27314-97-2,MFCD00132954
Catalog No.:AA01CBIB

27314-97-2 | 1,2,4-Benzotriazin-3-amine, 1,4-dioxide

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1mg
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10mg
98%
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50mg
≥98%
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$172.00   $120.00
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100mg
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  • Technical Information
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Technical Information
Catalog Number:
AA01CBIB
Chemical Name:
1,2,4-Benzotriazin-3-amine, 1,4-dioxide
CAS Number:
27314-97-2
Molecular Formula:
C7H6N4O2
Molecular Weight:
178.1481
MDL Number:
MFCD00132954
SMILES:
[O-][n+]1nc(=N)n(c2c1cccc2)O
Properties
Properties
 
BP:
493.581°C at 760 mmHg  
Form:
Solid  
MP:
220°C dec.  
Solubility:
DMSO: soluble10mg/mL, clear  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
191  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-0.3  

Literature

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Journal: Journal of theoretical biology 20121121

Title: Enhanced antitumor efficacy of cisplatin by tirapazamine-transferrin conjugate.

Journal: International journal of pharmaceutics 20120715

Title: Discovery and optimization of benzotriazine di-N-oxides targeting replicating and nonreplicating Mycobacterium tuberculosis.

Journal: Journal of medicinal chemistry 20120712

Title: A planned neck dissection is not necessary in all patients with N2-3 head-and-neck cancer after sequential chemoradiotherapy.

Journal: International journal of radiation oncology, biology, physics 20120701

Title: Dinitroazetidines are a novel class of anticancer agents and hypoxia-activated radiation sensitizers developed from highly energetic materials.

Journal: Cancer research 20120515

Title: Effects of tirapazamine on experimental colorectal liver metastases after radiofrequency ablation.

Journal: The British journal of surgery 20120401

Title: Effects of tirapazamine on experimental colorectal liver metastases after radiofrequency ablation (Br J Surg 2012; 99: 567-575).

Journal: The British journal of surgery 20120401

Title: On the reaction mechanism of tirapazamine reduction chemistry: unimolecular N-OH homolysis, stepwise dehydration, or triazene ring-opening.

Journal: Chemical research in toxicology 20120319

Title: Electron and spin-density analysis of tirapazamine reduction chemistry.

Journal: Chemical research in toxicology 20120319

Title: The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120315

Title: Prognostic and predictive significance of plasma HGF and IL-8 in a phase III trial of chemoradiation with or without tirapazamine in locoregionally advanced head and neck cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120315

Title: Molecular and cellular pharmacology of the hypoxia-activated prodrug TH-302.

Journal: Molecular cancer therapeutics 20120301

Title: Homologous recombination repair-dependent cytotoxicity of the benzotriazine di-N-oxide CEN-209: comparison with other hypoxia-activated prodrugs.

Journal: Biochemical pharmacology 20120301

Title: DNA strand cleavage by the phenazine di-N-oxide natural product myxin under both aerobic and anaerobic conditions.

Journal: Chemical research in toxicology 20120113

Title: Prognostic significance of plasma osteopontin in patients with locoregionally advanced head and neck squamous cell carcinoma treated on TROG 02.02 phase III trial.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120101

Title: Yeast toxicogenomics: genome-wide responses to chemical stresses with impact in environmental health, pharmacology, and biotechnology.

Journal: Frontiers in genetics 20120101

Title: Targeting tumor perfusion and oxygenation to improve the outcome of anticancer therapy.

Journal: Frontiers in pharmacology 20120101

Title: Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca²⁺ balance protein levels.

Journal: Oxidative medicine and cellular longevity 20120101

Title: Usefulness of combined treatment with continuous administration of tirapazamine and mild temperature hyperthermia in γ-ray irradiation in terms of local tumour response and lung metastatic potential.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20120101

Title: Enhanced antitumor effect of tirapazamine delivered intraperitoneally to VX2 liver tumor-bearing rabbits subjected to transarterial hepatic embolization.

Journal: Cardiovascular and interventional radiology 20111201

Title: Selenium is a modulator of circadian clock that protects mice from the toxicity of a chemotherapeutic drug via upregulation of the core clock protein, BMAL1.

Journal: Oncotarget 20111201

Title: Generation of oxygen gradients in microfluidic devices for cell culture using spatially confined chemical reactions.

Journal: Lab on a chip 20111107

Title: Quinoxalino[2,3-c]cinnolines and their 5-N-oxide: alkoxylation of methyl-substituted quinoxalino[2,3-c]cinnolines to acetals and orthoesters.

Journal: The Journal of organic chemistry 20111021

Title: Radiotherapy and temozolomide for newly diagnosed glioblastoma and anaplastic astrocytoma: validation of Radiation Therapy Oncology Group-Recursive Partitioning Analysis in the IMRT and temozolomide era.

Journal: Journal of neuro-oncology 20110801

Title: Hypoxia-targeting by tirapazamine (TPZ) induces preferential growth inhibition of nasopharyngeal carcinoma cells with Chk1/2 activation.

Journal: Investigational new drugs 20110601

Title: Targeting castration-induced tumour hypoxia enhances the acute effects of castration therapy in a rat prostate cancer model.

Journal: BJU international 20110601

Title: Hypoxia-dependent retinal toxicity of NLCQ-1 (NSC 709257) in BALB/c mice. Comparison with tirapazamine.

Journal: Basic & clinical pharmacology & toxicology 20110601

Title: Uroporphyrinogen decarboxylase: optimizing radiotherapy for head and neck cancer.

Journal: Future oncology (London, England) 20110501

Title: Early toxicity predicts long-term survival in high-grade glioma.

Journal: British journal of cancer 20110426

Title: Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives.

Journal: European journal of medicinal chemistry 20110301

Title: High-throughput 3D spheroid culture and drug testing using a 384 hanging drop array.

Journal: The Analyst 20110207

Title: Evaluation of the efficacy of radiation-modifying compounds using γH2AX as a molecular marker of DNA double-strand breaks.

Journal: Genome integrity 20110101

Title: Investigation of tumor hypoxia using a two-enzyme system for in vitro generation of oxygen deficiency.

Journal: Radiation oncology (London, England) 20110101

Title: Transport processes of radiopharmaceuticals and -modulators.

Journal: Radiation oncology (London, England) 20110101

Title: Pronounced hypoxia in models of murine and human leukemia: high efficacy of hypoxia-activated prodrug PR-104.

Journal: PloS one 20110101

Title: A mathematical model for targeting chemicals to tissues by exploiting complex degradation.

Journal: Biology direct 20110101

Title: Regulation of DNA repair mechanism in human glioma xenograft cells both in vitro and in vivo in nude mice.

Journal: PloS one 20110101

Title: Novel Phenazine 5,10-Dioxides Release OH in Simulated Hypoxia and Induce Reduction of Tumour Volume In Vivo.

Journal: ISRN pharmacology 20110101

Title: Targeting hypoxic tumour cells to overcome metastasis.

Journal: BMC cancer 20110101

Title: Metronomic Cyclophosphamide and Methotrexate Chemotherapy Combined with 1E10 Anti-Idiotype Vaccine in Metastatic Breast Cancer.

Journal: International journal of breast cancer 20110101

Title: Combined modality approaches in the management of adult glioblastoma.

Journal: Frontiers in oncology 20110101

Title: Strategies for discovery of small molecule radiation protectors and radiation mitigators.

Journal: Frontiers in oncology 20110101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20101201

Title: Henry S. Kaplan Distinguished Scientist Award Lecture 2007. The remarkable yin and yang of tumour hypoxia.

Journal: International journal of radiation biology 20101101

Title: Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20101015

Title: Strategies to promote translational research within the European Organisation for Research and Treatment of Cancer (EORTC) Head and Neck Cancer Group: a report from the Translational Research Subcommittee.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20101001

Title: Prognostic significance of p16INK4A and human papillomavirus in patients with oropharyngeal cancer treated on TROG 02.02 phase III trial.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100920

Title: p16 Expression as a predictive biomarker of hypoxic cell-sensitizing agents in oropharyngeal cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100920

Title: Substantial improvement in UK cervical cancer survival with chemoradiotherapy: results of a Royal College of Radiologists' audit.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain)) 20100901

Title: Medicinal electronomics bricolage design of hypoxia-targeting antineoplastic drugs and invention of boron tracedrugs as innovative future-architectural drugs.

Journal: Anticancer research 20100901

Title: Correlation of pharmacokinetic features and tissue distribution with toxicity of Q39, a hypoxic cell cytotoxic agent.

Journal: Die Pharmazie 20100901

Title: The hypoxia-selective cytotoxin NLCQ-1 (NSC 709257) controls metastatic disease when used as an adjuvant to radiotherapy.

Journal: British journal of cancer 20100713

Title: Phase 1 study of tirapazamine in combination with radiation and weekly cisplatin in patients with locally advanced cervical cancer.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20100701

Title: The tumor microenvironment in non-small-cell lung cancer.

Journal: Seminars in radiation oncology 20100701

Title: Critical impact of radiotherapy protocol compliance and quality in the treatment of advanced head and neck cancer: results from TROG 02.02.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100620

Title: Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): a phase III trial of the Trans-Tasman Radiation Oncology Group.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100620

Title: Review of positron emission tomography tracers for imaging of tumor hypoxia.

Journal: Cancer biotherapy & radiopharmaceuticals 20100601

Title: DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide.

Journal: Bioorganic & medicinal chemistry 20100501

Title: Characterization of radicals formed following enzymatic reduction of 3-substituted analogues of the hypoxia-selective cytotoxin 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Journal of the American Chemical Society 20100303

Title: Expression of hypoxia-inducible factor 1 alpha in thyroid carcinomas.

Journal: Endocrine-related cancer 20100301

Title: Regulation of hypoxia-induced mRNA expressions of HIF-1alpha and osteopontin and in vitro radiosensitization by tirapazamine in human nasopharyngeal carcinoma HNE-1 and CNE-1 cells.

Journal: Chinese journal of cancer 20100201

Title: Residual gammaH2AX foci as an indication of lethal DNA lesions.

Journal: BMC cancer 20100101

Title: Effectiveness of combined modality radiotherapy of orthotopic human squamous cell carcinomas in Nu/Nu mice using cetuximab, tirapazamine and MnSOD-plasmid liposome gene therapy.

Journal: In vivo (Athens, Greece) 20100101

Title: Hypoxia-inducible factor-1 as a therapeutic target in endometrial cancer management.

Journal: Obstetrics and gynecology international 20100101

Title: Design of novel hypoxia-targeting IDO hybrid inhibitors conjugated with an unsubstituted L-TRP as an IDO affinity moiety.

Journal: Advances in experimental medicine and biology 20100101

Title: Architectural heterogeneity in tumors caused by differentiation alters intratumoral drug distribution and affects therapeutic synergy of antiangiogenic organoselenium compound.

Journal: Journal of oncology 20100101

Title: XQ2, a novel TPZ derivative, induced G2/M phase arrest and apoptosis under hypoxia in non-small cell lung cancer cells.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Hypoxia-specific targets in cancer therapy: role of splice variants.

Journal: BMC medicine 20100101

Title: The contribution of cetuximab in the treatment of recurrent and/or metastatic head and neck cancer.

Journal: Biologics : targets & therapy 20100101

Title: A phase II randomized trial comparing radiotherapy with concurrent weekly cisplatin or weekly paclitaxel in patients with advanced cervical cancer.

Journal: Radiation oncology (London, England) 20100101

Title: Suppression of hypoxia-inducible factor 1α (HIF-1α) by tirapazamine is dependent on eIF2α phosphorylation rather than the mTORC1/4E-BP1 pathway.

Journal: PloS one 20100101

Title: VEGFR2 heterogeneity and response to anti-angiogenic low dose metronomic cyclophosphamide treatment.

Journal: BMC cancer 20100101

Title: A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy.

Journal: British journal of cancer 20091201

Title: Contribution of HIF-1 and drug penetrance to oxaliplatin resistance in hypoxic colorectal cancer cells.

Journal: British journal of cancer 20091020

Title: Spin trapping of radicals other than the *OH radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase.

Journal: Journal of the American Chemical Society 20091014

Title: Molecular imaging of hypoxia with radiolabelled agents.

Journal: European journal of nuclear medicine and molecular imaging 20091001

Title: Increased tumor oxygenation and drug uptake during anti-angiogenic weekly low dose cyclophosphamide enhances the anti-tumor effect of weekly tirapazamine.

Journal: Current cancer drug targets 20090901

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20090901

Title: Ultrasensitive electrochemical sensing of the anticancer drug tirapazamine using an ordered mesoporous carbon modified pyrolytic graphite electrode.

Journal: Biosensors & bioelectronics 20090715

Title: Detecting vascular-targeting effects of the hypoxic cytotoxin tirapazamine in tumor xenografts using magnetic resonance imaging.

Journal: International journal of radiation oncology, biology, physics 20090701

Title: Phase II study of tirapazamine, cisplatin, and etoposide and concurrent thoracic radiotherapy for limited-stage small-cell lung cancer: SWOG 0222.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090620

Title: Evaluation of the potential of hexamethylenetetramine, compared with tirapazamine, as a combined agent with {gamma}-irradiation and cisplatin treatment in vivo.

Journal: The British journal of radiology 20090501

Title: Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N).

Journal: Molecular cancer therapeutics 20090501

Title: Structural adaptation and heterogeneity of normal and tumor microvascular networks.

Journal: PLoS computational biology 20090501

Title: Cytotoxic palladium complexes of bioreductive quinoxaline N1,N4-dioxide prodrugs.

Journal: Bioorganic & medicinal chemistry 20090215

Title: Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxide antitumor agents: mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide.

Journal: Journal of the American Chemical Society 20090128

Title: A phase I pharmacokinetic study of hypoxic abdominal stop-flow perfusion with gemcitabine in patients with advanced pancreatic cancer and refractory malignant ascites.

Journal: Cancer chemotherapy and pharmacology 20090101

Title: Tirapazamine: a novel agent targeting hypoxic tumor cells.

Journal: Expert opinion on investigational drugs 20090101

Title: Synthesis, cytotoxic activity, and DNA binding properties of copper (II) complexes with hesperetin, naringenin, and apigenin.

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Title: A dialogue between the hypoxia-inducible factor and the tumor microenvironment.

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Journal: Analytical biochemistry 20081001

Title: Synthesis and biological activity of 1-methyl-tryptophan-tirapazamine hybrids as hypoxia-targeting indoleamine 2,3-dioxygenase inhibitors.

Journal: Bioorganic & medicinal chemistry 20080915

Title: iNOS as a therapeutic target for treatment of human tumors.

Journal: Nitric oxide : biology and chemistry 20080901

Title: Hypoxia-specific drug tirapazamine does not abrogate hypoxic tumor cells in combination therapy with irinotecan and methylselenocysteine in well-differentiated human head and neck squamous cell carcinoma a253 xenografts.

Journal: Neoplasia (New York, N.Y.) 20080801

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Title: [Can tumor hypoxia be turned into a chemotherapeutic advantage?].

Journal: Bulletin du cancer 20080501

Title: Carbonic anhydrase 9 (CA9) expression in tumor cells enhances sensitivity to tirapazamine.

Journal: Journal of cancer research and clinical oncology 20080301

Title: Exploring vascular dysfunction caused by tirapazamine.

Journal: Microvascular research 20080301

Title: Evaluation of the antiangiogenic potential of AQ4N.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080301

Title: Hypoxic tumor cell radiosensitization: role of the iNOS/NO pathway.

Journal: Bulletin du cancer 20080301

Title: Tirapazamine plus cisplatin and irradiation in a mouse model: improved tumor control at the cost of increased toxicity.

Journal: Journal of cancer research and clinical oncology 20080201

Title: A review of topotecan in combination chemotherapy for advanced cervical cancer.

Journal: Therapeutics and clinical risk management 20080201

Title: Homologous recombination is the principal pathway for the repair of DNA damage induced by tirapazamine in mammalian cells.

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Title: Pharmacokinetic/pharmacodynamic model-guided identification of hypoxia-selective 1,2,4-benzotriazine 1,4-dioxides with antitumor activity: the role of extravascular transport.

Journal: Journal of medicinal chemistry 20071213

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20071201

Title: DNA strand damage product analysis provides evidence that the tumor cell-specific cytotoxin tirapazamine produces hydroxyl radical and acts as a surrogate for O(2).

Journal: Journal of the American Chemical Society 20071024

Title: Oxygen dependence and extravascular transport of hypoxia-activated prodrugs: comparison of the dinitrobenzamide mustard PR-104A and tirapazamine.

Journal: International journal of radiation oncology, biology, physics 20071001

Title: Chemical radiosensitizers for use in radiotherapy.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain)) 20070801

Title: Bioreductive drugs: from concept to clinic.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain)) 20070801

Title: Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA cross-linking agent PR-104.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070701

Title: Adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts.

Journal: British journal of cancer 20070618

Title: Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards.

Journal: Radiation research 20070601

Title: Beyond detection: novel applications for PET imaging to guide cancer therapy.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070601

Title: Pretreatment 18F-FAZA PET predicts success of hypoxia-directed radiochemotherapy using tirapazamine.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070601

Title: Increased nanoparticle penetration in collagenase-treated multicellular spheroids.

Journal: International journal of nanomedicine 20070601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20070601

Title: [Inhibitory effect of tirapazamine combined with phosphatidylinositol 3-kinase inhibitor LY294002 to ovarian cancer cells].

Journal: Zhonghua yi xue za zhi 20070508

Title: Synthesis, structure and hypoxic cytotoxicity of 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives.

Journal: Archiv der Pharmazie 20070501

Title: On the mechanism of reaction of radicals with tirapazamine.

Journal: Journal of the American Chemical Society 20070418

Title: Phase I trial of tirapazamine, cisplatin, and concurrent accelerated boost reirradiation in patients with recurrent head and neck cancer.

Journal: International journal of radiation oncology, biology, physics 20070301

Title: Effects of fluctuating oxygenation on tirapazamine efficacy: Theoretical predictions.

Journal: International journal of radiation oncology, biology, physics 20070201

Title: The concurrent chemoradiation paradigm--general principles.

Journal: Nature clinical practice. Oncology 20070201

Title: Assessment of DNA damage at the dimer level: measurement of the formamide lesion.

Journal: Radiation research 20070201

Title: The usefulness of mild temperature hyperthermia combined with continuous tirapazamine administration under reduced dose-rate irradiation with gamma-rays.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20070201

Title: Dependency of the effect of a vascular disrupting agent on sensitivity to tirapazamine and gamma-ray irradiation upon the timing of its administration and tumor size, with reference to the effect on intratumor quiescent cells.

Journal: Journal of cancer research and clinical oncology 20070101

Title: Radiosensitization by 2-benzoyl-3-phenyl-6,7-dichloroquinoxaline 1,4-dioxide under oxia and hypoxia in human colon cancer cells.

Journal: Radiation oncology (London, England) 20070101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20070101

Title: DNA repair mechanisms are involved in the hypoxia-dependent toxicity of NLCQ-1 (NSC 709257) and its synergistic interaction with alkylating agents.

Journal: In vivo (Athens, Greece) 20070101

Title: Identifying and targeting hypoxia in head and neck cancer: a brief overview of current approaches.

Journal: International journal of radiation oncology, biology, physics 20070101

Title: Hypoxia in head and neck cancer: studies with hypoxic positron emission tomography imaging and hypoxic cytotoxins.

Journal: International journal of radiation oncology, biology, physics 20070101

Title: Tumor hypoxia in cancer therapy.

Journal: Methods in enzymology 20070101

Title: Breast tumour angiogenesis.

Journal: Breast cancer research : BCR 20070101

Title: Bevacizumab: the evidence for its clinical potential in the treatment of nonsmall cell lung cancer.

Journal: Core evidence 20070101

Title: The usefulness of a continuous administration of tirapazamine combined with reduced dose-rate irradiation using {gamma}-rays or reactor thermal neutrons.

Journal: The British journal of radiology 20061201

Title: New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides.

Journal: Bioorganic & medicinal chemistry 20061015

Title: Complete 1H, 13C and 15N NMR assignment of tirapazamine and related 1,2,4-benzotriazine N-oxides.

Journal: Magnetic resonance in chemistry : MRC 20061001

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20061001

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20060901

Title: Respecting cancer drug transportability: a basis for successful lead selection.

Journal: Journal of the National Cancer Institute 20060816

Title: Use of three-dimensional tissue cultures to model extravascular transport and predict in vivo activity of hypoxia-targeted anticancer drugs.

Journal: Journal of the National Cancer Institute 20060816

Title: Selective hypoxia-cytotoxins based on vanadyl complexes with 3-aminoquinoxaline-2-carbonitrile-N1,N4-dioxide derivatives.

Journal: Journal of inorganic biochemistry 20060801

Title: Hypoxia: targeting the tumour.

Journal: Anti-cancer agents in medicinal chemistry 20060701

Title: Concurrent chemoradiotherapy for locally advanced, nonmetastatic, squamous carcinoma of the head and neck: consensus, controversy, and conundrum.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20060610

Title: Mature results from a randomized Phase II trial of cisplatin plus 5-fluorouracil and radiotherapy with or without tirapazamine in patients with resectable Stage IV head and neck squamous cell carcinomas.

Journal: Cancer 20060501

Title: Prognostic significance of [18F]-misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: a substudy of Trans-Tasman Radiation Oncology Group Study 98.02.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20060501

Title: [Evaluation of the toxicity of tirapazamine plus cisplatin in a mouse tumor model].

Journal: Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al] 20060401

Title: A phase II evaluation of tirapazamine plus cisplatin in the treatment of recurrent platinum-sensitive ovarian or primary peritoneal cancer: a Gynecologic Oncology Group study.

Journal: Gynecologic oncology 20060301

Title: Radiation sensitization with redox modulators: a promising approach.

Journal: International journal of radiation oncology, biology, physics 20060201

Title: Low-dose metronomic daily cyclophosphamide and weekly tirapazamine: a well-tolerated combination regimen with enhanced efficacy that exploits tumor hypoxia.

Journal: Cancer research 20060201

Title: Tirapazamine causes vascular dysfunction in HCT-116 tumour xenografts.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20060201

Title: [Study on HPLC determination method and pharmacokinetics of tirapazaming in rabbits].

Journal: Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi 20060201

Title: Potentiation of the cytotoxicity of the anticancer agent tirapazamine by benzotriazine N-oxides: the role of redox equilibria.

Journal: Journal of the American Chemical Society 20060111

Title: Tirapazamine plus cisplatin in advanced or recurrent carcinoma of the uterine cervix: a Southwest Oncology Group study.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101

Title: Global analysis of gene function in yeast by quantitative phenotypic profiling.

Journal: Molecular systems biology 20060101

Title: Phase II study of tirapazamine plus cisplatin in patients with advanced or recurrent cervical cancer.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101

Title: Potentiation of alkylating agents by NLCQ-1 or TPZ in vitro and in vivo.

Journal: Journal of experimental therapeutics & oncology 20060101

Title: Tirapazamine: from bench to clinical trials.

Journal: Current clinical pharmacology 20060101

Title: Update on clinical radiobiology.

Journal: Biomedical imaging and intervention journal 20060101

Title: Phase III trial of paclitaxel plus carboplatin with or without tirapazamine in advanced non-small-cell lung cancer: Southwest Oncology Group Trial S0003.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20051220

Title: Utility of FMISO PET in advanced head and neck cancer treated with chemoradiation incorporating a hypoxia-targeting chemotherapy agent.

Journal: European journal of nuclear medicine and molecular imaging 20051201

Title: Synthesis of 3-amino-1,2,4-benzothiadi- azine 1,1-dioxides via a tandem aza-Wittig/heterocumulene annulation.

Journal: The Journal of organic chemistry 20051125

Title: Large-scale analysis of genes that alter sensitivity to the anticancer drug tirapazamine in Saccharomyces cerevisiae.

Journal: Molecular pharmacology 20051101

Title: Resistance to endocrine therapy in breast cancer.

Journal: Cancer chemotherapy and pharmacology 20051101

Title: [Determination of the related substances in tirapazamine by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20051101

Title: Anemia, tumor hypoxemia, and the cancer patient.

Journal: International journal of radiation oncology, biology, physics 20050901

Title: Combination of the antivascular agent ZD6126 with hypoxic cytotoxin treatment, with reference to the effect on quiescent tumor cells and the dependency on p53 status of tumor cells.

Journal: Oncology reports 20050801

Title: The role of bioreductive activation of doxorubicin in cytotoxic activity against leukaemia HL60-sensitive cell line and its multidrug-resistant sublines.

Journal: British journal of cancer 20050711

Title: Hypoxia in head and neck cancer: how much, how important?

Journal: Head & neck 20050701

Title: Observation of incipient tumor angiogenesis that is independent of hypoxia and hypoxia inducible factor-1 activation.

Journal: Cancer research 20050701

Title: Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides.

Journal: Organic & biomolecular chemistry 20050607

Title: Tirapazamine administered as a neoadjuvant to radiotherapy reduces metastatic dissemination.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050601

Title: The usefulness of continuous administration of hypoxic cytotoxin combined with mild temperature hyperthermia, with reference to effects on quiescent tumour cell populations.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20050601

Title: Tirapazamine cytotoxicity for neuroblastoma is p53 dependent.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050401

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20050401

Title: Time-resolved spectroscopy of the excited singlet states of tirapazamine and desoxytirapazamine.

Journal: The journal of physical chemistry. A 20050303

Title: Tirapazamine with cisplatin and vinorelbine in patients with advanced non-small-cell lung cancer: a phase I/II study.

Journal: Clinical lung cancer 20050301

Title: Extravascular transport of drugs in tumor tissue: effect of lipophilicity on diffusion of tirapazamine analogues in multicellular layer cultures.

Journal: Journal of medicinal chemistry 20050224

Title: Tirapazamine, Cisplatin, and Radiation versus Fluorouracil, Cisplatin, and Radiation in patients with locally advanced head and neck cancer: a randomized phase II trial of the Trans-Tasman Radiation Oncology Group (TROG 98.02).

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050101

Title: Improving survival and reducing toxicity with chemotherapy in advanced non-small cell lung cancer : a realistic goal?

Journal: Treatments in respiratory medicine 20050101

Title: Radiosensitising effect of electrochemotherapy with bleomycin in LPB sarcoma cells and tumors in mice.

Journal: BMC cancer 20050101

Title: Prodrug research: futile or fertile?

Journal: Biochemical pharmacology 20041201

Title: The Japanese experiences with hypoxia-targeting pharmacoradiotherapy: from hypoxic cell sensitisers to radiation-activated prodrugs.

Journal: Expert opinion on pharmacotherapy 20041201

Title: [Phase II-trial of tirapazamine in combination with cisplatin and gemcitabine in patients with advanced non-small-cell-lung-cancer (NSCLC)].

Journal: Pneumologie (Stuttgart, Germany) 20041201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20041201

Title: Enzyme-activated, hypoxia-selective DNA damage by 3-amino-2-quinoxalinecarbonitrile 1,4-di-N-oxide.

Journal: Chemical research in toxicology 20041101

Title: Combined chemotherapy and radiation therapy for cervical cancer.

Journal: Journal of the National Comprehensive Cancer Network : JNCCN 20041101

Title: Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo.

Journal: British journal of cancer 20041018

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20041001

Title: Microenvironmental adaptation of experimental tumours to chronic vs acute hypoxia.

Journal: British journal of cancer 20040913

Title: Prospects for hypoxia-activated anticancer drugs.

Journal: Current medicinal chemistry. Anti-cancer agents 20040901

Title: Cytochrome P450 CYP1B1 activity in renal cell carcinoma.

Journal: British journal of cancer 20040831

Title: Phase I study of tirapazamine plus cisplatin/etoposide and concurrent thoracic radiotherapy in limited-stage small cell lung cancer (S0004): a Southwest Oncology Group study.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040815

Title: Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide.

Journal: Cancer research 20040801

Title: Enhanced effectiveness of radiochemotherapy with tirapazamine by local application of electric pulses to tumors.

Journal: Radiation research 20040801

Title: Clinical studies of hypoxia modification in radiotherapy.

Journal: Seminars in radiation oncology 20040701

Title: Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides.

Journal: Journal of the American Chemical Society 20040630

Title: Oxygen dependence of the metabolic activation and cytotoxicity of tirapazamine: implications for extravascular transport and activity in tumors.

Journal: Radiation research 20040601

Title: New derivatives of quinazoline and 1, 2-dihydroquinazoline n3-oxide with expected antitumor activity.

Journal: Archiv der Pharmazie 20040501

Title: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part II.

Journal: Archiv der Pharmazie 20040501

Title: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part III.

Journal: Archiv der Pharmazie 20040501

Title: Phase I trial of tirapazamine and cyclophosphamide in children with refractory solid tumors: a pediatric oncology group study.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20040415

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20040401

Title: 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT.

Journal: British journal of cancer 20040308

Title: Enzyme-catalyzed activation of anticancer prodrugs.

Journal: Pharmacological reviews 20040301

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20040301

Title: Hypoxia targeted gene therapy to increase the efficacy of tirapazamine as an adjuvant to radiotherapy: reversing tumor radioresistance and effecting cure.

Journal: Cancer research 20040215

Title: DNA-targeted 1,2,4-benzotriazine 1,4-dioxides: potent analogues of the hypoxia-selective cytotoxin tirapazamine.

Journal: Journal of medicinal chemistry 20040115

Title: Selective potentiation of the hypoxic cytotoxicity of tirapazamine by its 1-N-oxide metabolite SR 4317.

Journal: Cancer research 20040115

Title: The importance of DT-diaphorase and hypoxia in the cytotoxicity of RH1 in human breast and non-small cell lung cancer cell lines.

Journal: Anti-cancer drugs 20040101

Title: Efficacy of cytotoxic agents used in the treatment of testicular germ cell tumours under normoxic and hypoxic conditions in vitro.

Journal: British journal of cancer 20031201

Title: Endogenous markers of tumor hypoxia predictors of clinical radiation resistance?

Journal: Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al] 20031201

Title: NLCQ-1 (NSC 709257): exploiting hypoxia with a weak DNA-intercalating bioreductive drug.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031115

Title: Enhanced conversion of DNA radical damage to double strand breaks by 1,2,4-benzotriazine 1,4-dioxides linked to a DNA binder compared to tirapazamine.

Journal: Chemical research in toxicology 20031101

Title: The expression of P-glycoprotein does influence the distribution of novel fluorescent compounds in solid tumour models.

Journal: British journal of cancer 20031020

Title: Human NADPH-cytochrome p450 reductase overexpression does not enhance the aerobic cytotoxicity of doxorubicin in human breast cancer cell lines.

Journal: Cancer research 20031015

Title: Tirapazamine plus carboplatin and paclitaxel in advanced malignant solid tumors: a california cancer consortium phase I and molecular correlative study.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031001

Title: DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Journal of the American Chemical Society 20030924

Title: Multicellular resistance to tirapazamine is due to restricted extravascular transport: a pharmacokinetic/pharmacodynamic study in HT29 multicellular layer cultures.

Journal: Cancer research 20030915

Title: Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK.

Journal: British journal of cancer 20030804

Title: A mass spectrometry study of tirapazamine and its metabolites. insights into the mechanism of metabolic transformations and the characterization of reaction intermediates.

Journal: Journal of the American Society for Mass Spectrometry 20030801

Title: A simple method of producing low oxygen conditions with oxyrase for cultured cells exposed to radiation and tirapazamine.

Journal: American journal of clinical oncology 20030801

Title: Expression of phosphorylated histone H2AX as a surrogate of cell killing by drugs that create DNA double-strand breaks.

Journal: Cancer research 20030801

Title: Tumour hypoxia, chemotherapeutic resistance and hypoxia-related therapies.

Journal: Cancer treatment reviews 20030801

Title: Comparison of the comet assay and the oxygen microelectrode for measuring tumor oxygenation in head-and-neck cancer patients.

Journal: International journal of radiation oncology, biology, physics 20030601

Title: Non-nuclear localized human NOSII enhances the bioactivation and toxicity of tirapazamine (SR4233) in vitro.

Journal: Molecular pharmacology 20030601

Title: Improved potency of the hypoxic cytotoxin tirapazamine by DNA-targeting.

Journal: Biochemical pharmacology 20030601

Title: Antagonism of buthionine sulfoximine cytotoxicity for human neuroblastoma cell lines by hypoxia is reversed by the bioreductive agent tirapazamine.

Journal: Cancer research 20030401

Title: Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-Di-N-oxide analogues.

Journal: Chemical research in toxicology 20030201

Title: Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction.

Journal: Journal of the American Chemical Society 20030122

Title: Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine.

Journal: Journal of medicinal chemistry 20030102

Title: Potential of alpha-amino alcohol p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, regarding its enantiomers.

Journal: Journal of cancer research and clinical oncology 20030101

Title: Usefulness of combined treatment with mild temperature hyperthermia and/or tirapazamine in the treatment of solid tumors: its independence of p53 status.

Journal: Cancer science 20030101

Title: Antiangiogenic hypoxic cytotoxin TX-402 inhibits hypoxia-inducible factor 1 signaling pathway.

Journal: Anticancer research 20030101

Title: Therapeutic advantage from combining paclitaxel with the hypoxia-selective cytotoxin NLCQ-1 in murine tumor- or human xenograft-bearing mice.

Journal: Cancer chemotherapy and pharmacology 20021201

Title: Platinum drugs in the treatment of non-small-cell lung cancer.

Journal: British journal of cancer 20021007

Title: Therapeutic advantage from combining 5-fluorouracil with the hypoxia-selective cytotoxin NLCQ-1 in vivo; comparison with tirapazamine.

Journal: Cancer chemotherapy and pharmacology 20021001

Title: Tirapazamine: a hypoxia-activated topoisomerase II poison.

Journal: Cancer research 20020915

Title: Oxidative DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Bioorganic & medicinal chemistry letters 20020902

Title: 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy.

Journal: Investigational new drugs 20020801

Title: Carbogen breathing after irradiation enhances the effectiveness of tirapazamine in SiHa tumors but not SCCVII tumors in mice.

Journal: Radiation research 20020701

Title: Design, synthesis and biological activities of antiangiogenic hypoxic cytotoxin, triazine-N-oxide derivatives.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20020501

Title: Photochemical electron transfer reactions of tirapazamine.

Journal: Photochemistry and photobiology 20020401

Title: Significance of the response of quiescent cell populations within solid tumors in cancer therapy.

Journal: Journal of radiation research 20020301

Title: The effect of functional groups on reduction and activation of quinone bioreductive agents by DT-diaphorase.

Journal: Cancer chemotherapy and pharmacology 20020201

Title: Local hypoxia is produced at sites of intratumour injection.

Journal: British journal of cancer 20020201

Title: Tirapazamine: prototype for a novel class of therapeutic agents targeting tumor hypoxia.

Journal: Seminars in oncology 20020201

Title: Synergistic enhancement of the antitumor effect of taxol by the bioreductive compound NLCQ-1, in vivo: comparison with tirapazamine.

Journal: Oncology research 20020101

Title: Hypoxic active drugs.

Journal: I supplementi di Tumori : official journal of Societa italiana di cancerologia ... [et al.] 20020101

Title: Tumor microenvironment and the response to anticancer therapy.

Journal: Cancer biology & therapy 20020101

Title: Metabolism of tirapazamine by multiple reductases in the nucleus.

Journal: Biochemical pharmacology 20011101

Title: Optimizing the use of combined radioimmunotherapy and hypoxic cytotoxin therapy as a function of tumor hypoxia.

Journal: International journal of cancer 20011101

Title: Evaluation of the potential of p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, referring to the effect on intratumor quiescent cells.

Journal: Japanese journal of cancer research : Gann 20010901

Title: Indications for chemotherapy in stage IV non-small cell lung cancer.

Journal: Lung cancer (Amsterdam, Netherlands) 20010901

Title: Modeling the action of an antitumor drug: a density functional theory study of the mechanism of tirapazamine.

Journal: Journal of the American Chemical Society 20010801

Title: Effects of anticancer drugs on the metabolism of the anticancer drug 5,6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes.

Journal: British journal of clinical pharmacology 20010801

Title: The chemopotentiation of cisplatin by the novel bioreductive drug AQ4N.

Journal: British journal of cancer 20010801

Title: Schedule-dependent potentiation of chemotherapeutic drugs by the bioreductive compounds NLCQ-1 and tirapazamine against EMT6 tumors in mice.

Journal: Cancer chemotherapy and pharmacology 20010801

Title: Selective interaction of tirapazamine with DNA bases and DNA. A comparison of cyclic voltammetry and electrolysis techniques.

Journal: Free radical research 20010801

Title: Radiosensitization effect by combination with paclitaxel in vivo, including the effect on intratumor quiescent cells.

Journal: International journal of radiation oncology, biology, physics 20010715

Title: Inhibition of DNA replication by tirapazamine.

Journal: Cancer research 20010715

Title: Phase I trial of i.v. administered tirapazamine plus cyclophosphamide.

Journal: Anti-cancer drugs 20010701

Title: Recent advances in the chemotherapy of non-small cell lung cancer.

Journal: Japanese journal of clinical oncology 20010701

Title: Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia.

Journal: Current medicinal chemistry 20010601

Title: Triplet combination chemotherapy and targeted therapy regimens.

Journal: Oncology (Williston Park, N.Y.) 20010301

Title: Therapeutic targets in radiotherapy.

Journal: International journal of radiation oncology, biology, physics 20010201

Title: Phase I trial of concurrent tirapazamine, cisplatin, and radiotherapy in patients with advanced head and neck cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20010115

Title: 3-amino-1,2,4-benzotriazine 4-oxide: characterization of a new metabolite arising from bioreductive processing of the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: The Journal of organic chemistry 20010112

Title: Analysis of DNA damage in individual cells.

Journal: Methods in cell biology 20010101

Title: An investigation of the molecular basis for the synergistic interaction of tirapazamine and cisplatin.

Journal: International journal of radiation oncology, biology, physics 20010101

Title: Mitochondrial dysfunction after aerobic exposure to the hypoxic cytotoxin tirapazamine.

Journal: Cancer research 20010101

Title: Cytotoxicity of bioreductive drug tirapazamine is increased by application of electric pulses in SA-1 tumours in mice.

Journal: Anticancer research 20010101

Title: 4-[3-(2-Nitro-1-imidazolyl)propylamino]-7-chloroquinoline hydrochloride (NLCQ-1), a novel bioreductive agent as radiosensitizer in vitro and in vivo: comparison with tirapazamine.

Journal: Oncology research 20010101

Title: Hypoxia and oxidative stress. Tumour hypoxia--therapeutic considerations.

Journal: Breast cancer research : BCR 20010101

Title: Targeting hypoxia in head and neck cancer.

Journal: Acta oncologica (Stockholm, Sweden) 20010101

Title: Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/P450-reductase-based cancer gene therapy.

Journal: Cancer research 20000715

Title: Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations.

Journal: British journal of cancer 19950401

Title: SR-4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells.

Journal: International journal of radiation oncology, biology, physics 19860701

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Tags:27314-97-2 Molecular Formula|27314-97-2 MDL|27314-97-2 SMILES|27314-97-2 1,2,4-Benzotriazin-3-amine, 1,4-dioxide
Catalog No.: AA01CBIB
27314-97-2,MFCD00132954
27314-97-2 | 1,2,4-Benzotriazin-3-amine, 1,4-dioxide
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Purity: 98%
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Technical Information
Catalog Number: AA01CBIB
Chemical Name: 1,2,4-Benzotriazin-3-amine, 1,4-dioxide
CAS Number: 27314-97-2
Molecular Formula: C7H6N4O2
Molecular Weight: 178.1481
MDL Number: MFCD00132954
SMILES: [O-][n+]1nc(=N)n(c2c1cccc2)O
Properties
BP: 493.581°C at 760 mmHg  
Form: Solid  
MP: 220°C dec.  
Solubility: DMSO: soluble10mg/mL, clear  
Storage: Keep in dry area;-20 ℃;  
Complexity: 191  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 13  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -0.3  
Literature fold

Title: Avascular tumour growth dynamics and the constraints of protein binding for drug transportation.

Journal: Journal of theoretical biology20121121

Title: Enhanced antitumor efficacy of cisplatin by tirapazamine-transferrin conjugate.

Journal: International journal of pharmaceutics20120715

Title: Discovery and optimization of benzotriazine di-N-oxides targeting replicating and nonreplicating Mycobacterium tuberculosis.

Journal: Journal of medicinal chemistry20120712

Title: A planned neck dissection is not necessary in all patients with N2-3 head-and-neck cancer after sequential chemoradiotherapy.

Journal: International journal of radiation oncology, biology, physics20120701

Title: Dinitroazetidines are a novel class of anticancer agents and hypoxia-activated radiation sensitizers developed from highly energetic materials.

Journal: Cancer research20120515

Title: Effects of tirapazamine on experimental colorectal liver metastases after radiofrequency ablation.

Journal: The British journal of surgery20120401

Title: Effects of tirapazamine on experimental colorectal liver metastases after radiofrequency ablation (Br J Surg 2012; 99: 567-575).

Journal: The British journal of surgery20120401

Title: On the reaction mechanism of tirapazamine reduction chemistry: unimolecular N-OH homolysis, stepwise dehydration, or triazene ring-opening.

Journal: Chemical research in toxicology20120319

Title: Electron and spin-density analysis of tirapazamine reduction chemistry.

Journal: Chemical research in toxicology20120319

Title: The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20120315

Title: Prognostic and predictive significance of plasma HGF and IL-8 in a phase III trial of chemoradiation with or without tirapazamine in locoregionally advanced head and neck cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20120315

Title: Molecular and cellular pharmacology of the hypoxia-activated prodrug TH-302.

Journal: Molecular cancer therapeutics20120301

Title: Homologous recombination repair-dependent cytotoxicity of the benzotriazine di-N-oxide CEN-209: comparison with other hypoxia-activated prodrugs.

Journal: Biochemical pharmacology20120301

Title: DNA strand cleavage by the phenazine di-N-oxide natural product myxin under both aerobic and anaerobic conditions.

Journal: Chemical research in toxicology20120113

Title: Prognostic significance of plasma osteopontin in patients with locoregionally advanced head and neck squamous cell carcinoma treated on TROG 02.02 phase III trial.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20120101

Title: Yeast toxicogenomics: genome-wide responses to chemical stresses with impact in environmental health, pharmacology, and biotechnology.

Journal: Frontiers in genetics20120101

Title: Targeting tumor perfusion and oxygenation to improve the outcome of anticancer therapy.

Journal: Frontiers in pharmacology20120101

Title: Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca²⁺ balance protein levels.

Journal: Oxidative medicine and cellular longevity20120101

Title: Usefulness of combined treatment with continuous administration of tirapazamine and mild temperature hyperthermia in γ-ray irradiation in terms of local tumour response and lung metastatic potential.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group20120101

Title: Enhanced antitumor effect of tirapazamine delivered intraperitoneally to VX2 liver tumor-bearing rabbits subjected to transarterial hepatic embolization.

Journal: Cardiovascular and interventional radiology20111201

Title: Selenium is a modulator of circadian clock that protects mice from the toxicity of a chemotherapeutic drug via upregulation of the core clock protein, BMAL1.

Journal: Oncotarget20111201

Title: Generation of oxygen gradients in microfluidic devices for cell culture using spatially confined chemical reactions.

Journal: Lab on a chip20111107

Title: Quinoxalino[2,3-c]cinnolines and their 5-N-oxide: alkoxylation of methyl-substituted quinoxalino[2,3-c]cinnolines to acetals and orthoesters.

Journal: The Journal of organic chemistry20111021

Title: Radiotherapy and temozolomide for newly diagnosed glioblastoma and anaplastic astrocytoma: validation of Radiation Therapy Oncology Group-Recursive Partitioning Analysis in the IMRT and temozolomide era.

Journal: Journal of neuro-oncology20110801

Title: Hypoxia-targeting by tirapazamine (TPZ) induces preferential growth inhibition of nasopharyngeal carcinoma cells with Chk1/2 activation.

Journal: Investigational new drugs20110601

Title: Targeting castration-induced tumour hypoxia enhances the acute effects of castration therapy in a rat prostate cancer model.

Journal: BJU international20110601

Title: Hypoxia-dependent retinal toxicity of NLCQ-1 (NSC 709257) in BALB/c mice. Comparison with tirapazamine.

Journal: Basic & clinical pharmacology & toxicology20110601

Title: Uroporphyrinogen decarboxylase: optimizing radiotherapy for head and neck cancer.

Journal: Future oncology (London, England)20110501

Title: Early toxicity predicts long-term survival in high-grade glioma.

Journal: British journal of cancer20110426

Title: Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives.

Journal: European journal of medicinal chemistry20110301

Title: High-throughput 3D spheroid culture and drug testing using a 384 hanging drop array.

Journal: The Analyst20110207

Title: Evaluation of the efficacy of radiation-modifying compounds using γH2AX as a molecular marker of DNA double-strand breaks.

Journal: Genome integrity20110101

Title: Investigation of tumor hypoxia using a two-enzyme system for in vitro generation of oxygen deficiency.

Journal: Radiation oncology (London, England)20110101

Title: Transport processes of radiopharmaceuticals and -modulators.

Journal: Radiation oncology (London, England)20110101

Title: Pronounced hypoxia in models of murine and human leukemia: high efficacy of hypoxia-activated prodrug PR-104.

Journal: PloS one20110101

Title: A mathematical model for targeting chemicals to tissues by exploiting complex degradation.

Journal: Biology direct20110101

Title: Regulation of DNA repair mechanism in human glioma xenograft cells both in vitro and in vivo in nude mice.

Journal: PloS one20110101

Title: Novel Phenazine 5,10-Dioxides Release OH in Simulated Hypoxia and Induce Reduction of Tumour Volume In Vivo.

Journal: ISRN pharmacology20110101

Title: Targeting hypoxic tumour cells to overcome metastasis.

Journal: BMC cancer20110101

Title: Metronomic Cyclophosphamide and Methotrexate Chemotherapy Combined with 1E10 Anti-Idiotype Vaccine in Metastatic Breast Cancer.

Journal: International journal of breast cancer20110101

Title: Combined modality approaches in the management of adult glioblastoma.

Journal: Frontiers in oncology20110101

Title: Strategies for discovery of small molecule radiation protectors and radiation mitigators.

Journal: Frontiers in oncology20110101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20101201

Title: Henry S. Kaplan Distinguished Scientist Award Lecture 2007. The remarkable yin and yang of tumour hypoxia.

Journal: International journal of radiation biology20101101

Title: Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20101015

Title: Strategies to promote translational research within the European Organisation for Research and Treatment of Cancer (EORTC) Head and Neck Cancer Group: a report from the Translational Research Subcommittee.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology20101001

Title: Prognostic significance of p16INK4A and human papillomavirus in patients with oropharyngeal cancer treated on TROG 02.02 phase III trial.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100920

Title: p16 Expression as a predictive biomarker of hypoxic cell-sensitizing agents in oropharyngeal cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100920

Title: Substantial improvement in UK cervical cancer survival with chemoradiotherapy: results of a Royal College of Radiologists' audit.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain))20100901

Title: Medicinal electronomics bricolage design of hypoxia-targeting antineoplastic drugs and invention of boron tracedrugs as innovative future-architectural drugs.

Journal: Anticancer research20100901

Title: Correlation of pharmacokinetic features and tissue distribution with toxicity of Q39, a hypoxic cell cytotoxic agent.

Journal: Die Pharmazie20100901

Title: The hypoxia-selective cytotoxin NLCQ-1 (NSC 709257) controls metastatic disease when used as an adjuvant to radiotherapy.

Journal: British journal of cancer20100713

Title: Phase 1 study of tirapazamine in combination with radiation and weekly cisplatin in patients with locally advanced cervical cancer.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society20100701

Title: The tumor microenvironment in non-small-cell lung cancer.

Journal: Seminars in radiation oncology20100701

Title: Critical impact of radiotherapy protocol compliance and quality in the treatment of advanced head and neck cancer: results from TROG 02.02.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100620

Title: Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): a phase III trial of the Trans-Tasman Radiation Oncology Group.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20100620

Title: Review of positron emission tomography tracers for imaging of tumor hypoxia.

Journal: Cancer biotherapy & radiopharmaceuticals20100601

Title: DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide.

Journal: Bioorganic & medicinal chemistry20100501

Title: Characterization of radicals formed following enzymatic reduction of 3-substituted analogues of the hypoxia-selective cytotoxin 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Journal of the American Chemical Society20100303

Title: Expression of hypoxia-inducible factor 1 alpha in thyroid carcinomas.

Journal: Endocrine-related cancer20100301

Title: Regulation of hypoxia-induced mRNA expressions of HIF-1alpha and osteopontin and in vitro radiosensitization by tirapazamine in human nasopharyngeal carcinoma HNE-1 and CNE-1 cells.

Journal: Chinese journal of cancer20100201

Title: Residual gammaH2AX foci as an indication of lethal DNA lesions.

Journal: BMC cancer20100101

Title: Effectiveness of combined modality radiotherapy of orthotopic human squamous cell carcinomas in Nu/Nu mice using cetuximab, tirapazamine and MnSOD-plasmid liposome gene therapy.

Journal: In vivo (Athens, Greece)20100101

Title: Hypoxia-inducible factor-1 as a therapeutic target in endometrial cancer management.

Journal: Obstetrics and gynecology international20100101

Title: Design of novel hypoxia-targeting IDO hybrid inhibitors conjugated with an unsubstituted L-TRP as an IDO affinity moiety.

Journal: Advances in experimental medicine and biology20100101

Title: Architectural heterogeneity in tumors caused by differentiation alters intratumoral drug distribution and affects therapeutic synergy of antiangiogenic organoselenium compound.

Journal: Journal of oncology20100101

Title: XQ2, a novel TPZ derivative, induced G2/M phase arrest and apoptosis under hypoxia in non-small cell lung cancer cells.

Journal: Bioscience, biotechnology, and biochemistry20100101

Title: Hypoxia-specific targets in cancer therapy: role of splice variants.

Journal: BMC medicine20100101

Title: The contribution of cetuximab in the treatment of recurrent and/or metastatic head and neck cancer.

Journal: Biologics : targets & therapy20100101

Title: A phase II randomized trial comparing radiotherapy with concurrent weekly cisplatin or weekly paclitaxel in patients with advanced cervical cancer.

Journal: Radiation oncology (London, England)20100101

Title: Suppression of hypoxia-inducible factor 1α (HIF-1α) by tirapazamine is dependent on eIF2α phosphorylation rather than the mTORC1/4E-BP1 pathway.

Journal: PloS one20100101

Title: VEGFR2 heterogeneity and response to anti-angiogenic low dose metronomic cyclophosphamide treatment.

Journal: BMC cancer20100101

Title: A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy.

Journal: British journal of cancer20091201

Title: Contribution of HIF-1 and drug penetrance to oxaliplatin resistance in hypoxic colorectal cancer cells.

Journal: British journal of cancer20091020

Title: Spin trapping of radicals other than the *OH radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase.

Journal: Journal of the American Chemical Society20091014

Title: Molecular imaging of hypoxia with radiolabelled agents.

Journal: European journal of nuclear medicine and molecular imaging20091001

Title: Increased tumor oxygenation and drug uptake during anti-angiogenic weekly low dose cyclophosphamide enhances the anti-tumor effect of weekly tirapazamine.

Journal: Current cancer drug targets20090901

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20090901

Title: Ultrasensitive electrochemical sensing of the anticancer drug tirapazamine using an ordered mesoporous carbon modified pyrolytic graphite electrode.

Journal: Biosensors & bioelectronics20090715

Title: Detecting vascular-targeting effects of the hypoxic cytotoxin tirapazamine in tumor xenografts using magnetic resonance imaging.

Journal: International journal of radiation oncology, biology, physics20090701

Title: Phase II study of tirapazamine, cisplatin, and etoposide and concurrent thoracic radiotherapy for limited-stage small-cell lung cancer: SWOG 0222.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20090620

Title: Evaluation of the potential of hexamethylenetetramine, compared with tirapazamine, as a combined agent with {gamma}-irradiation and cisplatin treatment in vivo.

Journal: The British journal of radiology20090501

Title: Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N).

Journal: Molecular cancer therapeutics20090501

Title: Structural adaptation and heterogeneity of normal and tumor microvascular networks.

Journal: PLoS computational biology20090501

Title: Cytotoxic palladium complexes of bioreductive quinoxaline N1,N4-dioxide prodrugs.

Journal: Bioorganic & medicinal chemistry20090215

Title: Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxide antitumor agents: mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide.

Journal: Journal of the American Chemical Society20090128

Title: A phase I pharmacokinetic study of hypoxic abdominal stop-flow perfusion with gemcitabine in patients with advanced pancreatic cancer and refractory malignant ascites.

Journal: Cancer chemotherapy and pharmacology20090101

Title: Tirapazamine: a novel agent targeting hypoxic tumor cells.

Journal: Expert opinion on investigational drugs20090101

Title: Synthesis, cytotoxic activity, and DNA binding properties of copper (II) complexes with hesperetin, naringenin, and apigenin.

Journal: Bioinorganic chemistry and applications20090101

Title: A Model for NAD(P)H:Quinoneoxidoreductase 1 (NQO1) Targeted Individualized Cancer Chemotherapy.

Journal: Drug target insights20090101

Title: A dialogue between the hypoxia-inducible factor and the tumor microenvironment.

Journal: Cancer microenvironment : official journal of the International Cancer Microenvironment Society20081201

Title: Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins.

Journal: Journal of medicinal chemistry20081113

Title: Lower osteopontin plasma levels are associated with superior outcomes in advanced non-small-cell lung cancer patients receiving platinum-based chemotherapy: SWOG Study S0003.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20081010

Title: Quantitative measure of cytotoxicity of anticancer drugs and other agents.

Journal: Analytical biochemistry20081001

Title: Synthesis and biological activity of 1-methyl-tryptophan-tirapazamine hybrids as hypoxia-targeting indoleamine 2,3-dioxygenase inhibitors.

Journal: Bioorganic & medicinal chemistry20080915

Title: iNOS as a therapeutic target for treatment of human tumors.

Journal: Nitric oxide : biology and chemistry20080901

Title: Hypoxia-specific drug tirapazamine does not abrogate hypoxic tumor cells in combination therapy with irinotecan and methylselenocysteine in well-differentiated human head and neck squamous cell carcinoma a253 xenografts.

Journal: Neoplasia (New York, N.Y.)20080801

Title: In vivo 1H magnetic resonance spectroscopy of lactate in patients with stage IV head and neck squamous cell carcinoma.

Journal: International journal of radiation oncology, biology, physics20080715

Title: [Can tumor hypoxia be turned into a chemotherapeutic advantage?].

Journal: Bulletin du cancer20080501

Title: Carbonic anhydrase 9 (CA9) expression in tumor cells enhances sensitivity to tirapazamine.

Journal: Journal of cancer research and clinical oncology20080301

Title: Exploring vascular dysfunction caused by tirapazamine.

Journal: Microvascular research20080301

Title: Evaluation of the antiangiogenic potential of AQ4N.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20080301

Title: Hypoxic tumor cell radiosensitization: role of the iNOS/NO pathway.

Journal: Bulletin du cancer20080301

Title: Tirapazamine plus cisplatin and irradiation in a mouse model: improved tumor control at the cost of increased toxicity.

Journal: Journal of cancer research and clinical oncology20080201

Title: A review of topotecan in combination chemotherapy for advanced cervical cancer.

Journal: Therapeutics and clinical risk management20080201

Title: Homologous recombination is the principal pathway for the repair of DNA damage induced by tirapazamine in mammalian cells.

Journal: Cancer research20080101

Title: [The Oxygen effect: an old new target?].

Journal: Cancer radiotherapie : journal de la Societe francaise de radiotherapie oncologique20080101

Title: Detection and specific targeting of hypoxic regions within solid tumors: current preclinical and clinical strategies.

Journal: Current medicinal chemistry20080101

Title: Pharmacokinetic/pharmacodynamic model-guided identification of hypoxia-selective 1,2,4-benzotriazine 1,4-dioxides with antitumor activity: the role of extravascular transport.

Journal: Journal of medicinal chemistry20071213

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20071201

Title: DNA strand damage product analysis provides evidence that the tumor cell-specific cytotoxin tirapazamine produces hydroxyl radical and acts as a surrogate for O(2).

Journal: Journal of the American Chemical Society20071024

Title: Oxygen dependence and extravascular transport of hypoxia-activated prodrugs: comparison of the dinitrobenzamide mustard PR-104A and tirapazamine.

Journal: International journal of radiation oncology, biology, physics20071001

Title: Chemical radiosensitizers for use in radiotherapy.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain))20070801

Title: Bioreductive drugs: from concept to clinic.

Journal: Clinical oncology (Royal College of Radiologists (Great Britain))20070801

Title: Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA cross-linking agent PR-104.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070701

Title: Adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts.

Journal: British journal of cancer20070618

Title: Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards.

Journal: Radiation research20070601

Title: Beyond detection: novel applications for PET imaging to guide cancer therapy.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine20070601

Title: Pretreatment 18F-FAZA PET predicts success of hypoxia-directed radiochemotherapy using tirapazamine.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine20070601

Title: Increased nanoparticle penetration in collagenase-treated multicellular spheroids.

Journal: International journal of nanomedicine20070601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20070601

Title: [Inhibitory effect of tirapazamine combined with phosphatidylinositol 3-kinase inhibitor LY294002 to ovarian cancer cells].

Journal: Zhonghua yi xue za zhi20070508

Title: Synthesis, structure and hypoxic cytotoxicity of 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives.

Journal: Archiv der Pharmazie20070501

Title: On the mechanism of reaction of radicals with tirapazamine.

Journal: Journal of the American Chemical Society20070418

Title: Phase I trial of tirapazamine, cisplatin, and concurrent accelerated boost reirradiation in patients with recurrent head and neck cancer.

Journal: International journal of radiation oncology, biology, physics20070301

Title: Effects of fluctuating oxygenation on tirapazamine efficacy: Theoretical predictions.

Journal: International journal of radiation oncology, biology, physics20070201

Title: The concurrent chemoradiation paradigm--general principles.

Journal: Nature clinical practice. Oncology20070201

Title: Assessment of DNA damage at the dimer level: measurement of the formamide lesion.

Journal: Radiation research20070201

Title: The usefulness of mild temperature hyperthermia combined with continuous tirapazamine administration under reduced dose-rate irradiation with gamma-rays.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group20070201

Title: Dependency of the effect of a vascular disrupting agent on sensitivity to tirapazamine and gamma-ray irradiation upon the timing of its administration and tumor size, with reference to the effect on intratumor quiescent cells.

Journal: Journal of cancer research and clinical oncology20070101

Title: Radiosensitization by 2-benzoyl-3-phenyl-6,7-dichloroquinoxaline 1,4-dioxide under oxia and hypoxia in human colon cancer cells.

Journal: Radiation oncology (London, England)20070101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20070101

Title: DNA repair mechanisms are involved in the hypoxia-dependent toxicity of NLCQ-1 (NSC 709257) and its synergistic interaction with alkylating agents.

Journal: In vivo (Athens, Greece)20070101

Title: Identifying and targeting hypoxia in head and neck cancer: a brief overview of current approaches.

Journal: International journal of radiation oncology, biology, physics20070101

Title: Hypoxia in head and neck cancer: studies with hypoxic positron emission tomography imaging and hypoxic cytotoxins.

Journal: International journal of radiation oncology, biology, physics20070101

Title: Tumor hypoxia in cancer therapy.

Journal: Methods in enzymology20070101

Title: Breast tumour angiogenesis.

Journal: Breast cancer research : BCR20070101

Title: Bevacizumab: the evidence for its clinical potential in the treatment of nonsmall cell lung cancer.

Journal: Core evidence20070101

Title: The usefulness of a continuous administration of tirapazamine combined with reduced dose-rate irradiation using {gamma}-rays or reactor thermal neutrons.

Journal: The British journal of radiology20061201

Title: New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides.

Journal: Bioorganic & medicinal chemistry20061015

Title: Complete 1H, 13C and 15N NMR assignment of tirapazamine and related 1,2,4-benzotriazine N-oxides.

Journal: Magnetic resonance in chemistry : MRC20061001

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20061001

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20060901

Title: Respecting cancer drug transportability: a basis for successful lead selection.

Journal: Journal of the National Cancer Institute20060816

Title: Use of three-dimensional tissue cultures to model extravascular transport and predict in vivo activity of hypoxia-targeted anticancer drugs.

Journal: Journal of the National Cancer Institute20060816

Title: Selective hypoxia-cytotoxins based on vanadyl complexes with 3-aminoquinoxaline-2-carbonitrile-N1,N4-dioxide derivatives.

Journal: Journal of inorganic biochemistry20060801

Title: Hypoxia: targeting the tumour.

Journal: Anti-cancer agents in medicinal chemistry20060701

Title: Concurrent chemoradiotherapy for locally advanced, nonmetastatic, squamous carcinoma of the head and neck: consensus, controversy, and conundrum.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20060610

Title: Mature results from a randomized Phase II trial of cisplatin plus 5-fluorouracil and radiotherapy with or without tirapazamine in patients with resectable Stage IV head and neck squamous cell carcinomas.

Journal: Cancer20060501

Title: Prognostic significance of [18F]-misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: a substudy of Trans-Tasman Radiation Oncology Group Study 98.02.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20060501

Title: [Evaluation of the toxicity of tirapazamine plus cisplatin in a mouse tumor model].

Journal: Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al]20060401

Title: A phase II evaluation of tirapazamine plus cisplatin in the treatment of recurrent platinum-sensitive ovarian or primary peritoneal cancer: a Gynecologic Oncology Group study.

Journal: Gynecologic oncology20060301

Title: Radiation sensitization with redox modulators: a promising approach.

Journal: International journal of radiation oncology, biology, physics20060201

Title: Low-dose metronomic daily cyclophosphamide and weekly tirapazamine: a well-tolerated combination regimen with enhanced efficacy that exploits tumor hypoxia.

Journal: Cancer research20060201

Title: Tirapazamine causes vascular dysfunction in HCT-116 tumour xenografts.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology20060201

Title: [Study on HPLC determination method and pharmacokinetics of tirapazaming in rabbits].

Journal: Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi20060201

Title: Potentiation of the cytotoxicity of the anticancer agent tirapazamine by benzotriazine N-oxides: the role of redox equilibria.

Journal: Journal of the American Chemical Society20060111

Title: Tirapazamine plus cisplatin in advanced or recurrent carcinoma of the uterine cervix: a Southwest Oncology Group study.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society20060101

Title: Global analysis of gene function in yeast by quantitative phenotypic profiling.

Journal: Molecular systems biology20060101

Title: Phase II study of tirapazamine plus cisplatin in patients with advanced or recurrent cervical cancer.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society20060101

Title: Potentiation of alkylating agents by NLCQ-1 or TPZ in vitro and in vivo.

Journal: Journal of experimental therapeutics & oncology20060101

Title: Tirapazamine: from bench to clinical trials.

Journal: Current clinical pharmacology20060101

Title: Update on clinical radiobiology.

Journal: Biomedical imaging and intervention journal20060101

Title: Phase III trial of paclitaxel plus carboplatin with or without tirapazamine in advanced non-small-cell lung cancer: Southwest Oncology Group Trial S0003.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20051220

Title: Utility of FMISO PET in advanced head and neck cancer treated with chemoradiation incorporating a hypoxia-targeting chemotherapy agent.

Journal: European journal of nuclear medicine and molecular imaging20051201

Title: Synthesis of 3-amino-1,2,4-benzothiadi- azine 1,1-dioxides via a tandem aza-Wittig/heterocumulene annulation.

Journal: The Journal of organic chemistry20051125

Title: Large-scale analysis of genes that alter sensitivity to the anticancer drug tirapazamine in Saccharomyces cerevisiae.

Journal: Molecular pharmacology20051101

Title: Resistance to endocrine therapy in breast cancer.

Journal: Cancer chemotherapy and pharmacology20051101

Title: [Determination of the related substances in tirapazamine by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography20051101

Title: Anemia, tumor hypoxemia, and the cancer patient.

Journal: International journal of radiation oncology, biology, physics20050901

Title: Combination of the antivascular agent ZD6126 with hypoxic cytotoxin treatment, with reference to the effect on quiescent tumor cells and the dependency on p53 status of tumor cells.

Journal: Oncology reports20050801

Title: The role of bioreductive activation of doxorubicin in cytotoxic activity against leukaemia HL60-sensitive cell line and its multidrug-resistant sublines.

Journal: British journal of cancer20050711

Title: Hypoxia in head and neck cancer: how much, how important?

Journal: Head & neck20050701

Title: Observation of incipient tumor angiogenesis that is independent of hypoxia and hypoxia inducible factor-1 activation.

Journal: Cancer research20050701

Title: Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides.

Journal: Organic & biomolecular chemistry20050607

Title: Tirapazamine administered as a neoadjuvant to radiotherapy reduces metastatic dissemination.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20050601

Title: The usefulness of continuous administration of hypoxic cytotoxin combined with mild temperature hyperthermia, with reference to effects on quiescent tumour cell populations.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group20050601

Title: Tirapazamine cytotoxicity for neuroblastoma is p53 dependent.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20050401

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20050401

Title: Time-resolved spectroscopy of the excited singlet states of tirapazamine and desoxytirapazamine.

Journal: The journal of physical chemistry. A20050303

Title: Tirapazamine with cisplatin and vinorelbine in patients with advanced non-small-cell lung cancer: a phase I/II study.

Journal: Clinical lung cancer20050301

Title: Extravascular transport of drugs in tumor tissue: effect of lipophilicity on diffusion of tirapazamine analogues in multicellular layer cultures.

Journal: Journal of medicinal chemistry20050224

Title: Tirapazamine, Cisplatin, and Radiation versus Fluorouracil, Cisplatin, and Radiation in patients with locally advanced head and neck cancer: a randomized phase II trial of the Trans-Tasman Radiation Oncology Group (TROG 98.02).

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20050101

Title: Improving survival and reducing toxicity with chemotherapy in advanced non-small cell lung cancer : a realistic goal?

Journal: Treatments in respiratory medicine20050101

Title: Radiosensitising effect of electrochemotherapy with bleomycin in LPB sarcoma cells and tumors in mice.

Journal: BMC cancer20050101

Title: Prodrug research: futile or fertile?

Journal: Biochemical pharmacology20041201

Title: The Japanese experiences with hypoxia-targeting pharmacoradiotherapy: from hypoxic cell sensitisers to radiation-activated prodrugs.

Journal: Expert opinion on pharmacotherapy20041201

Title: [Phase II-trial of tirapazamine in combination with cisplatin and gemcitabine in patients with advanced non-small-cell-lung-cancer (NSCLC)].

Journal: Pneumologie (Stuttgart, Germany)20041201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20041201

Title: Enzyme-activated, hypoxia-selective DNA damage by 3-amino-2-quinoxalinecarbonitrile 1,4-di-N-oxide.

Journal: Chemical research in toxicology20041101

Title: Combined chemotherapy and radiation therapy for cervical cancer.

Journal: Journal of the National Comprehensive Cancer Network : JNCCN20041101

Title: Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo.

Journal: British journal of cancer20041018

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20041001

Title: Microenvironmental adaptation of experimental tumours to chronic vs acute hypoxia.

Journal: British journal of cancer20040913

Title: Prospects for hypoxia-activated anticancer drugs.

Journal: Current medicinal chemistry. Anti-cancer agents20040901

Title: Cytochrome P450 CYP1B1 activity in renal cell carcinoma.

Journal: British journal of cancer20040831

Title: Phase I study of tirapazamine plus cisplatin/etoposide and concurrent thoracic radiotherapy in limited-stage small cell lung cancer (S0004): a Southwest Oncology Group study.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20040815

Title: Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide.

Journal: Cancer research20040801

Title: Enhanced effectiveness of radiochemotherapy with tirapazamine by local application of electric pulses to tumors.

Journal: Radiation research20040801

Title: Clinical studies of hypoxia modification in radiotherapy.

Journal: Seminars in radiation oncology20040701

Title: Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides.

Journal: Journal of the American Chemical Society20040630

Title: Oxygen dependence of the metabolic activation and cytotoxicity of tirapazamine: implications for extravascular transport and activity in tumors.

Journal: Radiation research20040601

Title: New derivatives of quinazoline and 1, 2-dihydroquinazoline n3-oxide with expected antitumor activity.

Journal: Archiv der Pharmazie20040501

Title: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part II.

Journal: Archiv der Pharmazie20040501

Title: 1, 2, 4-Triazine N-oxide derivatives: studies as potential hypoxic cytotoxins. Part III.

Journal: Archiv der Pharmazie20040501

Title: Phase I trial of tirapazamine and cyclophosphamide in children with refractory solid tumors: a pediatric oncology group study.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20040415

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20040401

Title: 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT.

Journal: British journal of cancer20040308

Title: Enzyme-catalyzed activation of anticancer prodrugs.

Journal: Pharmacological reviews20040301

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20040301

Title: Hypoxia targeted gene therapy to increase the efficacy of tirapazamine as an adjuvant to radiotherapy: reversing tumor radioresistance and effecting cure.

Journal: Cancer research20040215

Title: DNA-targeted 1,2,4-benzotriazine 1,4-dioxides: potent analogues of the hypoxia-selective cytotoxin tirapazamine.

Journal: Journal of medicinal chemistry20040115

Title: Selective potentiation of the hypoxic cytotoxicity of tirapazamine by its 1-N-oxide metabolite SR 4317.

Journal: Cancer research20040115

Title: The importance of DT-diaphorase and hypoxia in the cytotoxicity of RH1 in human breast and non-small cell lung cancer cell lines.

Journal: Anti-cancer drugs20040101

Title: Efficacy of cytotoxic agents used in the treatment of testicular germ cell tumours under normoxic and hypoxic conditions in vitro.

Journal: British journal of cancer20031201

Title: Endogenous markers of tumor hypoxia predictors of clinical radiation resistance?

Journal: Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al]20031201

Title: NLCQ-1 (NSC 709257): exploiting hypoxia with a weak DNA-intercalating bioreductive drug.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20031115

Title: Enhanced conversion of DNA radical damage to double strand breaks by 1,2,4-benzotriazine 1,4-dioxides linked to a DNA binder compared to tirapazamine.

Journal: Chemical research in toxicology20031101

Title: The expression of P-glycoprotein does influence the distribution of novel fluorescent compounds in solid tumour models.

Journal: British journal of cancer20031020

Title: Human NADPH-cytochrome p450 reductase overexpression does not enhance the aerobic cytotoxicity of doxorubicin in human breast cancer cell lines.

Journal: Cancer research20031015

Title: Tirapazamine plus carboplatin and paclitaxel in advanced malignant solid tumors: a california cancer consortium phase I and molecular correlative study.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20031001

Title: DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Journal of the American Chemical Society20030924

Title: Multicellular resistance to tirapazamine is due to restricted extravascular transport: a pharmacokinetic/pharmacodynamic study in HT29 multicellular layer cultures.

Journal: Cancer research20030915

Title: Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK.

Journal: British journal of cancer20030804

Title: A mass spectrometry study of tirapazamine and its metabolites. insights into the mechanism of metabolic transformations and the characterization of reaction intermediates.

Journal: Journal of the American Society for Mass Spectrometry20030801

Title: A simple method of producing low oxygen conditions with oxyrase for cultured cells exposed to radiation and tirapazamine.

Journal: American journal of clinical oncology20030801

Title: Expression of phosphorylated histone H2AX as a surrogate of cell killing by drugs that create DNA double-strand breaks.

Journal: Cancer research20030801

Title: Tumour hypoxia, chemotherapeutic resistance and hypoxia-related therapies.

Journal: Cancer treatment reviews20030801

Title: Comparison of the comet assay and the oxygen microelectrode for measuring tumor oxygenation in head-and-neck cancer patients.

Journal: International journal of radiation oncology, biology, physics20030601

Title: Non-nuclear localized human NOSII enhances the bioactivation and toxicity of tirapazamine (SR4233) in vitro.

Journal: Molecular pharmacology20030601

Title: Improved potency of the hypoxic cytotoxin tirapazamine by DNA-targeting.

Journal: Biochemical pharmacology20030601

Title: Antagonism of buthionine sulfoximine cytotoxicity for human neuroblastoma cell lines by hypoxia is reversed by the bioreductive agent tirapazamine.

Journal: Cancer research20030401

Title: Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-Di-N-oxide analogues.

Journal: Chemical research in toxicology20030201

Title: Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction.

Journal: Journal of the American Chemical Society20030122

Title: Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine.

Journal: Journal of medicinal chemistry20030102

Title: Potential of alpha-amino alcohol p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, regarding its enantiomers.

Journal: Journal of cancer research and clinical oncology20030101

Title: Usefulness of combined treatment with mild temperature hyperthermia and/or tirapazamine in the treatment of solid tumors: its independence of p53 status.

Journal: Cancer science20030101

Title: Antiangiogenic hypoxic cytotoxin TX-402 inhibits hypoxia-inducible factor 1 signaling pathway.

Journal: Anticancer research20030101

Title: Therapeutic advantage from combining paclitaxel with the hypoxia-selective cytotoxin NLCQ-1 in murine tumor- or human xenograft-bearing mice.

Journal: Cancer chemotherapy and pharmacology20021201

Title: Platinum drugs in the treatment of non-small-cell lung cancer.

Journal: British journal of cancer20021007

Title: Therapeutic advantage from combining 5-fluorouracil with the hypoxia-selective cytotoxin NLCQ-1 in vivo; comparison with tirapazamine.

Journal: Cancer chemotherapy and pharmacology20021001

Title: Tirapazamine: a hypoxia-activated topoisomerase II poison.

Journal: Cancer research20020915

Title: Oxidative DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: Bioorganic & medicinal chemistry letters20020902

Title: 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy.

Journal: Investigational new drugs20020801

Title: Carbogen breathing after irradiation enhances the effectiveness of tirapazamine in SiHa tumors but not SCCVII tumors in mice.

Journal: Radiation research20020701

Title: Design, synthesis and biological activities of antiangiogenic hypoxic cytotoxin, triazine-N-oxide derivatives.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology20020501

Title: Photochemical electron transfer reactions of tirapazamine.

Journal: Photochemistry and photobiology20020401

Title: Significance of the response of quiescent cell populations within solid tumors in cancer therapy.

Journal: Journal of radiation research20020301

Title: The effect of functional groups on reduction and activation of quinone bioreductive agents by DT-diaphorase.

Journal: Cancer chemotherapy and pharmacology20020201

Title: Local hypoxia is produced at sites of intratumour injection.

Journal: British journal of cancer20020201

Title: Tirapazamine: prototype for a novel class of therapeutic agents targeting tumor hypoxia.

Journal: Seminars in oncology20020201

Title: Synergistic enhancement of the antitumor effect of taxol by the bioreductive compound NLCQ-1, in vivo: comparison with tirapazamine.

Journal: Oncology research20020101

Title: Hypoxic active drugs.

Journal: I supplementi di Tumori : official journal of Societa italiana di cancerologia ... [et al.]20020101

Title: Tumor microenvironment and the response to anticancer therapy.

Journal: Cancer biology & therapy20020101

Title: Metabolism of tirapazamine by multiple reductases in the nucleus.

Journal: Biochemical pharmacology20011101

Title: Optimizing the use of combined radioimmunotherapy and hypoxic cytotoxin therapy as a function of tumor hypoxia.

Journal: International journal of cancer20011101

Title: Evaluation of the potential of p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, referring to the effect on intratumor quiescent cells.

Journal: Japanese journal of cancer research : Gann20010901

Title: Indications for chemotherapy in stage IV non-small cell lung cancer.

Journal: Lung cancer (Amsterdam, Netherlands)20010901

Title: Modeling the action of an antitumor drug: a density functional theory study of the mechanism of tirapazamine.

Journal: Journal of the American Chemical Society20010801

Title: Effects of anticancer drugs on the metabolism of the anticancer drug 5,6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes.

Journal: British journal of clinical pharmacology20010801

Title: The chemopotentiation of cisplatin by the novel bioreductive drug AQ4N.

Journal: British journal of cancer20010801

Title: Schedule-dependent potentiation of chemotherapeutic drugs by the bioreductive compounds NLCQ-1 and tirapazamine against EMT6 tumors in mice.

Journal: Cancer chemotherapy and pharmacology20010801

Title: Selective interaction of tirapazamine with DNA bases and DNA. A comparison of cyclic voltammetry and electrolysis techniques.

Journal: Free radical research20010801

Title: Radiosensitization effect by combination with paclitaxel in vivo, including the effect on intratumor quiescent cells.

Journal: International journal of radiation oncology, biology, physics20010715

Title: Inhibition of DNA replication by tirapazamine.

Journal: Cancer research20010715

Title: Phase I trial of i.v. administered tirapazamine plus cyclophosphamide.

Journal: Anti-cancer drugs20010701

Title: Recent advances in the chemotherapy of non-small cell lung cancer.

Journal: Japanese journal of clinical oncology20010701

Title: Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia.

Journal: Current medicinal chemistry20010601

Title: Triplet combination chemotherapy and targeted therapy regimens.

Journal: Oncology (Williston Park, N.Y.)20010301

Title: Therapeutic targets in radiotherapy.

Journal: International journal of radiation oncology, biology, physics20010201

Title: Phase I trial of concurrent tirapazamine, cisplatin, and radiotherapy in patients with advanced head and neck cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20010115

Title: 3-amino-1,2,4-benzotriazine 4-oxide: characterization of a new metabolite arising from bioreductive processing of the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine).

Journal: The Journal of organic chemistry20010112

Title: Analysis of DNA damage in individual cells.

Journal: Methods in cell biology20010101

Title: An investigation of the molecular basis for the synergistic interaction of tirapazamine and cisplatin.

Journal: International journal of radiation oncology, biology, physics20010101

Title: Mitochondrial dysfunction after aerobic exposure to the hypoxic cytotoxin tirapazamine.

Journal: Cancer research20010101

Title: Cytotoxicity of bioreductive drug tirapazamine is increased by application of electric pulses in SA-1 tumours in mice.

Journal: Anticancer research20010101

Title: 4-[3-(2-Nitro-1-imidazolyl)propylamino]-7-chloroquinoline hydrochloride (NLCQ-1), a novel bioreductive agent as radiosensitizer in vitro and in vivo: comparison with tirapazamine.

Journal: Oncology research20010101

Title: Hypoxia and oxidative stress. Tumour hypoxia--therapeutic considerations.

Journal: Breast cancer research : BCR20010101

Title: Targeting hypoxia in head and neck cancer.

Journal: Acta oncologica (Stockholm, Sweden)20010101

Title: Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/P450-reductase-based cancer gene therapy.

Journal: Cancer research20000715

Title: Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations.

Journal: British journal of cancer19950401

Title: SR-4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells.

Journal: International journal of radiation oncology, biology, physics19860701

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