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117570-53-3,MFCD00870555
Catalog No.:AA0035TX

117570-53-3 | 5,6-Dimethylxantheonone-4-acetic acid

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1mg
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10mg
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100mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0035TX
Chemical Name:
5,6-Dimethylxantheonone-4-acetic acid
CAS Number:
117570-53-3
Molecular Formula:
C17H14O4
Molecular Weight:
282.2907
MDL Number:
MFCD00870555
SMILES:
OC(=O)Cc1cccc2c1oc1c(C)c(C)ccc1c2=O
Properties
Properties
 
BP:
520.9 °C at 760 mmHg  
Form:
Solid  
MP:
>230°C (dec.)  
Solubility:
DMSO: 17 mg/mL, soluble  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
433  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
3.2  

Literature

Title: p38 mitogen-activated protein kinase is required for the antitumor activity of the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid.

Journal: The Journal of pharmacology and experimental therapeutics 20120601

Title: DMXAA (Vadimezan, ASA404) is a multi-kinase inhibitor targeting VEGFR2 in particular.

Journal: Clinical science (London, England : 1979) 20120501

Title: Mass balance, excretion and metabolism of [¹⁴C] ASA404 in cancer patients in a phase I trial.

Journal: Cancer chemotherapy and pharmacology 20120501

Title: Dissection of stromal and cancer cell-derived signals in melanoma xenografts before and after treatment with DMXAA.

Journal: British journal of cancer 20120313

Title: Vascular disruption in combination with mTOR inhibition in renal cell carcinoma.

Journal: Molecular cancer therapeutics 20120201

Title: High throughput screening for small molecule enhancers of the interferon signaling pathway to drive next-generation antiviral drug discovery.

Journal: PloS one 20120101

Title: The influence of the combined treatment with Vadimezan (ASA404) and taxol on the growth of U251 glioblastoma xenografts.

Journal: BMC cancer 20120101

Title: Vascular disrupting agent drug classes differ in effects on the cytoskeleton.

Journal: PloS one 20120101

Title: Monitoring antivascular therapy in head and neck cancer xenografts using contrast-enhanced MR and US imaging.

Journal: Angiogenesis 20111201

Title: Photodynamic therapy augments the efficacy of oncolytic vaccinia virus against primary and metastatic tumours in mice.

Journal: British journal of cancer 20111108

Title: Activation of mitogen-activated protein kinases by 5,6-dimethylxanthenone-4-acetic acid (DMXAA) plays an important role in macrophage stimulation.

Journal: Biochemical pharmacology 20111101

Title: Influence of the vascular damaging agents DMXAA and ZD6126 on hypericin distribution and accumulation in RIF-1 tumors.

Journal: Journal of cancer research and clinical oncology 20111101

Title: Pharmacokinetic evaluation of vadimezan (ASA404, 5,6-dimethylxanthenone-4-acetic acid, DMXAA).

Journal: Expert opinion on drug metabolism & toxicology 20111001

Title: Pharmacologic activation of the innate immune system to prevent respiratory viral infections.

Journal: American journal of respiratory cell and molecular biology 20110901

Title: The safety and tolerability of intravenous ASA404 when administered in combination with docetaxel (60 or 75 mg/m²) in Japanese patients with advanced or recurrent solid tumors.

Journal: Japanese journal of clinical oncology 20110901

Title: Clinical development of vascular disrupting agents: what lessons can we learn from ASA404?

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20110801

Title: Randomized phase III placebo-controlled trial of carboplatin and paclitaxel with or without the vascular disrupting agent vadimezan (ASA404) in advanced non-small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20110801

Title: Cardiovascular toxicity profiles of vascular-disrupting agents.

Journal: The oncologist 20110801

Title: Control of cervicovaginal HPV-16 E7-expressing tumors by the combination of therapeutic HPV vaccination and vascular disrupting agents.

Journal: Human gene therapy 20110701

Title: Aminolevulinic acid-photodynamic therapy combined with topically applied vascular disrupting agent vadimezan leads to enhanced antitumor responses.

Journal: Photochemistry and photobiology 20110701

Title: Developing a robust ultrafiltration-LC-MS/MS method for quantitative analysis of unbound vadimezan (ASA404) in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110701

Title: Clinical trials of vascular disrupting agents in advanced non--small-cell lung cancer.

Journal: Clinical lung cancer 20110501

Title: Phase I study of intravenous ASA404 (vadimezan) administered in combination with paclitaxel and carboplatin in Japanese patients with non-small cell lung cancer.

Journal: Cancer science 20110401

Title: The anti-tumor agent, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), induces IFN-beta-mediated antiviral activity in vitro and in vivo.

Journal: Journal of leukocyte biology 20110301

Title: 18F-fluromisonidazole PET imaging as a biomarker for the response to 5,6-dimethylxanthenone-4-acetic acid in colorectal xenograft tumors.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20110301

Title: Editorial: One small molecule: a new way to treat the flu?

Journal: Journal of leukocyte biology 20110301

Title: Vascular disrupting agent DMXAA enhances the antitumor effects generated by therapeutic HPV DNA vaccines.

Journal: Journal of biomedical science 20110101

Title: Interaction of a traditional Chinese Medicine (PHY906) and CPT-11 on the inflammatory process in the tumor microenvironment.

Journal: BMC medical genomics 20110101

Title: Flavonoids: A versatile source of anticancer drugs.

Journal: Pharmacognosy reviews 20110101

Title: Comparative outcomes of squamous and non-squamous non-small cell lung cancer (NSCLC) patients in phase II studies of ASA404 (DMXAA) - retrospective analysis of pooled data.

Journal: Journal of thoracic disease 20101201

Title: Temporal aspects of the action of ASA404 (vadimezan; DMXAA).

Journal: Expert opinion on investigational drugs 20101101

Title: ASA404: a tumor vascular-disrupting agent with broad potential for cancer therapy.

Journal: Future oncology (London, England) 20101001

Title: Labeling of oxidizable proteins with a photoactivatable analog of the antitumor agent DMXAA: evidence for redox signaling in its mode of action.

Journal: Neoplasia (New York, N.Y.) 20100901

Title: Phase I trial of CYT997, a novel cytotoxic and vascular-disrupting agent.

Journal: British journal of cancer 20100824

Title: Vadimezan: 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid.

Journal: Acta crystallographica. Section E, Structure reports online 20100801

Title: RECIST revised: implications for the radiologist. A review article on the modified RECIST guideline.

Journal: European radiology 20100601

Title: Guidelines for the welfare and use of animals in cancer research.

Journal: British journal of cancer 20100525

Title: Phase II study on the addition of ASA404 (vadimezan; 5,6-dimethylxanthenone-4-acetic acid) to docetaxel in CRMPC.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100515

Title: Disrupting established tumor blood vessels: an emerging therapeutic strategy for cancer.

Journal: Cancer 20100415

Title: Activation of the nucleotide oligomerization domain signaling pathway by the non-bacterially derived xanthone drug 5'6-dimethylxanthenone-4-acetic acid (Vadimezan).

Journal: The Journal of biological chemistry 20100402

Title: Novel agents target existing tumor vasculature.

Journal: Expert review of anticancer therapy 20100301

Title: [Advances in the study of the anti-tumor activity of small molecule vascular disrupting agents].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100301

Title: The development of the tumor vascular-disrupting agent ASA404 (vadimezan, DMXAA): current status and future opportunities.

Journal: Expert opinion on investigational drugs 20100201

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: Molecule of the month. Vadimezan.

Journal: Drug news & perspectives 20091101

Title: Molecular imaging of hypoxia with radiolabelled agents.

Journal: European journal of nuclear medicine and molecular imaging 20091001

Title: AVE8062: a new combretastatin derivative vascular disrupting agent.

Journal: Expert opinion on investigational drugs 20091001

Title: Acute vascular disruption by 5,6-dimethylxanthenone-4-acetic Acid in an orthotopic model of human head and neck cancer.

Journal: Translational oncology 20090818

Title: Phase II study of ASA404 (vadimezan, 5,6-dimethylxanthenone-4-acetic acid/DMXAA) 1800mg/m(2) combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer.

Journal: Lung cancer (Amsterdam, Netherlands) 20090801

Title: MRI-based characterization of vascular disruption by 5,6-dimethylxanthenone-acetic acid in gliomas.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20090801

Title: Neutrophil influx and chemokine production during the early phases of the antitumor response to the vascular disrupting agent DMXAA (ASA404).

Journal: Neoplasia (New York, N.Y.) 20090801

Title: Enhancement of the action of the antivascular drug 5,6-dimethylxanthenone-4-acetic acid (DMXAA; ASA404) by non-steroidal anti-inflammatory drugs.

Journal: Investigational new drugs 20090601

Title: Transient retinal effects of 5,6-dimethylxanthenone-4-acetic acid (DMXAA, ASA404), an antitumor vascular-disrupting agent in phase I clinical trials.

Journal: Investigative ophthalmology & visual science 20090601

Title: Vascular disrupting agents: a novel mechanism of action in the battle against non-small cell lung cancer.

Journal: The oncologist 20090601

Title: The vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid improves the antitumor efficacy and shortens treatment time associated with Photochlor-sensitized photodynamic therapy in vivo.

Journal: Photochemistry and photobiology 20090101

Title: Immune-modulating and anti-vascular activities of two xanthenone acetic acid analogues: A comparative study to DMXAA.

Journal: International journal of oncology 20090101

Title: Indexing TNF-alpha gene expression using a gene-targeted reporter cell line.

Journal: BMC biology 20090101

Title: Zolpidem, a clinical hypnotic that affects electronic transfer, alters synaptic activity through potential GABA receptors in the nervous system without significant free radical generation.

Journal: Oxidative medicine and cellular longevity 20090101

Title: Randomised phase II study of ASA404 combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer.

Journal: British journal of cancer 20081209

Title: Assessment of the early effects of 5,6-dimethylxanthenone-4-acetic acid using macromolecular contrast media-enhanced magnetic resonance imaging: ectopic versus orthotopic tumors.

Journal: International journal of radiation oncology, biology, physics 20081115

Title: ASA404: update on drug development.

Journal: Expert opinion on investigational drugs 20081001

Title: [Tumor vasculature as a therapeutic target in non-small cell lung cancer].

Journal: Magyar onkologia 20080901

Title: Vessel size index magnetic resonance imaging to monitor the effect of antivascular treatment in a rodent tumor model.

Journal: International journal of radiation oncology, biology, physics 20080801

Title: Macrophage proinflammatory response to Francisella tularensis live vaccine strain requires coordination of multiple signaling pathways.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20080515

Title: Exploration of the mechanism underlying the tumor necrosis avidity of hypericin.

Journal: Oncology reports 20080401

Title: Population pharmacokinetic-pharmacodynamic model of the vascular-disrupting agent 5,6-dimethylxanthenone-4-acetic acid in cancer patients.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080401

Title: Consequences of increased vascular permeability induced by treatment of mice with 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and thalidomide.

Journal: Cancer chemotherapy and pharmacology 20080301

Title: IFN-beta-dependent inhibition of tumor growth by the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research 20080301

Title: The potential of DMXAA (ASA404) in combination with docetaxel in advanced prostate cancer.

Journal: Expert opinion on investigational drugs 20080101

Title: The ability of coumarin-, flavanon- and flavonol-analogues of flavone acetic acid to stimulate human monocytes.

Journal: Oncology reports 20080101

Title: Molecular profiling of angiogenesis in hypericin mediated photodynamic therapy.

Journal: Molecular cancer 20080101

Title: The effect of combretastatin A4 disodium phosphate and 5,6-dimethylxanthenone-4-acetic acid on water diffusion and blood perfusion in tumours.

Journal: Acta oncologica (Stockholm, Sweden) 20080101

Title: Assessment of tumor response to the vascular disrupting agents 5,6-dimethylxanthenone-4-acetic acid or combretastatin-A4-phosphate by intrinsic susceptibility magnetic resonance imaging.

Journal: International journal of radiation oncology, biology, physics 20071115

Title: Early experience with novel immunomodulators for cancer treatment.

Journal: Expert opinion on investigational drugs 20070901

Title: Synthesis and biological activity of azido analogues of 5,6-dimethylxanthenone-4-acetic acid for use in photoaffinity labeling.

Journal: Journal of medicinal chemistry 20070809

Title: The vascular disrupting agent, DMXAA, directly activates dendritic cells through a MyD88-independent mechanism and generates antitumor cytotoxic T lymphocytes.

Journal: Cancer research 20070715

Title: The chemotherapeutic agent DMXAA potently and specifically activates the TBK1-IRF-3 signaling axis.

Journal: The Journal of experimental medicine 20070709

Title: N-(4-iodophenyl)-N'-(2-chloroethyl)urea as a microtubule disrupter: in vitro and in vivo profiling of antitumoral activity on CT-26 murine colon carcinoma cell line cultured and grafted to mice.

Journal: British journal of cancer 20070604

Title: Evidence for the involvement of p38 MAP kinase in the action of the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Investigational new drugs 20070601

Title: Development and validation of a liquid chromatography/tandem mass spectrometry method for the determination of DMXAA in human and mouse plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601

Title: Vascular disrupting agents in clinical development.

Journal: British journal of cancer 20070423

Title: Antitumour action of 5,6-dimethylxanthenone-4-acetic acid in rats bearing chemically induced primary mammary tumours.

Journal: Cancer chemotherapy and pharmacology 20070401

Title: Pharmacokinetics of 5,6-dimethylxanthenone-4-acetic acid (AS1404), a novel vascular disrupting agent, in phase I clinical trial.

Journal: Cancer chemotherapy and pharmacology 20070401

Title: Visualizing the acute effects of vascular-targeted therapy in vivo using intravital microscopy and magnetic resonance imaging: correlation with endothelial apoptosis, cytokine induction, and treatment outcome.

Journal: Neoplasia (New York, N.Y.) 20070201

Title: DCE-MRI biomarkers in the clinical evaluation of antiangiogenic and vascular disrupting agents.

Journal: British journal of cancer 20070129

Title: NF-kappaB-independent induction of endothelial cell apoptosis by the vascular disrupting agent DMXAA.

Journal: Anticancer research 20070101

Title: Oxygen sensitivity of reporter genes: implications for preclinical imaging of tumor hypoxia.

Journal: Molecular imaging 20070101

Title: Vascular disrupting agents.

Journal: Journal of cellular biochemistry 20061101

Title: 5,6-Dimethylxanthenone-4-acetic acid treatment of a non-immunogenic tumour does not synergize with active or passive CD8+ T-cell immunotherapy.

Journal: Immunology and cell biology 20060801

Title: Activity of the vascular-disrupting agent 5,6-dimethylxanthenone-4-acetic acid against human head and neck carcinoma xenografts.

Journal: Neoplasia (New York, N.Y.) 20060701

Title: New derivatives of xanthenone-4-acetic acid: synthesis, pharmacological profile and effect on TNF-alpha and NO production by human immune cells.

Journal: Bioorganic & medicinal chemistry 20060615

Title: Current development status of small-molecule vascular disrupting agents.

Journal: Current opinion in investigational drugs (London, England : 2000) 20060601

Title: 5,6-Dimethylxanthenone-4-acetic acid in the treatment of refractory tumors: a phase I safety study of a vascular disrupting agent.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060315

Title: Rat tumor response to the vascular-disrupting agent 5,6-dimethylxanthenone-4-acetic acid as measured by dynamic contrast-enhanced magnetic resonance imaging, plasma 5-hydroxyindoleacetic acid levels, and tumor necrosis.

Journal: Neoplasia (New York, N.Y.) 20060301

Title: The effects of the vascular disrupting agents combretastatin A-4 disodium phosphate, 5,6-dimethylxanthenone-4-acetic acid and ZD6126 in a murine tumour: a comparative assessment using MRI and MRS.

Journal: Acta oncologica (Stockholm, Sweden) 20060101

Title: Inhibition of DMXAA-induced tumor necrosis factor production in murine splenocyte cultures by NF-kappaB inhibitors.

Journal: Oncology research 20060101

Title: Activation of tumor-associated macrophages by the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid induces an effective CD8+ T-cell-mediated antitumor immune response in murine models of lung cancer and mesothelioma.

Journal: Cancer research 20051215

Title: Vascular-targeting agents and radiation therapy in lung cancer: where do we stand in 2005?

Journal: Clinical lung cancer 20051101

Title: Effects of platinum/taxane based chemotherapy on acute perfusion in human pelvic tumours measured by dynamic MRI.

Journal: British journal of cancer 20051031

Title: Fundamental, electron transfer mechanism by pyrylium-type ions for the anticancer drugs 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and flavone-8-acetic acid (FAA).

Journal: Current medicinal chemistry. Anti-cancer agents 20050901

Title: Mechanisms of tumor vascular shutdown induced by 5,6-dimethylxanthenone-4-acetic acid (DMXAA): Increased tumor vascular permeability.

Journal: International journal of cancer 20050820

Title: Inhibition of human CYP1A2 oxidation of 5,6-dimethyl-xanthenone-4-acetic acid by acridines: a molecular modelling study.

Journal: Clinical and experimental pharmacology & physiology 20050801

Title: Disrupting tumour blood vessels.

Journal: Nature reviews. Cancer 20050601

Title: Tumor vascular response to photodynamic therapy and the antivascular agent 5,6-dimethylxanthenone-4-acetic acid: implications for combination therapy.

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

Title: Tumor dose response to the vascular disrupting agent, 5,6-dimethylxanthenone-4-acetic acid, using in vivo magnetic resonance spectroscopy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050515

Title: The assessment of antiangiogenic and antivascular therapies in early-stage clinical trials using magnetic resonance imaging: issues and recommendations.

Journal: British journal of cancer 20050509

Title: Transport of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid and its acyl glucuronide by human intestinal Caco-2 cells.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20050401

Title: Novel vascular targeting/disrupting agents: combretastatin A4 phosphate and related compounds.

Journal: Current oncology reports 20050301

Title: Mono- or di-fluorinated analogues of flavone-8-acetic acid: synthesis and in vitro biological activity.

Journal: Anticancer research 20050101

Title: A comparison of the ability of DMXAA and xanthenone analogues to activate NF-kappaB in murine and human cell lines.

Journal: Oncology research 20050101

Title: Determination of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid and its acyl glucuronide in Caco-2 monolayers by liquid chromatography with fluorescence detection: application to transport studies.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040925

Title: Vascular-targeting therapies for treatment of malignant disease.

Journal: Cancer 20040615

Title: Tumour-specific enhancement of thermoradiotherapy at mild temperatures by the vascular targeting agent 5,6-dimethylxanthenone-4-acetic acid.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20040601

Title: Modulation of thalidomide pharmacokinetics by cyclophosphamide or 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in mice: the role of tumour necrosis factor.

Journal: Cancer chemotherapy and pharmacology 20040501

Title: Induction of tumour necrosis factor and interferon-gamma in cultured murine splenocytes by the antivascular agent DMXAA and its metabolites.

Journal: Biochemical pharmacology 20040301

Title: Relationship between tumour endothelial cell apoptosis and tumour blood flow shutdown following treatment with the antivascular agent DMXAA in mice.

Journal: British journal of cancer 20040223

Title: Vascular targeting agents as cancer therapeutics.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040115

Title: Angiogenesis inhibitors in clinical development; where are we now and where are we going?

Journal: British journal of cancer 20040112

Title: Improvement of the antitumor activity of intraperitoneally and orally administered 5,6-dimethylxanthenone-4-acetic acid by optimal scheduling.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031215

Title: Clostridia in cancer therapy.

Journal: Nature reviews. Microbiology 20031201

Title: Treatment with the tumor necrosis factor-alpha-inducing drug 5,6-dimethylxanthenone-4-acetic acid enhances the antitumor activity of the photodynamic therapy of RIF-1 mouse tumors.

Journal: Cancer research 20031115

Title: Synthesis and biological evaluation of 3-alkoxy analogues of flavone-8-acetic acid.

Journal: Journal of medicinal chemistry 20030814

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: Clinical aspects of a phase I trial of 5,6-dimethylxanthenone-4-acetic acid (DMXAA), a novel antivascular agent.

Journal: British journal of cancer 20030616

Title: Requirements for ICAM-1 immunogene therapy of lymphoma.

Journal: Cancer gene therapy 20030601

Title: Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid.

Journal: Biochemical pharmacology 20030601

Title: Tumour dose response to the antivascular agent ZD6126 assessed by magnetic resonance imaging.

Journal: British journal of cancer 20030519

Title: NF-kappa B activation in vivo in both host and tumour cells by the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: European journal of cancer (Oxford, England : 1990) 20030501

Title: 5,6-dimethylxanthenone-4-acetic acid (DMXAA), a novel antivascular agent: phase I clinical and pharmacokinetic study.

Journal: British journal of cancer 20030422

Title: Early detection of tumour immune-rejection using magnetic resonance imaging.

Journal: British journal of cancer 20030407

Title: The first international conference on vascular targeting: meeting overview.

Journal: Cancer research 20030301

Title: Antivascular therapy of cancer: DMXAA.

Journal: The Lancet. Oncology 20030301

Title: Preclinical factors influencing the relative contributions of Phase I and II enzymes to the metabolism of the experimental anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid.

Journal: Biochemical pharmacology 20030101

Title: Marked potentiation of the antitumour activity of chemotherapeutic drugs by the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Cancer chemotherapy and pharmacology 20030101

Title: Effect of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Oncology research 20030101

Title: DMXAA: an antivascular agent with multiple host responses.

Journal: International journal of radiation oncology, biology, physics 20021201

Title: Combination of vascular targeting agents with thermal or radiation therapy.

Journal: International journal of radiation oncology, biology, physics 20021201

Title: Enhancement of radiation therapy by vascular targeting agents.

Journal: Current opinion in investigational drugs (London, England : 2000) 20021101

Title: Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation.

Journal: Drug metabolism reviews 20021101

Title: Synthesis and antitumor activity of new derivatives of xanthen-9-one-4-acetic acid.

Journal: Journal of medicinal chemistry 20021024

Title: Potential of DMXAA combination therapy for solid tumors.

Journal: Expert review of anticancer therapy 20021001

Title: An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: European journal of medicinal chemistry 20021001

Title: Effects of 5,6-dimethylxanthenone-4-acetic acid on human tumor microcirculation assessed by dynamic contrast-enhanced magnetic resonance imaging.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020915

Title: Strain differences in the liver microsomal metabolism of the experimental anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid in mice.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020905

Title: The antitumour activity of 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in TNF receptor-1 knockout mice.

Journal: British journal of cancer 20020812

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

Journal: Investigational new drugs 20020801

Title: Non-specific binding of the experimental anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in liver microsomes from various species.

Journal: The Journal of pharmacy and pharmacology 20020701

Title: Induction of endothelial cell apoptosis by the antivascular agent 5,6-Dimethylxanthenone-4-acetic acid.

Journal: British journal of cancer 20020617

Title: A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs.

Journal: British journal of cancer 20020520

Title: Vascular targeting agents enhance chemotherapeutic agent activities in solid tumor therapy.

Journal: International journal of cancer 20020501

Title: Acute effects of vascular modifying agents in solid tumors assessed by noninvasive laser Doppler flowmetry and near infrared spectroscopy.

Journal: Neoplasia (New York, N.Y.) 20020501

Title: Differential sensitivity of two adenocarcinoma xenografts to the anti-vascular drugs combretastatin A4 phosphate and 5,6-dimethylxanthenone-4-acetic acid, assessed using MRI and MRS.

Journal: NMR in biomedicine 20020401

Title: Reproducibility of dynamic contrast-enhanced MRI in human muscle and tumours: comparison of quantitative and semi-quantitative analysis.

Journal: NMR in biomedicine 20020401

Title: High-throughput screening of potential inhibitors for the metabolism of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020205

Title: Gender differences in the metabolism and pharmacokinetics of the experimental anticancer agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Cancer chemotherapy and pharmacology 20020201

Title: Species differences in the metabolism of the antitumour agent 5,6-dimethylxanthenone-4-acetic acid in vitro: implications for prediction of metabolic interactions in vivo.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20020201

Title: Oral activity and pharmacokinetics of 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in mice.

Journal: Cancer chemotherapy and pharmacology 20020101

Title: Thalidomide in cancer treatment: a potential role in the elderly?

Journal: Drugs & aging 20020101

Title: 6-methylhydroxylation of the anti-cancer agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) by flavin-containing monooxygenase 3.

Journal: European journal of drug metabolism and pharmacokinetics 20020101

Title: Uptake of the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and activation of NF-kappaB in human tumor cell lines.

Journal: Oncology research 20020101

Title: Measurement of plasma 5-hydroxyindoleacetic acid as a possible clinical surrogate marker for the action of antivascular agents.

Journal: Clinica chimica acta; international journal of clinical chemistry 20011201

Title: Improved tumor response by combining radiation and the vascular-damaging drug 5,6-dimethylxanthenone-4-acetic acid.

Journal: Radiation research 20011101

Title: The antitumour agent 5,6-dimethylxanthenone-4-acetic acid acts in vitro on human mononuclear cells as a co-stimulator with other inducers of tumour necrosis factor.

Journal: European journal of cancer (Oxford, England : 1990) 20011001

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: Small-molecule cytokine inducers causing tumor necrosis.

Journal: Current opinion in investigational drugs (London, England : 2000) 20010701

Title: Determination of the covalent adducts of the novel anti-cancer agent 5,6-dimethylxanthenone-4-acetic acid in biological samples by high-performance liquid chromatography.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010615

Title: Determination of unbound concentration of the novel anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid in human plasma by ultrafiltration followed by high-performance liquid chromatography with fluorimetric detection.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010615

Title: Effects of the serotonin receptor antagonist cyproheptadine on the activity and pharmacokinetics of 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Cancer chemotherapy and pharmacology 20010601

Title: A difference between the rat and mouse in the pharmacokinetic interaction of 5,6-dimethylxanthenone-4-acetic acid with thalidomide.

Journal: Cancer chemotherapy and pharmacology 20010601

Title: Identification and reactivity of the major metabolite (beta-1-glucuronide) of the anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in humans.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20010501

Title: Reversible binding of the novel anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid to plasma proteins and its distribution into blood cells in various species.

Journal: The Journal of pharmacy and pharmacology 20010401

Title: In vitro and in vivo kinetic interactions of the antitumour agent 5,6-dimethylxanthenone-4-acetic acid with thalidomide and diclofenac.

Journal: Cancer chemotherapy and pharmacology 20010401

Title: Vascular attack by 5,6-dimethylxanthenone-4-acetic acid combined with B7.1 (CD80)-mediated immunotherapy overcomes immune resistance and leads to the eradication of large tumors and multiple tumor foci.

Journal: Cancer research 20010301

Title: Interferon-inducible protein 10 induction and inhibition of angiogenesis in vivo by the antitumor agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Journal: Cancer research 20010215

Title: Comparative effects of combretastatin A-4 disodium phosphate and 5,6-dimethylxanthenone-4-acetic acid on blood perfusion in a murine tumour and normal tissues.

Journal: International journal of radiation biology 20010201

Title: Potentiation of the anti-tumour effect of hyperthermia by combining with the vascular targeting agent 5,6-dimethylxanthenone-4-acetic acid.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20010101

Title: Downey CM, et al. DMXAA causes tumor site-specific vascular disruption in murine non-small cell lung cancer, and like the endogenous non-canonical cyclic dinucleotide STING agonist, 2'3'-cGAMP, induces M2 macrophage repolarization. PLoS One. 2014 Jun 18;9(6):e99988.

Title: Shirey KA, et al. The anti-tumor agent, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), induces IFN-beta-mediated antiviral activity in vitro and in vivo. J Leukoc Biol. 2011 Mar;89(3):351-7.

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Tags:117570-53-3 Molecular Formula|117570-53-3 MDL|117570-53-3 SMILES|117570-53-3 5,6-Dimethylxantheonone-4-acetic acid