Home Amines 20535-83-5
20535-83-5,MFCD00133009
Catalog No.:AA0029YJ

20535-83-5 | 6-Methoxy-7h-purin-2-amine

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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0029YJ
Chemical Name:
6-Methoxy-7h-purin-2-amine
CAS Number:
20535-83-5
Molecular Formula:
C6H7N5O
Molecular Weight:
165.1527
MDL Number:
MFCD00133009
SMILES:
COc1nc(N)nc2c1nc[nH]2
NSC Number:
37364
Properties
Properties
 
BP:
288.6°C at 760 mmHg  
Form:
Solid  
MP:
>300 °C(lit.)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
166  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
-0.2  

Downstream Synthesis Route
20535-83-5    144490-03-9   
Aceticacid(2S,3S,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(2-amino-6-methoxy-purin-9-yl)-tetrahydro-furan-3-ylester 
  852553-83-4 

[1]Herbal,Karim;Kitteringham,John;Voyle,Martyn;Whitehead,AndrewJ.[TetrahedronLetters,2005,vol.46,#17,p.2961-2964]

[1]JournaloftheKoreanChemicalSociety,2010,vol.54,p.429-436

[1]JournaloftheKoreanChemicalSociety,2010,vol.54,p.429-436

[1]JournaloftheKoreanChemicalSociety,2010,vol.54,p.429-436

[1]JournaloftheKoreanChemicalSociety,2010,vol.54,p.429-436

Literature

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Title: Dihydromethysticin (DHM) Blocks Tobacco Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-Induced O(6)-Methylguanine in a Manner Independent of the Aryl Hydrocarbon Receptor (AhR) Pathway in C57BL/6 Female Mice.

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Title: Atl1 regulates choice between global genome and transcription-coupled repair of O(6)-alkylguanines.

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Journal: British journal of cancer 20110906

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Journal: Physical biology 20110801

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Title: Targeted deletion of GSNOR in hepatocytes of mice causes nitrosative inactivation of O6-alkylguanine-DNA alkyltransferase and increased sensitivity to genotoxic diethylnitrosamine.

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Title: Synergistic cytotoxicity of N-methyl-N'-nitro-N-nitrosoguanidine and absence of poly(ADP-ribose) glycohydrolase involves chromatin decondensation.

Journal: International journal of oncology 20110701

Title: Quantitative analysis of O6-methylguanine DNA methyltransferase (MGMT) promoter methylation in patients with low-grade gliomas.

Journal: Journal of neuro-oncology 20110601

Title: O6-methylguanine DNA methyltransferase expression in tumor cells predicts outcome of radiotherapy plus concomitant and adjuvant temozolomide therapy in patients with primary glioblastoma.

Journal: Brain tumor pathology 20110401

Title: Phenethyl isothiocyanate exhibits antileukemic activity in vitro and in vivo by inactivation of Akt and activation of JNK pathways.

Journal: Cell death & disease 20110401

Title: Role of alkyltransferase-like (ATL) protein in repair of methylated DNA lesions in Thermus thermophilus.

Journal: Mutagenesis 20110301

Title: MGMT is a molecular determinant for potency of the DNA-EGFR-combi-molecule ZRS1.

Journal: Molecular cancer research : MCR 20110301

Title: O6-methylguanine DNA methyltransferase status determined by promoter methylation and immunohistochemistry in gliosarcoma and their clinical implications.

Journal: Journal of neuro-oncology 20110201

Title: MGMT promoter hypermethylation is a frequent, early, and consistent event in astrocytoma progression, and not correlated with TP53 mutation.

Journal: Journal of neuro-oncology 20110201

Title: Tubular adenomas with minor villous changes show molecular features characteristic of tubulovillous adenomas.

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Title: Extent and patterns of MGMT promoter methylation in glioblastoma- and respective glioblastoma-derived spheres.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110115

Title: Development and validation of a new, sensitive immunochemical assay for O⁶-methylguanine in DNA and its application in a population study.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110101

Title: Comprehensive analysis of MGMT promoter methylation: correlation with MGMT expression and clinical response in GBM.

Journal: PloS one 20110101

Title: Morphological and molecular alterations in 1,2 dimethylhydrazine and azoxymethane induced colon carcinogenesis in rats.

Journal: Journal of biomedicine & biotechnology 20110101

Title: O6-Methylguanine-DNA methyltransferase protein expression by immunohistochemistry in brain and non-brain systemic tumours: systematic review and meta-analysis of correlation with methylation-specific polymerase chain reaction.

Journal: BMC cancer 20110101

Title: Lysyl oxidase, a critical intra- and extra-cellular target in the lung for cigarette smoke pathogenesis.

Journal: International journal of environmental research and public health 20110101

Title: NNK-Induced Lung Tumors: A Review of Animal Model.

Journal: Journal of oncology 20110101

Title: Peritoneal carcinomatosis from ovarian cancer: chemosensitivity test and tissue markers as predictors of response to chemotherapy.

Journal: Journal of translational medicine 20110101

Title: Promoter methylation of p16(INK4A), hMLH1, and MGMT in liquid-based cervical cytology samples compared with clinicopathological findings and HPV presence.

Journal: Infectious diseases in obstetrics and gynecology 20110101

Title: The human RECQ1 helicase is highly expressed in glioblastoma and plays an important role in tumor cell proliferation.

Journal: Molecular cancer 20110101

Title: Multiple ATR-Chk1 pathway proteins preferentially associate with checkpoint-inducing DNA substrates.

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Title: Rad51 and BRCA2--New molecular targets for sensitizing glioma cells to alkylating anticancer drugs.

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Title: Innovative Therapies against Human Glioblastoma Multiforme.

Journal: ISRN oncology 20110101

Title: Both hMutSα and hMutSß DNA mismatch repair complexes participate in 5-fluorouracil cytotoxicity.

Journal: PloS one 20110101

Title: Direct detection and sequencing of damaged DNA bases.

Journal: Genome integrity 20110101

Title: The prognostic impact of O6-methylguanine DNA methyltransferase and epidermal growth factor receptor expressions on primary gliosarcoma: a clinicopathologic and immunohistochemical study of seven cases at a single institution.

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Title: [Induction of repair enzyme O6-methylguanine-DNA methyltransferase gene expression under the influence of cytokine EMAP II in human cells in vitro].

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Journal: The Journal of biological chemistry 20101224

Title: Both base excision repair and O6-methylguanine-DNA methyltransferase protect against methylation-induced colon carcinogenesis.

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Title: O6-methylguanine DNA methyltransferase gene promoter methylation status in gliomas and its correlation with other molecular alterations: first Indian report with review of challenges for use in customized treatment.

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Title: Quantitative relationship between guanine O(6)-alkyl lesions produced by Onrigin™ and tumor resistance by O(6)-alkylguanine-DNA alkyltransferase.

Journal: Biochemical pharmacology 20101101

Title: Nijmegen breakage syndrome protein (NBN) causes resistance to methylating anticancer drugs such as temozolomide.

Journal: Molecular pharmacology 20101101

Title: Methylation tolerance due to an O6-methylguanine DNA methyltransferase (MGMT) field defect in the colonic mucosa: an initiating step in the development of mismatch repair-deficient colorectal cancers.

Journal: Gut 20101101

Title: Activity of irinotecan and temozolomide in the presence of O6-methylguanine-DNA methyltransferase inhibition in neuroblastoma pre-clinical models.

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Title: Absence of the MGMT protein as well as methylation of the MGMT promoter predict the sensitivity for temozolomide.

Journal: British journal of cancer 20100629

Title: Epigenetic aberrations and therapeutic implications in gliomas.

Journal: Cancer science 20100601

Title: Loss expression of O6-methylguanine DNA methyltransferase by promoter hypermethylation and its relationship to betel quid chewing in oral squamous cell carcinoma.

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Journal: Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases 20100601

Title: CpG methylation and reduced expression of O6-methylguanine DNA methyltransferase is associated with Helicobacter pylori infection.

Journal: Gastroenterology 20100501

Title: Structural basis of O6-alkylguanine recognition by a bacterial alkyltransferase-like DNA repair protein.

Journal: The Journal of biological chemistry 20100430

Title: RAD51D protects against MLH1-dependent cytotoxic responses to O(6)-methylguanine.

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Title: Interaction of murine dnmt3a with DNA containing o6-methylguanine.

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Title: Acquired resistance to 6-thioguanine in melanoma cells involves the repair enzyme O6-methylguanine-DNA methyltransferase (MGMT).

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Title: Processing of O6-methylguanine into DNA double-strand breaks requires two rounds of replication whereas apoptosis is also induced in subsequent cell cycles.

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Title: O6-Methylguanine DNA methyltransferase protein expression in tumor cells predicts outcome of temozolomide therapy in glioblastoma patients.

Journal: Neuro-oncology 20100101

Title: Promoter methylation analysis of O6-methylguanine-DNA methyltransferase in glioblastoma: detection by locked nucleic acid based quantitative PCR using an imprinted gene (SNURF) as a reference.

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Title: Cruciferous vegetable intake is inversely associated with lung cancer risk among smokers: a case-control study.

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Title: Repair of DNA Alkylation Damage by the Escherichia coli Adaptive Response Protein AlkB as Studied by ESI-TOF Mass Spectrometry.

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Title: Biological rationale for the use of DNA methyltransferase inhibitors as new strategy for modulation of tumor response to chemotherapy and radiation.

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Title: Combining modularity, conservation, and interactions of proteins significantly increases precision and coverage of protein function prediction.

Journal: BMC genomics 20100101

Title: Role of bevacizumab therapy in the management of glioblastoma.

Journal: Cancer management and research 20100101

Title: Inhibition of 1, 2-dimethylhydrazine-induced mucin-depleted foci and O⁶-methylguanine DNA adducts in the rat colorectum by boiled garlic powder.

Journal: Asian Pacific journal of cancer prevention : APJCP 20100101

Title: Different threshold levels for 2-amino-3,8 dimethylimidazo[4,5-f]quinoxaline (MelQx) initiation of lung and colon carcinogenesis and the effects of an additional initiation by 4 (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mice.

Journal: Molecular medicine reports 20100101

Title: O6-methylguanine repair by O6-alkylguanine-DNA alkyltransferase.

Journal: The journal of physical chemistry. B 20091224

Title: Is inactivation of O6-methylguanine DNA methyltransferase still a favorable prognostic factor of patients with diffuse large B-cell lymphoma in the era of R-CHOP chemotherapy?

Journal: Leukemia & lymphoma 20091201

Title: A quantum chemical study of repair of O6-methylguanine to guanine by tyrosine: evaluation of the winged helix-turn-helix model.

Journal: Journal of molecular modeling 20091101

Title: Gas-phase thermochemical properties of the damaged base O(6)-methylguanine versus adenine and guanine.

Journal: The Journal of organic chemistry 20091002

Title: The translesion polymerase Rev3L in the tolerance of alkylating anticancer drugs.

Journal: Molecular pharmacology 20091001

Title: Repair of O6-methylguanine to guanine by cysteine in the absence and presence of histidine and by cysteine thiolate anion: a quantum chemical study.

Journal: Physical chemistry chemical physics : PCCP 20091001

Title: Recognition of O6MeG lesions by MGMT and mismatch repair proficiency may be a prerequisite for low-dose radiation hypersensitivity.

Journal: Radiation research 20091001

Title: Epigenetic cross-talk between DNA methylation and histone modifications in human cancers.

Journal: Yonsei medical journal 20090831

Title: Cytosine methylation effects on the repair of O6-methylguanines within CG dinucleotides.

Journal: The Journal of biological chemistry 20090821

Title: Correlation of chromosomes 1p and 19q status and expressions of O6-methylguanine DNA methyltransferase (MGMT), p53 and Ki-67 in diffuse gliomas of World Health Organization (WHO) grades II and III: a clinicopathological study.

Journal: Neuropathology and applied neurobiology 20090801

Title: Extent of MGMT promoter methylation correlates with outcome in glioblastomas given temozolomide and radiotherapy.

Journal: British journal of cancer 20090707

Title: MGMT and MLH1 promoter methylation versus APC, KRAS and BRAF gene mutations in colorectal cancer: indications for distinct pathways and sequence of events.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20090701

Title: Correlation of promoter hypermethylation in hTERT, DAPK and MGMT genes with cervical oncogenesis progression.

Journal: Oncology reports 20090701

Title: Flipping of alkylated DNA damage bridges base and nucleotide excision repair.

Journal: Nature 20090611

Title: Methylation of estrogen receptor 1 in colorectal adenomas is not age-dependent, but is correlated with K-ras mutation.

Journal: Cancer science 20090601

Title: Comparative levels of O6-methylguanine, pyridyloxobutyl-, and pyridylhydroxybutyl-DNA adducts in lung and liver of rats treated chronically with the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20090601

Title: Toward a molecular equivalent dose: use of the medaka model in comparative risk assessment.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20090301

Title: A novel protein, MAPO1, that functions in apoptosis triggered by O6-methylguanine mispair in DNA.

Journal: Oncogene 20090226

Title: Temozolomide and carmustine cause large-scale heterochromatin reorganization in glioma cells.

Journal: Biochemical and biophysical research communications 20090206

Title: The L84F polymorphic variant of human O6-methylguanine-DNA methyltransferase alters stability in U87MG glioma cells but not temozolomide sensitivity.

Journal: Neuro-oncology 20090201

Title: Prognostic significance of O6-methylguanine DNA methyltransferase and p57 methylation in patients with diffuse large B-cell lymphomas.

Journal: APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20090201

Title: Brca2/Xrcc2 dependent HR, but not NHEJ, is required for protection against O(6)-methylguanine triggered apoptosis, DSBs and chromosomal aberrations by a process leading to SCEs.

Journal: DNA repair 20090101

Title: Epidemiology of brain tumors.

Journal: Methods in molecular biology (Clifton, N.J.) 20090101

Title: O6-methylguanine DNA methyltransferase deficiency and response to temozolomide-based therapy in patients with neuroendocrine tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090101

Title: Homogeneous MGMT immunoreactivity correlates with an unmethylated MGMT promoter status in brain metastases of various solid tumors.

Journal: PloS one 20090101

Title: Molecular neuropathology of gliomas.

Journal: International journal of molecular sciences 20090101

Title: Treatment of recurrent malignant gliomas with fotemustine monotherapy: impact of dose and correlation with MGMT promoter methylation.

Journal: BMC cancer 20090101

Title: Temozolomide and cisplatin in relapsed/refractory acute leukemia.

Journal: Journal of hematology & oncology 20090101

Title: Transcriptome and proteome analyses of adaptive responses to methyl methanesulfonate in Escherichia coli K-12 and ada mutant strains.

Journal: BMC microbiology 20090101

Title: Inhibitory effects of high temperature- and pressure-treated garlic on formation of 1,2-dimethylhydrazine-induced mucin-depleted foci and O(6)-methylguanine DNA adducts in the rat colorectum.

Journal: Asian Pacific journal of cancer prevention : APJCP 20090101

Title: Degradation of BRCA2 in alkyltransferase-mediated DNA repair and its clinical implications.

Journal: Cancer research 20081201

Title: IFN-beta sensitizes neuroblastoma to the antitumor activity of temozolomide by modulating O6-methylguanine DNA methyltransferase expression.

Journal: Molecular cancer therapeutics 20081201

Title: Survival and tumorigenesis in O6-methylguanine DNA methyltransferase-deficient mice following cyclophosphamide exposure.

Journal: Mutagenesis 20080901

Title: Human MLH1 protein participates in genomic damage checkpoint signaling in response to DNA interstrand crosslinks, while MSH2 functions in DNA repair.

Journal: PLoS genetics 20080901

Title: Model of human aging: recent findings on Werner's and Hutchinson-Gilford progeria syndromes.

Journal: Clinical interventions in aging 20080901

Title: An O6-methylguanine-DNA methyltransferase-like protein from Thermus thermophilus interacts with a nucleotide excision repair protein.

Journal: Journal of biochemistry 20080801

Title: Transcriptional repression of O6-methylguanine DNA methyltransferase gene rendering cells hypersensitive to N,N'-bis(2-chloroethyl)-N-nitrosurea in camptothecin-resistant cells.

Journal: Molecular pharmacology 20080801

Title: Different initial steps of apoptosis induced by two types of antineoplastic drugs.

Journal: Biochemical pharmacology 20080801

Title: Epigenetic silencing of O6-methylguanine DNA methyltransferase gene in NiS-transformed cells.

Journal: Carcinogenesis 20080601

Title: A methylation-specific and SYBR-green-based quantitative polymerase chain reaction technique for O6-methylguanine DNA methyltransferase promoter methylation analysis.

Journal: Analytical biochemistry 20080601

Title: Inhibition of the 5' to 3' exonuclease activity of hEXO1 by 8-oxoguanine.

Journal: Environmental and molecular mutagenesis 20080601

Title: Effect of O6-methylguanine on the stability of G-quadruplex DNA.

Journal: Journal of the American Chemical Society 20080528

Title: Mechanisms of chemoresistance to alkylating agents in malignant glioma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080515

Title: Monitoring of dimethyl sulphate-induced N3-methyladenine, N7-methylguanine and O(6)-methylguanine DNA adducts using reversed-phase high performance liquid chromatography and mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080501

Title: [Methylnitrosourea as challenge mutagen in assessment of the DNA mismatch repair (MMR) activity: association with some types of cancer].

Journal: Genetika 20080501

Title: Binding of MutS protein to oligonucleotides containing a methylated or an ethylated guanine residue, and correlation with mutation frequency.

Journal: Mutation research 20080402

Title: Ras regulation of DNA-methylation and cancer.

Journal: Experimental cell research 20080401

Title: Prognostic significance of DNA repair proteins MLH1, MSH2 and MGMT expression in non-small-cell lung cancer and precursor lesions.

Journal: Histopathology 20080401

Title: Protective effects of vanadium against DMH-induced genotoxicity and carcinogenesis in rat colon: removal of O(6)-methylguanine DNA adducts, p53 expression, inducible nitric oxide synthase downregulation and apoptotic induction.

Journal: Mutation research 20080227

Title: Genetic markers predictive of chemosensitivity and outcome in gliomatosis cerebri.

Journal: Neurology 20080219

Title: Mismatch repair proteins collaborate with methyltransferases in the repair of O(6)-methylguanine.

Journal: DNA repair 20080201

Title: Molecular diagnostic testing in malignant gliomas: a practical update on predictive markers.

Journal: Journal of neuropathology and experimental neurology 20080101

Title: K-ras mutations in sinonasal cancers in relation to wood dust exposure.

Journal: BMC cancer 20080101

Title: Acetylation regulates WRN catalytic activities and affects base excision DNA repair.

Journal: PloS one 20080101

Title: B-MYB is essential for normal cell cycle progression and chromosomal stability of embryonic stem cells.

Journal: PloS one 20080101

Title: Promoter methylation inhibits BRD7 expression in human nasopharyngeal carcinoma cells.

Journal: BMC cancer 20080101

Title: Improved generation of rat gene knockouts by target-selected mutagenesis in mismatch repair-deficient animals.

Journal: BMC genomics 20080101

Title: High-fidelity correction of genomic uracil by human mismatch repair activities.

Journal: BMC molecular biology 20080101

Title: Cell death upon epigenetic genome methylation: a novel function of methyl-specific deoxyribonucleases.

Journal: Genome biology 20080101

Title: Cilengitide induces cellular detachment and apoptosis in endothelial and glioma cells mediated by inhibition of FAK/src/AKT pathway.

Journal: Journal of experimental & clinical cancer research : CR 20080101

Title: Human DNA polymerase lambda is a proficient extender of primer ends paired to 7,8-dihydro-8-oxoguanine.

Journal: DNA repair 20071201

Title: Tamoxifen accelerates proteasomal degradation of O6-methylguanine DNA methyltransferase in human cancer cells.

Journal: International journal of cancer 20071115

Title: From old organisms to new molecules: integrative biology and therapeutic targets in accelerated human ageing.

Journal: Cellular and molecular life sciences : CMLS 20071001

Title: Nelarabine: a novel purine antimetabolite antineoplastic agent.

Journal: Clinical therapeutics 20070901

Title: Determination of the role of target tissue metabolism in lung carcinogenesis using conditional cytochrome P450 reductase-null mice.

Journal: Cancer research 20070815

Title: Mouse embryonic stem cells are hypersensitive to apoptosis triggered by the DNA damage O(6)-methylguanine due to high E2F1 regulated mismatch repair.

Journal: Cell death and differentiation 20070801

Title: MGMT: a personal perspective.

Journal: DNA repair 20070801

Title: Correlation between promoter hypermethylation of GSTP1 and response to chemotherapy in diffuse large B cell lymphoma.

Journal: Annals of hematology 20070801

Title: Inhibition of nuclear factor-kappaB activity by temozolomide involves O6-methylguanine induced inhibition of p65 DNA binding.

Journal: Cancer research 20070715

Title: The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.

Journal: Bioorganic & medicinal chemistry 20070515

Title: Methylation of O6-methylguanine DNA methyltransferase and loss of heterozygosity on 19q and/or 17p are overlapping features of secondary glioblastomas with prolonged survival.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070501

Title: Silencing of O6-methylguanine DNA methyltransferase in the absence of promoter hypermethylation in hepatocellular carcinomas from Australia and South Africa.

Journal: Oncology reports 20070401

Title: Low frequency of promoter methylation of O6-methylguanine DNA methyltransferase and hMLH1 in ulcerative colitis-associated tumors: comparison with sporadic colonic tumors.

Journal: American journal of clinical pathology 20070301

Title: Dose response relationship in anti-stress gene regulatory networks.

Journal: PLoS computational biology 20070301

Title: Sulfolobus solfataricus DNA polymerase Dpo4 is partially inhibited by 'wobble' pairing between O6-methylguanine and cytosine, but accurate bypass is preferred.

Journal: The Journal of biological chemistry 20070112

Title: Apoptosis in malignant glioma cells triggered by the temozolomide-induced DNA lesion O6-methylguanine.

Journal: Oncogene 20070111

Title: A distinct epigenetic signature at targets of a leukemia protein.

Journal: BMC genomics 20070101

Title: Paradoxical DNA repair and peroxide resistance gene conservation in Bacillus pumilus SAFR-032.

Journal: PloS one 20070101

Title: Transcriptional networks in S. cerevisiae linked to an accumulation of base excision repair intermediates.

Journal: PloS one 20070101

Title: The synthesis and properties of tricyclic analogues of S6-methylthioguanine and O6-methylguanine.

Journal: Nucleosides, nucleotides & nucleic acids 20070101

Title: Prostate cancer epigenetics: a review on gene regulation.

Journal: Gene regulation and systems biology 20070101

Title: Polymorphisms in O6-methylguanine DNA methyltransferase and endometrial cancer risk.

Journal: Carcinogenesis 20061101

Title: Correlations between O6-methylguanine DNA methyltransferase promoter methylation status, 1p and 19q deletions, and response to temozolomide in anaplastic and recurrent oligodendroglioma: a prospective GICNO study.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20061010

Title: DNA stability in the gas versus solution phases: a systematic study of thirty-one duplexes with varying length, sequence, and charge level.

Journal: Journal of the American Society for Mass Spectrometry 20061001

Title: A pilot study of dose-intensified procarbazine, CCNU, vincristine for poor prognosis brain tumors utilizing fibronectin-assisted, retroviral-mediated modification of CD34+ peripheral blood cells with O6-methylguanine DNA methyltransferase.

Journal: Cancer gene therapy 20060901

Title: DNA damage-induced cell death by apoptosis.

Journal: Trends in molecular medicine 20060901

Title: Mismatch repair-dependent iterative excision at irreparable O6-methylguanine lesions in human nuclear extracts.

Journal: The Journal of biological chemistry 20060811

Title: Role of temozolomide in pediatric brain tumors.

Journal: Child's nervous system : ChNS : official journal of the International Society for Pediatric Neurosurgery 20060701

Title: Polymorphisms in O6-methylguanine DNA methyltransferase and breast cancer risk.

Journal: Pharmacogenetics and genomics 20060701

Title: DNA methyltransferases messenger RNA expression and aberrant methylation of CpG islands in non-small-cell lung cancer: association and prognostic value.

Journal: Clinical lung cancer 20060701

Title: High frequency and strong prognostic relevance of O6-methylguanine DNA methyltransferase silencing in diffuse large B-cell lymphomas from the Middle East.

Journal: Human pathology 20060601

Title: ATR kinase activation mediated by MutSalpha and MutLalpha in response to cytotoxic O6-methylguanine adducts.

Journal: Molecular cell 20060519

Title: The syntheses and properties of tricyclic pyrrolo[2,3-d]pyrimidine analogues of S6-methylthioguanine and O6-methylguanine.

Journal: Organic & biomolecular chemistry 20060507

Title: In vivo effects of myeloablative alkylator therapy on survival and differentiation of MGMTP140K-transduced human G-CSF-mobilized peripheral blood cells.

Journal: Molecular therapy : the journal of the American Society of Gene Therapy 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Progressive low-grade oligodendrogliomas: response to temozolomide and correlation between genetic profile and O6-methylguanine DNA methyltransferase protein expression.

Journal: Cancer 20060415

Title: Simultaneous quantitation of 7-methyl- and O6-methylguanine adducts in DNA by liquid chromatography-positive electrospray tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060403

Title: DNA repair enzyme, O6-methylguanine DNA methyltransferase, modulates cytotoxicity of camptothecin-derived topoisomerase I inhibitors.

Journal: The Journal of pharmacology and experimental therapeutics 20060201

Title: O6-methylguanine DNA methyltransferase and p53 status predict temozolomide sensitivity in human malignant glioma cells.

Journal: Journal of neurochemistry 20060201

Title: Mutually exclusive promoter hypermethylation patterns of hMLH1 and O6-methylguanine DNA methyltransferase in colorectal cancer.

Journal: The Journal of molecular diagnostics : JMD 20060201

Title: Inhibitory effects of caraway (Carum carvi L. ) and its component on N-methyl-N'-nitro-N-nitrosoguanidine-induced mutagenicity.

Journal: The journal of medical investigation : JMI 20060201

Title: Effect of chemotherapy-induced DNA repair on oncolytic herpes simplex viral replication.

Journal: Journal of the National Cancer Institute 20060104

Title: [Comparison of geno- and cytotoxicity of methylnitrosourea on MMR-proficient and MMR-deficient human tumor cell lines].

Journal: Tsitologiia 20060101

Title: Promoter hypermethylation of DNA repair gene MGMT in laryngeal squamous cell carcinoma.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20060101

Title: Analysis of gene expression and chemoresistance of CD133+ cancer stem cells in glioblastoma.

Journal: Molecular cancer 20060101

Title: Predictive utility of circulating methylated DNA in serum of melanoma patients receiving biochemotherapy.

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

Title: Exon 3 polymorphisms and haplotypes of O6-methylguanine-DNA methyltransferase and risk of bladder cancer in southern China: a case-control analysis.

Journal: Cancer letters 20050908

Title: Epigenetic silencing of the MGMT gene in cancer.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20050801

Title: Nelarabine: a nucleoside analog with efficacy in T-cell and other leukemias.

Journal: The Annals of pharmacotherapy 20050601

Title: Loss of DNA minor groove interactions by exonuclease-deficient Klenow polymerase inhibits O6-methylguanine and abasic site translesion synthesis.

Journal: Biochemistry 20050510

Title: [Effect of beta-carotene supplementation on DNA oxidative and alkylation damage in rats].

Journal: Wei sheng yan jiu = Journal of hygiene research 20050501

Title: Mitochondrial targeting of human O6-methylguanine DNA methyltransferase protects against cell killing by chemotherapeutic alkylating agents.

Journal: Cancer research 20050415

Title: Genetic pathways to glioblastomas.

Journal: Neuropathology : official journal of the Japanese Society of Neuropathology 20050301

Title: Lack of EGF receptor contributes to drug sensitivity of human germline cells.

Journal: British journal of cancer 20050131

Title: Inhibition by allyl sulfides and crushed garlic of O6-methylguanine formation in liver DNA of dimethylnitrosamine-treated rats.

Journal: Nutrition and cancer 20050101

Title: Electrochemical detection of lesions in DNA.

Journal: Bioconjugate chemistry 20050101

Title: PCNA-MutSalpha-mediated binding of MutLalpha to replicative DNA with mismatched bases to induce apoptosis in human cells.

Journal: Nucleic acids research 20050101

Title: Epigenetics of cervical cancer. An overview and therapeutic perspectives.

Journal: Molecular cancer 20050101

Title: Intra- and intercellular variations in the repair efficiency of O6-methylguanine, and their contribution to kinetic complexity.

Journal: Mutation research 20041221

Title: The combi-targeting concept: dissection of the binary mechanism of action of the combi-triazene SMA41 in vitro and antitumor activity in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20041201

Title: Inhibitory effects of Centella asiatica on azoxymethane-induced aberrant crypt focus formation and carcinogenesis in the intestines of F344 rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20041201

Title: Mutational-reporter transgenes rescued from mice lacking either Mgmt, or both Mgmt and Msh6 suggest that O6-alkylguanine-induced miscoding does not contribute to the spontaneous mutational spectrum.

Journal: Oncogene 20040805

Title: Proofreading activity of Pfu thermostable DNA polymerase on a 6-O-methylguanine-containing template monitored by ESI-FTICR mass spectrometry.

Journal: Chembiochem : a European journal of chemical biology 20040705

Title: DNA damage and repair measured in different genomic regions using the comet assay with fluorescent in situ hybridization.

Journal: Mutagenesis 20040701

Title: Synthesis and characterization of bifunctional probes for the specific labeling of fusion proteins.

Journal: Bioorganic & medicinal chemistry letters 20040607

Title: The Werner syndrome protein confers resistance to the DNA lesions N3-methyladenine and O6-methylguanine: implications for WRN function.

Journal: DNA repair 20040603

Title: Therapeutic impact of methoxyamine: blocking repair of abasic sites in the base excision repair pathway.

Journal: Current opinion in investigational drugs (London, England : 2000) 20040601

Title: Profiling epigenetic inactivation of tumor suppressor genes in tumors and plasma from cutaneous melanoma patients.

Journal: Oncogene 20040513

Title: Loss of ATM sensitizes against O6-methylguanine triggered apoptosis, SCEs and chromosomal aberrations.

Journal: DNA repair 20040401

Title: Detection of O6-carboxymethyl-2'-deoxyguanosine in DNA following reaction of nitric oxide with glycine and in human blood DNA using a quantitative immunoslot blot assay.

Journal: Chemical research in toxicology 20040301

Title: The repair of the tobacco specific nitrosamine derived adduct O6-[4-Oxo-4-(3-pyridyl)butyl]guanine by O6-alkylguanine-DNA alkyltransferase variants.

Journal: Chemical research in toxicology 20040301

Title: [Promoter hypermethylation of DNA repair gene O6-methylguanine DNA methyltransferase in laryngeal squamous cell carcinoma].

Journal: Zhonghua er bi yan hou ke za zhi 20040301

Title: Guanine 6-O-methylation pattern within the dioxin responsive element of the CYP1A1 enhancer shows two critical guanines for AhR/ARNT binding.

Journal: Chemistry & biodiversity 20040301

Title: Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides.

Journal: Journal of medicinal chemistry 20040129

Title: Endogenous 5-methylcytosine protects neighboring guanines from N7 and O6-methylation and O6-pyridyloxobutylation by the tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.

Journal: Biochemistry 20040120

Title: Apoptosis triggered by DNA damage O6-methylguanine in human lymphocytes requires DNA replication and is mediated by p53 and Fas/CD95/Apo-1.

Journal: Oncogene 20040115

Title: Generating mutations but providing chemosensitivity: the role of O6-methylguanine DNA methyltransferase in human cancer.

Journal: Oncogene 20040108

Title: Promoter methylation status of multiple genes in brain metastases of solid tumors.

Journal: International journal of molecular medicine 20040101

Title: O6-3-[131I]iodobenzylguanine: improved synthesis and further evaluation of a potential agent for imaging of alkylguanine-DNA alkyltransferase.

Journal: Bioconjugate chemistry 20040101

Title: Mechanisms and consequences of methylating agent-induced SCEs and chromosomal aberrations: a long road traveled and still a far way to go.

Journal: Cytogenetic and genome research 20040101

Title: DNA damage processing and aberration formation in plants.

Journal: Cytogenetic and genome research 20040101

Title: Dexamethasone protected human glioblastoma U87MG cells from temozolomide induced apoptosis by maintaining Bax:Bcl-2 ratio and preventing proteolytic activities.

Journal: Molecular cancer 20040101

Title: BRAF/K-ras mutation, microsatellite instability, and promoter hypermethylation of hMLH1/MGMT in human gastric carcinomas.

Journal: Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association 20040101

Title: The syntheses of tricyclic analogues of O6-methylguanine.

Journal: Organic & biomolecular chemistry 20031207

Title: The N2-ethylguanine and the O6-ethyl- and O6-methylguanine lesions in DNA: contrasting responses from the 'bypass' DNA polymerase eta and the replicative DNA polymerase alpha.

Journal: Chemical research in toxicology 20031201

Title: O6-alkylguanine-DNA alkyltransferases repair O6-methylguanine in DNA with Michaelis-Menten-like kinetics.

Journal: Chemical research in toxicology 20031101

Title: Alkylation damage repair protein O6-alkylguanine-DNA alkyltransferase from the hyperthermophiles Aquifex aeolicus and Archaeoglobus fulgidus.

Journal: The Biochemical journal 20031015

Title: The mutational spectrum of the HPRT gene from human T cells in vivo shares a significant concordant set of hot spots with MNNG-treated human cells.

Journal: Cancer research 20030915

Title: Mutations in putative mutator genes of Mycobacterium tuberculosis strains of the W-Beijing family.

Journal: Emerging infectious diseases 20030701

Title: In vivo protection of hematopoietic cells from alkylator-mediated DNA damage.

Journal: Current hematology reports 20030701

Title: Stereospecific deuterium substitution attenuates the tumorigenicity and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).

Journal: Chemical research in toxicology 20030601

Title: K-ras gene sequence effects on the formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-DNA adducts.

Journal: Chemical research in toxicology 20030401

Title: DNA repair enzymes and cytotoxic effects of temozolomide: comparative studies between tumor cells and normal cells of the immune system.

Journal: Journal of chemotherapy (Florence, Italy) 20030401

Title: Mutation analysis of K-ras and beta-catenin genes related to O6-methylguanin-DNA methyltransferase and mismatch repair protein status in human gallbladder carcinoma.

Journal: International journal of molecular medicine 20030101

Title: Evaluation of O6-methylguanine DNA methyltransferase activity in patients with gastric cancer.

Journal: Oncology research 20030101

Title: Genotoxic methylating agents modulate extracellular signal regulated kinase activity through MEK-dependent, glutathione-, and DNA methylation-independent mechanisms in lung epithelial cells.

Journal: Chemical research in toxicology 20030101

Title: Inhibition of azoxymethane-induced DNA adduct formation by Aloe arborescens var. natalensis.

Journal: Asian Pacific journal of cancer prevention : APJCP 20030101

Title: Methylenetetrahydrofolate reductase genotype in diffuse large B-cell lymphomas with and without hypermethylation of the DNA repair gene O6-methylguanine DNA methyltransferase.

Journal: The International journal of biological markers 20030101

Title: Comparison of the chemopreventive efficacies of 1,4-phenylenebis(methylene)selenocyanate and selenium-enriched yeast on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced lung tumorigenesis in A/J mouse.

Journal: Nutrition and cancer 20030101

Title: Mechanisms of carcinogenicity/chemotherapy by O6-methylguanine.

Journal: Mutagenesis 20021101

Title: O6-benzylguanine-mediated enhancement of chemotherapy.

Journal: Molecular cancer therapeutics 20020901

Title: Probing the ATP ribose-binding domain of cyclin-dependent kinases 1 and 2 with O(6)-substituted guanine derivatives.

Journal: Journal of medicinal chemistry 20020801

Title: DNA repair in resistance to alkylating anticancer drugs.

Journal: International journal of clinical pharmacology and therapeutics 20020801

Title: Pharmacological strategies to increase the antitumor activity of methylating agents.

Journal: Current medicinal chemistry 20020701

Title: DNA adducts and liver DNA replication in rats during chronic exposure to N-nitrosodimethylamine (NDMA) and their relationships to the dose-dependence of NDMA hepatocarcinogenesis.

Journal: Mutation research 20020320

Title: Antimutagenicity of Murdannia loriformis in the Salmonella mutation assay and its inhibitory effects on azoxymethane-induced DNA methylation and aberrant crypt focus formation in male F344 rats.

Journal: The journal of medical investigation : JMI 20020201

Title: Effect of the O6 substituent on misincorporation kinetics catalyzed by DNA polymerases at O(6)-methylguanine and O(6)-benzylguanine.

Journal: Biochemistry 20020122

Title: Misincorporation and stalling at O(6)-methylguanine and O(6)-benzylguanine: evidence for inactive polymerase complexes.

Journal: Biochemistry 20020122

Title: Monitoring for DNA damage of humans occupationally exposed to methyl bromide.

Journal: Anticancer research 20020101

Title: Correlation of nucleoside and nucleobase transporter gene expression with antimetabolite drug cytotoxicity.

Journal: Journal of experimental therapeutics & oncology 20020101

Title: Glutathione S-transferase and O6-methylguanine DNA methyl transferase activities in patients with thyroid papillary carcinoma.

Journal: Cancer investigation 20020101

Title: Differential effects of CYP2E1 status on the metabolic activation of the colon carcinogens azoxymethane and methylazoxymethanol.

Journal: Cancer research 20011201

Title: Expression and prognostic significance of O6-methylguanine-DNA methyltransferase in hepatocellular, gastric, and breast cancers.

Journal: Annals of surgical oncology 20011201

Title: The effect of a 2-h exposure to cigarette smoke on the metabolic activation of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mice.

Journal: Chemico-biological interactions 20011128

Title: Repair of O(6)-methylguanine is not affected by thymine base pairing and the presence of MMR proteins.

Journal: Mutation research 20011101

Title: Host determinants of DNA alkylation and DNA repair activity in human colorectal tissue: O(6)-methylguanine levels are associated with GSTT1 genotype and O(6)-alkylguanine-DNA alkyltransferase activity with CYP2D6 genotype.

Journal: Mutation research 20010822

Title: Chemoprevention of esophageal tumorigenesis by dietary administration of lyophilized black raspberries.

Journal: Cancer research 20010815

Title: Ethanol enhances the formation of endogenously and exogenously derived adducts in rat hepatic DNA.

Journal: Mutation research 20010808

Title: High-performance liquid chromatographic method with electrochemical detection for the analysis of O6-methylguanine.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010805

Title: Interactions between methylating and pyridyloxobutylating agents in A/J mouse lungs: implications for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis.

Journal: Cancer research 20010801

Title: Modulation of 1,3-bis-(2-chloroethyl)-1-nitrosourea resistance in human tumor cells using hammerhead ribozymes designed to degrade O6-methylguanine DNA methyltransferase mRNA.

Journal: The Journal of pharmacology and experimental therapeutics 20010701

Title: Mutagenesis by O(6)-methyl-, O(6)-ethyl-, and O(6)-benzylguanine and O(4)-methylthymine in human cells: effects of O(6)-alkylguanine-DNA alkyltransferase and mismatch repair.

Journal: Chemical research in toxicology 20010701

Title: The 3' --> 5' exonuclease of T4 DNA polymerase removes premutagenic alkyl mispairs and contributes to futile cycling at O6-methylguanine lesions.

Journal: The Journal of biological chemistry 20010629

Title: Possible involvement of O6-methylguanine formation and p53 dysfunction in mouse urinary bladder carcinogenesis.

Journal: Mutation research 20010602

Title: [Repair of alkylated DNA and consequences of its failure].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20010601

Title: Micellar electrokinetic capillary chromatography quantification of cytosine arabinoside and its metabolite, uracil arabinoside, in human serum.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010415

Title: Diversity of the damage recognition step in the global genomic nucleotide excision repair in vitro.

Journal: Mutation research 20010404

Title: Effects of single or split exposure of leukemic cells to temozolomide, combined with poly(ADP-ribose) polymerase inhibitors on cell growth, chromosomal aberrations and base excision repair components.

Journal: Cancer chemotherapy and pharmacology 20010401

Title: Health span and life span in transgenic mice with modulated DNA repair.

Journal: Annals of the New York Academy of Sciences 20010401

Title: Role of cytochrome P450 in DNA damage produced by treatment of colon cells with 1,2-dimethylhydrazine.

Journal: International journal of oncology 20010301

Title: Inhibition of N-nitrosomethylbenzylamine-induced tumorigenesis in the rat esophagus by dietary freeze-dried strawberries.

Journal: Carcinogenesis 20010301

Title: p53 effects both the duration of G2/M arrest and the fate of temozolomide-treated human glioblastoma cells.

Journal: Cancer research 20010301

Title: Inhibitory effects of bitter melon (Momordica charantia Linn.) on bacterial mutagenesis and aberrant crypt focus formation in the rat colon.

Journal: The journal of medical investigation : JMI 20010201

Title: Topoisomerase I-mediated cytotoxicity of N-methyl-N'-nitro-N-nitrosoguanidine: trapping of topoisomerase I by the O6-methylguanine.

Journal: Cancer research 20010101

Title: DNA damage recognition and repair pathway coordination revealed by the structural biochemistry of DNA repair enzymes.

Journal: Progress in nucleic acid research and molecular biology 20010101

Title: BER, MGMT, and MMR in defense against alkylation-induced genotoxicity and apoptosis.

Journal: Progress in nucleic acid research and molecular biology 20010101

Title: O6-alkylguanines, dietary N-nitroso compounds, and their precursors in gastric cancer.

Journal: Nutrition and cancer 20010101

Title: Novel DNA repair alkyltransferase from Caenorhabditis elegans.

Journal: Environmental and molecular mutagenesis 20010101

Title: DNA repair: counteragent in mutagenesis and carcinogenesis-- accomplice in cancer therapy resistance.

Journal: Mutation research 20000401

Title: Toxicity, mutation frequency and mutation spectrum induced by dacarbazine in CHO cells expressing different levels of O(6)-methylguanine-DNA methyltransferase.

Journal: Mutation research 20000214

Title: Chromium(III) decreases the fidelity of human DNA polymerase beta.

Journal: Biochemistry 19980630

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Tags:20535-83-5 Molecular Formula|20535-83-5 MDL|20535-83-5 SMILES|20535-83-5 6-Methoxy-7h-purin-2-amine |Organic_Building_Blocks