(Q28305438)

English

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

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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 (English)

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author name string

Venkatraman Junnotula

1

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Ujjal Sarkar

2

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Sarmistha Sinha

3

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Kent S Gates

4

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language of work or name

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publication date

28 January 2009

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Journal of the American Chemical Society

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131

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3

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1015-24

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Exploiting tumour hypoxia in cancer treatment

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20 March 2017

Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling

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20 March 2017

Structure and potential mutagenicity of new hydantoin products from guanosine and 8-oxo-7,8-dihydroguanine oxidation by transition metals.

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20 March 2017

Oxidants, oxidative stress and the biology of ageing

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20 March 2017

57 Sequencing end-labeled DNA with base-specific chemical cleavages

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20 March 2017

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

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20 March 2017

Role of free radicals and catalytic metal ions in human disease: an overview

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7 April 2017

Tirapazamine: from bench to clinical trials.

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https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Hypoxia-selective 3-alkyl 1,2,4-benzotriazine 1,4-dioxides: the influence of hydrogen bond donors on extravascular transport and antitumor activity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogues

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Collateral damage in cancer chemotherapy: oxidative stress in nontargeted tissues

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Elucidating DNA damage and repair processes by independently generating reactive and metastable intermediates

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Synthesis and hypoxic-cytotoxic activity of some 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Oxidative DNA damage and disease: induction, repair and significance

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean?

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Cellular thiols and reactive oxygen species in drug-induced apoptosis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

The hypoxic cell: a target for selective cancer therapy--eighteenth Bruce F. Cain Memorial Award lecture.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Tirapazamine-induced DNA damage measured using the comet assay correlates with cytotoxicity towards hypoxic tumour cells in vitro

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Reactions of oxyl radicals with DNA.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: a review.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Quantitative measurement of single- and double-strand breakage of DNA in Escherichia coli by the antitumor antibiotics bleomycin and talisomycin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

SR 4233 cytotoxicity and metabolism in DNA repair-competent and repair-deficient cell cultures

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Photogeneration of hydroxyl radicals for footprinting

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

Electrophoresis of DNA in agarose gels. Optimizing separations of conformational isomers of double- and single-stranded DNAs

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

29 September 2017

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).

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

Hydroxylation of salicylate and phenylalanine as assays for hydroxyl radicals: a cautionary note visited for the third time

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

Chemical properties which control selectivity and efficacy of aromatic N-oxide bioreductive drugs

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

The interaction of closed circular DNA with intercalative dyes. I. The superhelix density of SV40 DNA in the presence and absence of dye.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

Metabolism of SR 4233 by Chinese hamster ovary cells: basis of selective hypoxic cytotoxicity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

Structure-activity relationships for benzotriazine di-N-oxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

2 June 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Photochemical electron transfer reactions of tirapazamine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Metabolism of tirapazamine by multiple reductases in the nucleus

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

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).

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

The tumor microenvironment: a double-edged sword.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Reduction of 3-amino-1,2,4-benzotriazine-1,4-di-N-oxide (tirapazamine, WIN 59075, SR 4233) to a DNA-damaging species: a direct role for NADPH:cytochrome P450 oxidoreductase.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2819123

27 November 2018

Guanine oxidation: one- and two-electron reactions

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Investigating nucleic acid damage processes via independent generation of reactive intermediates

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-l,2,4-benzotriazine-l ,4-dioxide (SR 4233, WIN 59075) by mouse liver

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Photosensitization of guanine-specific DNA damage by a cyano-substituted quinoxaline di-N-oxide

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Direct evidence for bimodal DNA damage induced by tirapazamine

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Second-generation 1,2,4-benzotriazine 1,4-di-N-oxide bioreductive anti-tumor agents: pharmacology and activity in vitro and in vivo

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Detection and quantitation of hydroxyl radical using dimethyl sulfoxide as molecular probe

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Enzymology of tirapazamine metabolism: a review

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Oxidative Nucleobase Modifications Leading to Strand Scission

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Dual action of tirapazamine in the induction of DNA strand breaks

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Reaction of the hypoxia-selective antitumor agent tirapazamine with a C1'-radical in single-stranded and double-stranded DNA: the drug and its metabolites can serve as surrogates for molecular oxygen in radical-mediated DNA damage reactions

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Kinetics of reductive N-O bond fragmentation: the role of a conical intersection

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Quantitation of the hydroxyl radical by reaction with dimethyl sulfoxide

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Simple procedure for distinguishing CCC, OC, and L forms of plasmid DNA by agarose gel electrophoresis

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The one-electron reduction potential of 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine): a hypoxia-selective bioreductive drug

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

High-performance liquid chromatographic determination of methanesulphinic acid as a method for the determination of hydroxyl radicals

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233)

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Production of formaldehyde during metabolism of dimethyl sulfoxide by hydroxyl radical-generating systems

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identification of two major reduction products of the hypoxic cell toxin 3-amino-1,2,4-benzotriazine-1,4-dioxide

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Detection of hydroxyl radicals by aromatic hydroxylation

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

1,2,4-Benzotriazine 1,4-dioxides. An important class of hypoxic cytotoxins with antitumor activity

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Measurement of tumor oxygenation

1 reference

https://pubmed.ncbi.nlm.nih.gov/19117394

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/JA8049645

1 reference

Consolidated OpenCitations Corpus – April 2017

OpenCitations bibliographic resource ID

OpenCitations bibliographic resource ID

1 reference

Consolidated OpenCitations Corpus – April 2017

OpenCitations bibliographic resource ID

1 reference

Consolidated OpenCitations Corpus – April 2017

OpenCitations bibliographic resource ID

1 reference

Consolidated OpenCitations Corpus – April 2017

OpenCitations bibliographic resource ID

ResearchGate publication ID

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