(Q41808209)

English

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).

scientific article published on 27 September 2007

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scholarly article

1 reference

Europe PubMed Central

12 October 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). (English)

1 reference

Europe PubMed Central

12 October 2017

author name string

Goutam Chowdhury

1

1 reference

Europe PubMed Central

12 October 2017

Venkatraman Junnotula

2

1 reference

Europe PubMed Central

12 October 2017

J Scott Daniels

3

1 reference

Europe PubMed Central

12 October 2017

Marc M Greenberg

4

1 reference

Europe PubMed Central

12 October 2017

Kent S Gates

5

1 reference

Europe PubMed Central

12 October 2017

language of work or name

0 references

publication date

27 September 2007

1 reference

Europe PubMed Central

12 October 2017

Journal of the American Chemical Society

1 reference

Europe PubMed Central

12 October 2017

129

1 reference

Europe PubMed Central

12 October 2017

42

1 reference

Europe PubMed Central

12 October 2017

12870-12877

1 reference

Europe PubMed Central

12 October 2017

Tirapazamine: from bench to clinical trials.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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=2821206

6 June 2018

Exploiting tumour hypoxia in cancer treatment

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Half-life and DNA strand scission products of 2-deoxyribonolactone oxidative DNA damage lesions

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Tandem Lesions Are the Major Products Resulting from a Pyrimidine Nucleobase Radical

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

The role of hypoxia-activated prodrugs in cancer therapy

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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=2821206

6 June 2018

Mitochondrial dysfunction after aerobic exposure to the hypoxic cytotoxin tirapazamine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Mechanisms of DNA cleavage by copper complexes of 3-clip-phen and of its conjugate with a distamycin analogue

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Oxidants, oxidative stress and the biology of ageing

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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=2821206

6 June 2018

The reactivity of the 2-deoxyribonolactone lesion in single-stranded DNA and its implication in reaction mechanisms of DNA damage and repair

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Tirapazamine: laboratory data relevant to clinical activity.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Adaptation of human tumor cells to tirapazamine under aerobic conditions: implications of increased antioxidant enzyme activity to mechanism of aerobic cytotoxicity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 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=2821206

6 June 2018

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=2821206

6 June 2018

SR 4233 (tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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=2821206

6 June 2018

Mitomycin C: a prototype bioreductive agent.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

gamma Ray induced deoxyribonucleic acid strand breaks. 3' Glycolate termini

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Malondialdehyde precursors in gamma-irradiated DNA, deoxynucleotides and deoxynucleosides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 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=2821206

6 June 2018

Nuclease activity of 1,10-phenanthroline-copper ion: reaction with CGCGAATTCGCG and its complexes with netropsin and EcoRI.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

3'-Formyl phosphate-ended DNA: high-energy intermediate in antibiotic-induced DNA sugar damage

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

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=2821206

6 June 2018

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=2821206

6 June 2018

Neocarzinostatin-induced hydrogen atom abstraction from C-4' and C-5' of the T residue at a d(GT) step in oligonucleotides: shuttling between deoxyribose attack sites based on isotope selection effects

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Mechanism of DNA cleavage by cationic manganese porphyrins: hydroxylations at the 1'-carbon and 5'-carbon atoms of deoxyriboses as initial damages

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Neocarzinostatin-mediated DNA damage in a model AGT.ACT site: mechanistic studies of thiol-sensitive partitioning of C4' DNA damage products

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Neocarzinostatin acts as a sensitive probe of DNA microheterogeneity: switching of chemistry from C-1' to C-4' by a G.T mismatch 5' to the site of DNA damage

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

6 June 2018

Chemical and biological evidence for base propenals as the major source of the endogenous M1dG adduct in cellular DNA.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

18 August 2018

Contribution of aldehyde oxidase, xanthine oxidase, and aldehyde dehydrogenase on the oxidation of aromatic aldehydes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

18 August 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=2821206

18 August 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=2821206

18 August 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=2821206

18 August 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=2821206

18 August 2018

Reaction of malondialdehyde-DNA adducts with hydrazines-development of a facile assay for quantification of malondialdehyde equivalents in DNA.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

18 August 2018

Oxygen-dependent DNA damage amplification involving 5,6-dihydrothymidin-5-yl in a structurally minimal system

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2821206

18 August 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=2821206

18 August 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=2821206

18 August 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=2821206

18 August 2018

Investigating nucleic acid damage processes via independent generation of reactive intermediates

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

O2-dependent cleavage of DNA by tetrazomine

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Bleomycin-induced strand-scission of DNA. Mechanism of deoxyribose cleavage

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Characterization and mechanism of formation of tandem lesions in DNA by a nucleobase peroxyl radical

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Mismatch-induced switch of neocarzinostatin attack sites in the DNA minor groove

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Potential bioreductive alkylating agents. 1. Benzoquinone derivatives

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

On the mechanism of reaction of radicals with tirapazamine

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Analysis of products formed during bleomycin-mediated DNA degradation

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Oxygen transfer from the nitro group of a nitroaromatic radiosensitizer to a DNA sugar damage product

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Bioreductive therapies: an overview of drugs and their mechanisms of action

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Bleomycin versus OH-radical-induced malonaldehydic-product formation in DNA

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

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/17900117

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/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Studies on the specificity toward aldehyde substrates and steady-state kinetics of xanthine oxidase

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Electron paramagnetic resonance spectrometry evidence for bioreduction of tirapazamine to oxidising free radicals under anaerobic conditions

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Sequence-dependent variations of DNA structure modulate radiation-induced strand breakage

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Strand breaks and sugar release by .gamma.-irradiation of DNA in aqueous solution

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Measurement of tumor oxygenation

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Bleomycin-iron damage to DNA with formation of 8-hydroxydeoxyguanosine and base propenals. Indications that xanthine oxidase generates superoxide from DNA degradation products

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical

1 reference

https://pubmed.ncbi.nlm.nih.gov/17900117

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/JA074432M

1 reference

Europe PubMed Central

12 October 2017

1 reference

Europe PubMed Central

12 October 2017

1 reference

Europe PubMed Central

12 October 2017

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