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Free Radical Research Volume 25, 1996 - Issue 5
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Original Article

The One-Electron Reduction Potential of 3-Amino-1, 2, 4-benzotriazine 1, 4-dioxide (Tirapazamine): A Hypoxia-Selective Bioreductive Drug

K. Indira Priyadarsini Gray Laboratory Cancer Research Trust, Mount Vernon Hospital, PO Box 100, Northwood, Middx, HA6 2JR, UK
,
Michael Tracy Bio-Organic Chemistry Laboratory, SRI Usaional, Menlo Park, CA, 94025, USA; Chemistry Division, Bhabha Atomic Research Centre, Trombay, Bombay, 400085, India
&
Peter Wardman Gray Laboratory Cancer Research Trust, Mount Vernon Hospital, PO Box 100, Northwood, Middx, HA6 2JR, UK
Pages 393-399 | Received 19 Mar 1996, Published online: 07 Jul 2009

Citations (23)

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Read on this site (2)

Peter O'Neill & Peter Wardman. (2009) Radiation chemistry comes before radiation biology. International Journal of Radiation Biology 85:1, pages 9-25.
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William A Denny & William R Wilson. (2000) Tirapazamine: a bioreductive anticancer drug that exploits tumour hypoxia. Expert Opinion on Investigational Drugs 9:12, pages 2889-2901.
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Articles from other publishers (21)

Achille Nassi, Sergeot Delor Kungo Sop, Jules-Blaise Mabou Leuna, Suzanne Makota, Martin Pengou & Emmanuel Ngameni. (2022) Electrochemical reactivity of thin film of plumbagin at ionic liquid | water interface. Monatshefte für Chemie - Chemical Monthly 153:7-8, pages 569-576.
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Wen Qi, Pooja Yadav, Cho R. Hong, Ralph J. Stevenson, Michael P. Hay & Robert F. Anderson. (2022) Spin Trapping Hydroxyl and Aryl Radicals of One-Electron Reduced Anticancer Benzotriazine 1,4-Dioxides. Molecules 27:3, pages 812.
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Xiulong Shen & Kent S. Gates. (2019) Enzyme-Activated Generation of Reactive Oxygen Species from Heterocyclic N -Oxides under Aerobic and Anaerobic Conditions and Its Relevance to Hypoxia-Selective Prodrugs . Chemical Research in Toxicology 32:3, pages 348-361.
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Xu Wang, Dan Wan, Awais Ihsan, Qianying Liu, Guyue Cheng, Juan Li, Zhenli Liu & Zonghui Yuan. (2015) Mechanism of adrenocortical toxicity induced by quinocetone and its bidesoxy-quinocetone metabolite in porcine adrenocortical cells in vitro. Food and Chemical Toxicology 84, pages 115-124.
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Xiulong Shen, Anuruddha Rajapakse, Fabio Gallazzi, Venkatraman Junnotula, Tarra Fuchs-Knotts, Rainer Glaser & Kent S. Gates. (2013) Isotopic Labeling Experiments That Elucidate the Mechanism of DNA Strand Cleavage by the Hypoxia-Selective Antitumor Agent 1,2,4-Benzotriazine 1,4-Di- N -oxide . Chemical Research in Toxicology 27:1, pages 111-118.
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Pooja Yadav, Andrew J. Marshall, Jóhannes Reynisson, William A. Denny, Michael P. Hay & Robert F. Anderson. (2014) Fragmentation of the quinoxaline N-oxide bond to the ˙OH radical upon one-electron bioreduction. Chem. Commun. 50:89, pages 13729-13731.
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Jian Yin, Rainer Glaser & Kent S. Gates. (2012) On the Reaction Mechanism of Tirapazamine Reduction Chemistry: Unimolecular N–OH Homolysis, Stepwise Dehydration, or Triazene Ring-Opening. Chemical Research in Toxicology 25:3, pages 634-645.
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Jian Yin, Rainer Glaser & Kent S. Gates. (2012) Electron and Spin-Density Analysis of Tirapazamine Reduction Chemistry. Chemical Research in Toxicology 25:3, pages 620-633.
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Goutam Chowdhury, Ujjal Sarkar, Susan Pullen, William R. Wilson, Anuruddha Rajapakse, Tarra Fuchs-Knotts & Kent S. Gates. (2011) DNA Strand Cleavage by the Phenazine Di- N -oxide Natural Product Myxin under Both Aerobic and Anaerobic Conditions . Chemical Research in Toxicology 25:1, pages 197-206.
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Venkatraman Junnotula, Anuruddha Rajapakse, Leire Arbillaga, Adela López de Cerain, Beatriz Solano, Raquel Villar, Antonio Monge & Kent S. Gates. (2010) DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide. Bioorganic & Medicinal Chemistry 18:9, pages 3125-3132.
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Sujata S. Shinde, Andrej Maroz, Michael P. Hay, Adam V. Patterson, William A. Denny & Robert F. Anderson. (2010) Characterization of Radicals Formed Following Enzymatic Reduction of 3-Substituted Analogues of the Hypoxia-Selective Cytotoxin 3-Amino-1,2,4-Benzotriazine 1,4-Dioxide (Tirapazamine). Journal of the American Chemical Society 132:8, pages 2591-2599.
Crossref
Venkatraman Junnotula, Ujjal Sarkar, Sarmistha Sinha & Kent S. Gates. (2008) Initiation of DNA Strand Cleavage by 1,2,4-Benzotriazine 1,4-Dioxide Antitumor Agents: Mechanistic Insight from Studies of 3-Methyl-1,2,4-benzotriazine 1,4-Dioxide. Journal of the American Chemical Society 131:3, pages 1015-1024.
Crossref
Michael P. Hay, Kevin O. Hicks, Frederik B. Pruijn, Karin Pchalek, Bronwyn G. Siim, William R. Wilson & William A. Denny. (2007) Pharmacokinetic/Pharmacodynamic Model-Guided Identification of Hypoxia-Selective 1,2,4-Benzotriazine 1,4-Dioxides with Antitumor Activity: The Role of Extravascular Transport. Journal of Medicinal Chemistry 50:25, pages 6392-6404.
Crossref
P. Wardman. (2007) Chemical Radiosensitizers for Use in Radiotherapy. Clinical Oncology 19:6, pages 397-417.
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Maruta Boyd, Michael P. Hay & Peter D. W. Boyd. (2006) Complete1H,13C and15N NMR assignment of tirapazamine and related 1,2,4-benzotriazineN-oxides. Magnetic Resonance in Chemistry 44:10, pages 948-954.
Crossref
Robert F. Anderson, Sujata S. Shinde, Michael P. Hay, Swarna A. Gamage & William A. Denny. (2005) Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides. Organic & Biomolecular Chemistry 3:11, pages 2167.
Crossref
Dmitri Zagorevskii, Minghu Song, Curt Breneman, Yang Yuan, Tarra Fuchs, Kent S. Gates & C. Michael Greenlief. (2003) A mass spectrometry study of tirapazamine and its metabolites: Insights into the mechanism of metabolic transformations and the characterization of reaction intermediates. Journal of the American Society for Mass Spectrometry 14:8, pages 881-892.
Crossref
Michael P Hay & William A Denny. (2002) New and versatile syntheses of 3-alkyl- and 3-aryl-1,2,4-benzotriazine 1,4-dioxides: preparation of the bioreductive cytotoxins SR 4895 and SR 4941. Tetrahedron Letters 43:52, pages 9569-9571.
Crossref
James S. Poole, Christopher M. Hadad, Matthew S. Platz, Zachary P. Fredin, Laura Pickard, Elisa Levya Guerrero, Margarita Kessler, Goutam Chowdhury, Delshanee Kotandeniya & Kent S. Gates. (2007) Photochemical Electron Transfer Reactions of Tirapazamine¶. Photochemistry and Photobiology 75:4, pages 339-345.
Crossref
James S. Poole, Christopher M. Hadad, Matthew S. Platz, Zachary P. Fredin, Laura Pickard, Elisa Levya Guerrero, Margarita Kessler, Goutam Chowdhury, Delshanee Kotandeniya & Kent S. Gates. (2002) Photochemical Electron Transfer Reactions of Tirapazamine¶. Photochemistry and Photobiology 75:4, pages 339.
Crossref
P. Wardman. 2001. Radiation Chemistry - Present Status and Future Trends. Radiation Chemistry - Present Status and Future Trends 623 655 .

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