Literature DB >> 12161126

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

Delshanee Kotandeniya1, Brian Ganley, Kent S Gates.   

Abstract

Tirapazamine is a bioreductively activated DNA-damaging agent that selectively kills the hypoxic cells found in solid tumors. In this work, base excision repair enzymes were used to provide evidence that tirapazamine causes significant amounts of damage to both purine and pyrimidine residues in double-stranded DNA.

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Year:  2002        PMID： 12161126     DOI： 10.1016/s0960-894x(02)00468-7

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  11 in total

1.  DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide.

Authors:  Venkatraman Junnotula; Anuruddha Rajapakse; Leire Arbillaga; Adela López de Cerain; Beatriz Solano; Raquel Villar; Antonio Monge; Kent S Gates
Journal:  Bioorg Med Chem       Date:  2010-03-19       Impact factor: 3.641

2.  Synthesis and Crystal Structure of the Azoxydichinyl Helicene, Pyrido[3,2-f]quinolino[6,5-c]cinnoline 5-Oxide Monohydrate.

Authors:  Anuruddha Rajapakse; Charles L Barnes; Kent S Gates
Journal:  J Chem Crystallogr       Date:  2011-11       Impact factor: 0.603

3.  Synthesis, Crystal Structure, and Rotational Energy Profile of 3-Cyclopropyl-1,2,4-benzotriazine 1,4-Di-N-oxide.

Authors:  Ujjal Sarkar; Rainer Glaser; Zack D Parsons; Charles L Barnes; Kent S Gates
Journal:  J Chem Crystallogr       Date:  2010-07       Impact factor: 0.603

Review 4.  Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents.

Authors:  A M Mfuh; O V Larionov
Journal:  Curr Med Chem       Date:  2015       Impact factor: 4.530

5.  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.

Authors:  Xiulong Shen; Anuruddha Rajapakse; Fabio Gallazzi; Venkatraman Junnotula; Tarra Fuchs-Knotts; Rainer Glaser; Kent S Gates
Journal:  Chem Res Toxicol       Date:  2013-12-19       Impact factor: 3.739

6.  Application of Suzuki-Miyaura and Buchwald-Hartwig Cross-coupling Reactions to the Preparation of Substituted 1,2,4-Benzotriazine 1-Oxides Related to the Antitumor Agent Tirapazamine.

Authors:  Ujjal Sarkar; Roman Hillebrand; Kevin M Johnson; Andrea H Cummings; Ngoc Linh Phung; Anuruddha Rajapakse; Haiying Zhou; Jordan R Willis; Charles L Barnes; Kent S Gates
Journal:  J Heterocycl Chem       Date:  2015-11-25       Impact factor: 2.193

7.  Electronic structures and spin topologies of gamma-picoliniumyl radicals. A study of the homolysis of N-methyl-gamma-picolinium and of benzo-, dibenzo-, and naphthoannulated analogs.

Authors:  Rainer Glaser; Yongqiang Sui; Ujjal Sarkar; Kent S Gates
Journal:  J Phys Chem A       Date:  2008-05-29       Impact factor: 2.781

8.  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).

Authors:  Goutam Chowdhury; Venkatraman Junnotula; J Scott Daniels; Marc M Greenberg; Kent S Gates
Journal:  J Am Chem Soc       Date:  2007-09-27       Impact factor: 15.419

9.  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.

Authors:  Venkatraman Junnotula; Ujjal Sarkar; Sarmistha Sinha; Kent S Gates
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

Review 10.  Quinoxaline 1,4-di-N-Oxides: Biological Activities and Mechanisms of Actions.

Authors:  Guyue Cheng; Wei Sa; Chen Cao; Liangliang Guo; Haihong Hao; Zhenli Liu; Xu Wang; Zonghui Yuan
Journal:  Front Pharmacol       Date:  2016-03-21       Impact factor: 5.810
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