Literature DB >> 19757819

An overview of chemical processes that damage cellular DNA: spontaneous hydrolysis, alkylation, and reactions with radicals.

Kent S Gates1.   

Abstract

The sequence of heterocyclic bases on the interior of the DNA double helix constitutes the genetic code that drives the operation of all living organisms. With this said, it is not surprising that chemical modification of cellular DNA can have profound biological consequences. Therefore, the organic chemistry of DNA damage is fundamentally important to diverse fields including medicinal chemistry, toxicology, and biotechnology. This review is designed to provide a brief overview of the common types of chemical reactions that lead to DNA damage under physiological conditions.

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Year:  2009        PMID： 19757819      PMCID： PMC2806061          DOI： 10.1021/tx900242k

Source DB:  PubMed          Journal:  Chem Res Toxicol        ISSN： 0893-228X            Impact factor:   3.739


  170 in total

1.  Gamma-radiolysis and hydroxyl radical produce interstrand cross-links in DNA involving thymidine.

Authors:  Hui Ding; Marc M Greenberg
Journal:  Chem Res Toxicol       Date:  2007-10-17       Impact factor: 3.739

Review 2.  Formation and repair of interstrand cross-links in DNA.

Authors:  David M Noll; Tracey McGregor Mason; Paul S Miller
Journal:  Chem Rev       Date:  2006-02       Impact factor: 60.622

3.  A sensitive genetic assay for the detection of cytosine deamination: determination of rate constants and the activation energy.

Authors:  L A Frederico; T A Kunkel; B R Shaw
Journal:  Biochemistry       Date:  1990-03-13       Impact factor: 3.162

4.  Kinetics of bisulfite-induced cytosine deamination in single-stranded DNA.

Authors:  H Chen; B R Shaw
Journal:  Biochemistry       Date:  1993-04-13       Impact factor: 3.162

5.  A study of DNA spontaneous degradation.

Authors:  P Crine; W G Verly
Journal:  Biochim Biophys Acta       Date:  1976-08-02

6.  Theoretical studies of the hydroxide-catalyzed P-O cleavage reactions of neutral phosphate triesters and diesters in aqueous solution: examination of the changes induced by H/Me substitution.

Authors:  Nathalie Iché-Tarrat; Jean-Claude Barthelat; Daniel Rinaldi; Alain Vigroux
Journal:  J Phys Chem B       Date:  2005-12-01       Impact factor: 2.991

7.  Cross-linked thymine-purine base tandem lesions: synthesis, characterization, and measurement in gamma-irradiated isolated DNA.

Authors:  Sophie Bellon; Jean-Luc Ravanat; Didier Gasparutto; Jean Cadet
Journal:  Chem Res Toxicol       Date:  2002-04       Impact factor: 3.739

8.  Efficient nitroso group transfer from N-nitrosoindoles to nucleotides and 2'-deoxyguanosine at physiological pH. A new pathway for N-nitrosocompounds to exert genotoxicity.

Authors:  L T Lucas; D Gatehouse; D E Shuker
Journal:  J Biol Chem       Date:  1999-06-25       Impact factor: 5.157

9.  Absence of 2'-deoxyoxanosine and presence of abasic sites in DNA exposed to nitric oxide at controlled physiological concentrations.

Authors:  Min Dong; Chen Wang; William M Deen; Peter C Dedon
Journal:  Chem Res Toxicol       Date:  2003-09       Impact factor: 3.739

10.  Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2-deoxy-beta-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS.

Authors:  Brock Matter; Danuta Malejka-Giganti; A Saari Csallany; Natalia Tretyakova
Journal:  Nucleic Acids Res       Date:  2006-10-04       Impact factor: 16.971
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  138 in total

1.  Revisiting the reactivity of uracil during collision induced dissociation: tautomerism and charge-directed processes.

Authors:  Daniel G Beach; Wojciech Gabryelski
Journal:  J Am Soc Mass Spectrom       Date:  2012-02-14       Impact factor: 3.109

2.  Generation of DNA-damaging reactive oxygen species via the autoxidation of hydrogen sulfide under physiologically relevant conditions: chemistry relevant to both the genotoxic and cell signaling properties of H(2)S.

Authors:  Marjorie Hoffman; Anuruddha Rajapakse; Xiulong Shen; Kent S Gates
Journal:  Chem Res Toxicol       Date:  2012-06-04       Impact factor: 3.739

3.  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

4.  Noncovalent DNA binding drives DNA alkylation by leinamycin: evidence that the Z,E-5-(thiazol-4-yl)-penta-2,4-dienone moiety of the natural product serves as an atypical DNA intercalator.

Authors:  Mostafa I Fekry; Jozsef Szekely; Sanjay Dutta; Leonid Breydo; Hong Zang; Kent S Gates
Journal:  J Am Chem Soc       Date:  2011-10-18       Impact factor: 15.419

5.  Direct and Topoisomerase II Mediated DNA Damage by Bis-3-chloropiperidines: The Importance of Being an Earnest G.

Authors:  Alice Sosic; Ivonne Zuravka; Nina-Katharina Schmitt; Angelica Miola; Richard Göttlich; Dan Fabris; Barbara Gatto
Journal:  ChemMedChem       Date:  2017-08-10       Impact factor: 3.466

6.  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

7.  Effect of N7-methylation on base pairing patterns of guanine: a DFT study.

Authors:  Swarnadeep Biswas; Pradeep Kumar Shukla
Journal:  J Mol Model       Date:  2021-05-25       Impact factor: 1.810

8.  Pathways of Metabolite-Related Damage to a Synthetic p53 Gene Exon 7 Oligonucleotide Using Magnetic Enzyme Bioreactor Beads and LC-MS/MS Sequencing.

Authors:  Spundana Malla; Karteek Kadimisetty; Di Jiang; Dharamainder Choudhary; James F Rusling
Journal:  Biochemistry       Date:  2018-05-23       Impact factor: 3.162

9.  Quantitation of Apurinic/Apyrimidinic Sites in Isolated DNA and in Mammalian Tissue with a Reduced Level of Artifacts.

Authors:  Haoqing Chen; Lihua Yao; Christina Brown; Carmelo J Rizzo; Robert J Turesky
Journal:  Anal Chem       Date:  2019-05-13       Impact factor: 6.986

10.  Depurination of N7-methylguanine by DNA glycosylase AlkD is dependent on the DNA backbone.

Authors:  Emily H Rubinson; Plamen P Christov; Brandt F Eichman
Journal:  Biochemistry       Date:  2013-10-07       Impact factor: 3.162
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