Literature DB >> 17256856

Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine.

James S Stover1, Madalina Ciobanu, David E Cliffel, Carmelo J Rizzo.   

Abstract

The electrochemical and chemical oxidation of a series of C8-arylamine adducts of 2'-deoxyguanosine has been examined. The oxidations were found to be reversible by cyclic and square-wave voltammetry in both aqueous buffer and aprotic organic solvent. The mechanism of the oxidation in protic media was either one- or two-electron, depending on the aryl group. The chemical oxidation resulted in guanidinohydantoin and spiroiminodihydantoin rearrangement products similar to those observed for 8-oxo-7,8-dihydro-2'-deoxyguanosine.

Entities:  

Mesh:

Substances:

Year:  2007        PMID: 17256856      PMCID: PMC2526121          DOI: 10.1021/ja066404u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  55 in total

1.  In vitro nucleotide misinsertion opposite the oxidized guanosine lesions spiroiminodihydantoin and guanidinohydantoin and DNA synthesis past the lesions using Escherichia coli DNA polymerase I (Klenow fragment).

Authors:  Olga Kornyushyna; Aym M Berges; James G Muller; Cynthia J Burrows
Journal:  Biochemistry       Date:  2002-12-24       Impact factor: 3.162

Review 2.  Nutrition and dietary carcinogens.

Authors:  T Sugimura
Journal:  Carcinogenesis       Date:  2000-03       Impact factor: 4.944

3.  Direct oxidation of guanine and 7,8-dihydro-8-oxoguanine in DNA by a high-valent chromium complex: a possible mechanism for chromate genotoxicity.

Authors:  K D Sugden; C K Campo; B D Martin
Journal:  Chem Res Toxicol       Date:  2001-09       Impact factor: 3.739

Review 4.  Tobacco smoke carcinogens and breast cancer.

Authors:  Stephen S Hecht
Journal:  Environ Mol Mutagen       Date:  2002       Impact factor: 3.216

5.  Base pairing of 8-oxoguanosine and 8-oxo-2'-deoxyguanosine with 2'-deoxyadenosine, 2'-deoxycytosine, 2'-deoxyguanosine, and thymidine.

Authors:  P M Gannett; T P Sura
Journal:  Chem Res Toxicol       Date:  1993 Sep-Oct       Impact factor: 3.739

6.  Preparation of C8-amine and acetylamine adducts of 2'-deoxyguanosine suitably protected for DNA synthesis.

Authors:  Ludovic C J Gillet; Orlando D Schärer
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

7.  NMR structural studies of a 15-mer DNA sequence from a ras protooncogene, modified at the first base of codon 61 with the carcinogen 4-aminobiphenyl.

Authors:  B P Cho; F A Beland; M M Marques
Journal:  Biochemistry       Date:  1992-10-13       Impact factor: 3.162

Review 8.  Heterocyclic aromatic amine metabolism, DNA adduct formation, mutagenesis, and carcinogenesis.

Authors:  Robert J Turesky
Journal:  Drug Metab Rev       Date:  2002-08       Impact factor: 4.518

9.  Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG.

Authors:  S Shibutani; M Takeshita; A P Grollman
Journal:  Nature       Date:  1991-01-31       Impact factor: 49.962

Review 10.  Structure and potential mutagenicity of new hydantoin products from guanosine and 8-oxo-7,8-dihydroguanine oxidation by transition metals.

Authors:  Cynthia J Burrows; James G Muller; Olga Kornyushyna; Wenchen Luo; Victor Duarte; Michael D Leipold; Sheila S David
Journal:  Environ Health Perspect       Date:  2002-10       Impact factor: 9.031

View more
  5 in total

1.  Biologically relevant oxidants cause bound proteins to readily oxidatively cross-link at Guanine.

Authors:  Morwena J Solivio; Dessalegn B Nemera; Larry Sallans; Edward J Merino
Journal:  Chem Res Toxicol       Date:  2012-02-06       Impact factor: 3.739

2.  Biomonitoring DNA Adducts of Cooked Meat Carcinogens in Human Prostate by Nano Liquid Chromatography-High Resolution Tandem Mass Spectrometry: Identification of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine DNA Adduct.

Authors:  Shun Xiao; Jingshu Guo; Byeong Hwa Yun; Peter W Villalta; Suprita Krishna; Resha Tejpaul; Paari Murugan; Christopher J Weight; Robert J Turesky
Journal:  Anal Chem       Date:  2016-12-01       Impact factor: 6.986

3.  Lesion specificity in the base excision repair enzyme hNeil1: modeling and dynamics studies.

Authors:  Lei Jia; Vladimir Shafirovich; Nicholas E Geacintov; Suse Broyde
Journal:  Biochemistry       Date:  2007-04-14       Impact factor: 3.162

4.  Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide.

Authors:  Yuyuan Zhang; Jordan Dood; Ashley A Beckstead; Xi-Bo Li; Khiem V Nguyen; Cynthia J Burrows; Roberto Improta; Bern Kohler
Journal:  Proc Natl Acad Sci U S A       Date:  2014-07-28       Impact factor: 11.205

5.  Spirodi(iminohydantoin) products from oxidation of 2'-deoxyguanosine in the presence of NH4Cl in nucleoside and oligodeoxynucleotide contexts.

Authors:  Aaron M Fleming; Erin I Armentrout; Judy Zhu; James G Muller; Cynthia J Burrows
Journal:  J Org Chem       Date:  2015-01-07       Impact factor: 4.354

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.