8-Hydroxy-2′-deoxyguanosine formation during the catalytic oxidation of hydrazines in the presence of 2′-deoxyguanosine

Peter M. Gannett, Naresh S. Dalal, Xianglin Shi, Bela Toth

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The reaction of 2′-deoxyguanosine (1), substituted hydrazines (Hy) and oxygen, in the presence of Cu(II) as catalyst, yields 8-hydroxy-2′-deoxyguanosine (2). The rate of formation of 2 was found to be dependent upon the oxidation potential of the Hy and on structural factors of the Hy. The conversion of 1 to 2 under these conditions suggested that a Haber-Weiss/Fenton type of process was involved with Hy acting as reductant. However, the dependence of the rate of the conversion of 1 to 2 upon the structure of Hy suggested that the Hy substrates studied may be more directly involved in the process than that of a reducing agent. Additional studies of this reaction system, including the oxygen consumption, radical trapping studies and direct ESR measurements suggest that the conversion of 1 to 2, under the conditions used, involves the intermediacy of complex composed of the metal catalyst, 1, Hy and oxygen. The rate data for the conversion of 1 to 2 appear to be correlated with the carcinogenicity of Hy and therefore 2 may be an important DNA adduct in the carcinogenesis of hydrazines.

Original languageEnglish
Pages (from-to)57-72
Number of pages16
JournalChemico-Biological Interactions
Volume80
Issue number1
DOIs
StatePublished - 1991

Keywords

  • 8-Hydroxy-2′-deoxyguanine
  • Carcinogenesis
  • Hydrazine oxidation
  • Hydroxyl radical

ASJC Scopus subject areas

  • Toxicology

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