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

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.

journal_name

Chem Biol Interact

authors

Gannett PM,Dalal NS,Shi XL,Toth B

doi

10.1016/0009-2797(91)90031-2

subject

Has Abstract

pub_date

1991-01-01 00:00:00

pages

57-72

issue

1

eissn

0009-2797

issn

1872-7786

pii

0009-2797(91)90031-2

journal_volume

80

pub_type

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