Cross-link dimer formation of the acetaldehyde-derived cyclic 1,N(2)-Propano-2'-deoxyguanosine adduct using electrochemical oxidation.

Abstract:

:The electrochemically oxidative lesion of the acetaldehyde-derived cyclic propano adduct 2 of 2'-deoxyguanosine 1 was identified as the cross-linked dimer 4 of adduct 2. Cross-link formation is explained by the nucleophilic preference of the exocyclic amino group in 2 to the carbocation 3 electrogenerated by 1-proton and 2-electron transfers. Dimer formation was also detected in duplex DNA during exposure to acetaldehyde followed by electrochemical oxidation. The dimer has been deduced to be an intrastrand cross-link generated specifically in the G-G sequence in duplex DNA, which is expected to contribute to acetaldehyde-mediated genotoxicity.

authors

Murakami H,Esaka Y,Uno B

doi

10.1248/cpb.57.1434

subject

Has Abstract

pub_date

2009-12-01 00:00:00

pages

1434-6

issue

12

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/57.1434

journal_volume

57

pub_type

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