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.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Murakami H,Esaka Y,Uno Bdoi
10.1248/cpb.57.1434subject
Has Abstractpub_date
2009-12-01 00:00:00pages
1434-6issue
12eissn
0009-2363issn
1347-5223pii
JST.JSTAGE/cpb/57.1434journal_volume
57pub_type
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