Cross-link dimer formation of the acetaldehyde-derived cyclic 1,N(2)-Propano-2'-deoxyguanosine adduct using electrochemical oxidation.
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.
Murakami
Hiroya
H
Gifu Pharmaceutical University, Mitahora-higashi, Japan.
Esaka
Yukihiro
Y
Uno
Bunji
B
D000079:Acetaldehyde / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D003839:Deoxyadenosines / Q000737:chemistry*; D019281:Dimerization; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011407:Propane / Q000737:chemistry*
D003432:Cross-Linking Reagents; D003839:Deoxyadenosines; D000079:Acetaldehyde; D011407:Propane