Studies of the reaction of acetaldehyde with deoxynucleosides

The reaction of acetaldehyde with deoxynucleosides was studied in buffered solutions at room temperature (22–24°C) and neutral pH. Reaction products were obtained with all deoxynucleosides with the exception of thymidine, as shown by reversed-phase HPLC analysis. The order of reactivity was dGuo>...

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Bibliographic Details
Published in:Chemico-biological interactions 1995-10, Vol.98 (1), p.51-67
Main Authors: Vaca, Carlos E., Fang, Jia-Long, Schweda, Elke K.H.
Format: Article
Language:English
Subjects:
Acetaldehyde
Acetaldehyde - chemistry
Biological and medical sciences
Carcinogenesis, carcinogens and anticarcinogens
Chemical agents
Chromatography, High Pressure Liquid
Deoxyadenosines - chemistry
Deoxycytidine - chemistry
Deoxyguanosine - chemistry
Deoxynucleoside adduct
Deoxyribonucleosides - chemistry
Drug Stability
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Medical sciences
Reaction mechanism
Spectrometry, Mass, Fast Atom Bombardment
Spectrophotometry, Ultraviolet
Temperature
Tumors
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Summary:The reaction of acetaldehyde with deoxynucleosides was studied in buffered solutions at room temperature (22–24°C) and neutral pH. Reaction products were obtained with all deoxynucleosides with the exception of thymidine, as shown by reversed-phase HPLC analysis. The order of reactivity was dGuo>dAdo>dCyd, for which three, two and one reaction products, respectively, were obtained. We report here data on the kinetics of the reactions, the stability of the adducts at physiolgical pH, product yields, UV-spectroscopic data at different pH values, and describe the synthesis, isolation and structural characterization by FAB/MS and NMR of the stable adducts of acetaldehyde with dGuo. Furthermore, the formation of adducts with dGuo by the cooperative reaction of Aa with ethanol was studied.
ISSN:0009-2797
1872-7786
DOI:10.1016/0009-2797(95)03632-V