One-Electron Oxidation of the Guanine Moiety of 2‘-Deoxyguanosine:  Influence of 8-Oxo-7,8-dihydro-2‘-deoxyguanosine

The influence of 8-oxo-7,8-dihydro-2‘-deoxyguanosine (8-oxodGuo) on riboflavin and UVA-mediated one-electron oxidation of an aqueous aerated solution of 2‘-deoxyguanosine (dGuo) has been studied. Using labeled experiments, we have demonstrated that, despite not being able to detect significant amoun...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-02, Vol.125 (8), p.2030-2031
Main Authors: Ravanat, Jean-Luc, Saint-Pierre, Christine, Cadet, Jean
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical Sciences
Chemistry
Chromatography, High Pressure Liquid
Deoxyguanosine - analogs & derivatives
Deoxyguanosine - chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
General and physical chemistry
Guanine - chemistry
Kinetics
Mass Spectrometry
Molecular biophysics
Organic chemistry
Oxidation-Reduction
Photochemistry
Photochemistry. Photosynthesis. Bioluminescence
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Radiation-biomolecule interaction
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Summary:The influence of 8-oxo-7,8-dihydro-2‘-deoxyguanosine (8-oxodGuo) on riboflavin and UVA-mediated one-electron oxidation of an aqueous aerated solution of 2‘-deoxyguanosine (dGuo) has been studied. Using labeled experiments, we have demonstrated that, despite not being able to detect significant amounts of 8-oxodGuo upon one-electron oxidation of dGuo, 8-oxodGuo is indeed produced but is further rapidly degraded to oxidized nucleosides. Evidence is provided showing that an efficient electron transfer reaction from 8-oxodGuo to the guanine radical cation or rather its deprotonated form occurs, giving rise to the specific decomposition of 8-oxodGuo together with the restitution of dGuo. It could be concluded that 8-oxodGuo efficiently protects dGuo from decomposition by the one-electron oxidation reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja028608q