One-electron oxidation of the guanine moiety of 2'-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2'-deoxyguanosine

J Am Chem Soc. 2003 Feb 26;125(8):2030-1. doi: 10.1021/ja028608q.

Abstract

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.

MeSH terms

  • 8-Hydroxy-2'-Deoxyguanosine
  • Chromatography, High Pressure Liquid
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry*
  • Guanine / chemistry*
  • Kinetics
  • Mass Spectrometry
  • Oxidation-Reduction

Substances

  • Guanine
  • 8-Hydroxy-2'-Deoxyguanosine
  • Deoxyguanosine