Formation of tricyclic [4.3.3.0] adducts between 8-oxoguanosine and tyrosine under conditions of oxidative DNA-protein cross-linking

J Am Chem Soc. 2008 Aug 6;130(31):10080-1. doi: 10.1021/ja803896d. Epub 2008 Jul 9.

Abstract

8-Oxo-7,8-dihydro-2'-deoxyguanosine (OG), a prevalent product of oxidative stress on cellular DNA, is readily further oxidized forming adducts with nucleophiles. In the presence of tyrosine or p-cresol, an unusual tricyclo[4.3.3.0] adduct has been characterized in both nucleoside and oligodeoxynucleotide studies. The adduct is more stable in oligomers than nucleosides and undergoes slow reversion and hydration to spiroiminodihydantoin.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • DNA / chemistry*
  • DNA Adducts
  • DNA Damage
  • Guanosine / analogs & derivatives*
  • Guanosine / chemistry
  • Oligodeoxyribonucleotides
  • Oxidative Stress
  • Proteins / chemistry*
  • Spiro Compounds
  • Tyrosine / chemistry*

Substances

  • DNA Adducts
  • Oligodeoxyribonucleotides
  • Proteins
  • Spiro Compounds
  • spiroiminodihydantoin
  • Guanosine
  • 8-hydroxyguanosine
  • Tyrosine
  • DNA