Spiroiminodihydantoin as an oxo-atom transfer product of 8-oxo-2'-deoxyguanosine oxidation by chromium(V)

Org Lett. 2007 Oct 25;9(22):4411-4. doi: 10.1021/ol701667t. Epub 2007 Oct 4.

Abstract

Oxidation of the DNA lesion 8-oxo-2'-deoxyguanosine by the two electron oxidants N,N'-ethylenebis(salicylideneanimato)oxochromium(V) (Cr(V)-salen) and bis(2-ethyl-2-hydroxybutyrato)oxochromium(V) (Cr(V)-ehba) at neutral pH forms spiroiminodihydantoin by an oxo-atom transfer mechanism. The chromium complexes are models of a DNA oxidation pathway caused by the carcinogen chromate.

Publication types

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

MeSH terms

  • 8-Hydroxy-2'-Deoxyguanosine
  • Chromium / chemistry*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry
  • Guanosine / analogs & derivatives*
  • Guanosine / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Spiro Compounds / chemistry*

Substances

  • Spiro Compounds
  • spiroiminodihydantoin
  • Chromium
  • Guanosine
  • 8-Hydroxy-2'-Deoxyguanosine
  • Deoxyguanosine