The formation of 9-hydroxychrysene-1,2-diol as an intermediate in the metabolic activation of chrysene

Carcinogenesis. 1985 Jan;6(1):135-9. doi: 10.1093/carcin/6.1.135.

Abstract

9-Hydroxy-trans-1,2-dihydro-1,2-dihydroxychrysene (9-hydroxychrysene-1,2-diol), which may be the triol involved in the formation of a chrysene triol-epoxide-DNA adduct in mouse skin, was not detected when chrysene was incubated with rat-liver microsomal preparations. In separate experiments an excess of synthetic 9-hydroxychrysene-1,2-diol was added during the incubation of 3H-labelled chrysene with rat-liver microsomes and was then re-isolated. The triol was found to contain a radioactive product that had chromatographic properties identical to those of 9-hydroxychrysene-1,2-diol when examined by reverse-phase h.p.l.c., both before and after acetylation, by normal-phase h.p.l.c. and by t.l.c. both before and after oxidation. When treated with m-chloroperoxybenzoic acid, the synthetic 9-hydroxychrysene-1,2-diol formed products that possessed alkylating activity and that reacted with DNA in vitro. Examination of the triol-epoxides produced by oxidation of a mixture of synthetic and metabolic 9-hydroxychrysene-1,2-diol by t.l.c. suggested that the anti-isomer was formed.

Publication types

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

MeSH terms

  • Animals
  • Biotransformation
  • Chrysenes / metabolism*
  • DNA / metabolism
  • Male
  • Microsomes, Liver / metabolism
  • Phenanthrenes / metabolism*
  • Rats
  • Rats, Inbred Strains
  • Skin / metabolism

Substances

  • Chrysenes
  • Phenanthrenes
  • chrysene
  • DNA
  • 9-hydroxy-1,2-dihydro-1,2-dihydroxychrysene