Comparison of epoxide and free-radical mechanisms for activation of benzo[a]pyrene by Sprague-Dawley rat liver microsomes

J Natl Cancer Inst. 1980 Apr;64(4):771-4.

Abstract

Coincubation of [6-3H]benzo[a]pyrene ([6-3H]BP) and [14C]BP with SD rat liver microsomes produced metabolic profiles that showed that the C-6 of BP was not affected by formation of 4,5-dihydro-4,5-dihydroxy-BP, 7,8-dihydro-7,8-dihydroxy-BP, and 9,10-dihydro-9,10-dihydroxy-BP nor the 3- and 9-phenols of BP. Complete retention of tritium at C-6, except in the three quinones, confirmed the radical-cation model for formation of the 6-oxo-radical followed by oxidation to quinones. Epoxide formation at the carcinogenically active regions of BP appeared to biochemically isolate from 6-position activation and suggested that the microsomal epoxide pathway is unrelated to the radicalcation scheme. These molar ratios derived from double-label experiments reinforced the current literature that indicates the epoxide mechanism as the major pathway toward carcinogenic forms of BP.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benzopyrene Hydroxylase / metabolism
  • Benzopyrenes / metabolism*
  • Biotransformation
  • Catalysis
  • Epoxy Compounds / pharmacology
  • Free Radicals
  • Inactivation, Metabolic
  • Male
  • Methylcholanthrene / pharmacology
  • Microsomes, Liver / metabolism*
  • Mixed Function Oxygenases / metabolism
  • Quinones
  • Rats

Substances

  • Benzopyrenes
  • Epoxy Compounds
  • Free Radicals
  • Quinones
  • Methylcholanthrene
  • Mixed Function Oxygenases
  • Benzopyrene Hydroxylase