Benzo(a)pyrene metabolism in mouse epidermis. Analysis by high pressure liquid chromatography and DNA binding

Chem Biol Interact. 1977 Aug;18(2):129-42. doi: 10.1016/0009-2797(77)90001-1.

Abstract

Mouse epidermal homogenates contain an inducible aryl hydrocarbon hydroxylase (AHH) complex that catalyzes the formation of benzo(a)pyrene-7,8-dihydrodiol from benzo(a)pyrene (BP) as assessed by high pressure liquid chromatography (HPLC). 5,6-Benzoflavone (5,6-BF), 7,8-benzoflavone (7,8-BF) and 17-beta-estradiol decreased and butylated hydroxytoluene (BHT) enhanced oxidative metabolism of BP when added in vitro. Epoxide hydrase activity (hydration of benzo(a)pyrene-4,5-epoxide) (BP-4,5-epoxide) was enhanced by 17-beta-estradiol, 5,6-BF, and 7,8-BF. BHT exhibited no significant effect and 1,2-epoxy-3,3,3-trichloropropane (TCPO) inhibited hydrase activity. The capacity of epidermal homogenates to catalyze the covalent binding of BP to DNA indicated that addition of both 5,6-BF and 7,8-BF decreased binding. BHT and TCPO did not significantly affect DNA-binding.

Publication types

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

MeSH terms

  • Animals
  • Aryl Hydrocarbon Hydroxylases / metabolism
  • Benzopyrans / metabolism*
  • Binding Sites
  • Butylated Hydroxytoluene / pharmacology
  • Chromatography, High Pressure Liquid
  • DNA / metabolism*
  • Epoxide Hydrolases / metabolism
  • Epoxy Compounds / pharmacology
  • Estradiol / pharmacology
  • Female
  • Flavonoids / pharmacology
  • Methylcholanthrene / pharmacology
  • Mice
  • Phenols / metabolism
  • Propane / analogs & derivatives
  • Propane / pharmacology
  • Quinones / metabolism
  • Skin / metabolism

Substances

  • Benzopyrans
  • Epoxy Compounds
  • Flavonoids
  • Phenols
  • Quinones
  • Butylated Hydroxytoluene
  • Estradiol
  • Methylcholanthrene
  • DNA
  • Aryl Hydrocarbon Hydroxylases
  • Epoxide Hydrolases
  • Propane