Peroxyl radical-mediated oxidation of 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene (BP-7,8-Diol) in mouse skin

Conference · Fri Feb 28 23:00:00 EST 1986 · Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)

OSTI ID:5001827

Marnett, L J; Battista, J R; Curtis, J; Eling, T E

To determine if peroxyl radical-mediated expoxidation of BP-7,8-Diol occurs in a target tissue for benzo(a)pyrene carcinogenesis, the authors incubated (+)-BP-7,8-Diol with freshly isolated epidermal cells from hairless mice. The major metabolites isolated after 90 min. incubations were tetrahydrotetraol hydrolysis products of the anti-diolepoxide. Anti-diolepoxide formation was potently inhibited by anti-oxidants but unaffected by pretreatment of mice with inducers of epidermal cytochrome P-450. In contrast, formation of hydrolysis products derived from the syn-diolepoxide, a major product of P-450-dependent oxidation, was greatly increased in cells isolated from animals pretreated with ..beta..-naphthoflavone. The time course of epoxidation of (+)-BP-7,8-Diol to the anti-diolepoxide paralleled exactly the time course of lipid peroxidation. When (+)-BP-7,8-Diol is topically administered to mice and the skin recovered for metabolite analysis, the major products of oxidation are derived from the anti-diolepoxide. These observations suggest that peroxyl radicals play a quantitatively significant role in epidermal metabolism of BP-7,8-Diol to the ultimate carcinogenic form of benzo(a)pyrene.

• Research Organization: Wayne State Univ., Detroit, MI
• OSTI ID: 5001827
• Report Number(s): CONF-8604222-
• Journal Information: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Vol. 45:3; ISSN FEPRA
• Country of Publication: United States
• Language: English

Related Subjects

560305* -- Chemicals Metabolism & Toxicology-- Vertebrates-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANIMAL TISSUES
ANIMALS
AROMATICS
BENZOPYRENE
BODY
CARCINOGENESIS
CONDENSED AROMATICS
EPIDERMIS
EPITHELIUM
HYDROCARBONS
MAMMALS
METABOLISM
METABOLITES
MICE
ORGANIC COMPOUNDS
ORGANS
PATHOGENESIS
PEROXY RADICALS
RADICALS
RODENTS
SKIN
TISSUES
VERTEBRATES