Biotransformation of 7-methylbenz (a)anthracene (7-methylba) to cholanthrene and related compounds in rat tissue cytosol preparations, and in vivo

Conference · Sat Mar 01 04:00:00 EST 1986 · Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)

OSTI ID:5317286

Flesher, J W; Myers, S R; Blake, J W

Previous studies from this laboratory demonstrated that benz (a)anthracene, (BA), an unsubstituted carcinogenic hydrocarbon (preprocarcinogen) undergoes bioalkylation in tissue cytosol preparations fortified with S-adenosyl-L-methionine (SAM) to the procarcinogens 7-methylBA, 12-methylBA, and 7,12-dimethylBA and that the reaction takes place most favorably in the mesoanthracenic position(s). The procarcinogens formed are more carcinogenic than BA, a weak preprocarcinogen. In this study 7-methylBA (200 nmole) was incubated with cytosol preparations of rat liver, lung, or dorsal subcutaneous tissues fortified with SAM (500 nmole), 3 ..mu..mole MgCl/sub 2/, and 20 ..mu..mole of potassium phosphate buffer (pH 7.4) for 1 hour in air at 37/sup 0/C. The reactions were stopped with cold acetone and the products extracted with ethyl acetate, washed with water and evaporated under reduced pressure. Biotransformation of 7-methylBA to BA, 7,12-dimethylBA, and cholanthrene was detected by HPLC and confirmed by GC/MS. Biotransformation of 7-methylBA (0.4 ..mu..mole) in dorsal subcutis tissue to cholanthrene and related compounds was detected in vivo. The results suggest that bioalkylation also occurs in positions other than the reactive meso-anthracenic positions.

• Research Organization: Univ. of Lexington, KY
• OSTI ID: 5317286
• Report Number(s): CONF-8604222-
• Conference Information: Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Journal Volume: 45:3
• Country of Publication: United States
• Language: English

Related Subjects

560301* -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
560305 -- Chemicals Metabolism & Toxicology-- Vertebrates-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALKYLATION
AMINO ACIDS
ANIMALS
AROMATICS
BENZANTHRACENE
BODY
CARBOXYLIC ACIDS
CARCINOGENESIS
CHEMICAL REACTIONS
CHOLANTHRENE
CHROMATOGRAPHY
CONDENSED AROMATICS
DIGESTIVE SYSTEM
DRUGS
GLANDS
HYDROCARBONS
IN VITRO
IN VIVO
LIPOTROPIC FACTORS
LIQUID COLUMN CHROMATOGRAPHY
LIVER
LUNGS
MAMMALS
METABOLISM
METHIONINE
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANS
PATHOGENESIS
RATS
RESPIRATORY SYSTEM
RODENTS
SEPARATION PROCESSES
TISSUE CULTURES
VERTEBRATES