Differential stereoselectivity in the metabolism of benzo[a]pyrene and anthracene by rabbit epidermal and hepatic microsomes.
The stereoselective metabolism of benzo[a]pyrene (BP) to its 7,8-dihydrodiol and of anthracene to its 1,2-dihydrodiol by microsomal fractions of the liver and skin of the rabbit were examined. For both tissues, more anthracene-1,2-dihydrodiol than BP-7,8-dihydrodiol was extracted from these incubations. The BP-7R,8R and anthracene-1S,2S enantiomers were found to predominate with optical purities of greater than or equal to 90% and 32%, respectively. The latter result is in contrast to previous observations made in incubations with rat liver microsomes and might be due to differences in stereoselectivities of cytochromes P-450 between the two species.
Chester Beatty Laboratories, Institute of Cancer Research, Royal Cancer Hospital, London, U.K.
M
M
Hall
P L
PL
Grover
D000818:Animals; D000873:Anthracenes / Q000378:metabolism*; D001564:Benzo(a)pyrene / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D066298:In Vitro Techniques; D008297:Male; D008861:Microsomes / Q000378:metabolism; D008862:Microsomes, Liver / Q000378:metabolism*; D011817:Rabbits; D051381:Rats; D012867:Skin / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism
D000873:Anthracenes; D001564:Benzo(a)pyrene; C034020:anthracene