Metabolism of the bay-region trans-1,2-dihydrodiol of benz[a]anthracene in rat liver microsomes occurs primarily at the 3,4-double bond.
The bay-region hydroxyl groups of benz[a]anthracene (+/-)trans-1,2-dihydrodiol are known to be exclusively in quasi-axial conformations. This dihydrodiol was stereoselectively metabolized in rat liver microsomes to form two optically active 1,2,3,4-tetrahydrotetrols as the predominant products. Thus, the bay-region axial hydroxyl groups of benz[a]anthracene trans-1,2-dihydrodiol do not direct metabolism away from the vicinal 3,4-double bond.
Yang
S K
SK
Department of Pharmacology, School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, MD 20014, USA.
Chou
M W
MW
D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D008862:Microsomes, Liver / Q000378:metabolism*; D008968:Molecular Conformation; D051381:Rats; D013237:Stereoisomerism
D001551:Benz(a)Anthracenes; C021624:benzanthracene-1,2-dihydrodiol