Microsomal metabolism of dibenz[a,c]anthracene, dibenz[a,h]anthracene and dibenz[a,j]anthracene to bis-dihydrodiols and polyhydroxylated products.
Polar, ethyl acetate soluble metabolites formed in incubations of dibenz[a,c]anthracene (DB[a,c]A), dibenz[a,h]anthracene (DB[a,h]A) and the related DB[a,h]A 3,4-diol and dibenz[a,j]anthracene (DB[a,j]A) with 3-methylcholanthrene (3-MC)-induced rat liver microsomal preparations have been separated by HPLC and examined using fluorescence, UV and NMR spectroscopy. Metabolites with spectral properties consistant with their identification as the 3,4:8,9-bis-diol of DB[a,j]A and a 1,2,3,4,12,13-hexol derived from DB[a,c]A were found. DB[a,h]A was metabolized to three polar products identified as the 3,4:10,11-bis-diol and the related 1,2,3,4,8,9- and 1,2,3,4,10,11-hexols, which were also formed, together with the related 1,2,3,4-tetrol, from the DB[a,h]A 3,4-diol. The possible role of bis-diols in the metabolic activation of these three dibenzanthracenes is discussed.
Lecoq
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Haddow Laboratories, Institute of Cancer Research, Sutton, Surrey, U.K.
Chalvet
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Strapelias
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Grover
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PL
Phillips
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DH
Duquesne
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D000818:Animals; D001551:Benz(a)Anthracenes / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D008297:Male; D008748:Methylcholanthrene; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains
D001551:Benz(a)Anthracenes; C056428:3,4-dihydrodioldibenz(a,j)anthracene; C006710:benzotriphenylene; C041515:dibenzo(aj)anthracene; C021626:benzanthracene-8,9-dihydrodiol; D008748:Methylcholanthrene; C026486:1,2,5,6-dibenzanthracene