Metabolism of 9-nitroanthracene by rat liver microsomes: identification and mutagenicity of metabolites.
Aerobic metabolism of 9-nitroanthracene by uninduced rat liver microsomes produced four metabolites identified as trans-1,2- and 3,4-dihydrodiols, 1,2,3,4-tetrahydrotetrol of 9-nitroanthracene, and anthraquinone. Further metabolism of the predominant metabolite, 9-nitroanthracene trans-3,4-dihyrodiol, yielded a 1,2,3,4-tetrahydrotetrol with a trans-cis-trans configuration, indicating that a trans-dihydrodiol anti-epoxide is formed as an intermediate. The mutagenic activities of both dihydrodiols and 9-nitroanthracene in strains TA98 and TA100, both in the presence and in the absence of S9 enzymes, were very low. When 9-nitroanthracene was metabolized under anaerobic conditions, nitroreduction did not occur. The results thus explain the weak mutagenic activity of 9-nitroanthracene.
D000818:Animals; D000873:Anthracenes / Q000378:metabolism* / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D066298:In Vitro Techniques; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009153:Mutagens / Q000302:isolation & purification*; D051381:Rats; D011919:Rats, Inbred Strains
D000873:Anthracenes; D009153:Mutagens; C045823:3,4-dihydroxy-9-nitro-3,4-dihydroanthracene; C045822:1,2-dihydroxy-9-nitro-1,2-dihydroanthracene; C035016:9-nitroanthracene