Liver microsomal metabolism of the environmental carcinogen 3-nitrofluoranthene. I. Phenolic metabolites.
The liver microsomal metabolism of the environmental carcinogen 3-nitrofluoranthene has been investigated. Five phenolic metabolites were isolated and characterized by their mass and NMR spectra as: 3-nitrofluoranthen-1-ol, 3-nitrofluoranthen-6-ol, 3-nitrofluoranthen-(7 or 10)-ol, 3-nitrofluoranthen-8-ol and 3-nitrofluoranthen-9-ol. While the microsomes isolated from Sprague-Dawley rat liver and C57B16 mouse liver preferentially metabolized the 3-nitrofluoranthene to 3-nitrofluoranthen-8-ol and 3-nitrofluoranthen-9-ol, the microsomes from Hartley guinea-pig liver preferentially metabolized 3-nitrofluoranthene to 3-nitrofluoranthen-6-ol. 3-Nitrofluoranthen-1-ol was a minor metabolite in each of the incubations. The results indicate the presence of the nitro group on fluoranthene directs the metabolism away from the C1-C5 positions, and more towards the C6-C10 positions.
Howard
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Department of Environmental Health Sciences, Case Western Reserve University, Cleveland, OH 44106.
Mateescu
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Consolo
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D000393:Air Pollutants; D000818:Animals; D006224:Cricetinae; D005260:Female; D005449:Fluorenes / Q000378:metabolism*; D006041:Goats; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008647:Mesocricetus; D051379:Mice; D008810:Mice, Inbred C57BL; D008862:Microsomes, Liver / Q000378:metabolism*; D010636:Phenols / Q000302:isolation & purification; D051381:Rats; D011919:Rats, Inbred Strains
D000393:Air Pollutants; D005449:Fluorenes; D010636:Phenols; C049030:2-nitrofluoranthene