Studies by fluorescence and n.m.r. spectroscopy of the major product formed after further metabolism of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
Racemic 7 beta,8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE) is further metabolized by liver microsomes obtained from 3-methylcholanthrene pretreated rats in the presence of NADPH to at least four products as revealed by h.p.l.c. Data obtained from measurements by fluorescence spectroscopy under neutral and alkaline conditions and high resolution two-dimensional 1H n.m.r. spectroscopy on the major metabolite derived from anti-BPDE are consistent with aromatic hydroxylation at the 3-position either directly or indirectly via transient epoxide intermediates.
Gräslund
A
A
Waern
F
F
Jernström
B
B
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D000818:Animals; D001580:Benzopyrenes / Q000378:metabolism*; D001711:Biotransformation; D002273:Carcinogens / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008748:Methylcholanthrene / Q000494:pharmacology; D008862:Microsomes, Liver / Q000378:metabolism*; D009249:NADP / Q000378:metabolism; D051381:Rats; D013050:Spectrometry, Fluorescence / Q000379:methods
D001580:Benzopyrenes; D002273:Carcinogens; D009249:NADP; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D008748:Methylcholanthrene