Stereoselective metabolism of benzo[c]phenanthrene to the procarcinogenic tras-3,4-dihydrodiol
- 1 May 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Carcinogenesis: Integrative Cancer Research
- Vol. 8 (5) , 705-709
- https://doi.org/10.1093/carcin/8.5.705
Abstract
The enantiomeric compositions of benzo[c]phenanthrene trans -3,4-dihydrodiol, a metabolic precursor of the ultimate carcinogenic bay-region 3,4-dihydrodiol-1,2-epoxides, formed in the metabolism of BcPh by liver microsomes from untreated, phenobarbital (PB)-treated, 3-methylcholanthrene (MC)-treated and polychlorinated biphenyls (PCB; Aroclor 1254)-treated rats of the Sprague-Dawley and Long-Evans strain were each determined by chiral stationary-phase h.p.l.c. and circular dichroism spectral analyses. The percentage of 3R,4R enantiomer in the tras -3,4-dihydrodiol metabolite of BcPh varies, depending on the concentration of liver microsomal enzymes used and the time of incubation: 29–30% (control), 46–54% (PB), 94–100% (MC) and 90–99% (PCB).This publication has 9 references indexed in Scilit:
- TUMORIGENICITY OF OPTICAL ISOMERS OF THE DIASTEREOMERIC BAY-REGION 3,4-DIOL-1,2-EPOXIDES OF BENZO(C)PHENANTHRENE IN MURINE TUMOR-MODELS1986
- Stereoselective metabolism of the (+)-(S,S)- and (-)-(R,R)-enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]-phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system.Journal of Biological Chemistry, 1986
- Metabolic and stereoselective formations of non-K-region benz[a]anthracene 8,9- and 10,11-epoxidesArchives of Biochemistry and Biophysics, 1986
- Stereoselective metabolism of chrysene by rat liver microsomes. Direct separation of diol enantiomers by chiral stationary phase h.p.l.c.Carcinogenesis: Integrative Cancer Research, 1986
- Metabolism of benzo[c]phenanthrene by rat liver microsomes and by a purified monooxygenase system reconstituted with different isozymes of cytochrome P-450Chemico-Biological Interactions, 1983
- Heterogeneity of cytochrome P-450s induced by polychlorinated biphenyls.Journal of Biological Chemistry, 1977
- Enzymic mechanism of benzo[a]pyrene conversion to phenols and diols and an improved high-pressure liquid chromatographic separation of benzo[a]pyrene derivativesBiochemistry, 1977
- The Carbon Monoxide-binding Pigment of Liver MicrosomesJournal of Biological Chemistry, 1964
- PROTEIN MEASUREMENT WITH THE FOLIN PHENOL REAGENTJournal of Biological Chemistry, 1951