| Stereoselectivity of styrene oxidation in microsomes and in purified cytochrome P-450 enzymes from rat liver. | |
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MedLine Citation:
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PMID: 2918465 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The stereochemistry of the cytochrome P-450(P-450)-dependent oxidation of styrene to styrene 7,8-oxide (SO) enantiomers was evaluated with rat hepatic microsomes and with individual rat liver P-450 enzymes in reconstituted monooxygenase systems. The stereoselectivity of the monooxygenase reaction with styrene was determined by high-performance liquid chromatographic analysis of the glutathione conjugates formed quantitatively from SO, the product of the monooxygenase reaction. Hepatic microsomes from control rats oxidized styrene at a rate of 13.1 +/- 4.5 nmol/min/nmol of P-450 and with a ratio of the amount of the (R)-styrene 7,8-oxide enantiomer to the amount of the (S)-styrene 7,8-oxide enantiomer (R/S) SO ratio of 0.65 +/- 0.1. These values were determined under incubation conditions in which epoxide hydrolase activity was inhibited by cyclohexene oxide, and at least 95% of the SO formed was converted enzymatically to glutathione conjugates. Treatment of rats i.p. with phenobarbital (PB) or beta-naphthoflavone (beta NF) caused changes in both parameters. Whereas the rates of oxidation in hepatic microsomes prepared from PB-treated rats was unchanged at 15.4 +/- 7.5 nmol/min/nmol of P-450 and decreased in hepatic microsomes from beta NF-treated rats to 9.4 +/- 2.8 nmol/min/nmol of P-450, the preference for formation of the R-enantiomer increased as the R/S ratio changed to 0.92 +/- 0.1 for PB and 1.25 +/- 0.1 for beta NF.(ABSTRACT TRUNCATED AT 250 WORDS) |
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Authors:
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G L Foureman; C Harris; F P Guengerich; J R Bend |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of pharmacology and experimental therapeutics Volume: 248 ISSN: 0022-3565 ISO Abbreviation: J. Pharmacol. Exp. Ther. Publication Date: 1989 Feb |
Date Detail:
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Created Date: 1989-04-03 Completed Date: 1989-04-03 Revised Date: 2003-11-14 |
Medline Journal Info:
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Nlm Unique ID: 0376362 Medline TA: J Pharmacol Exp Ther Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 492-7 Citation Subset: IM |
Affiliation:
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Laboratory of Pharmacology, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Benzoflavones / pharmacology Cytochrome P-450 Enzyme System / physiology* Glutathione / metabolism Liver / enzymology* Male Microsomes, Liver / metabolism* Oxidation-Reduction Phenobarbital / pharmacology Rats Rats, Inbred Strains Stereoisomerism Styrene Styrenes / metabolism* beta-Naphthoflavone |
| Chemical | |
Reg. No./Substance:
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0/Benzoflavones; 0/Styrenes; 100-42-5/Styrene; 50-06-6/Phenobarbital; 6051-87-2/beta-Naphthoflavone; 70-18-8/Glutathione; 9035-51-2/Cytochrome P-450 Enzyme System |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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