Stereoselective metabolism of 7-nitrobenz(a)anthracene to 3,4- and 8,9- trans-dihydrodiols |
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Authors: | P P Fu S K Yang |
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Institution: | 1. National Center for Toxicological Research, Jefferson, Arkansas 72079 USA;2. Department of Pharmacology, School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, Maryland 20814 USA |
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Abstract: | Metabolism of 7-nitrobenz(a)anthracene (7-NO2-BA) by rat liver microsomes yielded 7-NO2-BA trans-3,4-dihydrodiol and 7-NO2-BA trans-8,9-dihydrodiol as major metabolites. Proton NMR spectral analyses indicate that 7-NO2-BA trans-3,4-dihydrodiol preferentially adopts a quasidiequatorial conformation and that 7-NO2-BA trans-8,9-dihydrodiol adopts a mixture of quasidiequatorial and quasidiaxial conformations. Circular dichroism spectral analyses of these compounds and their diacetoxy derivatives indicated that the major enantiomers of both dihydrodiols have R,R absolute stereochemistries. The identification of 7-NO2-BA trans-8,9-dihydrodiol as a metabolite of 7-NO2-BA indicates that oxidative metabolism can occur at position peri to the nitro substituent. |
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Keywords: | nitro-PAH nitro-polycyclic aromatic hydrocarbon BA benz(a)anthracene 7-nitrobenz(a)anthracene HPLC high performance liquid chromatography NMR nuclear magnetic resonance CD circular dichroism |
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