Hydroperoxidation by cytochrome P-450 oxygenase: metabolism of 9-methylfluorene

Archives of Biochemistry and Biophysics
C ChenD P Gurka


9-Methylfluorene was metabolized by rat liver microsomes to 9-hydroperoxy-9-methylfluorene and 9-hydroxy-9-methylfluorene. The results were confirmed by using a reconstituted cytochrome P-450 oxygenase system purified from phenobarbital-induced rat liver which established its involvement. SKF-525A strongly inhibited the formation of both oxygenation products. Cytochrome P-450 alone brought about the conversion of the hydroperoxide to its alcohol. NADPH augmented the peroxidative reaction, but the presence of NADPH-cytochrome P-450 reductase was without effect. Certain microsomal preparations and reconstituted enzyme yielded little or no detectable amounts of hydroperoxide. This was due to a too rapid conversion of the hydroperoxide to its alcohol. The addition of metyrapone, a compound that inhibited such conversion, resulted in accumulation of 9-hydroperoxy-9-methylfluorene for positive identification. Incubation of 9-methylfluorene with microsomes and NADPH resulted in covalent binding of its metabolite to microsomal proteins. Incubation of 14C-labeled 9-hydroperoxy-9-methylfluorene caused covalent binding of label to proteins, RNA, and DNA.


Jan 1, 1984·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·J CapdevilaJ R Falck
Jan 1, 1980·Annual Review of Biochemistry·R E White, M J Coon

Related Concepts

High Pressure Liquid Chromatography Procedure
Cytochrome P-450 Oxygenase
Microsomes, Liver

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