Studies on the chiral isomers of fonofos and fonofos oxon: II. In vitro metabolism |
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| Authors: | Philip W Lee Reza Allahyari TRoy Fukuto |
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| Institution: | Division of Toxicology and Physiology, Department of Entomology, University of California, Riverside, California 92521 USA |
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| Abstract: | The in vitro metabolism of the chiral isomers of fonofos and fonofos oxon in the presence of mouse liver mixed-function oxidase and serum esterase was investigated. The metabolism of 35S-labeled phenyl-(S)P-fonofos mediated by mixed-function oxidase took place stereoselectively, resulting predominantly in (R)P-fonofos oxon. Similarly, (R)P-fonofos was converted to (S)P-oxon. In each case, however, a significant amount of racemization occurred. Other products were diphenyl disulfide and diphenyl disulfide oxide. In addition to stereospecificity, the oxidative metabolism of (R)P-fonofos proceeded at a rate faster than that of (S)P-fonofos. Stereoselective rate differences also were observed in mouse or rat serum-catalzyed degradation of the fonofos oxon enantiomers, the (S)P isomer being degraded about twofold faster than its enantiomer. The differences in toxicities of the isomers of fonofos and fonofos oxon were consistent with the in vitro metabolism data. |
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