Reductive metabolism of 1,1,1,2-tetrachloroethane and related chloroethanes by rat liver microsomes
Chemico-Biological Interactions, ISSN: 0009-2797, Vol: 51, Issue: 3, Page: 321-333
1984
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Article Description
The susceptibility of polychlorinated ethanes to reductive metabolism was evaluated by measuring the amount of each compound consumed during anaerobic incubations with rat liver microsomes; 1,1,1,2-tetrachloroethane, pentachloroethane and hexachloroethane were metabolized extensively, 1,1,1,2-tetrachloroethane and the trichloroethanes were metabolized very slowly and the dichloroethanes were not metabolized at a detectable rate. The electron affinity of the chloroethanes was determined by measuring electrochemical half-wave reduction potentials. Chloroethanes with an E12 of −1.35 V or less negative were reduced readily in microsomes while those with an E12 equal to or more negative than −1.90 V were not good substrates for enzymatic reduction. Metabolites produced from 1,1,1,2-tetrachloroethane in vitro were 1,1-dichloroethylene (DCE) and 1,1,2-trichloroethane (TCEA) and the ratio DCETCEA was about 25:1. These conversions were NADPH-dependent and were inhibited by air, CO and metyrapone. In the presence of SKF 525-A, DCE formation was inhibited by 47%. Microsomes from untreated or β-naphthoflavone-treated rats were 70–90% less active than microsomes from phenobarbital-treated rats. The K m was 0.50 mM and the V max was 66 nmol min −1 mg −1 protein for DCE formation. The results are consistent with the proposal that 1,1,1,2-tetrachloroethane is reduced by hepatic cytochrome(s) P -450 to a free radical intermediate which, for the most part, remains closely associated with the enzyme, is reduced further and undergoes β-elimination of a chloride ion to form DCE. The occurrence of this reductive pathway in vivo was demonstrated by the quantitation of DCE and TCEA in blood from rats treated with 1,1,1,2-tetrachloroethane.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/0009279784901571; http://dx.doi.org/10.1016/0009-2797(84)90157-1; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=0021125189&origin=inward; http://www.ncbi.nlm.nih.gov/pubmed/6488393; https://linkinghub.elsevier.com/retrieve/pii/0009279784901571; http://dx.doi.org/10.1016/0009-2797%2884%2990157-1; https://dx.doi.org/10.1016/0009-2797%2884%2990157-1
Elsevier BV
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