Spectral evidence for 2,2,3-trichloro-oxirane formation during microsomal trichloroethylene oxidation View Full Text


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Article Info

DATE

1977-01

AUTHORS

H. Uehleke, Sonja Tabarelli-Poplawski, G. Bonse, D. Henschler

ABSTRACT

During aerobic incubation of trichloroethylene with rabbit liver microsomes and NADPH a difference absorption peak appears at 451–452 nm. Trichloroethylene does not form a ligand absorption spectrum with hepatic microsomes reduced by dithionite, or in anaerobic incubates in the presence of NADPH.Addition of trichloroethylene epoxide (2,2,3-trichloro-oxirane) to reduced suspensions of rabbit liver microsomes produces high difference absorption at 452 nm, the optical Ks being approximately 2 mM. Of all possible metabolites of trichloroethylene only trichloroethanol forms absorption in the vicinity of 480 nm, and the broad absorption band reveals relatively low absorption near 450 nm. Dichloroacetyl chloride is the main thermal rearrangement product of trichloroethylene epoxide, and also produces 452 nm absorption in reduced microsomes. However, the difference absorption is 5 times smaller than the absorption produced by the intermediate formed during incubation of trichloroethylene in metabolising liver microsomes.These observations include strong evidence for epoxide formation during microsomal oxidation of trichloroethylene. 14C-labelled trichloroethylene binds irreversibly to hepatic macromolecules in vivo and in vitro. Possible rearrangement pathways of 2,2,3-trichloro-oxirane and reactive intermediates are presented. More... »

PAGES

95-105

References to SciGraph publications

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  • 1972-09. Bildung von Chloroform aus Tetrachlorkohlenstoff in Lebermikrosomen, Lipidperoxidation und Zerstörung von Cytochrom P-450 in FÜHNER-WEILANDS SAMMLUNG VON VERGIFTUNGSFÄLLEN ARCHIV FÜR TOXIKOLOGIE
  • 1977. Binding of Haloalkanes to Liver Microsomes in BIOLOGICAL REACTIVE INTERMEDIATES
  • 1967-05. Die Schwingungsspektren von Tetrachloräthylenoxid,cis-undtrans-1,2-Dichloräthylenoxid in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 1974-12. Metabolism of trichloroethylene in man in ARCHIVES OF TOXICOLOGY
  • 1972-09. Metabolism of trichloroethylene in man in FÜHNER-WEILANDS SAMMLUNG VON VERGIFTUNGSFÄLLEN ARCHIV FÜR TOXIKOLOGIE
  • 1974-12. The mechanism of halothane binding to microsomal cytochrome P450 in NAUNYN-SCHMIEDEBERG'S ARCHIVES OF PHARMACOLOGY
  • 1975-12. A comparative study on the irreversible binding of labeled halothane trichlorofluoromethane, chloroform, and carbon tetrachloride to hepatic protein and lipids in vitro and in vivo in ARCHIVES OF TOXICOLOGY
  • 1972-12. Trichloroethylene exposure and trichloroethylene metabolites in urine and blood in FÜHNER-WEILANDS SAMMLUNG VON VERGIFTUNGSFÄLLEN ARCHIV FÜR TOXIKOLOGIE
  • 1973-01. Metabolism, excretion and toxicology of trichloroethylene after inhalation in FÜHNER-WEILANDS SAMMLUNG VON VERGIFTUNGSFÄLLEN ARCHIV FÜR TOXIKOLOGIE
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    URI

    http://scigraph.springernature.com/pub.10.1007/bf00293858

    DOI

    http://dx.doi.org/10.1007/bf00293858

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1005950999

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/18130


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