{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T01:46:37Z","timestamp":1790732797563,"version":"4.1.0"},"reference-count":63,"publisher":"American Chemical Society (ACS)","issue":"1","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem. Res. Toxicol."],"published-print":{"date-parts":[[1996,1,1]]},"DOI":"10.1021\/tx950075u","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T01:30:15Z","timestamp":1027647015000},"page":"41-49","source":"Crossref","is-referenced-by-count":47,"title":["Sulfoxidation of Mercapturic Acids Derived from Tri- and Tetrachloroethene by Cytochromes P450 3A:\u2009 A Bioactivation Reaction in Addition to Deacetylation and Cysteine Conjugate \u03b2-Lyase Mediated Cleavage"],"prefix":"10.1021","volume":"9","author":[{"given":"Michael","family":"Werner","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Toxikologie der Universt\u00e4t W\u00fcrzburg, Versbacherstrasse 9, 97078 W\u00fcrzburg, FRG"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gerhard","family":"Birner","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Toxikologie der Universt\u00e4t W\u00fcrzburg, Versbacherstrasse 9, 97078 W\u00fcrzburg, FRG"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wolfgang","family":"Dekant","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Toxikologie der Universt\u00e4t W\u00fcrzburg, Versbacherstrasse 9, 97078 W\u00fcrzburg, FRG"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[1996,1,15]]},"reference":[{"key":"tx950075ub00001\/tx950075ub00001_1","unstructured":"NTP (1988) National Toxicology Program. Toxicology and carcinogenesis studies of trichloroethylene in four strains of rats (ACI, August, Marshall, Osborne-Mendel) (gavage studies). U.S. Department of Health and Human Services, Technical Report 273."},{"key":"tx950075ub00002\/tx950075ub00002_1","unstructured":"NTP (1986) National Toxicology Program. Carcinogenesis bioassay of tetrachloroethylene. U.S. Department of Health and Human Services, Technical Report 232."},{"key":"tx950075ub00003\/tx950075ub00003_1","volume-title":"The metabolism of 36Cl-labelled trichloroethylene and tetrachloroethylene in the rat. Biochem. Pharmacol. 12, 795\u2212802","author":"Daniel J. W.","year":"1963"},{"key":"tx950075ub00004\/tx950075ub00004_1","volume-title":"The pharmacokinetics and macromolecular interactions of perchloroethylene in mice and rats as related to oncogenicity. Toxicol. Appl. Pharmacol. 55, 207\u2212219","author":"Schumann A. M.","year":"1980"},{"key":"tx950075ub00005\/tx950075ub00005_1","volume-title":"The pharmacokinetics and macromolecular interactions of trichloroethylene in mice and rats. Toxicol. Appl. Pharmacol. 62, 137\u2212151","author":"Stott W. T.","year":"1982"},{"key":"tx950075ub00006\/tx950075ub00006_1","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1002\/jbt.2570010206","volume":"1","author":"Dekant W.","year":"1986","journal-title":"J. Biochem. Toxicol."},{"key":"tx950075ub00007\/tx950075ub00007_1","doi-asserted-by":"crossref","unstructured":"Dekant, W., Metzler, M., and Henschler, D. (1986) Identification of\n                      S\n                      -1,2-dichlorovinyl-\n                      N\n                      -acety\n                      l\n                      -cysteine as a urinary metabolite of trichloroethylene:\u2009 A possible explanation for its nephrocarcinogenicity in male rats.\n                      Biochem. Pharmacol.\n                      35\n                      , 2455\u22122458.","DOI":"10.1016\/0006-2952(86)90039-0"},{"key":"tx950075ub00008\/tx950075ub00008_1","volume-title":"Bioactivation of tetrachloroethyleneRole of glutathione S-transferase-catalyzed conjugation versus cytochrome P-450-dependent phospholipid alkylation. Drug Metab. Dispos. 15, 702\u2212709","author":"Dekant W.","year":"1987"},{"key":"tx950075ub00009\/tx950075ub00009_1","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/0041-008X(90)90264-U","volume":"103","author":"Green T.","year":"1990","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"tx950075ub00010\/tx950075ub00010_1","volume-title":"Identification of N-acetyl(1,1-dichlorovinyl)- and N-acetyl(1,2-dichlorovinyl)-l-cysteine as two regioisomeric mercapturic acids of trichloroethylene in the rat. Chem. Res. Toxicol. 3, 212\u2212218","author":"Commandeur J. N. M.","year":"1990"},{"key":"tx950075ub00011\/tx950075ub00011_1","doi-asserted-by":"crossref","first-page":"83","DOI":"10.3109\/03602538908994144","volume":"20","author":"Dekant W.","year":"1989","journal-title":"Drug Metab. Rev."},{"key":"tx950075ub00012\/tx950075ub00012_1","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/S0009-2797(85)80149-6","volume":"54","author":"Green T.","year":"1985","journal-title":"Chem.-Biol. Interact."},{"key":"tx950075ub00013\/tx950075ub00013_1","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/0009-2797(86)90015-3","volume":"60","author":"Dekant W.","year":"1986","journal-title":"Chem.-Biol. Interact."},{"key":"tx950075ub00014\/tx950075ub00014_1","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/0165-1218(88)90144-9","volume":"206","author":"Vamvakas S.","year":"1988","journal-title":"Mutat. Res."},{"key":"tx950075ub00015\/tx950075ub00015_1","volume-title":"Vitro 3, 151\u2212156.","author":"Vamvakas S.","year":"1989"},{"key":"tx950075ub00016\/tx950075ub00016_1","volume-title":"Mutagenicity and cytotoxicity of two regioisomeric mercapturic acids and cysteine S-conjugates of trichloroethylene. Arch. Toxicol. 65, 373\u2212380","author":"Commandeur J. N. M.","year":"1991"},{"key":"tx950075ub00017\/tx950075ub00017_1","doi-asserted-by":"crossref","DOI":"10.1021\/ja00013a090","volume":"113","author":"Dekant W.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"tx950075ub00018\/tx950075ub00018_1","volume-title":"Metabolism of tetrachloroethene in rats:\u2009 identification of N\u03b5-(dichloroacetyl)-l-lysine and N\u03b5-(trichloroacetyl)-l-lysine as protein adducts. Chem. Res. Toxicol. 7, 724\u2212732","author":"Birner G.","year":"1994"},{"key":"tx950075ub00019\/tx950075ub00019_1","volume-title":"Sex-differences in hexachlorobutadiene biotransformation and nephrotoxicity. Toxicol. Appl. Pharmacol. 132, 203\u2212212","author":"Birner G.","year":"1995"},{"key":"tx950075ub00020\/tx950075ub00020_1","volume-title":"Metabolic basis of detoxication","author":"Ziegler D. M.","year":"1982"},{"key":"tx950075ub00021\/tx950075ub00021_1","volume-title":"Cytochrome P450 and FAD-monooxygenase mediated S- and N-oxygenations. Drug Metab. Drug Interact. 6, 350\u2212363","author":"Damani L. A.","year":"1988"},{"key":"tx950075ub00022\/tx950075ub00022_1","first-page":"49","volume":"3","author":"Poulsen L. L.","year":"1981","journal-title":"Rev. Biochem. Toxicol."},{"key":"tx950075ub00023\/tx950075ub00023_1","doi-asserted-by":"crossref","DOI":"10.1021\/ja00195a041","volume":"111","author":"Cashman J. R.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"tx950075ub00024\/tx950075ub00024_1","doi-asserted-by":"crossref","unstructured":"Light, D. R., Waxman, D. J., and Walsh, C. T. (1982) Studies on the chirality of sulfoxidation catalyzed by bacterial flavoenzyme cyclohexanone monooxygenase and hog liver flavine adenine dinucleotide containing monooxygenase.\n                      Biochemistry\n                      21\n                      , 2490\u22122498.","DOI":"10.1021\/bi00539a031"},{"key":"tx950075ub00025\/tx950075ub00025_1","volume-title":"Biological reactive intermediates. II. Chemical Mechanisms and biological effects","author":"Hunt P. A.","year":"1982"},{"key":"tx950075ub00026\/tx950075ub00026_1","volume-title":"Enzymic basis of detoxification","author":"Ziegler D. M.","year":"1980"},{"key":"tx950075ub00027\/tx950075ub00027_1","doi-asserted-by":"crossref","unstructured":"Waxman, D. J., Light, D. R., and Walsh, C. (1982) Chiral sulfoxidations catalyzed by rat liver cytochromes P-450.\n                      Biochemistry\n                      21\n                      , 2499\u22122507.","DOI":"10.1021\/bi00539a032"},{"key":"tx950075ub00028\/tx950075ub00028_1","volume":"81","author":"McKinney L. L.","year":"1959","journal-title":"J. Am. Chem. Soc."},{"key":"tx950075ub00029\/tx950075ub00029_1","volume":"31","author":"Stoll A.","year":"1948","journal-title":"Helv. Chim. Acta"},{"key":"tx950075ub00030\/tx950075ub00030_1","volume-title":"Specific and enantioselective sulfoxidation of an aryl-trifluoromethyl sulfide by rat liver cytochromes P-450. Drug Metab. Dispos. 20, 877\u2212881","author":"Benoit E.","year":"1992"},{"key":"tx950075ub00031\/tx950075ub00031_1","volume-title":"Methods in Enzymology","author":"Yang C. S."},{"key":"tx950075ub00032\/tx950075ub00032_1","volume-title":"Assay of cysteine conjugate \u03b2-lyase activity with S-(2-benzothiazolyl)cysteine as the substrate. Anal. Biochem. 120, 379\u2212386","author":"Dohn D. R.","year":"1982"},{"key":"tx950075ub00033\/tx950075ub00033_1","volume":"228","author":"Wolf C. R.","year":"1984","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"tx950075ub00034\/tx950075ub00034_1","doi-asserted-by":"crossref","DOI":"10.1093\/oxfordjournals.jbchem.a122124","volume":"102","author":"Imaoka S.","year":"1987","journal-title":"J. Biochem."},{"key":"tx950075ub00035\/tx950075ub00035_1","volume":"926","author":"Funae Y.","year":"1987","journal-title":"Biochim. Biophys. Acta"},{"key":"tx950075ub00036\/tx950075ub00036_1","doi-asserted-by":"crossref","unstructured":"Burke, M. D., and Mayer, R. T. (1983) Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal metabolism in cytochrome P-450 binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresorufins).\n                      Chem.Biol. Interact.\n                      45\n                      , 243\u2212258.","DOI":"10.1016\/0009-2797(83)90072-8"},{"key":"tx950075ub00037\/tx950075ub00037_1","volume-title":"Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem. Res. Toxicol. 3, 566\u2212573","author":"Peter R.","year":"1990"},{"key":"tx950075ub00038\/tx950075ub00038_1","volume-title":"Microsomal oxidation of thiobenzamide. A photometric assay for the flavin-containing monooxygenase. Biochem. Biophys. Res. Commun. 98, 147\u2212153","author":"Cashman J. R.","year":"1981"},{"key":"tx950075ub00039\/tx950075ub00039_1","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/0003-9861(85)90010-4","volume":"240","author":"Tynes R. E.","year":"1985","journal-title":"Arch. Biochem. Biophys."},{"key":"tx950075ub00040\/tx950075ub00040_1","doi-asserted-by":"crossref","DOI":"10.1016\/S0021-9258(20)82245-5","volume":"239","author":"Omura T.","year":"1964","journal-title":"J. Biol. Chem."},{"key":"tx950075ub00041\/tx950075ub00041_1","volume-title":"A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principal of protein\u2212dye binding. Anal. Biochem. 72, 248\u2212254","author":"Bradford M. M.","year":"1976"},{"key":"tx950075ub00042\/tx950075ub00042_1","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/0009-2797(89)90091-4","volume":"71","author":"Vamvakas S.","year":"1989","journal-title":"Chem.-Biol. Interact."},{"key":"tx950075ub00043\/tx950075ub00043_1","volume-title":"Enzymatic transformation of mercapturic acids derived from halogenated alkenes to reactive and mutagenic intermediates. Biochem. Pharmacol. 36, 2741\u22122748","author":"Vamvakas S.","year":"1987"},{"key":"tx950075ub00044\/tx950075ub00044_1","doi-asserted-by":"crossref","DOI":"10.1021\/jo00051a036","volume":"57","author":"Carre\u00f1o M. C.","year":"1992","journal-title":"J. Org. Chem."},{"key":"tx950075ub00045\/tx950075ub00045_1","volume-title":"Regulation of two members of the steroid-inducible cytochrome P450 subfamily (3A) in rats. Arch. Biochem. Biophys. 301, 345\u2212354","author":"Cooper K. O.","year":"1993"},{"key":"tx950075ub00046\/tx950075ub00046_1","volume-title":"Pregnenolone 16\u03b1-carbonitrile-inducible P-450 gene family:\u2009 gene conversion and differential regulation. Mol. Cell. Biol. 6, 2969\u22122976","author":"Gonzalez F. J.","year":"1986"},{"key":"tx950075ub00047\/tx950075ub00047_1","doi-asserted-by":"crossref","DOI":"10.1093\/oxfordjournals.jbchem.a122494","volume":"104","author":"Imaoka S.","year":"1988","journal-title":"J. Biochem."},{"key":"tx950075ub00048\/tx950075ub00048_1","volume-title":"Self-induction by triacetyloleandomycin of its own transformation into a metabolite forming a stable 456 nm-absorbing complex with cytochrome P-450. Biochem. Pharmacol. 30, 553\u2212558","author":"Pessayre D.","year":"1981"},{"key":"tx950075ub00049\/tx950075ub00049_1","doi-asserted-by":"crossref","unstructured":"Pessayre, D., Konstantinova-Mitcheva, M., Descatoire, V., Cobert, B., Wandscheer, J.C., Level, R., Feldmann, G., Mansuy, D., and Benhamou, J.P. (1981) Hypoactivity of cytochrome P-450 after triacetyloleandomycin administration.\n                      Biochem. Pharmacol.\n                      30\n                      , 559\u2212564.","DOI":"10.1016\/0006-2952(81)90126-X"},{"key":"tx950075ub00050\/tx950075ub00050_1","volume-title":"Proc. Natl. Acad. Sci. U.S.A. 82","author":"Watkins P. B.","year":"1985"},{"key":"tx950075ub00051\/tx950075ub00051_1","doi-asserted-by":"crossref","unstructured":"Guengerich, F. P., Dannan, G. A., Wright, S. T., Martin, M. V., and Kaminsky, L. S. (1982) Purification and characterization of liver microsomal cytochromes P-450:\u2009 electrophoretic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or \u03b2-naphtoflavone.\n                      Biochemistry\n                      21\n                      , 6019\u22126030.","DOI":"10.1021\/bi00266a045"},{"key":"tx950075ub00052\/tx950075ub00052_1","volume":"19","author":"Adesnik M.","year":"1985","journal-title":"Crit. Rev. Toxicol."},{"key":"tx950075ub00053\/tx950075ub00053_1","volume-title":"Ligand interactions with cytochrome P-450. Binding of primary amines. Biochemistry 8, 3455\u22123465","author":"Jeffcoate C. R. E.","year":"1969"},{"key":"tx950075ub00054\/tx950075ub00054_1","doi-asserted-by":"crossref","unstructured":"Sausen, P. J., and Elfarra, A. A. (1991) Reactivity of cysteine\n                      S\n                      -conjugate sulfoxides:\u2009 Formation of\n                      S\n                      -(1-chloro-2-(\n                      S\n                      -glutathionyl)vinyl)-\n                      l\n                      -cysteine sulfoxide by the reaction of\n                      S\n                      -(1,2-dichlorovinyl)-\n                      l\n                      -cysteine sulfoxide with glutathione.\n                      Chem. Res. Toxicol.\n                      4\n                      , 655\u2212660.","DOI":"10.1021\/tx00024a010"},{"key":"tx950075ub00055\/tx950075ub00055_1","volume":"261","author":"Lash L. H.","year":"1986","journal-title":"J. Biol. Chem."},{"key":"tx950075ub00056\/tx950075ub00056_1","volume":"261","author":"Lash L. H.","year":"1986","journal-title":"J. Biol. Chem."},{"key":"tx950075ub00057\/tx950075ub00057_1","volume-title":"Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. Biochem. Pharmacol. 35, 283\u2212288","author":"Elfarra A. A.","year":"1986"},{"key":"tx950075ub00058\/tx950075ub00058_1","first-page":"101","volume":"42","author":"Murray M.","year":"1990","journal-title":"Pharmacol. Rev."},{"key":"tx950075ub00059\/tx950075ub00059_1","volume-title":"Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 percent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 22, 3099\u22123108","author":"Cheng Y. C.","year":"1973"},{"key":"tx950075ub00060\/tx950075ub00060_1","volume-title":"The sulfoxidation of the hexachlorobutadiene metabolite N-acetyl-(S-1,2,3,4,4-pentachlorobutadienyl)-l-cysteine is catalyzed by human cytochrome P450 3A enzymes. Chem. Res. Toxicol. (in press)","author":"Werner M.","year":"1995"},{"key":"tx950075ub00061\/tx950075ub00061_1","volume":"269","author":"Lash L. H.","year":"1994","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"tx950075ub00062\/tx950075ub00062_1","volume":"108","author":"Kahn S. D.","year":"1986","journal-title":"J. Am. Chem. Soc."},{"key":"tx950075un00001\/tx950075un00001_1","volume-title":"flavin-containing monooxygenase","author":"Abbreviations FMO"}],"container-title":["Chemical Research in Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/tx950075u","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,13]],"date-time":"2023-03-13T19:35:54Z","timestamp":1678736154000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/tx950075u"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1996,1,1]]},"references-count":63,"journal-issue":{"issue":"1","published-print":{"date-parts":[[1996,1,1]]}},"alternative-id":["10.1021\/tx950075u"],"URL":"https:\/\/doi.org\/10.1021\/tx950075u","relation":{},"ISSN":["0893-228X","1520-5010"],"issn-type":[{"value":"0893-228X","type":"print"},{"value":"1520-5010","type":"electronic"}],"subject":[],"published":{"date-parts":[[1996,1,1]]}}}