References
- Abraham D. G., Patel P. P., Cooper A. J.L. Isolation from rat kidney of a cytosolic high molecular weight cysteine‐S‐conjugate β‐lyase with activity toward leukotriene E4. J. Biol. Chem. 1995; 270: 180–188, [PUBMED], [INFOTRIEVE]
- Ahmed A. E., Anders M. W. Metabolism of dihalomethanes to formaldehyde and inorganic halide. II. Studies on the mechanism of the reaction. Biochem. Pharmacol. 1978; 27: 2021–2025, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Anders M. W., Dekant W. Glutathione‐dependent bioactivation of haloalkenes. Annu. Rev. Pharmacol. Toxicol. 1998; 38: 501–537, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Casanova M., Bell D. A., Heck H. d.A. Dichloromethane metabolism to formaldehyde and reaction of formaldehyde with nucleic acids in hepatocytes of rodents and humans with and without glutathione S‐transferase T1 and M1 genes. Fundam. Appl. Toxicol. 1997; 37: 168–180, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Chen Q., Jones T. W., Brown P. C., Stevens J. L. The mechanism of cysteine conjugate cytotoxicity in renal epithelial cells. Covalent binding leads to thiol depletion and lipid peroxidation. J. Biol. Chem. 1990; 265: 21603–21611, [PUBMED], [INFOTRIEVE]
- Cmarik J. L., Humphreys W. G., Bruner K. L., Lloyd R. S., Tibbetts C., Guengerich F. P. Mutation spectrum and sequence alkylation selectivity resulting from modification of bacteriophage M13mp18 DNA with S‐(2‐chloroethyl)glutathione. J. Biol. Chem. 1992; 267: 6672–6679, [PUBMED], [INFOTRIEVE]
- Commandeur J. N.M., Brakenhoff J. P.G., De Kanter F. J.J., Vermeulen N. P.E. Nephrotoxicity of mercapturic acids of three structurally related 2,2‐difluoroethylenes in the rat. Biochem. Pharmacol. 1988; 37: 4495–4504, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Commandeur J. N.M., King L. J., Koymans L., Vermeulen N. P.E. Bioactivation of S‐(2,2‐dihalo‐1,1‐difluoroethyl)‐L‐cysteines and S‐(trihalovinyl)‐L‐cysteines by cysteine S‐conjugate β‐lyase: indications for formation of both thionoacylating species and thiiranes as reactive intermediates. Chem. Res. Toxicol. 1996; 9: 1092–1102, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Cooper A., Bruschi S., Anders M. Toxic, halogenated cysteine S‐conjugates and targeting of mitochondrial enzymes of energy metabolism. Biochem. Pharmacol. 2002; 64: 553–564, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Cummings B. S., Parker J. C., Lash L. H. Role of cytochrome P450 and glutathione S‐transferase alpha in the metabolism and cytotoxicity of trichloroethylene in rat kidney. Biochem. Pharmacol. 2000; 59: 531–543, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Davis M. E. Effects of AT‐125 on the nephrotoxicity of hexachloro‐1,3‐butadiene in rats. Toxicol. Appl. Pharmacol. 1988; 95: 44–52, [PUBMED], [INFOTRIEVE], [CSA]
- Dekant W., Lash L. H., Anders M. W. Bioactivation mechanism of the cytotoxic and nephrotoxic S‐conjugate S‐(2‐chloro‐1,1,2‐trifluoroethyl)‐L‐cysteine. Proc. Natl. Acad. Sci. U. S. A. 1987; 84: 7443–7447, [PUBMED], [INFOTRIEVE]
- Dekant W., Berthold K., Vamvakas S., Henschler D., Anders M. W. Thioacylating intermediates as metabolites of S‐(1,2‐dichlorovinyl)‐L‐cysteine and S‐(1,2,2‐trichlorovinyl)‐L‐cysteine formed by cysteine conjugate β‐lyase. Chem. Res. Toxicol. 1988; 1: 175–178, [PUBMED], [INFOTRIEVE]
- Dekant W., Vamvakas S., Anders M. W. Bioactivation of nephrotoxic haloalkenes by glutathione conjugation: formation of toxic and mutagenic intermediates by cysteine conjugate β‐lyase. Drug Metab. Rev. 1989; 20: 43–83, [PUBMED], [INFOTRIEVE]
- Dekant W., Urban G., Görsmann C., Anders M. W. Thioketene formation from α‐haloalkenyl 2‐nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S‐conjugates. J. Am. Chem. Soc. 1991; 113: 5120–5122
- Dekant W., Vamvakas S., Anders M. W. Formation and fate of nephrotoxic and cytotoxic glutathione S‐conjugates: cysteine conjugate β‐lyase pathway. Adv. Pharmacol. 1994; 27: 115–162, [PUBMED], [INFOTRIEVE]
- Dohn D. R., Casida J. E. Thiiranium ion intermediates in the formation and reactions of S‐(2‐haloethyl)‐L‐cysteines. Bioorg. Chem. 1987; 15: 115–124, [CROSSREF]
- Elfarra A. A., Baggs R. B., Anders M. W. Structure‐nephrotoxicity relationships of S‐(2‐chloroethyl)‐DL‐cysteine and analogs: role for an episulfonium ion. J. Pharmacol. Exp. Ther. 1985; 233: 512–516, [PUBMED], [INFOTRIEVE]
- Elfarra A. A., Jakobson I., Anders M. W. Mechanism of S‐(1,2‐dichlorovinyl)glutathione‐induced nephrotoxicity. Biochem. Pharmacol. 1986; 35: 283–288, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Finkelstein M. B., Baggs R. B., Anders M. W. Nephrotoxicity of the glutathione and cysteine conjugates of 2‐bromo‐2‐chloro‐1,1‐difluoroethene. J. Pharmacol. Exp. Ther. 1992; 261: 1248–1252, [PUBMED], [INFOTRIEVE], [CSA]
- Finkelstein M. B., Vamvakas S., Bittner D., Anders M. W. Structure‐mutagenicity and structure‐cytotoxicity studies on bromine‐containing cysteine S‐conjugates and related compounds. Chem. Res. Toxicol. 1994; 7: 157–163, [PUBMED], [INFOTRIEVE], [CSA]
- Finkelstein M. B., Dekant W., Kende A. S., Anders M. W. α‐Thiolactones as novel intermediates in the cysteine conjugate β‐lyase‐catalyzed bioactivation of bromine‐containing cysteine S‐conjugates. J. Am. Chem. Soc. 1995; 117: 9590–9591
- Finkelstein M. B., Dekant W., Anders M. W. Cysteine conjugate β‐lyase‐catalyzed bioactivation of bromine‐containing cysteine S‐conjugates: stoichiometry and formation of 2,2‐difluoro‐3‐halothiiranes. Chem. Res. Toxicol. 1996; 9: 227–231, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Guengerich F. P. Activation of dihaloalkanes by thiol‐dependent mechanisms. J. Biochem. Mol. Biol. 2003; 36: 20–27, [PUBMED], [INFOTRIEVE]
- Guengerich F. P., Persmark M. Mechanism of formation of ethenoguanine adducts from 2‐haloacetaldehydes: 13C‐labeling patterns with 2‐bromoacetaldehyde. Chem. Res. Toxicol. 1994; 7: 205–208, [PUBMED], [INFOTRIEVE], [CSA]
- Hargus S. J., Anders M. W. Immunochemical detection of covalently modified kidney proteins in S‐(1,1,2,2‐tetrafluoroethyl)‐L‐cysteine‐treated rats. Biochem. Pharmacol. 1991; 42: R17–R20, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Harris J. W., Dekant W., Anders M. W. In vivo detection and characterization of protein adducts resulting from bioactivation of haloethene cysteine S‐conjugates by 19F NMR: chlorotrifluoroethene and tetrafluoroethene. Chem. Res. Toxicol. 1992; 5: 34–41, [PUBMED], [INFOTRIEVE]
- Hashmi M., Dechert S., Dekant W., Anders M. W. Bioactivation of [13C]dichloromethane in mouse, rat, and human liver cytosol: 13C nuclear magnetic resonance spectroscopic studies. Chem. Res. Toxicol. 1994; 7: 291–296, [PUBMED], [INFOTRIEVE], [CSA]
- Hayden P. J., Welsh C. J., Yang Y., Schaefer W. H., Ward A. J.I., Stevens J. L. Formation of mitochondrial phospholipid adducts by nephrotoxic cysteine conjugate metabolites. Chem. Res. Toxicol. 1992; 5: 231–237
- Humphreys W. G., Kim D. H., Guengerich F. P. Isolation and characterization of N7‐guanyl adducts derived from 1,2‐dibromo‐3‐chloropropane. Chem. Res. Toxicol. 1991; 4: 445–453, [PUBMED], [INFOTRIEVE], [CSA]
- Inskeep P. B., Guengerich F. P. Glutathione‐mediated binding of dibromoalkanes to DNA: specificity of rat glutathione S‐transferases and dibromoalkane structure. Carcinogenesis 1984; 5: 805–808, [PUBMED], [INFOTRIEVE]
- Jolivette L. J., Anders M. W. Structure‐activity relationship for the biotransformation of haloalkenes by rat liver microsomal glutathione transferase 1. Chem. Res. Toxicol. 2002; 15: 1036–1041, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Jolivette L. J., Anders M. W. Computational and experimental studies on the distribution of addition and substitution products of the microsomal glutathione transferase 1‐catalyzed conjugation of glutathione with fluoroalkenes. Chem. Res. Toxicol. 2003; 16: 137–144, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Kharasch E. D., Thorning D., Garton K., Hankins D. C., Kilty G. C. Role of renal cysteine conjugate β‐lyase in the mechanism of compound A nephrotoxicity in rats. Anesthesiology 1997; 86: 160–171, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Kharasch E. D., Hoffman G. M., Thorning D., Hankins D. C., Kilty C. G. Role of the renal cysteine conjugate β‐lyase pathway in inhaled compound A nephrotoxicity in rats. Anesthesiology 1998; 88: 1624–1633, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Kim D‐H., Humphreys W. G., Guengerich F. P. Characterization of S‐[2‐(N1‐adenyl)ethyl]glutathione as an adduct formed in RNA and DNA from 1,2‐dibromoethane. Chem. Res. Toxicol. 1990; 3: 587–594, [PUBMED], [INFOTRIEVE]
- Kubic V. L., Anders M. W. Metabolism of dihalomethanes to carbon monoxide–III. Studies on the mechanisms of the reaction. Biochem. Pharmacol. 1978; 27: 2349–2355, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Lantum H. B.M., Iyer R. A., Anders M. W. Acivicin‐induced alterations in renal and hepatic glutathione concentrations and in γ‐glutamyltransferase activities. Biochem. Pharmacol. 2004; 67: 1421–1426, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Lash L. H., Anders M. W. Cytotoxicity of S‐(1,2‐dichlorovinyl)glutathione and S‐(1,2‐dichlorovinyl)‐L‐cysteine in isolated rat kidney cells. J. Biol. Chem. 1986; 261: 13076–13081, [PUBMED], [INFOTRIEVE]
- Lash L. H., Anders M. W. Mechanism of S‐(1,2‐dichlorovinyl)‐L‐cysteine‐ and S‐(1,2‐dichlorovinyl)‐L‐homocysteine‐induced renal mitochondrial toxicity. Mol. Pharmacol. 1987; 32: 549–556, [PUBMED], [INFOTRIEVE], [CSA]
- Lash L. H., Anders M. W. Uptake of nephrotoxic S‐conjugates by isolated rat renal proximal tubular cells. J. Pharmacol. Exp. Ther. 1989; 248: 531–537, [PUBMED], [INFOTRIEVE], [CSA]
- Livesey J. C., Anders M. W., Langvardt P. W., Putzig C. L., Reitz R. H. Stereochemistry of the glutathione‐dependent biotransformation of vicinal‐dihaloalkanes to alkenes. Drug Metab. Dispos. 1982; 10: 201–204, [PUBMED], [INFOTRIEVE]
- Marsch G. A., Botta S., Martin M. V., McCormick W. A., Guengerich F. P. Formation and mass spectrometric analysis of DNA and nucleoside adducts by S‐(1‐acetoxymethyl)glutathione and by glutathione S‐transferase‐mediated activation of dihalomethanes. Chem. Res. Toxicol. 2004; 17: 45–54, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Martin J. L., Laster M. J., Kandel L., Kerschmann R. L., Reed G. F., Eger E. I., II. Metabolism of compound A by renal cysteine‐S‐conjugate β‐lyase is not the mechanism of compound A‐induced renal injury in the rat. Anesth. Analg. 1996; 82: 770–774, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Martin J. L., Kandel L., Laster M. J., Kerschmann R. L., Eger E. I., II. Studies on the mechanism of nephrotoxicity of compound A in rats. J. Anesthesiol. 1997; 11: 32–37
- Ozawa N., Guengerich F. P. Evidence for formation of an S‐[2‐(N7‐guanyl)ethyl]glutathione adduct in glutathione‐mediated binding of the carcinogen 1,2‐dibromoethane to DNA. Proc. Natl. Acad. Sci. U. S. A. 1983; 80: 5266–5270, [PUBMED], [INFOTRIEVE], [CSA]
- Peterson L. A., Harris T. M., Guengerich F. P. Evidence for an episulfonium ion intermediate in the formation of S‐[2‐(N7‐guanyl)ethyl]glutathione in DNA. J. Am. Chem. Soc. 1988; 110: 3284–3291
- Rannug U., Beije B. The mutagenic effect of 1,2‐dichloroethane on Salmonella typhimurium. II. Activation by the isolated perfused rat liver. Chem. Biol. Interact. 1979; 24: 265–285, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Reitz R. H., Mendrala A. L., Guengerich F. P. In vitro metabolism of methylene chloride in human and animal tissues: use in physiologically based pharmacokinetic models. Toxicol. Appl. Pharmacol. 1989; 97: 230–246, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Schaeffer V. H., Stevens J. L. Mechanism of transport for toxic cysteine conjugates in rat kidney cortex membrane vesicles. Mol. Pharmacol. 1987a; 32: 293–298, [PUBMED], [INFOTRIEVE]
- Schaeffer V. H., Stevens J. L. The transport of S‐cysteine conjugates in LLC‐PK1 cells and its role in toxicity. Mol. Pharmacol. 1987b; 31: 506–512, [PUBMED], [INFOTRIEVE], [CSA]
- Shim J.‐Y., Richard A. M. Theoretical evaluation of two plausible routes for bioactivation of S‐(1,1‐difluoro‐2,2‐dihaloethyl)‐L‐cysteine conjugates: thiirane vs. thionoacyl fluoride pathway. Chem. Res. Toxicol. 1997; 10: 103–110, [PUBMED], [INFOTRIEVE], [CSA]
- Stevens J. L., Robbins J. D., Byrd R. A. A purified cysteine conjugate β‐lyase from rat kidney cytosol. Requirement for an α‐keto acid or an amino acid oxidase for activity and identity with soluble glutamine transaminase K. J. Biol. Chem. 1986a; 261: 15529–15537, [PUBMED], [INFOTRIEVE]
- Stevens J., Hayden P., Taylor G. The role of glutathione conjugate metabolism and cysteine conjugate β‐lyase in the mechanism of S‐cysteine conjugate toxicity in LLC‐PK1 cells. J. Biol. Chem. 1986b; 261: 3325–3332, [PUBMED], [INFOTRIEVE]
- Thier R., Taylor J. B., Pemble S. E., Humphreys W. G., Persmark M., Ketterer B., Guengerich F. P. Expression of mammalian glutathione S‐transferase 5‐5 in Salmonella typhimurium TA1535 leads to base‐pair mutations upon exposure to dihalomethanes. Proc. Natl. Acad. Sci. U. S. A. 1993; 90: 8576–8580, [PUBMED], [INFOTRIEVE], [CSA]
- van Bladeren P. J., van der Gen A., Breimer D. D., Mohn G. R. Stereoselective activation of vicinal dihalogen compounds to mutagens by glutathione conjugation. Biochem. Pharmacol. 1979; 28: 2521–2524, [PUBMED], [INFOTRIEVE], [CROSSREF]
- van Bladeren P. J., Breimer D. D., van Huijgevoort J. A.T.C.M., Vermeulen N. P.E., van der Gen A. The metabolic formation of N‐acetyl‐S‐2‐hydroxyethyl‐L‐cysteine from tetradeutero‐1,2‐dibromoethane. Relative importance of oxidation and glutathione conjugation in vivo. Biochem. Pharmacol. 1981; 30: 2499–2502, [CROSSREF]
- Völkel W., Dekant W. Chlorothioketene, the ultimate reactive intermediate formed by cysteine conjugate β‐lyase‐mediated cleavage of the trichloroethene metabolite S‐(1,2‐Dichlorovinyl)‐L‐cysteine, forms cytosine adducts in organic solvents, but not in aqueous solution. Chem. Res. Toxicol. 1998; 11: 1082–1088, [CSA], [CROSSREF]
- Webb W. W., Elfarra A. A., Webster K. D., Thom R. E., Anders M. W. Role for an episulfonium ion in S‐(2‐chloroethyl)‐DL‐cysteine‐induced cytotoxicity and its reaction with glutathione. Biochemistry 1987; 26: 3017–3023, [PUBMED], [INFOTRIEVE]
- Wheeler J. B., Stourman N. V., Thier R., Dommermuth A., Vuilleumier S., Rose J. A., Armstrong R. N., Guengerich F. P. Conjugation of haloalkanes by bacterial and mammalian glutathione transferases: mono‐ and dihalomethanes. Chem. Res. Toxicol. 2001; 14: 1118–1127, [PUBMED], [INFOTRIEVE], [CSA], [CROSSREF]
- Zhang T.‐L., Wang L., Hashmi M., Anders M. W., Thorpe C., Ridge D. P. Fourier‐transform ion cyclotron resonance mass spectrometric evidence for the formation of α‐chloroethenethiolates and thioketenes from chloroalkene‐derived, cytotoxic 4‐thiaalkanoates. Chem. Res. Toxicol. 1995; 8: 907–910, [PUBMED], [INFOTRIEVE], [CSA]