메뉴 건너뛰기




Volumn 36, Issue 3-4, 2004, Pages 583-594

Glutathione-dependent bioactivation of haloalkanes and haloalkenes

Author keywords

Betalyase; Glutathione; Glutathione transferase; Haloalkanes; Haloalkenes

Indexed keywords

1,2 DIBROMOETHANE; 1,2 DICHLOROETHANE; ALKANE DERIVATIVE; CHLOROTRIFLUOROETHYLENE; CYSTEINE CONJUGATE BETA LYASE; CYTOCHROME P450; DICHLOROMETHANE; GLUTATHIONE; GLUTATHIONE DERIVATIVE; GLUTATHIONE TRANSFERASE; HALOGENATED HYDROCARBON; HALOOLEFIN; HEXACHLOROBUTADIENE; KETENE DERIVATIVE; SULFONIUM DERIVATIVE; TETRAFLUOROETHYLENE; THIOL DERIVATIVE; TRICHLOROETHYLENE; UNCLASSIFIED DRUG;

EID: 7544236966     PISSN: 03602532     EISSN: None     Source Type: Journal    
DOI: 10.1081/DMR-200033451     Document Type: Review
Times cited : (59)

References (61)
  • 2
    • 0018176867 scopus 로고
    • Metabolism of dihalomethanes to formaldehyde and inorganic halide. II. Studies on the mechanism of the reaction
    • Ahmed, A. E., Anders, M. W. (1978). Metabolism of dihalomethanes to formaldehyde and inorganic halide. II. Studies on the mechanism of the reaction. Biochem. Pharmacol. 27:2021-2025.
    • (1978) Biochem. Pharmacol. , vol.27 , pp. 2021-2025
    • Ahmed, A.E.1    Anders, M.W.2
  • 3
    • 0031748545 scopus 로고    scopus 로고
    • Glutathione-dependent bioactivation of haloalkenes
    • Anders, M. W., Dekant, W. (1998). Glutathione-dependent bioactivation of haloalkenes. Annu. Rev. Pharmacol. Toxicol. 38:501-537.
    • (1998) Annu. Rev. Pharmacol. Toxicol. , vol.38 , pp. 501-537
    • Anders, M.W.1    Dekant, W.2
  • 4
    • 9944244304 scopus 로고    scopus 로고
    • 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
    • Casanova, M., Bell, D. A., Heck, H. d. A. (1997). 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. 37:168-180.
    • (1997) Fundam. Appl. Toxicol. , vol.37 , pp. 168-180
    • Casanova, M.1    Bell, D.A.2    Heck, H.D.A.3
  • 5
    • 0025685477 scopus 로고
    • The mechanism of cysteine conjugate cytotoxicity in renal epithelial cells. Covalent binding leads to thiol depletion and lipid peroxidation
    • Chen, Q., Jones, T. W., Brown, P. C., Stevens, J. L. (1990). The mechanism of cysteine conjugate cytotoxicity in renal epithelial cells. Covalent binding leads to thiol depletion and lipid peroxidation. J. Biol. Chem. 265:21603-21611.
    • (1990) J. Biol. Chem. , vol.265 , pp. 21603-21611
    • Chen, Q.1    Jones, T.W.2    Brown, P.C.3    Stevens, J.L.4
  • 6
    • 0026657542 scopus 로고
    • Mutation spectrum and sequence alkylation selectivity resulting from modification of bacteriophage M13mp18 DNA with S-(2-chloroethyl)glutathione
    • Cmarik, J. L., Humphreys, W. G., Bruner, K. L., Lloyd, R. S., Tibbetts, C., Guengerich, F. P. (1992). Mutation spectrum and sequence alkylation selectivity resulting from modification of bacteriophage M13mp18 DNA with S-(2-chloroethyl)glutathione. J. Biol. Chem. 267:6672-6679.
    • (1992) J. Biol. Chem. , vol.267 , pp. 6672-6679
    • Cmarik, J.L.1    Humphreys, W.G.2    Bruner, K.L.3    Lloyd, R.S.4    Tibbetts, C.5    Guengerich, F.P.6
  • 7
    • 0024268840 scopus 로고
    • Nephrotoxicity of mercapturic acids of three structurally related 2, 2-difluoroethylenes in the rat
    • Commandeur, J. N. M., Brakenhoff, J. P. G., De Kanter, F. J. J., Vermeulen, N. P. E. (1988). Nephrotoxicity of mercapturic acids of three structurally related 2, 2-difluoroethylenes in the rat. Biochem. Pharmacol. 37:4495-4504.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 4495-4504
    • Commandeur, J.N.M.1    Brakenhoff, J.P.G.2    De Kanter, F.J.J.3    Vermeulen, N.P.E.4
  • 8
    • 0029958578 scopus 로고    scopus 로고
    • 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
    • Commandeur, J. N. M., King, L. J., Koymans, L., Vermeulen, N. P. E. (1996). 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. 9:1092-1102.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1092-1102
    • Commandeur, J.N.M.1    King, L.J.2    Koymans, L.3    Vermeulen, N.P.E.4
  • 9
    • 0037103561 scopus 로고    scopus 로고
    • Toxic, halogenated cysteine S-conjugates and targeting of mitochondrial enzymes of energy metabolism
    • Cooper, A., Bruschi, S., Anders, M. (2002). Toxic, halogenated cysteine S-conjugates and targeting of mitochondrial enzymes of energy metabolism. Biochem. Pharmacol. 64:553-564.
    • (2002) Biochem. Pharmacol. , vol.64 , pp. 553-564
    • Cooper, A.1    Bruschi, S.2    Anders, M.3
  • 10
    • 0033958342 scopus 로고    scopus 로고
    • Role of cytochrome P450 and glutathione S-transferase alpha in the metabolism and cytotoxicity of trichloroethylene in rat kidney
    • Cummings, B. S., Parker, J. C., Lash, L. H. (2000). Role of cytochrome P450 and glutathione S-transferase alpha in the metabolism and cytotoxicity of trichloroethylene in rat kidney. Biochem. Pharmacol. 59:531-543.
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 531-543
    • Cummings, B.S.1    Parker, J.C.2    Lash, L.H.3
  • 11
    • 0023753913 scopus 로고
    • Effects of AT-125 on the nephrotoxicity of hexachloro-1, 3-butadiene in rats
    • Davis, M. E. (1988). Effects of AT-125 on the nephrotoxicity of hexachloro-1, 3-butadiene in rats. Toxicol. Appl. Pharmacol. 95:44-52.
    • (1988) Toxicol. Appl. Pharmacol. , vol.95 , pp. 44-52
    • Davis, M.E.1
  • 12
    • 0023447097 scopus 로고
    • Bioactivation mechanism of the cytotoxic and nephrotoxic S-conjugate S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine
    • Dekant, W., Lash, L. H., Anders, M. W. (1987). 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. 84:7443-7447.
    • (1987) Proc. Natl. Acad. Sci. U. S. A. , vol.84 , pp. 7443-7447
    • Dekant, W.1    Lash, L.H.2    Anders, M.W.3
  • 13
    • 0023937244 scopus 로고
    • 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
    • Dekant, W., Berthold, K., Vamvakas, S., Henschler, D., Anders, M. W. (1988). 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. 1:175-178.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 175-178
    • Dekant, W.1    Berthold, K.2    Vamvakas, S.3    Henschler, D.4    Anders, M.W.5
  • 14
    • 0024604605 scopus 로고
    • Bioactivation of nephrotoxic haloalkenes by glutathione conjugation: Formation of toxic and mutagenic intermediates by cysteine conjugate β-lyase
    • Dekant, W., Vamvakas, S., Anders, M. W. (1989). Bioactivation of nephrotoxic haloalkenes by glutathione conjugation: formation of toxic and mutagenic intermediates by cysteine conjugate β-lyase. Drug Metab. Rev. 20:43-83.
    • (1989) Drug Metab. Rev. , vol.20 , pp. 43-83
    • Dekant, W.1    Vamvakas, S.2    Anders, M.W.3
  • 15
    • 0000666578 scopus 로고
    • Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: Models for biological reactive intermediates of cytotoxic S-conjugates
    • Dekant, W., Urban, G., Görsmann, C., Anders, M. W. (1991). Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S-conjugates. J. Am. Chem. Soc. 113:5120-5122.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5120-5122
    • Dekant, W.1    Urban, G.2    Görsmann, C.3    Anders, M.W.4
  • 16
    • 0028190695 scopus 로고
    • Formation and fate of nephrotoxic and cytotoxic glutathione S-conjugates: Cysteine conjugate β-lyase pathway
    • Dekant, W., Vamvakas, S., Anders, M. W. (1994). Formation and fate of nephrotoxic and cytotoxic glutathione S-conjugates: cysteine conjugate β-lyase pathway. Adv. Pharmacol. 27:115-162.
    • (1994) Adv. Pharmacol. , vol.27 , pp. 115-162
    • Dekant, W.1    Vamvakas, S.2    Anders, M.W.3
  • 17
    • 0001086729 scopus 로고
    • Thiiranium ion intermediates in the formation and reactions of S-(2-haloethyl)-L-cysteines
    • Dohn, D. R., Casida, J. E. (1987). Thiiranium ion intermediates in the formation and reactions of S-(2-haloethyl)-L-cysteines. Bioorg. Chem. 15:115-124.
    • (1987) Bioorg. Chem. , vol.15 , pp. 115-124
    • Dohn, D.R.1    Casida, J.E.2
  • 18
    • 0021979132 scopus 로고
    • Structure-nephrotoxicity relationships of S-(2-chloroethyl)-DL-cysteine and analogs: Role for an episulfonium ion
    • Elfarra, A. A., Baggs, R. B., Anders, M. W. (1985). Structure- nephrotoxicity relationships of S-(2-chloroethyl)-DL-cysteine and analogs: role for an episulfonium ion. J. Pharmacol. Exp. Ther. 233:512-516.
    • (1985) J. Pharmacol. Exp. Ther. , vol.233 , pp. 512-516
    • Elfarra, A.A.1    Baggs, R.B.2    Anders, M.W.3
  • 19
    • 0022492563 scopus 로고
    • Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity
    • Elfarra, A. A., Jakobson, I., Anders, M. W. (1986). Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. Biochem. Pharmacol. 35:283-288.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 283-288
    • Elfarra, A.A.1    Jakobson, I.2    Anders, M.W.3
  • 20
    • 0026772846 scopus 로고
    • Nephrotoxicity of the glutathione and cysteine conjugates of 2-bromo-2-chloro-1,1-difluoroethene
    • Finkelstein, M. B., Baggs, R. B., Anders, M. W. (1992). Nephrotoxicity of the glutathione and cysteine conjugates of 2-bromo-2-chloro-1,1-difluoroethene. J. Pharmacol. Exp. Ther. 261:1248-1252.
    • (1992) J. Pharmacol. Exp. Ther. , vol.261 , pp. 1248-1252
    • Finkelstein, M.B.1    Baggs, R.B.2    Anders, M.W.3
  • 21
    • 0028350975 scopus 로고
    • Structure-mutagenicity and structure-cytotoxicity studies on bromine-containing cysteine S-conjugates and related compounds
    • Finkelstein, M. B., Vamvakas, S., Bittner, D., Anders, M. W. (1994). Structure-mutagenicity and structure-cytotoxicity studies on bromine-containing cysteine S-conjugates and related compounds. Chem. Res. Toxicol. 7:157-163.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 157-163
    • Finkelstein, M.B.1    Vamvakas, S.2    Bittner, D.3    Anders, M.W.4
  • 22
    • 0028982297 scopus 로고
    • α-Thiolactones as novel intermediates in the cysteine conjugate β-lyase-catalyzed bioactivation of bromine-containing cysteine S-conjugates
    • Finkelstein, M. B., Dekant, W., Kende, A. S., Anders, M. W. (1995). α-Thiolactones as novel intermediates in the cysteine conjugate β-lyase-catalyzed bioactivation of bromine-containing cysteine S-conjugates. J. Am. Chem. Soc. 117:9590-9591.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9590-9591
    • Finkelstein, M.B.1    Dekant, W.2    Kende, A.S.3    Anders, M.W.4
  • 23
    • 0030053915 scopus 로고    scopus 로고
    • Cysteine conjugate β-lyase-catalyzed bioactivation of bromine-containing cysteine S-conjugates: Stoichiometry and formation of 2,2-difluoro-3-halothiiranes
    • Finkelstein, M. B., Dekant, W., Anders, M. W. (1996). Cysteine conjugate β-lyase-catalyzed bioactivation of bromine-containing cysteine S-conjugates: stoichiometry and formation of 2,2-difluoro-3-halothiiranes. Chem. Res. Toxicol. 9:227-231.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 227-231
    • Finkelstein, M.B.1    Dekant, W.2    Anders, M.W.3
  • 24
    • 0038544198 scopus 로고    scopus 로고
    • Activation of dihaloalkanes by thiol-dependent mechanisms
    • Guengerich, F. P. (2003). Activation of dihaloalkanes by thiol-dependent mechanisms. J. Biochem. Mol. Biol. 36:20-27.
    • (2003) J. Biochem. Mol. Biol. , vol.36 , pp. 20-27
    • Guengerich, F.P.1
  • 26
    • 0025935633 scopus 로고
    • Immunochemical detection of covalently modified kidney proteins in S-(1,1,2,2-tetrafluoroethyl)-L-cysteine-treated rats
    • Hargus, S. J., Anders, M. W. (1991). Immunochemical detection of covalently modified kidney proteins in S-(1,1,2,2-tetrafluoroethyl)-L-cysteine- treated rats. Biochem. Pharmacol. 42:R17-R20.
    • (1991) Biochem. Pharmacol. , vol.42
    • Hargus, S.J.1    Anders, M.W.2
  • 29
    • 0026832048 scopus 로고
    • Formation of mitochondrial phospholipid adducts by nephrotoxic cysteine conjugate metabolites
    • Hayden, P. J., Welsh, C. J., Yang, Y., Schaefer, W. H., Ward, A. J. I., Stevens, J. L. (1992). Formation of mitochondrial phospholipid adducts by nephrotoxic cysteine conjugate metabolites. Chem. Res. Toxicol. 5:231-237.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 231-237
    • Hayden, P.J.1    Welsh, C.J.2    Yang, Y.3    Schaefer, W.H.4    Ward, A.J.I.5    Stevens, J.L.6
  • 31
    • 0021241496 scopus 로고
    • Glutathione-mediated binding of dibromoalkanes to DNA: Specificity of rat glutathione S-transferases and dibromoalkane structure
    • Inskeep, P. B., Guengerich, F. P. (1984). Glutathione-mediated binding of dibromoalkanes to DNA: specificity of rat glutathione S-transferases and dibromoalkane structure. Carcinogenesis 5:805-808.
    • (1984) Carcinogenesis , vol.5 , pp. 805-808
    • Inskeep, P.B.1    Guengerich, F.P.2
  • 32
    • 0036667457 scopus 로고    scopus 로고
    • Structure-activity relationship for the biotransformation of haloalkenes by rat liver microsomal glutathione transferase 1
    • Jolivette, L. J., Anders, M. W. (2002). Structure-activity relationship for the biotransformation of haloalkenes by rat liver microsomal glutathione transferase 1. Chem. Res. Toxicol. 15:1036-1041.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1036-1041
    • Jolivette, L.J.1    Anders, M.W.2
  • 33
    • 0037328128 scopus 로고    scopus 로고
    • Computational and experimental studies on the distribution of addition and substitution products of the microsomal glutathione transferase 1-catalyzed conjugation of glutathione with fluoroalkenes
    • Jolivette, L. J., Anders, M. W. (2003). 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. 16:137-144.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 137-144
    • Jolivette, L.J.1    Anders, M.W.2
  • 34
    • 0031020994 scopus 로고    scopus 로고
    • Role of renal cysteine conjugate β-lyase in the mechanism of compound A nephrotoxicity in rats
    • Kharasch, E. D., Thorning, D., Garton, K., Hankins, D. C., Kilty, G. C. (1997). Role of renal cysteine conjugate β-lyase in the mechanism of compound A nephrotoxicity in rats. Anesthesiology 86:160-171.
    • (1997) Anesthesiology , vol.86 , pp. 160-171
    • Kharasch, E.D.1    Thorning, D.2    Garton, K.3    Hankins, D.C.4    Kilty, G.C.5
  • 35
    • 0031777738 scopus 로고    scopus 로고
    • Role of the renal cysteine conjugate β-lyase pathway in inhaled compound A nephrotoxicity in rats
    • Kharasch, E. D., Hoffman, G. M., Thorning, D., Hankins, D. C., Kilty, C. G. (1998). Role of the renal cysteine conjugate β-lyase pathway in inhaled compound A nephrotoxicity in rats. Anesthesiology 88:1624-1633.
    • (1998) Anesthesiology , vol.88 , pp. 1624-1633
    • Kharasch, E.D.1    Hoffman, G.M.2    Thorning, D.3    Hankins, D.C.4    Kilty, C.G.5
  • 36
    • 0025204386 scopus 로고
    • 1-adenyl)ethyl]glutathione as an adduct formed in RNA and DNA from 1, 2-dibromoethane
    • 1-adenyl)ethyl]glutathione as an adduct formed in RNA and DNA from 1, 2-dibromoethane. Chem. Res. Toxicol. 3:587-594.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 587-594
    • Kim, D.-H.1    Humphreys, W.G.2    Guengerich, F.P.3
  • 37
    • 0018085060 scopus 로고
    • Metabolism of dihalomethanes to carbon monoxide-III. Studies on the mechanisms of the reaction
    • Kubic, V. L., Anders, M. W. (1978). Metabolism of dihalomethanes to carbon monoxide-III. Studies on the mechanisms of the reaction. Biochem. Pharmacol. 27:2349-2355.
    • (1978) Biochem. Pharmacol. , vol.27 , pp. 2349-2355
    • Kubic, V.L.1    Anders, M.W.2
  • 38
    • 1542285469 scopus 로고    scopus 로고
    • Acivicin-induced alterations in renal and hepatic glutathione concentrations and in β-glutamyltransferase activities
    • Lantum, H. B. M., Iyer, R. A., Anders, M. W. (2004). Acivicin-induced alterations in renal and hepatic glutathione concentrations and in β-glutamyltransferase activities. Biochem. Pharmacol. 67:1421-1426.
    • (2004) Biochem. Pharmacol. , vol.67 , pp. 1421-1426
    • Lantum, H.B.M.1    Iyer, R.A.2    Anders, M.W.3
  • 39
    • 0022870699 scopus 로고
    • Cytotoxicity of 5-(1,2-dichlorovinyl)glutathione and S-(1,2- dichlorovinyl)-L-cysteine in isolated rat kidney cells
    • Lash, L. H., Anders, M. W. (1986). Cytotoxicity of 5-(1,2-dichlorovinyl) glutathione and S-(1,2-dichlorovinyl)-L-cysteine in isolated rat kidney cells. J. Biol. Chem. 261:13076-13081.
    • (1986) J. Biol. Chem. , vol.261 , pp. 13076-13081
    • Lash, L.H.1    Anders, M.W.2
  • 40
    • 0023492515 scopus 로고
    • Mechanism of S-(1,2-dichlorovinyl)-L-cysteine- and S-(1,2-dichlorovinyl)- L-homocysteine-induced renal mitochondrial toxicity
    • Lash, L. H., Anders, M. W. (1987). Mechanism of S-(1,2-dichlorovinyl)-L- cysteine- and S-(1,2-dichlorovinyl)-L-homocysteine-induced renal mitochondrial toxicity. Mol. Pharmacol. 32:549-556.
    • (1987) Mol. Pharmacol. , vol.32 , pp. 549-556
    • Lash, L.H.1    Anders, M.W.2
  • 41
    • 0024513664 scopus 로고
    • Uptake of nephrotoxic S-conjugates by isolated rat renal proximal tubular cells
    • Lash, L. H., Anders, M. W. (1989). Uptake of nephrotoxic S-conjugates by isolated rat renal proximal tubular cells. J. Pharmacol. Exp. Ther. 248:531-537.
    • (1989) J. Pharmacol. Exp. Ther. , vol.248 , pp. 531-537
    • Lash, L.H.1    Anders, M.W.2
  • 42
    • 0019958662 scopus 로고
    • Stereochemistry of the glutathione-dependent biotransformation of vicinal-dihaloalkanes to alkenes
    • Livesey, J. C., Anders, M. W., Langvardt, P. W., Putzig, C. L., Reitz, R. H. (1982). Stereochemistry of the glutathione-dependent biotransformation of vicinal-dihaloalkanes to alkenes. Drug Metab. Dispos. 10:201-204.
    • (1982) Drug Metab. Dispos. , vol.10 , pp. 201-204
    • Livesey, J.C.1    Anders, M.W.2    Langvardt, P.W.3    Putzig, C.L.4    Reitz, R.H.5
  • 43
    • 1642539123 scopus 로고    scopus 로고
    • Formation and mass spectrometric analysis of DNA and nucleoside adducts by S-(1-acetoxymethyl)glutathione and by glutathione S-transferase-mediated activation of dihalomethanes
    • Marsch, G. A., Botta, S., Martin, M. V., McCormick, W. A., Guengerich, F. P. (2004). 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. 17:45-54.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 45-54
    • Marsch, G.A.1    Botta, S.2    Martin, M.V.3    McCormick, W.A.4    Guengerich, F.P.5
  • 44
    • 0029916396 scopus 로고    scopus 로고
    • Metabolism of compound A by renal cysteine-S-conjugate β-lyase is not the mechanism of compound A-induced renal injury in the rat
    • Martin, J. L., Laster, M. J., Kandel, L., Kerschmann, R. L., Reed, G. F., Eger, E. I. II. (1996). 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. 82:770-774.
    • (1996) Anesth. Analg. , vol.82 , pp. 770-774
    • Martin, J.L.1    Laster, M.J.2    Kandel, L.3    Kerschmann, R.L.4    Reed, G.F.5    Eger II, E.I.6
  • 46
    • 0008252723 scopus 로고
    • 7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of the carcinogen 1,2-dibromoethane to DNA
    • 7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of the carcinogen 1,2-dibromoethane to DNA. Proc. Natl. Acad. Sci. U. S. A. 80:5266-5270.
    • (1983) Proc. Natl. Acad. Sci. U. S. A. , vol.80 , pp. 5266-5270
    • Ozawa, N.1    Guengerich, F.P.2
  • 48
    • 0018425602 scopus 로고
    • The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. II. Activation by the isolated perfused rat liver
    • Rannug, U., Beije, B. (1979). The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. II. Activation by the isolated perfused rat liver. Chem. Biol. Interact. 24:265-285.
    • (1979) Chem. Biol. Interact. , vol.24 , pp. 265-285
    • Rannug, U.1    Beije, B.2
  • 49
    • 0024515167 scopus 로고
    • In vitro metabolism of methylene chloride in human and animal tissues: Use in physiologically based pharmacokinetic models
    • Reitz, R. H., Mendrala, A. L., Guengerich, F. P. (1989). In vitro metabolism of methylene chloride in human and animal tissues: use in physiologically based pharmacokinetic models. Toxicol. Appl. Pharmacol. 97:230-246.
    • (1989) Toxicol. Appl. Pharmacol. , vol.97 , pp. 230-246
    • Reitz, R.H.1    Mendrala, A.L.2    Guengerich, F.P.3
  • 50
    • 0023546625 scopus 로고
    • Mechanism of transport for toxic cysteine conjugates in rat kidney cortex membrane vesicles
    • Schaeffer, V. H., Stevens, J. L. (1987a). Mechanism of transport for toxic cysteine conjugates in rat kidney cortex membrane vesicles. Mol. Pharmacol. 32:293-298.
    • (1987) Mol. Pharmacol. , vol.32 , pp. 293-298
    • Schaeffer, V.H.1    Stevens, J.L.2
  • 51
    • 0023228063 scopus 로고
    • The transport of S-cysteine conjugates in LLC-PK1 cells and its role in toxicity
    • Schaeffer, V. H., Stevens, J. L. (1987b). The transport of S-cysteine conjugates in LLC-PK1 cells and its role in toxicity. Mol. Pharmacol. 31:506-512.
    • (1987) Mol. Pharmacol. , vol.31 , pp. 506-512
    • Schaeffer, V.H.1    Stevens, J.L.2
  • 52
    • 0031012632 scopus 로고    scopus 로고
    • Theoretical evaluation of two plausible routes for bioactivation of S-(1,1-difluoro-2,2-dihaloethyl)-L-cysteine conjugates: Thiirane vs. thionoacyl fluoride pathway
    • Shim, J.-Y., Richard, A. M. (1997). 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. 10:103-110.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 103-110
    • Shim, J.-Y.1    Richard, A.M.2
  • 53
    • 0022979951 scopus 로고
    • 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
    • Stevens, J. L., Robbins, J. D., Byrd, R. A. (1986a). 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. 261:15529-15537.
    • (1986) J. Biol. Chem. , vol.261 , pp. 15529-15537
    • Stevens, J.L.1    Robbins, J.D.2    Byrd, R.A.3
  • 54
    • 0023031995 scopus 로고
    • The role of glutathione conjugate metabolism and cysteine conjugate β-lyase in the mechanism of S-cysteine conjugate toxicity in LLC-PK1 cells
    • Stevens, J., Hayden, P., Taylor, G. (1986b). 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. 261:3325-3332.
    • (1986) J. Biol. Chem. , vol.261 , pp. 3325-3332
    • Stevens, J.1    Hayden, P.2    Taylor, G.3
  • 55
    • 0027321555 scopus 로고
    • Expression of mammalian glutathione S-transferase 5-5 in Salmonella typhimurium TA1535 leads to base-pair mutations upon exposure to dihalomethanes
    • Thier, R., Taylor, J. B., Pemble, S. E., Humphreys, W. G., Persmark, M., Ketterer, B., Guengerich, F. P. (1993). 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. 90:8576-8580.
    • (1993) Proc. Natl. Acad. Sci. U. S. A. , vol.90 , pp. 8576-8580
    • Thier, R.1    Taylor, J.B.2    Pemble, S.E.3    Humphreys, W.G.4    Persmark, M.5    Ketterer, B.6    Guengerich, F.P.7
  • 56
    • 0018724657 scopus 로고
    • Stereoselective activation of vicinal dihalogen compounds to mutagens by glutathione conjugation
    • van Bladeren, P. J., van der Gen, A., Breimer, D. D., Mohn, G. R. (1979). Stereoselective activation of vicinal dihalogen compounds to mutagens by glutathione conjugation. Biochem. Pharmacol. 28:2521-2524.
    • (1979) Biochem. Pharmacol. , vol.28 , pp. 2521-2524
    • Van Bladeren, P.J.1    Van Der Gen, A.2    Breimer, D.D.3    Mohn, G.R.4
  • 57
    • 0019404603 scopus 로고
    • 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
    • van Bladeren, P. J., Breimer, D. D., van Huijgevoort, J. A. T. C. M., Vermeulen, N. P. E., van der Gen, A. (1981). 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. 30:2499-2502.
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 2499-2502
    • Van Bladeren, P.J.1    Breimer, D.D.2    Van Huijgevoort, J.A.T.C.M.3    Vermeulen, N.P.E.4    Van Der Gen, A.5
  • 58
    • 0031670446 scopus 로고    scopus 로고
    • 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
    • Völkel, W., Dekant, W. (1998). 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. 11:1082-1088.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1082-1088
    • Völkel, W.1    Dekant, W.2
  • 59
    • 0023642305 scopus 로고
    • Role for an episulfonium ion in S-(2-chloroethyl)-DL-cysteine-induced cytotoxicity and its reaction with glutathione
    • Webb, W. W., Elfarra, A. A., Webster, K. D., Thom, R. E., Anders, M. W. (1987). Role for an episulfonium ion in S-(2-chloroethyl)-DL-cysteine-induced cytotoxicity and its reaction with glutathione. Biochemistry 26:3017-3023.
    • (1987) Biochemistry , vol.26 , pp. 3017-3023
    • Webb, W.W.1    Elfarra, A.A.2    Webster, K.D.3    Thom, R.E.4    Anders, M.W.5
  • 61
    • 0028802455 scopus 로고
    • Fourier-transform ion cyclotron resonance mass spectrometric evidence for the formation of α-chloroethenethiolates and thioketenes from chloroalkene-derived, cytotoxic 4-thiaalkanoates
    • Zhang, T.-L., Wang, L., Hashmi, M., Anders, M. W., Thorpe, C., Ridge, D. P. (1995). 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. 8:907-910.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 907-910
    • Zhang, T.-L.1    Wang, L.2    Hashmi, M.3    Anders, M.W.4    Thorpe, C.5    Ridge, D.P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.