메뉴 건너뛰기




Volumn 16, Issue 10, 2003, Pages 1287-1297

Detoxication Pathways Involving Glutathione and Epoxide Hydrolase in the in Vitro Metabolism of Chloroprene

Author keywords

[No Author keywords available]

Indexed keywords

(1 CHLOROETHENYL)OXIRANE; 1 CHLORO 4 (GLUTATHIONYL)BUTAN 2 ONE; 1 HYDROXY 4 (GLUTATHIONYL)BUTAN 2 ONE; 1,4 BIS(GLUTATHIONYL)BUTAN 2 ONE; 2 (GLUTATHIONYL)BUTAN 2 ONE; 2 CHLORO 2 ETHENYLOXIRANE; 2 CHLORO 3 HYDROXY 4 (GLUTATHIONYL)BUTENE; ALDEHYDE DERIVATIVE; CLOROFENE; EPOXIDE; EPOXIDE HYDROLASE; ETHYLENE OXIDE; GLUTATHIONE; GLUTATHIONE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0142232002     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034107m     Document Type: Article
Times cited : (28)

References (36)
  • 1
    • 0035369994 scopus 로고    scopus 로고
    • Manufacture and use of chloroprene monomer
    • Lynch, M. (2001) Manufacture and use of chloroprene monomer. Chem.-Biol. Interact. 135/136, 155-167.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 155-167
    • Lynch, M.1
  • 2
    • 0035369988 scopus 로고    scopus 로고
    • Occupational exposure to butadiene, isoprene, and chloroprene
    • Lynch, J. (2001) Occupational exposure to butadiene, isoprene, and chloroprene. Chem.-Biol. Interact. 135/136, 207-214.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 207-214
    • Lynch, J.1
  • 3
    • 0000063228 scopus 로고    scopus 로고
    • Reevaluation of some organic chemicals, hydrazine and hydrogen peroxide
    • International Agency for Research on Cancer, Lyon, France
    • International Agency for Research on Cancer (1999) Reevaluation of some organic chemicals, hydrazine and hydrogen peroxide. In IARC Monographs on the Evaluation of the Carcinogenic Risks to Humans, Vol. 71 (Part 1), pp 227-250, International Agency for Research on Cancer, Lyon, France.
    • (1999) IARC Monographs on the Evaluation of the Carcinogenic Risks to Humans , vol.71 , Issue.PART 1 , pp. 227-250
  • 4
    • 0032903865 scopus 로고    scopus 로고
    • Multiple organ carcinogenicity of inhaled chloroprene (2-chloro-1,3-butadiene) in F344/N rats and B6C3F1 mice and comparison of dose response with 1,3-butadiene in mice
    • Melnick, R. L., Sills, R. C., Portier, C. J., Roycroft, J. H., Chou, B.J., Grumbein, S. L., and Miller, R. A. (1999) Multiple organ carcinogenicity of inhaled chloroprene (2-chloro-1,3-butadiene) in F344/N rats and B6C3F1 mice and comparison of dose response with 1,3-butadiene in mice. Carcinogenesis 20, 867-878.
    • (1999) Carcinogenesis , vol.20 , pp. 867-878
    • Melnick, R.L.1    Sills, R.C.2    Portier, C.J.3    Roycroft, J.H.4    Chou, B.J.5    Grumbein, S.L.6    Miller, R.A.7
  • 5
    • 0035369097 scopus 로고    scopus 로고
    • Comparative carcinogenicity of 1,3-butadiene, isoprene, and chloroprene in rats and mice
    • Melnick, R. L., and Sills, R. C. (2001) Comparative carcinogenicity of 1,3-butadiene, isoprene, and chloroprene in rats and mice. Chem.-Biol. Interact. 135/136, 27-42.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 27-42
    • Melnick, R.L.1    Sills, R.C.2
  • 6
    • 0035369827 scopus 로고    scopus 로고
    • A review of the epidemiology of 1,3-butadiene and chloroprene
    • Acquavella, J. F., and Leonard, R. C. (2001) A review of the epidemiology of 1,3-butadiene and chloroprene. Chem.-Biol. Interact. 135/136, 43-52.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 43-52
    • Acquavella, J.F.1    Leonard, R.C.2
  • 7
    • 0035369996 scopus 로고    scopus 로고
    • A cohort study of workers exposed to chloroprene in the department of Isere, France
    • Colonna, M., and Laydevant, G. (2001) A cohort study of workers exposed to chloroprene in the department of Isere, France. Chem.-Biol. Interact. 135/136, 505-514.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 505-514
    • Colonna, M.1    Laydevant, G.2
  • 10
    • 0035177945 scopus 로고    scopus 로고
    • In vitro metabolism of chloroprene: Species differences, epoxide stereochemistry and a de-chlorination pathway
    • Cottrell, L., Golding, B. T., Munter, T., and Watson, W. P. (2001) In vitro metabolism of chloroprene: species differences, epoxide stereochemistry and a de-chlorination pathway. Chem. Res. Toxicol. 14, 1552-1562.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1552-1562
    • Cottrell, L.1    Golding, B.T.2    Munter, T.3    Watson, W.P.4
  • 11
    • 0035369980 scopus 로고    scopus 로고
    • In vitro genotoxicity testing of (1-chloroethenyl)oxirane, a metabolite of β-chloroprene
    • Himmelstein, M. W., Gladnick, N. L., Donner, E. M., Snyder, R. D., and Valentine, R. (2001) In vitro genotoxicity testing of (1-chloroethenyl)oxirane, a metabolite of β-chloroprene. Chem.-Biol. Interact. 135/136, 703-713.
    • (2001) Chem.-Biol. Interact. , vol.135-136 , pp. 703-713
    • Himmelstein, M.W.1    Gladnick, N.L.2    Donner, E.M.3    Snyder, R.D.4    Valentine, R.5
  • 12
    • 0027964856 scopus 로고
    • Genotoxicity of 2-halosubstituted enals and 2-chloroacrylonitrile in the Ames test and the SOS-chromotest
    • Eder, E., Deininger, C., Deininger, D., and Weinfurtner, E. (1994) Genotoxicity of 2-halosubstituted enals and 2-chloroacrylonitrile in the Ames test and the SOS-chromotest. Mutat. Res. 322, 321-328.
    • (1994) Mutat. Res. , vol.322 , pp. 321-328
    • Eder, E.1    Deininger, C.2    Deininger, D.3    Weinfurtner, E.4
  • 13
    • 12244302243 scopus 로고    scopus 로고
    • Identification of adducts derived from reactions of (1-chloroethenyl)oxirane with nucleosides and calf thymus DNA
    • Munter, T., Cottrell, L., Hill, S., Kronberg, L., Watson, W. P., and Golding, B. T. (2002) Identification of adducts derived from reactions of (1-chloroethenyl)oxirane with nucleosides and calf thymus DNA. Chem. Res. Toxicol. 15, 1549-1560.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1549-1560
    • Munter, T.1    Cottrell, L.2    Hill, S.3    Kronberg, L.4    Watson, W.P.5    Golding, B.T.6
  • 14
    • 0342327333 scopus 로고    scopus 로고
    • The role of human glutathione transferases and epoxide hydrolases in the metabolism of xenobiotics
    • Seidegård, J., and Ekström, G. (1997) The role of human glutathione transferases and epoxide hydrolases in the metabolism of xenobiotics. Environ. Health Perspect. 105 (Suppl. 4), 791-799.
    • (1997) Environ. Health Perspect. , vol.105 , Issue.SUPPL. 4 , pp. 791-799
    • Seidegård, J.1    Ekström, G.2
  • 15
    • 0019170151 scopus 로고
    • Detoxification of chloroprene (2-chloro-1,3-butadiene) with glutathione in the rat
    • Summer, K.-H., and Greim, H. (1980) Detoxification of chloroprene (2-chloro-1,3-butadiene) with glutathione in the rat. Biochem. Biophys. Res. Commun. 96, 566-573.
    • (1980) Biochem. Biophys. Res. Commun. , vol.96 , pp. 566-573
    • Summer, K.-H.1    Greim, H.2
  • 16
    • 0025719230 scopus 로고
    • Mutagenicity of 2-methylacrolein, 2-ethylacrolein and 2-propylacrolein in Salmonella typhimurium TA100. A comparative study
    • Neudecker, T., Eder, E., Deininger, C., and Henschler, D. (1991) Mutagenicity of 2-methylacrolein, 2-ethylacrolein and 2-propylacrolein in Salmonella typhimurium TA100. A comparative study. Mutat. Res. 264, 193-196.
    • (1991) Mutat. Res. , vol.264 , pp. 193-196
    • Neudecker, T.1    Eder, E.2    Deininger, C.3    Henschler, D.4
  • 17
    • 0028018206 scopus 로고
    • Species differences in urinary butadiene metabolites: Comparisons of metabolite ratios between mice, rats, and humans
    • Bechtold, W. E., Strunk, M. R., Chang, I.-Y., Ward, J. B., and Henderson, R. F. (1994) Species differences in urinary butadiene metabolites: comparisons of metabolite ratios between mice, rats, and humans. Toxicol. Appl. Pharmacol. 127, 44-49.
    • (1994) Toxicol. Appl. Pharmacol. , vol.127 , pp. 44-49
    • Bechtold, W.E.1    Strunk, M.R.2    Chang, I.-Y.3    Ward, J.B.4    Henderson, R.F.5
  • 19
    • 0035663082 scopus 로고    scopus 로고
    • Hydroxymethylvinyl ketone: A reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes
    • Krause, R. J., Kemper, R. A., and Elfarra, A. A. (2001) Hydroxymethylvinyl ketone: a reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes. Chem. Res. Toxicol. 14, 1590-1595.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1590-1595
    • Krause, R.J.1    Kemper, R.A.2    Elfarra, A.A.3
  • 20
    • 0015849224 scopus 로고
    • Mammalian epoxide hydrases: Inducible enzymes catalyzing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds
    • Oesch, F. (1973) Mammalian epoxide hydrases: inducible enzymes catalyzing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 3, 305-340.
    • (1973) Xenobiotica , vol.3 , pp. 305-340
    • Oesch, F.1
  • 21
    • 33947484543 scopus 로고
    • Epoxidations with m-chloroperbenzoic acid
    • Schwartz, N. N., and Blumbergs, J. H. (1964) Epoxidations with m-chloroperbenzoic acid. J. Org. Chem. 29, 1976-1979.
    • (1964) J. Org. Chem. , vol.29 , pp. 1976-1979
    • Schwartz, N.N.1    Blumbergs, J.H.2
  • 22
    • 0001644105 scopus 로고
    • The thermally induced rearrangements of 2-vinyloxirane
    • Crawford, R. J., Lutener, S. B., and Cockcroft, R. D. (1976) The thermally induced rearrangements of 2-vinyloxirane. Can. J. Chem. 54, 3364-3376.
    • (1976) Can. J. Chem. , vol.54 , pp. 3364-3376
    • Crawford, R.J.1    Lutener, S.B.2    Cockcroft, R.D.3
  • 23
    • 33847086841 scopus 로고
    • 1-(Arylthio)cyclopro-panecarboxaldehydes. Conjunctive reagents for secoalkylation
    • Trost, B. M., and Jungheim, L. N. (1980) 1-(Arylthio)cyclopro-panecarboxaldehydes. Conjunctive reagents for secoalkylation. J. Am. Chem. Soc. 102, 7910-7925.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7910-7925
    • Trost, B.M.1    Jungheim, L.N.2
  • 25
    • 0027223845 scopus 로고
    • Glutathione and N-acetylcysteine inactivations of mutagenic 2(5H)-furanones from the chlorination of humics in water
    • LaLonde, R. T., and Xie, S. (1993) Glutathione and N-acetylcysteine inactivations of mutagenic 2(5H)-furanones from the chlorination of humics in water. Chem. Res. Toxicol. 6, 445-451.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 445-451
    • LaLonde, R.T.1    Xie, S.2
  • 26
    • 0028181096 scopus 로고
    • α,β-Unsaturated carbonyl compounds: Inhibition of rat liver glutathione S-transferase isozymes and chemical reaction with reduced glutathione
    • Chien, C., Kirollos, K. S., Linderman, R. J., and Dauterman, W. C. (1994) α,β-Unsaturated carbonyl compounds: inhibition of rat liver glutathione S-transferase isozymes and chemical reaction with reduced glutathione. Biochim. Biophys. Acta 1204, 175-180.
    • (1994) Biochim. Biophys. Acta , vol.1204 , pp. 175-180
    • Chien, C.1    Kirollos, K.S.2    Linderman, R.J.3    Dauterman, W.C.4
  • 28
    • 0025368304 scopus 로고
    • Metabolic activation of 1,2-dibromo-3-chloropropane: Evidence for the formation of reactive episulfonium ion intermediates
    • Pearson, P. G., Soderlund, E. J., Dybing, E., and Nelson, S. D. (1990) Metabolic activation of 1,2-dibromo-3-chloropropane: evidence for the formation of reactive episulfonium ion intermediates. Biochemistry 29, 4971-4981.
    • (1990) Biochemistry , vol.29 , pp. 4971-4981
    • Pearson, P.G.1    Soderlund, E.J.2    Dybing, E.3    Nelson, S.D.4
  • 31
    • 0003322295 scopus 로고
    • Synthesis and PMR properties of some dehydroalanine derivatives
    • Asquith, R. S., and Carthew, P. (1972) Synthesis and PMR properties of some dehydroalanine derivatives. Tetrahedron 28, 4769-4773.
    • (1972) Tetrahedron , vol.28 , pp. 4769-4773
    • Asquith, R.S.1    Carthew, P.2
  • 32
    • 0020615804 scopus 로고
    • The formation of dehydroalanine residues in alkali-treated insulin and oxidized glutathione
    • Jones, A. J., Helmerhorst, E., and Stokes, G. B. (1983) The formation of dehydroalanine residues in alkali-treated insulin and oxidized glutathione. Biochem. J. 211, 499-502.
    • (1983) Biochem. J. , vol.211 , pp. 499-502
    • Jones, A.J.1    Helmerhorst, E.2    Stokes, G.B.3
  • 34
    • 0028223369 scopus 로고
    • Stereoselectivity of in vitro isoprene metabolism
    • Wistuba, D., Weigand, K., and Peter, H. (1994) Stereoselectivity of in vitro isoprene metabolism. Chem. Res. Toxicol. 7, 336-343.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 336-343
    • Wistuba, D.1    Weigand, K.2    Peter, H.3
  • 35
    • 0029116450 scopus 로고
    • Disposition of butadiene manoepoxide and butadiene diepoxide in various tissues of rats and mice following a low-level inhalation exposure to 1,3-butadiene
    • Thornton-Manning, J. R., Dahl, A. R., Bechtold, W. E., and Henderson, R. F. (1995) Disposition of butadiene manoepoxide and butadiene diepoxide in various tissues of rats and mice following a low-level inhalation exposure to 1,3-butadiene. Carcinogenesis 16, 1723-1731.
    • (1995) Carcinogenesis , vol.16 , pp. 1723-1731
    • Thornton-Manning, J.R.1    Dahl, A.R.2    Bechtold, W.E.3    Henderson, R.F.4
  • 36
    • 0026741034 scopus 로고
    • Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans rats and mice
    • Csanàdy, G. A., Guengerich, F. P., and Bond, J. A. (1992) Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans rats and mice. Carcinogenesis 13, 1143-1153.
    • (1992) Carcinogenesis , vol.13 , pp. 1143-1153
    • Csanàdy, G.A.1    Guengerich, F.P.2    Bond, J.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.