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Volumn 36, Issue 1, 2003, Pages 20-27

Activation of dihaloalkanes by thiol-dependent mechanisms

Author keywords

Bioactivation; Dihalomethanes; Ethylene dibromide; Glutathione; Mutations; O6 Alkylguanine transferase

Indexed keywords

1,2 DIBROMOETHANE; ALKANE DERIVATIVE; GLUTATHIONE; METHANE; THIOL DERIVATIVE; TRANSFERASE; HALOGENATED HYDROCARBON; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE;

EID: 0038544198     PISSN: 12258687     EISSN: None     Source Type: Journal    
DOI: 10.5483/bmbrep.2003.36.1.020     Document Type: Review
Times cited : (47)

References (51)
  • 1
    • 0031408141 scopus 로고    scopus 로고
    • Bacterial and mammalian DNA alkyltransferases sensitize Escherichia coli to the lethal and mutagenic effects of dibromoalkanes
    • Abril, N., Luque-Romero, F. L., Prieto-Alamo, M.-J., Rafferty, J. A., Margison, G. P. and Pueyo, C. (1997) Bacterial and mammalian DNA alkyltransferases sensitize Escherichia coli to the lethal and mutagenic effects of dibromoalkanes. Carcinogenesis 18, 1883-1888.
    • (1997) Carcinogenesis , vol.18 , pp. 1883-1888
    • Abril, N.1    Luque-Romero, F.L.2    Prieto-Alamo, M.-J.3    Rafferty, J.A.4    Margison, G.P.5    Pueyo, C.6
  • 2
    • 0028987529 scopus 로고
    • ogt alkyltransferase enhances dibromoalkane mutagenicity in excision repair-deficient Escherichia coli K-12
    • Abril, N., Luqueromero, F. L., Prieto-Alamo, M. J., Margison, G. P. and Pueyo, C. (1995) ogt alkyltransferase enhances dibromoalkane mutagenicity in excision repair-deficient Escherichia coli K-12. Mol. Carcinogen. 12, 110-117.
    • (1995) Mol. Carcinogen. , vol.12 , pp. 110-117
    • Abril, N.1    Luqueromero, F.L.2    Prieto-Alamo, M.J.3    Margison, G.P.4    Pueyo, C.5
  • 3
    • 0032979605 scopus 로고    scopus 로고
    • 6-alkylguanine-DNA alkyltransferases are hypersensitive to dibromoalkanes
    • 6-alkylguanine-DNA alkyltransferases are hypersensitive to dibromoalkanes. Chem. Res. Toxicol. 12, 544-551.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 544-551
    • Abril, N.1    Margison, G.P.2
  • 4
    • 0017186325 scopus 로고
    • Metabolism of dihalomethanes to formaldehyde and inorganic halide. I. In vitro studies
    • Ahmed, A. E. and Anders, M. W. (1976) Metabolism of dihalomethanes to formaldehyde and inorganic halide. I. In vitro studies. Drug Metab. Dispos. 4, 357-361.
    • (1976) Drug Metab. Dispos. , vol.4 , pp. 357-361
    • Ahmed, A.E.1    Anders, M.W.2
  • 5
    • 0017574137 scopus 로고
    • Metabolism of haloforms to carbon monoxide. I. In vitro studies
    • Ahmed, A. E., Kubic, V. L. and Anders, M. W. (1977) Metabolism of haloforms to carbon monoxide. I. In vitro studies. Drug Metab. Dispos. 5, 198-204.
    • (1977) Drug Metab. Dispos. , vol.5 , pp. 198-204
    • Ahmed, A.E.1    Kubic, V.L.2    Anders, M.W.3
  • 6
    • 0023158895 scopus 로고
    • Physiologically based pharmacokinetics and the risk assessment process for methylene chloride
    • Andersen, M. E., Clewell, H. J., III, Gargas, M. L., Smith, F. A. and Reitz, R. H. (1987) Physiologically based pharmacokinetics and the risk assessment process for methylene chloride. Toxicol. Appl. Pharmacol. 87, 185-205.
    • (1987) Toxicol. Appl. Pharmacol. , vol.87 , pp. 185-205
    • Andersen, M.E.1    Clewell H.J. III2    Gargas, M.L.3    Smith, F.A.4    Reitz, R.H.5
  • 7
    • 0027207603 scopus 로고
    • Methylene chloride-induced tumorigenesis
    • Anderson, M. W. and Maronpot, R. R. (1993) Methylene chloride-induced tumorigenesis. Carcinogenesis 14, 787-788.
    • (1993) Carcinogenesis , vol.14 , pp. 787-788
    • Anderson, M.W.1    Maronpot, R.R.2
  • 8
    • 0000313919 scopus 로고    scopus 로고
    • Glutathione transferases
    • Guengerich, F. P., ed., Elsevier Science Ltd., Oxford
    • Armstrong, R. N. (1997) Glutathione transferases. In Biotransformafion, Vol. 3, Comprehensive Toxicology (Guengerich, F. P., ed.) 307-327, Elsevier Science Ltd., Oxford.
    • (1997) Biotransformafion, Vol. 3, Comprehensive Toxicology , vol.3 , pp. 307-327
    • Armstrong, R.N.1
  • 9
    • 0028003312 scopus 로고
    • Mutation spectra of 1,2-dibromoethane, 1,2-dichloroethane and 1-bromo-2-chloroethane in excision repair proficient and repair deficient strains of Drosophila melanogaster
    • Ballering, L. A. P., Nivard, M. J. M. and Vogel, E. W. (1994) Mutation spectra of 1,2-dibromoethane, 1,2-dichloroethane and 1-bromo-2-chloroethane in excision repair proficient and repair deficient strains of Drosophila melanogaster. Carcinogenesis 15, 869-875.
    • (1994) Carcinogenesis , vol.15 , pp. 869-875
    • Ballering, L.A.P.1    Nivard, M.J.M.2    Vogel, E.W.3
  • 12
    • 0028806420 scopus 로고
    • Mutation spectrum of 2-chloroethyl methanesulfonate in Drosophila melanogaster premeiotic germ cells
    • Fossett, N. G., Byrne, B. J., Tucker, A. B., Arbour-Reily, P., Chang, S. and Lee, W. R. (1995) Mutation spectrum of 2-chloroethyl methanesulfonate in Drosophila melanogaster premeiotic germ cells. Mutat. Res. 331, 213-224.
    • (1995) Mutat. Res. , vol.331 , pp. 213-224
    • Fossett, N.G.1    Byrne, B.J.2    Tucker, A.B.3    Arbour-Reily, P.4    Chang, S.5    Lee, W.R.6
  • 13
    • 0023797379 scopus 로고
    • An analysis of the mutagenicity of 1,2-dibromoethane to Escherichia coli: Influence of DNA repair activities and metabolic pathways
    • Foster, P. L., Wilkinson, W. G., Miller, J. K., Sullivan, A. D. and Barnes, W. M. (1988) An analysis of the mutagenicity of 1,2-dibromoethane to Escherichia coli: influence of DNA repair activities and metabolic pathways. Mutat. Res. 194, 171-181.
    • (1988) Mutat. Res. , vol.194 , pp. 171-181
    • Foster, P.L.1    Wilkinson, W.G.2    Miller, J.K.3    Sullivan, A.D.4    Barnes, W.M.5
  • 14
    • 0024588467 scopus 로고
    • Spectroscopic and kinetic evidence for the thiolate anion of glutathione at the active site of glutathione S-transferase
    • Graminski, G. F., Kubo, Y. and Armstrong, R. N. (1989) Spectroscopic and kinetic evidence for the thiolate anion of glutathione at the active site of glutathione S-transferase. Biochemistry 28, 3562-3568.
    • (1989) Biochemistry , vol.28 , pp. 3562-3568
    • Graminski, G.F.1    Kubo, Y.2    Armstrong, R.N.3
  • 15
    • 0029160231 scopus 로고
    • Methylene chloride-induced DNA damage: An interspecies comparison
    • Graves, R. J., Coutts, C. and Green, T. (1995) Methylene chloride-induced DNA damage: an interspecies comparison. Carcinogenesis 16, 1919-1926.
    • (1995) Carcinogenesis , vol.16 , pp. 1919-1926
    • Graves, R.J.1    Coutts, C.2    Green, T.3
  • 16
    • 0020510027 scopus 로고
    • The metabolic activation of dichloromethane and chlorofluoromethane in a bacterial mutation assay using Salmonella typhimurium
    • Green, T. (1983) The metabolic activation of dichloromethane and chlorofluoromethane in a bacterial mutation assay using Salmonella typhimurium. Mutat. Res. 118, 277-288.
    • (1983) Mutat. Res. , vol.118 , pp. 277-288
    • Green, T.1
  • 19
    • 0029664724 scopus 로고    scopus 로고
    • Methylene chloride
    • Huff, J., Bucher, J. and Barrett, J. C. (1996) Methylene chloride. Science 272, 1083-1084.
    • (1996) Science , vol.272 , pp. 1083-1084
    • Huff, J.1    Bucher, J.2    Barrett, J.C.3
  • 21
    • 0025075387 scopus 로고
    • Comparison of the DNA alkylating properties and mutagenic responses caused by a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives
    • Humphreys, W. G., Kim, D.-H., Cmarik, J. L., Shimada, T. and Guengerich, F. P. (1990) Comparison of the DNA alkylating properties and mutagenic responses caused by a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives. Biochemistry 29, 10342-10350.
    • (1990) Biochemistry , vol.29 , pp. 10342-10350
    • Humphreys, W.G.1    Kim, D.-H.2    Cmarik, J.L.3    Shimada, T.4    Guengerich, F.P.5
  • 22
    • 0021241496 scopus 로고
    • Glutathione-mediated binding of dibromoalkanes to DNA: Specificity of rat glutathione S-transferases and dibromoalkane structure
    • Inskeep, P. B. and 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
  • 25
    • 0034884901 scopus 로고    scopus 로고
    • Dehalogenation of dichloromethane by dichloromethane dehalogenase/glutathione S-transferase leads to formation of DNA adducts
    • Kayser, M. F. and Vuilleumier, S. (2001) Dehalogenation of dichloromethane by dichloromethane dehalogenase/glutathione S-transferase leads to formation of DNA adducts. J. Bacteriol. 183, 5209-5212.
    • (2001) J. Bacteriol. , vol.183 , pp. 5209-5212
    • Kayser, M.F.1    Vuilleumier, S.2
  • 26
    • 0024424137 scopus 로고
    • 7-guanyl)ethyl]-N-acetylcysteine in urine following administration of ethylene dibromide to rats
    • 7-guanyl)ethyl]-N-acetylcysteine in urine following administration of ethylene dibromide to rats. Cancer Res. 49, 5843-5851.
    • (1989) Cancer Res. , vol.49 , pp. 5843-5851
    • Kim, D.H.1    Guengerich, F.P.2
  • 31
    • 84944363601 scopus 로고
    • Two fatalities after acute occupational exposure to ethylene dibromide
    • Letz, G. A., Pond, S. M., Osterloh, J. D., Wade, R. L. and Becker, C. E. (1984) Two fatalities after acute occupational exposure to ethylene dibromide. J. Am. Med. Assoc. 252, 2428-2431.
    • (1984) J. Am. Med. Assoc. , vol.252 , pp. 2428-2431
    • Letz, G.A.1    Pond, S.M.2    Osterloh, J.D.3    Wade, R.L.4    Becker, C.E.5
  • 33
    • 0035023205 scopus 로고    scopus 로고
    • Characterization of nucleoside and DNA adducts formed by S-(1-acetoxymethyl)glutathione and implications for dihalomethane-glutathione conjugates
    • Marsch, G. A., Mundkowski, R. G., Morris, B. J., Manier, M. L., Hartman, M. K. and Guengerich, F. P. (2001) Characterization of nucleoside and DNA adducts formed by S-(1-acetoxymethyl)glutathione and implications for dihalomethane-glutathione conjugates. Chem. Res. Toxicol. 14, 600-608.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 600-608
    • Marsch, G.A.1    Mundkowski, R.G.2    Morris, B.J.3    Manier, M.L.4    Hartman, M.K.5    Guengerich, F.P.6
  • 34
    • 0031004763 scopus 로고    scopus 로고
    • UV-induced mutagenesis of human p53 in a vector replicated in Saccharomyces cerevisiae
    • Moshinsky, D. J. and Wogan, G. N. (1997) UV-induced mutagenesis of human p53 in a vector replicated in Saccharomyces cerevisiae. Proc. Natl. Acad. Sci. USA 94, 2266-2271.
    • (1997) Proc. Natl. Acad. Sci. USA , vol.94 , pp. 2266-2271
    • Moshinsky, D.J.1    Wogan, G.N.2
  • 35
    • 0029925074 scopus 로고    scopus 로고
    • A new Salmonella typhimurium NM5004 strain expressing rat glutathione S-transferase 5-5: Use in detection of genotoxicity of dihaloalkanes using an SOS/umu test system
    • Oda, Y., Yamazaki, H., Thier, R., Ketterer, B., Guengerich, F. P. and Shimada, T. (1996) A new Salmonella typhimurium NM5004 strain expressing rat glutathione S-transferase 5-5: use in detection of genotoxicity of dihaloalkanes using an SOS/umu test system. Carcinogenesis 17, 297-302.
    • (1996) Carcinogenesis , vol.17 , pp. 297-302
    • Oda, Y.1    Yamazaki, H.2    Thier, R.3    Ketterer, B.4    Guengerich, F.P.5    Shimada, T.6
  • 36
    • 0008252723 scopus 로고
    • 7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of 1,2-dibromoethane to DNA
    • 7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of 1,2-dibromoethane to DNA. Proc. Natl. Acad. Sci. USA 80, 5266-5270.
    • (1983) Proc. Natl. Acad. Sci. USA , vol.80 , pp. 5266-5270
    • Ozawa, N.1    Guengerich, F.P.2
  • 37
    • 0031149578 scopus 로고    scopus 로고
    • Glutathione S-transferase-mediated mutagenicity of trihalomethanes in Salmonella typhimurium: Contrasting results with bromodichloromethane and chloroform
    • Pegram, R. A., Andersen, M. E., Warren, S. H., Ross, T. M. and Claxton, L. D. (1997) Glutathione S-transferase-mediated mutagenicity of trihalomethanes in Salmonella typhimurium: contrasting results with bromodichloromethane and chloroform. Toxicol. Appl. Pharmacol. 144, 183-188.
    • (1997) Toxicol. Appl. Pharmacol. , vol.144 , pp. 183-188
    • Pegram, R.A.1    Andersen, M.E.2    Warren, S.H.3    Ross, T.M.4    Claxton, L.D.5
  • 39
    • 0018425602 scopus 로고
    • The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. II. Activation by the isolated perfused rat liver
    • Rannug, U. and 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
  • 40
    • 0017883678 scopus 로고
    • The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. I. Activation through conjugation with glutathione in vitro
    • Rannug, U., Sundvall, A. and Ramel, C. (1978) The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. I. Activation through conjugation with glutathione in vitro. Chem.-Biol. Interact. 20, 1-16.
    • (1978) Chem.-Biol. Interact. , vol.20 , pp. 1-16
    • Rannug, U.1    Sundvall, A.2    Ramel, C.3
  • 41
    • 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. and 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.2    Guengerich, F.P.3
  • 42
    • 0029161453 scopus 로고
    • Use of quantitative modelling in methylene chloride risk assessment
    • Rhomberg, L. (1995) Use of quantitative modelling in methylene chloride risk assessment. Toxicology 102, 95-114.
    • (1995) Toxicology , vol.102 , pp. 95-114
    • Rhomberg, L.1
  • 43
    • 0021102422 scopus 로고
    • Insertion of nucleotides opposite apurinic/apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: Uniqueness of adenine nucleotides
    • Sagher, D. and Strauss, B. (1983) Insertion of nucleotides opposite apurinic/apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: uniqueness of adenine nucleotides. Biochemistry 22, 4518-4526.
    • (1983) Biochemistry , vol.22 , pp. 4518-4526
    • Sagher, D.1    Strauss, B.2
  • 44
    • 0021754016 scopus 로고
    • EDB contamination kindles federal action
    • Sun, M. (1984) EDB contamination kindles federal action. Science 223, 464-466.
    • (1984) Science , vol.223 , pp. 464-466
    • Sun, M.1
  • 45
    • 0028930987 scopus 로고
    • Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase
    • Thier, R., Müller, M., Taylor, J. B., Pemble, S. E., Ketterer, B. and Guengerich, F. P. (1995) Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase. Chem. Res. Toxicol. 8, 465-472.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 465-472
    • Thier, R.1    Müller, M.2    Taylor, J.B.3    Pemble, S.E.4    Ketterer, B.5    Guengerich, F.P.6
  • 46
    • 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., Pemble, S. E., Taylor, J. B., Humphreys, W. G., Persmark, M., Ketterer, B. and 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. USA 90, 8576-8580.
    • (1993) Proc. Natl. Acad. Sci. USA , vol.90 , pp. 8576-8580
    • Thier, R.1    Pemble, S.E.2    Taylor, J.B.3    Humphreys, W.G.4    Persmark, M.5    Ketterer, B.6    Guengerich, F.P.7
  • 47
    • 0029947171 scopus 로고    scopus 로고
    • Human glutathione S-transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane, and 1,2,3,4-diepoxybutane in Salmonella typhimurium
    • Thier, R., Pemble, S., Kramer, H., Taylor, J. B., Guengerich, F. P., and Ketterer, B. (1996) Human glutathione S-transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane, and 1,2,3,4-diepoxybutane in Salmonella typhimurium. Carcinogenesis 17, 163-166.
    • (1996) Carcinogenesis , vol.17 , pp. 163-166
    • Thier, R.1    Pemble, S.2    Kramer, H.3    Taylor, J.B.4    Guengerich, F.P.5    Ketterer, B.6
  • 48
    • 0018862116 scopus 로고
    • Mutagenic activation of dibromomethane and diiodomethane by mammalian microsomes and glutathione S-transferases
    • van Bladeren, P. J., Breimer, D. D., Rotteveel-Smijs, G. M. T. and Mohn, G. R. (1980) Mutagenic activation of dibromomethane and diiodomethane by mammalian microsomes and glutathione S-transferases. Mutat. Res. 74, 341-346.
    • (1980) Mutat. Res. , vol.74 , pp. 341-346
    • Van Bladeren, P.J.1    Breimer, D.D.2    Rotteveel-Smijs, G.M.T.3    Mohn, G.R.4
  • 49
    • 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. and 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
  • 50
    • 0034868397 scopus 로고    scopus 로고
    • Conjugation of haloalkanes by bacterial and mammalian glutathione transferases: Mono- and vicinal dehaloethanes
    • Wheeler, J. B., Stourman, N. V., Armstrong, R. N. and Guengerich, F. P. (2001a) Conjugation of haloalkanes by bacterial and mammalian glutathione transferases: mono- and vicinal dehaloethanes. Chem. Res. Toxicol. 14, 1107-1117.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1107-1117
    • Wheeler, J.B.1    Stourman, N.V.2    Armstrong, R.N.3    Guengerich, F.P.4


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