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Volumn 224, Issue 2, 2014, Pages 272-281

Effect of human glutathione S-transferase hGSTP1-1 polymorphism on the detoxification of reactive metabolites of clozapine, diclofenac and acetaminophen

Author keywords

Adverse drug reactions; Bioinactivation; Cytochrome P450; Glutathione S transferase P1 1; Polymorphism; Reactive metabolites

Indexed keywords

1 CHLORO 2,4 DINITROBENZENE; 4 CHLORO 7 NITROBENZOFURAZAN; 5 METHYLCHRYSENE DIPOLXIDE; ACROLEIN; AMINO ACID; ATRAZINE; BENZO[A]PYRENE DIOLEPOXIDE; BENZO[C]CHRYSENE DIOLEPOXIDE 1; BENZO[C]CHRYSENE DIOLEPOXIDE 2; CHLORAMBUCIL; CHRYSENE DIOLEPOXIDE; CLOZAPINE; CLOZAPINE NITRENIUM ION; CROTONALDEHYDE; CYTOCHROME P450; CYTOCHROME P450 BM3; DICLOFENAC; DICLOFENAC 1,4 QUINONEIMINE; DICLOFENAC 2,5 QUINONEIMINE; DRUG METABOLITE; ETACRYNIC ACID; GLUTATHIONE TRANSFERASE; N ACETYL P BENZOQUINONEIMINE; PARACETAMOL; THIOTEPA; UNCLASSIFIED DRUG; GLUTATHIONE; GLUTATHIONE TRANSFERASE P1; GSTP1 PROTEIN, HUMAN;

EID: 84888397847     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2013.10.023     Document Type: Article
Times cited : (23)

References (56)
  • 1
    • 4344666283 scopus 로고    scopus 로고
    • Characterization of atrazine biotransformation by human and murine glutathione S-transferases
    • Abel E.L., Opp S.M., Verlinde C.L.M.J., Bammler T.K., Eaton D.L. Characterization of atrazine biotransformation by human and murine glutathione S-transferases. Toxicological Sciences 2004, 80:230-238.
    • (2004) Toxicological Sciences , vol.80 , pp. 230-238
    • Abel, E.L.1    Opp, S.M.2    Verlinde, C.L.M.J.3    Bammler, T.K.4    Eaton, D.L.5
  • 3
    • 79952446700 scopus 로고    scopus 로고
    • Hepatotoxicity related to antirheumatic drugs
    • Aithal G.P. Hepatotoxicity related to antirheumatic drugs. Nature Reviews Rheumatology 2011, 7:139-150.
    • (2011) Nature Reviews Rheumatology , vol.7 , pp. 139-150
    • Aithal, G.P.1
  • 4
    • 0030899372 scopus 로고    scopus 로고
    • Molecular cloning, characterization, and expression in Escherichia coli of full-length cDNAs of three human glutathione S-transferase Pi gene variants - evidence for differential catalytic activity of the encoded proteins
    • AliOsman F., Akande O., Antoun G., Mao J.X., Buolamwini J. Molecular cloning, characterization, and expression in Escherichia coli of full-length cDNAs of three human glutathione S-transferase Pi gene variants - evidence for differential catalytic activity of the encoded proteins. Journal of Biological Chemistry 1997, 272:10004-10012.
    • (1997) Journal of Biological Chemistry , vol.272 , pp. 10004-10012
    • AliOsman, F.1    Akande, O.2    Antoun, G.3    Mao, J.X.4    Buolamwini, J.5
  • 5
    • 0035132183 scopus 로고    scopus 로고
    • Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches
    • Bessems J.G.M., Vermeulen N.P.E. Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches. Critical Reviews in Toxicology 2001, 31:55-138.
    • (2001) Critical Reviews in Toxicology , vol.31 , pp. 55-138
    • Bessems, J.G.M.1    Vermeulen, N.P.E.2
  • 6
    • 84869408727 scopus 로고    scopus 로고
    • Mass spectrometric characterization of protein adducts of multiple P450-dependent reactive intermediates of diclofenac to human glutathione-S-transferase P 1-1
    • Boerma J.S., Dragovic S., Vermeulen N.P.E., Commandeur J.N.M. Mass spectrometric characterization of protein adducts of multiple P450-dependent reactive intermediates of diclofenac to human glutathione-S-transferase P 1-1. Chemical Research in Toxicology 2012, 25:2532-2541.
    • (2012) Chemical Research in Toxicology , vol.25 , pp. 2532-2541
    • Boerma, J.S.1    Dragovic, S.2    Vermeulen, N.P.E.3    Commandeur, J.N.M.4
  • 7
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 1976, 72:248-254.
    • (1976) Analytical Biochemistry , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 9
  • 10
    • 0033968033 scopus 로고    scopus 로고
    • Quantitive analysis of interindividual variation of glutathione-S-transferase expression in human pancreas and the ambiquity of correlating genotype with phenotype
    • Coles B.F., Anderson K.E., Doerge D.R., Churchwell M.I., Lang N.P., Kadlubar F.F. Quantitive analysis of interindividual variation of glutathione-S-transferase expression in human pancreas and the ambiquity of correlating genotype with phenotype. Cancer Research 2000, 60:573-579.
    • (2000) Cancer Research , vol.60 , pp. 573-579
    • Coles, B.F.1    Anderson, K.E.2    Doerge, D.R.3    Churchwell, M.I.4    Lang, N.P.5    Kadlubar, F.F.6
  • 11
    • 0037099541 scopus 로고    scopus 로고
    • Interindividual variation and organ-specific patterns of glutathione S-transferase alpha, mu, and pi expression in gastrointestinal tract mucosa of normal individuals
    • Coles B.F., Chen G., Kadlubar F.F., Radominska-Pandya R. Interindividual variation and organ-specific patterns of glutathione S-transferase alpha, mu, and pi expression in gastrointestinal tract mucosa of normal individuals. Archives of Biochemistry and Biophysics 2002, 403:270-276.
    • (2002) Archives of Biochemistry and Biophysics , vol.403 , pp. 270-276
    • Coles, B.F.1    Chen, G.2    Kadlubar, F.F.3    Radominska-Pandya, R.4
  • 15
    • 84888026053 scopus 로고    scopus 로고
    • Effect of human glutathione S-transferases on glutathione-dependent inactivation of cytochrome P450-dependent reactive intermediates of diclofenac
    • PMID 24083800
    • Dragovic S., Boerma J.S., Vermeulen N.P.E., Commandeur J.N.M. Effect of human glutathione S-transferases on glutathione-dependent inactivation of cytochrome P450-dependent reactive intermediates of diclofenac. Chemical Research in Toxicology 2013, 26:1632-1641. PMID 24083800.
    • (2013) Chemical Research in Toxicology , vol.26 , pp. 1632-1641
    • Dragovic, S.1    Boerma, J.S.2    Vermeulen, N.P.E.3    Commandeur, J.N.M.4
  • 18
    • 84859777006 scopus 로고    scopus 로고
    • Variants of glutathione s-transferase pi 1 exhibit differential enzymatic activity and inhibition by heavy metals
    • Goodrich J.M., Basu N. Variants of glutathione s-transferase pi 1 exhibit differential enzymatic activity and inhibition by heavy metals. Toxicology in Vitro 2012, 26:630-635.
    • (2012) Toxicology in Vitro , vol.26 , pp. 630-635
    • Goodrich, J.M.1    Basu, N.2
  • 19
    • 50049132591 scopus 로고    scopus 로고
    • A novel bioactivation pathway for 2-[2-(2,6-dichlorophenyl)aminophenyl] ethanoic acid (diclofenac) initiated by cytochrome P450-mediated oxidative decarboxylation
    • Grillo M.P., Ma J., Teffera Y., Waldon D.J. A novel bioactivation pathway for 2-[2-(2,6-dichlorophenyl)aminophenyl] ethanoic acid (diclofenac) initiated by cytochrome P450-mediated oxidative decarboxylation. Drug Metabolism and Disposition 2008, 36:1740-1744.
    • (2008) Drug Metabolism and Disposition , vol.36 , pp. 1740-1744
    • Grillo, M.P.1    Ma, J.2    Teffera, Y.3    Waldon, D.J.4
  • 20
    • 0016275313 scopus 로고
    • Glutathione S-transferases - first enzymatic step in mercapturic acid formation
    • Habig W.H., Pabst M.J., Jakoby W.B. Glutathione S-transferases - first enzymatic step in mercapturic acid formation. Journal of Biological Chemistry 1974, 249:7130-7139.
    • (1974) Journal of Biological Chemistry , vol.249 , pp. 7130-7139
    • Habig, W.H.1    Pabst, M.J.2    Jakoby, W.B.3
  • 22
    • 0029561598 scopus 로고
    • The glutathione S-transferase supergene family: regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance
    • Hayes J.D., Pulford D.J. The glutathione S-transferase supergene family: regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance. Critical Reviews in Biochemistry and Molecular Biology 1995, 30:445-600.
    • (1995) Critical Reviews in Biochemistry and Molecular Biology , vol.30 , pp. 445-600
    • Hayes, J.D.1    Pulford, D.J.2
  • 23
    • 0031716994 scopus 로고    scopus 로고
    • Specificities of human glutathione S-transferase isozymes toward anti-diol epoxides of methylchrysenes
    • Hu X., Pal A., Krzeminski J., Amin S., Awasthi Y.C., Zimniak P., Singh S.V. Specificities of human glutathione S-transferase isozymes toward anti-diol epoxides of methylchrysenes. Carcinogenesis 1998, 19:1685-1689.
    • (1998) Carcinogenesis , vol.19 , pp. 1685-1689
    • Hu, X.1    Pal, A.2    Krzeminski, J.3    Amin, S.4    Awasthi, Y.C.5    Zimniak, P.6    Singh, S.V.7
  • 26
    • 0033543218 scopus 로고    scopus 로고
    • Structure and function of residue 104 and water molecules in the xenobiotic substrate-binding site in human glutathione S-transferase P 1-1
    • Ji X.H., Blaszczyk J., Xiao B., O'Donnell R., Hu X., Herzog C., Singh S.V., Zimniak P. Structure and function of residue 104 and water molecules in the xenobiotic substrate-binding site in human glutathione S-transferase P 1-1. Biochemistry 1999, 38:10231-10238.
    • (1999) Biochemistry , vol.38 , pp. 10231-10238
    • Ji, X.H.1    Blaszczyk, J.2    Xiao, B.3    O'Donnell, R.4    Hu, X.5    Herzog, C.6    Singh, S.V.7    Zimniak, P.8
  • 27
    • 0032496408 scopus 로고    scopus 로고
    • Structure-activity relationships and thermal stability of human glutathione transferase P 1-1 governed by the H-site residue 105
    • Johansson A.-S., Stenberg G., Widersten M., Mannervik B. Structure-activity relationships and thermal stability of human glutathione transferase P 1-1 governed by the H-site residue 105. Journal of Molecular Biology 1998, 278:687-698.
    • (1998) Journal of Molecular Biology , vol.278 , pp. 687-698
    • Johansson, A.-S.1    Stenberg, G.2    Widersten, M.3    Mannervik, B.4
  • 30
    • 0029555342 scopus 로고
    • Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells
    • Liu Z.C., Uetrecht J.P. Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells. Journal of Pharmacology and Experimental Therapeutics 1995, 275:1476-1483.
    • (1995) Journal of Pharmacology and Experimental Therapeutics , vol.275 , pp. 1476-1483
    • Liu, Z.C.1    Uetrecht, J.P.2
  • 33
    • 84870312437 scopus 로고    scopus 로고
    • Allelic variants of glutathione S-transferase P 1-1 differentially mediate the peroxidase function of peroxiredoxin VI and alter membrane lipid peroxidation
    • Manevich Y., Hutchens S., Tew K.D., Townsend D.M. Allelic variants of glutathione S-transferase P 1-1 differentially mediate the peroxidase function of peroxiredoxin VI and alter membrane lipid peroxidation. Free Radical Biology and Medicine 2013, 54:62-70.
    • (2013) Free Radical Biology and Medicine , vol.54 , pp. 62-70
    • Manevich, Y.1    Hutchens, S.2    Tew, K.D.3    Townsend, D.M.4
  • 36
    • 0034624247 scopus 로고    scopus 로고
    • Location of the epoxide function determines specificity of the allelic variants of human glutathione transferase Pi toward benzo[c]chrysene diol epoxide isomers
    • Pal A., Desai D.H., Amin S., Srivastava S.K., Hu X., Herzog C., Zimniak P., Singh S.V. Location of the epoxide function determines specificity of the allelic variants of human glutathione transferase Pi toward benzo[c]chrysene diol epoxide isomers. FEBS Letters 2000, 486:163-166.
    • (2000) FEBS Letters , vol.486 , pp. 163-166
    • Pal, A.1    Desai, D.H.2    Amin, S.3    Srivastava, S.K.4    Hu, X.5    Herzog, C.6    Zimniak, P.7    Singh, S.V.8
  • 37
    • 0034213865 scopus 로고    scopus 로고
    • Catalytic efficiencies of allelic variants of human glutathione S-transferase Pi in the glutathione conjugation of alpha,beta-unsaturated aldehydes
    • Pal A., Hu X., Zimniak P., Singh S.V. Catalytic efficiencies of allelic variants of human glutathione S-transferase Pi in the glutathione conjugation of alpha,beta-unsaturated aldehydes. Cancer Letters 2000, 154:39-43.
    • (2000) Cancer Letters , vol.154 , pp. 39-43
    • Pal, A.1    Hu, X.2    Zimniak, P.3    Singh, S.V.4
  • 40
    • 44649175626 scopus 로고    scopus 로고
    • The anti-cancer drug chlorambucil as a substrate for the human polymorphic enzyme glutathione transferase P1-1: kinetic properties and crystallographic characterisation of allelic variants
    • Parker L.J., Ciccone S., Italiano L.C., Primavera A., Oakley A.J., Morton C.J., Hancock N.C., Lo Bello M., Parker M.W. The anti-cancer drug chlorambucil as a substrate for the human polymorphic enzyme glutathione transferase P1-1: kinetic properties and crystallographic characterisation of allelic variants. Journal of Molecular Biology 2008, 380:131-144.
    • (2008) Journal of Molecular Biology , vol.380 , pp. 131-144
    • Parker, L.J.1    Ciccone, S.2    Italiano, L.C.3    Primavera, A.4    Oakley, A.J.5    Morton, C.J.6    Hancock, N.C.7    Lo Bello, M.8    Parker, M.W.9
  • 43
    • 81855173536 scopus 로고    scopus 로고
    • Role of residue 87 in the activity and regioselectivity of clozapine metabolism by drug-metabolizing CYP102A1 M11H: application for structural characterization of clozapine GSH conjugates
    • Rea V., Dragovic S., Boerma J.S., de Kanter F.J.J., Vermeulen N.P.E., Commandeur J.N.M. Role of residue 87 in the activity and regioselectivity of clozapine metabolism by drug-metabolizing CYP102A1 M11H: application for structural characterization of clozapine GSH conjugates. Drug Metabolism and Disposition 2011, 39:2411-2420.
    • (2011) Drug Metabolism and Disposition , vol.39 , pp. 2411-2420
    • Rea, V.1    Dragovic, S.2    Boerma, J.S.3    de Kanter, F.J.J.4    Vermeulen, N.P.E.5    Commandeur, J.N.M.6
  • 45
    • 0030744050 scopus 로고    scopus 로고
    • Subunit diversity and tissue distribution of human glutathione S-transferases: interpretations based on electrospray ionization MS and peptide sequence-specific antisera
    • Rowe J.D., Nieves E., Listowsky I. Subunit diversity and tissue distribution of human glutathione S-transferases: interpretations based on electrospray ionization MS and peptide sequence-specific antisera. Biochemical Journal 1997, 325:481-486.
    • (1997) Biochemical Journal , vol.325 , pp. 481-486
    • Rowe, J.D.1    Nieves, E.2    Listowsky, I.3
  • 46
    • 0033150617 scopus 로고    scopus 로고
    • Differential catalytic efficiency of allelic variants of human glutathione S-transferase Pi in catalyzing the glutathione conjugation of thiotepa
    • Srivastava S.K., Singhal S.S., Hu X., Awasthi Y.C., Zimniak P., Singh S.V. Differential catalytic efficiency of allelic variants of human glutathione S-transferase Pi in catalyzing the glutathione conjugation of thiotepa. Archives of Biochemistry and Biophysics 1999, 366:89-94.
    • (1999) Archives of Biochemistry and Biophysics , vol.366 , pp. 89-94
    • Srivastava, S.K.1    Singhal, S.S.2    Hu, X.3    Awasthi, Y.C.4    Zimniak, P.5    Singh, S.V.6
  • 47
    • 0034653362 scopus 로고    scopus 로고
    • Glutathione S-transferase: genetics and role in toxicology
    • Strange R.C., Jones P.W., Fryer A.A. Glutathione S-transferase: genetics and role in toxicology. Toxicology Letters 2000, 112:357-363.
    • (2000) Toxicology Letters , vol.112 , pp. 357-363
    • Strange, R.C.1    Jones, P.W.2    Fryer, A.A.3
  • 49
    • 0025048493 scopus 로고
    • An immunohistochemical study of Pi-class glutathione-S-transferase expression in normal human tissue
    • Terrier P., Townsend A.J., Coindre J.M., Triche T.J., Cowan K.H. An immunohistochemical study of Pi-class glutathione-S-transferase expression in normal human tissue. American Journal of Pathology 1990, 137:845-853.
    • (1990) American Journal of Pathology , vol.137 , pp. 845-853
    • Terrier, P.1    Townsend, A.J.2    Coindre, J.M.3    Triche, T.J.4    Cowan, K.H.5
  • 50
    • 79954617745 scopus 로고    scopus 로고
    • Regulatory functions of glutathione S-transferase P 1-1 unrelated to detoxification
    • Tew K.D., Townsend D.M. Regulatory functions of glutathione S-transferase P 1-1 unrelated to detoxification. Drug Metabolism Reviews 2011, 43:179-193.
    • (2011) Drug Metabolism Reviews , vol.43 , pp. 179-193
    • Tew, K.D.1    Townsend, D.M.2
  • 52
    • 84864992699 scopus 로고    scopus 로고
    • Regio- and stereoselective hydroxylation of optically active alpha-ionone enantiomers by engineered cytochrome P450 BM3 mutants
    • Venkataraman H., de Beer S.B.A., Geerke D.P., Vermeulen N.P.E., Commandeur J.N.M. Regio- and stereoselective hydroxylation of optically active alpha-ionone enantiomers by engineered cytochrome P450 BM3 mutants. Advanced Synthesis and Catalysis 2012, 354:2172-2184.
    • (2012) Advanced Synthesis and Catalysis , vol.354 , pp. 2172-2184
    • Venkataraman, H.1    de Beer, S.B.A.2    Geerke, D.P.3    Vermeulen, N.P.E.4    Commandeur, J.N.M.5
  • 54
    • 0032934961 scopus 로고    scopus 로고
    • Genetic polymorphisms of human N-acetyltransferase, cytochrome P450, glutathione-S-transferase, and epoxide hydrolase enzymes: relevance to xenobiotic metabolism and toxicity
    • Wormhoudt L.W., Commandeur J.N.M., Vermeulen N.P.E. Genetic polymorphisms of human N-acetyltransferase, cytochrome P450, glutathione-S-transferase, and epoxide hydrolase enzymes: relevance to xenobiotic metabolism and toxicity. Critical Reviews in Toxicology 1999, 29:59-124.
    • (1999) Critical Reviews in Toxicology , vol.29 , pp. 59-124
    • Wormhoudt, L.W.1    Commandeur, J.N.M.2    Vermeulen, N.P.E.3
  • 56
    • 84867583625 scopus 로고    scopus 로고
    • Role of intestinal cytochrome P450 enzymes in diclofenac-induced toxicity in the small intestine
    • Zhu Y., Zhang Q.Y. Role of intestinal cytochrome P450 enzymes in diclofenac-induced toxicity in the small intestine. Journal of Pharmacology and Experimental Therapeutics 2012, 343:362-370.
    • (2012) Journal of Pharmacology and Experimental Therapeutics , vol.343 , pp. 362-370
    • Zhu, Y.1    Zhang, Q.Y.2


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