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Volumn 319, Issue 1, 2006, Pages 497-505

Enzyme-mediated protein haptenation of dapsone and sulfamethoxazole in human keratinocytes: II. Expression and role of flavin-containing monooxygenases and peroxidases

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBENZOHYDRAZIDE; DAPSONE; DIMETHYLANILINE MONOOXYGENASE; HYDRAZIDE DERIVATIVE; LACTOPEROXIDASE; MYELOPEROXIDASE; PEROXIDASE; PROTEIN; SULFAMETHOXAZOLE; THYROID PEROXIDASE; UNCLASSIFIED DRUG;

EID: 33749010103     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.105874     Document Type: Article
Times cited : (65)

References (40)
  • 1
    • 0023645785 scopus 로고
    • Structure and catalytic mechanism of horseradish peroxidase: Regiospecific meso alkylation of the prosthetic heme group by alkylhydrazines
    • Ator MA, David SK, and Ortiz de Montellano PR (1987) Structure and catalytic mechanism of horseradish peroxidase: regiospecific meso alkylation of the prosthetic heme group by alkylhydrazines. J Biol Chem 262:14954-14960.
    • (1987) J Biol Chem , vol.262 , pp. 14954-14960
    • Ator, M.A.1    David, S.K.2    Ortiz De Montellano, P.R.3
  • 2
    • 0020540731 scopus 로고
    • Subcellular localization of the β-cytochrome component of the human neutrophil microbicidal oxidase: Translocation during activation
    • Borregaard N, Heiple JM, Simons ER, and Clark RA (1983) Subcellular localization of the β-cytochrome component of the human neutrophil microbicidal oxidase: translocation during activation. J Cell Biol 97:52-61.
    • (1983) J Cell Biol , vol.97 , pp. 52-61
    • Borregaard, N.1    Heiple, J.M.2    Simons, E.R.3    Clark, R.A.4
  • 3
    • 0034280122 scopus 로고    scopus 로고
    • Human flavin-containing monooxygenase: Substrate specificity and role in drug metabolism
    • Cashman JR (2000) Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab 1:181-191.
    • (2000) Curr Drug Metab , vol.1 , pp. 181-191
    • Cashman, J.R.1
  • 4
    • 0033763393 scopus 로고    scopus 로고
    • Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450
    • Chung WG, Park CS, Roh HK, Lee WK, and Cha YN (2000) Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn J Pharmacol 84:213-220.
    • (2000) Jpn J Pharmacol , vol.84 , pp. 213-220
    • Chung, W.G.1    Park, C.S.2    Roh, H.K.3    Lee, W.K.4    Cha, Y.N.5
  • 7
    • 0025245841 scopus 로고
    • Peroxidase-dependent oxidation of sulfonamides by monocytes and neutrophils from humans and dogs
    • Cribb AE, Miller M, Tesoro A, and Spielberg SP (1990) Peroxidase-dependent oxidation of sulfonamides by monocytes and neutrophils from humans and dogs. Mol Pharmacol 38:744-751.
    • (1990) Mol Pharmacol , vol.38 , pp. 744-751
    • Cribb, A.E.1    Miller, M.2    Tesoro, A.3    Spielberg, S.P.4
  • 8
    • 0028986887 scopus 로고
    • N4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes
    • Cribb AE, Spielberg SP, and Griffin GP (1995) N4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes. Drug Metab Dispos 23:406-414.
    • (1995) Drug Metab Dispos , vol.23 , pp. 406-414
    • Cribb, A.E.1    Spielberg, S.P.2    Griffin, G.P.3
  • 9
  • 12
    • 3843070896 scopus 로고    scopus 로고
    • S-oxygenation of the thioether organophosphate insecticides phorate and disulfoton by human lung flavin-containing monooxygenase 2
    • Henderson MC, Krueger SK, Siddens LK, Stevens JF, and Williams DE (2004) S-oxygenation of the thioether organophosphate insecticides phorate and disulfoton by human lung flavin-containing monooxygenase 2. Biochem Pharmacol 68:959-967.
    • (2004) Biochem Pharmacol , vol.68 , pp. 959-967
    • Henderson, M.C.1    Krueger, S.K.2    Siddens, L.K.3    Stevens, J.F.4    Williams, D.E.5
  • 13
    • 0035885281 scopus 로고    scopus 로고
    • Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenases and cytochromes P450
    • Janmohamed A, Dolphin CT, Phillips IR, and Shephard EA (2001) Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenases and cytochromes P450. Biochem Pharmacol 62:777-786.
    • (2001) Biochem Pharmacol , vol.62 , pp. 777-786
    • Janmohamed, A.1    Dolphin, C.T.2    Phillips, I.R.3    Shephard, E.A.4
  • 15
    • 0031029267 scopus 로고    scopus 로고
    • Mechanism of inactivation of myeloperoxidase by 4-aminobenzoic acid hydrazide
    • Kettle AJ, Gedye CA, and Winterbourn CC (1997) Mechanism of inactivation of myeloperoxidase by 4-aminobenzoic acid hydrazide. Biochem J 321:503-508.
    • (1997) Biochem J , vol.321 , pp. 503-508
    • Kettle, A.J.1    Gedye, C.A.2    Winterbourn, C.C.3
  • 16
    • 0028233559 scopus 로고
    • Assays for the chlorination activity of myeloperoxidase
    • Kettle AJ and Winterbourn CC (1994) Assays for the chlorination activity of myeloperoxidase. Meth Enzymol 233:502-512.
    • (1994) Meth Enzymol , vol.233 , pp. 502-512
    • Kettle, A.J.1    Winterbourn, C.C.2
  • 17
    • 28444441585 scopus 로고    scopus 로고
    • Flavin-containing monooxygenase genetic polymorphism: Impact on chemical metabolism and drug development
    • Koukouritaki SB and Hines RN (2005) Flavin-containing monooxygenase genetic polymorphism: impact on chemical metabolism and drug development. Pharmacogenomics 6:807-822.
    • (2005) Pharmacogenomics , vol.6 , pp. 807-822
    • Koukouritaki, S.B.1    Hines, R.N.2
  • 18
    • 0642303632 scopus 로고    scopus 로고
    • Skin penetration of sulfamethoxazole and trimethoprim after oral administration
    • Krolicki A (2002) Skin penetration of sulfamethoxazole and trimethoprim after oral administration. Ann Acad Med Stetin 48:59-73.
    • (2002) Ann Acad Med Stetin , vol.48 , pp. 59-73
    • Krolicki, A.1
  • 20
    • 0014949207 scopus 로고
    • Cleavage of structural proteins during the assembly of the head of the bacteriophage T4
    • Laemmli U (1970) Cleavage of structural proteins during the assembly of the head of the bacteriophage T4. Nature (Lond) 227:680-685.
    • (1970) Nature (Lond) , vol.227 , pp. 680-685
    • Laemmli, U.1
  • 21
    • 32944475737 scopus 로고    scopus 로고
    • Identification of proteins adducted by reactive metabolites of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques
    • Lin CY, Boland BC, Lee YJ, Salemi MR, Morin D, Miller LA, Plopper CG, and Buckpitt AR (2006) Identification of proteins adducted by reactive metabolites of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. Proteomics 6:972-982.
    • (2006) Proteomics , vol.6 , pp. 972-982
    • Lin, C.Y.1    Boland, B.C.2    Lee, Y.J.3    Salemi, M.R.4    Morin, D.5    Miller, L.A.6    Plopper, C.G.7    Buckpitt, A.R.8
  • 23
    • 85033517545 scopus 로고    scopus 로고
    • Effect of methimazole, an FMO substrate and competitive inhibitor, on the neurotoxicity of 3,3′-iminodipropionitrile in male rats
    • Nace CG, Genter MB, Sayre LM, and Crofton KM (1997) Effect of methimazole, an FMO substrate and competitive inhibitor, on the neurotoxicity of 3,3′-iminodipropionitrile in male rats. Fundam Appl Toxicol 37:131-140.
    • (1997) Fundam Appl Toxicol , vol.37 , pp. 131-140
    • Nace, C.G.1    Genter, M.B.2    Sayre, L.M.3    Crofton, K.M.4
  • 25
    • 0020533077 scopus 로고
    • Biochemical and immunologic analysis of hereditary myeloperoxidase deficiency
    • Nauseef WM, Root RK, and Malech HL (1983) Biochemical and immunologic analysis of hereditary myeloperoxidase deficiency. J Clin Investig 71:1297-1307.
    • (1983) J Clin Investig , vol.71 , pp. 1297-1307
    • Nauseef, W.M.1    Root, R.K.2    Malech, H.L.3
  • 26
    • 0033656847 scopus 로고    scopus 로고
    • Association analysis of drug metabolizing enzyme gene polymorphisms in HIV-positive patients with co-trimoxazole hypersensitivity
    • Pirmohamed M, Alfirevic A, Vilar J, Stalford A, Wilkins EGL, Sim E, and Park BK (2000) Association analysis of drug metabolizing enzyme gene polymorphisms in HIV-positive patients with co-trimoxazole hypersensitivity. Pharmacogenetics 10:705-713.
    • (2000) Pharmacogenetics , vol.10 , pp. 705-713
    • Pirmohamed, M.1    Alfirevic, A.2    Vilar, J.3    Stalford, A.4    Wilkins, E.G.L.5    Sim, E.6    Park, B.K.7
  • 27
    • 0034123730 scopus 로고    scopus 로고
    • A role for bioactivation and covalent binding within epidermal keratinocytes in sulfonamide-induced cutaneous drug reactions
    • Reilly TP, Lash LH, Doll MA, Hein D, W Woster PM, and Svensson CK (2000) A role for bioactivation and covalent binding within epidermal keratinocytes in sulfonamide-induced cutaneous drug reactions. J Investig Dermatol 114:1164-1173.
    • (2000) J Investig Dermatol , vol.114 , pp. 1164-1173
    • Reilly, T.P.1    Lash, L.H.2    Doll, M.A.3    Hein, D.W.4    Woster, P.M.5    Svensson, C.K.6
  • 28
    • 33747103575 scopus 로고    scopus 로고
    • Mechanisms of drug-induced delayed-type hypersensitivity reactions in the skin
    • Roychowdhury S and Svensson CK (2005) Mechanisms of drug-induced delayed-type hypersensitivity reactions in the skin. AAPS J 7:E834-E846
    • (2005) AAPS J , vol.7
    • Roychowdhury, S.1    Svensson, C.K.2
  • 29
    • 23044473576 scopus 로고    scopus 로고
    • Characterization of the formation and localization of sulfamethoxazole and dapsone-associated drug-protein adducts in human epidermal keratinocytes
    • Roychowdhury S, Vyas PM, Reilly TP, Gaspari AA, and Svensson CK (2005) Characterization of the formation and localization of sulfamethoxazole and dapsone-associated drug-protein adducts in human epidermal keratinocytes. J Pharmacol Exp Ther 314:43-52.
    • (2005) J Pharmacol Exp Ther , vol.314 , pp. 43-52
    • Roychowdhury, S.1    Vyas, P.M.2    Reilly, T.P.3    Gaspari, A.A.4    Svensson, C.K.5
  • 31
    • 0141625021 scopus 로고    scopus 로고
    • Do arylhydroxylamine metabolites mediate the idiosyncratic reactions associated with sulfonamides and sulfones?
    • Svensson CK (2003) Do arylhydroxylamine metabolites mediate the idiosyncratic reactions associated with sulfonamides and sulfones? Chem Res Toxicol 16:1034-1043.
    • (2003) Chem Res Toxicol , vol.16 , pp. 1034-1043
    • Svensson, C.K.1
  • 33
    • 0009482260 scopus 로고
    • Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: Procedure and some applications
    • Towbin H, Staehelin T, and Gordon J (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc Natl Acad Sci USA 76:4350-4354.
    • (1979) Proc Natl Acad Sci USA , vol.76 , pp. 4350-4354
    • Towbin, H.1    Staehelin, T.2    Gordon, J.3
  • 34
    • 0023264655 scopus 로고
    • Characterization of a new human diploid myeloid leukemia cell line (PLB-985) with granulocytic and monocytic differentiating capacity
    • Tucker KA, Lilly MB, Heck L, and Rado TA (1987) Characterization of a new human diploid myeloid leukemia cell line (PLB-985) with granulocytic and monocytic differentiating capacity. Blood 70:372-378.
    • (1987) Blood , vol.70 , pp. 372-378
    • Tucker, K.A.1    Lilly, M.B.2    Heck, L.3    Rado, T.A.4
  • 35
    • 0024801405 scopus 로고
    • Drug metabolism by leukocytes and its role in drug-induced lupus and other idiosyncratic drug reactions
    • Uetrecht JP (1990) Drug metabolism by leukocytes and its role in drug-induced lupus and other idiosyncratic drug reactions. Crit Rev Toxicol 20:213-235.
    • (1990) Crit Rev Toxicol , vol.20 , pp. 213-235
    • Uetrecht, J.P.1
  • 36
    • 0026645711 scopus 로고
    • The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions
    • Uetrecht JP (1992) The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions. Drug Metab Rev 24:299-366.
    • (1992) Drug Metab Rev , vol.24 , pp. 299-366
    • Uetrecht, J.P.1
  • 37
    • 0023886192 scopus 로고
    • Metabolism of dapsone to a hydroxylamine by human neutrophils and mononuclear cells
    • Uetrecht J, Zahid N, Shear NH, and Biggar WD (1988) Metabolism of dapsone to a hydroxylamine by human neutrophils and mononuclear cells. J Pharmacol Exp Ther 245:274-279.
    • (1988) J Pharmacol Exp Ther , vol.245 , pp. 274-279
    • Uetrecht, J.1    Zahid, N.2    Shear, N.H.3    Biggar, W.D.4
  • 38
    • 29944436759 scopus 로고    scopus 로고
    • Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole
    • Vyas PM, Roychowdhury S, and Svensson CK (2006) Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole. Drug Metab Dispos 34:16-18.
    • (2006) Drug Metab Dispos , vol.34 , pp. 16-18
    • Vyas, P.M.1    Roychowdhury, S.2    Svensson, C.K.3
  • 39
    • 20444459901 scopus 로고    scopus 로고
    • Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes
    • Vyas PM, Roychowdhury S, Woster PM, and Svensson CK (2005) Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes. Biochem Pharmacol 70:275-286.
    • (2005) Biochem Pharmacol , vol.70 , pp. 275-286
    • Vyas, P.M.1    Roychowdhury, S.2    Woster, P.M.3    Svensson, C.K.4
  • 40
    • 0033855822 scopus 로고    scopus 로고
    • CYP 2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone
    • Winter HR, Wang Y, and Unadkat JD (2000) CYP 2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos 28:865-868.
    • (2000) Drug Metab Dispos , vol.28 , pp. 865-868
    • Winter, H.R.1    Wang, Y.2    Unadkat, J.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.