메뉴 건너뛰기




Volumn 39, Issue 12, 2011, Pages 2411-2420

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

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 BM3; GLUTATHIONE; GLUTATHIONE TRANSFERASE P1; HISTIDINE; METHIONINE; RECOMBINANT ENZYME;

EID: 81855173536     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.041046     Document Type: Article
Times cited : (14)

References (27)
  • 1
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
    • (1976) Anal Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 2
    • 0028787171 scopus 로고
    • Clozapine: Efficacy and safety
    • Buchanan RW (1995) Clozapine: efficacy and safety. Schizophr Bull 21:579-591.
    • (1995) Schizophr Bull , vol.21 , pp. 579-591
    • Buchanan, R.W.1
  • 3
    • 0034819837 scopus 로고    scopus 로고
    • Protein engineering of Bacillus megaterium CYP102A1. The oxidation of polycyclic aromatic hydrocarbons
    • Carmichael AB and Wong LL (2001) Protein engineering of Bacillus megaterium CYP102A1. The oxidation of polycyclic aromatic hydrocarbons. Eur J Biochem 268:3117-3125.
    • (2001) Eur J Biochem , vol.268 , pp. 3117-3125
    • Carmichael, A.B.1    Wong, L.L.2
  • 5
    • 77956900535 scopus 로고    scopus 로고
    • Role of human glutathione S-transferases in the inactivation of reactive metabolites of clozapine
    • Dragovic S, Boerma JS, van Bergen L, Vermeulen NP, and Commandeur JN (2010) Role of human glutathione S-transferases in the inactivation of reactive metabolites of clozapine. Chem Res Toxicol 23:1467-1476.
    • (2010) Chem Res Toxicol , vol.23 , pp. 1467-1476
    • Dragovic, S.1    Boerma, J.S.2    Van Bergen, L.3    Vermeulen, N.P.4    Commandeur, J.N.5
  • 6
    • 0033569516 scopus 로고    scopus 로고
    • Pharmacogenomics: Translating functional genomics into rational therapeutics
    • Evans WE and Relling MV (1999) Pharmacogenomics: translating functional genomics into rational therapeutics. Science 286:487-491.
    • (1999) Science , vol.286 , pp. 487-491
    • Evans, W.E.1    Relling, M.V.2
  • 7
    • 0025746640 scopus 로고
    • Possible role of free radical formation in clozapine (clorazil) induced agranulocytosis
    • Fischer V, Haar JA, Greiner L, Lloyd RV, and Mason RP (1991) Possible role of free radical formation in clozapine (clorazil) induced agranulocytosis. Mol Pharmacol 40:846-853.
    • (1991) Mol Pharmacol , vol.40 , pp. 846-853
    • Fischer, V.1    Haar, J.A.2    Greiner, L.3    Lloyd, R.V.4    Mason, R.P.5
  • 8
    • 0016275313 scopus 로고
    • Glutathione S-transferases. The first enzymatic step in mercapturic acid formation
    • Habig WH, Pabst MJ, and Jakoby WB (1974) Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 249:7130-7139.
    • (1974) J Biol Chem , vol.249 , pp. 7130-7139
    • Habig, W.H.1    Pabst, M.J.2    Jakoby, W.B.3
  • 11
    • 33646505950 scopus 로고    scopus 로고
    • Enantio-selective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3
    • Landwehr M, Hochrein L, Otey CR, Kasrayan A, Bäckvall JE, and Arnold FH (2006) Enantio-selective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3. J Am Chem Soc 128:6058-6059.
    • (2006) J Am Chem Soc , vol.128 , pp. 6058-6059
    • Landwehr, M.1    Hochrein, L.2    Otey, C.R.3    Kasrayan, A.4    Bäckvall, J.E.5    Arnold, F.H.6
  • 12
    • 0035653258 scopus 로고    scopus 로고
    • Engineering Cytochrome P450 BM-3 for Oxidation of Polycyclic Aromatic Hydrocarbons
    • DOI 10.1128/AEM.67.12.5735-5739.2001
    • Li QS, Ogawa J, Schmid RD, and Shimizu S (2001) Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons. Appl Environ Microbiol 67:5735-5739. (Pubitemid 33641012)
    • (2001) Applied and Environmental Microbiology , vol.67 , Issue.12 , pp. 5735-5739
    • Li, Q.S.1    Ogawa, J.2    Schmid, R.D.3    Shimizu, S.4
  • 13
    • 0029555342 scopus 로고
    • Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells
    • Liu ZC and Uetrecht JP (1995) Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells. J Pharmacol Exp Ther 275:1476-1483.
    • (1995) J Pharmacol Exp Ther , vol.275 , pp. 1476-1483
    • Liu, Z.C.1    Uetrecht, J.P.2
  • 14
    • 18144389824 scopus 로고    scopus 로고
    • Evaluation of alkoxyresorufins as fluorescent substrates for cytochrome P450 BM3 and site-directed mutants
    • DOI 10.1016/j.ab.2005.02.025
    • Lussenburg BM, Babel LC, Vermeulen NP, and Commandeur JN (2005) Evaluation of alkoxyresorufins as fluorescent substrates for cytochrome P450 BM3 and site-directed mutants. Anal Biochem 341:148-155. (Pubitemid 40615731)
    • (2005) Analytical Biochemistry , vol.341 , Issue.1 , pp. 148-155
    • Lussenburg, B.M.A.1    Babel, L.C.2    Vermeulen, N.P.E.3    Commandeur, J.N.M.4
  • 15
    • 34250731278 scopus 로고    scopus 로고
    • Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: Correlation to in vitro drug metabolism
    • DOI 10.1021/tx700029u
    • Madsen KG, Olsen J, Skonberg C, Hansen SH, and Jurva U (2007) Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism. Chem Res Toxicol 20:821-831. (Pubitemid 46953690)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.5 , pp. 821-831
    • Madsen, K.G.1    Olsen, J.2    Skonberg, C.3    Hansen, S.H.4    Jurva, U.5
  • 16
    • 0029416850 scopus 로고
    • The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man
    • Maggs JL, Williams D, Pirmohamed M, and Park BK (1995) The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man. J Pharmacol Exp Ther 275:1463-1475.
    • (1995) J Pharmacol Exp Ther , vol.275 , pp. 1463-1475
    • Maggs, J.L.1    Williams, D.2    Pirmohamed, M.3    Park, B.K.4
  • 20
    • 70350518093 scopus 로고    scopus 로고
    • A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds
    • Sawayama AM, Chen MM, Kulanthaivel P, Kuo MS, Hemmerle H, and Arnold FH (2009) A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds. Chemistry 15:11723-11729.
    • (2009) Chemistry , vol.15 , pp. 11723-11729
    • Sawayama, A.M.1    Chen, M.M.2    Kulanthaivel, P.3    Kuo, M.S.4    Hemmerle, H.5    Arnold, F.H.6
  • 21
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada T, Yamazaki H, Mimura M, Inui Y, and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423. (Pubitemid 24229655)
    • (1994) Journal of Pharmacology and Experimental Therapeutics , vol.270 , Issue.1 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 22
    • 62249177821 scopus 로고    scopus 로고
    • Metabolites in safety testing (MIST): Considerations of mechanisms of toxicity with dose, abundance, and duration of treatment
    • Smith DA and Obach RS (2009) Metabolites in safety testing (MIST): considerations of mechanisms of toxicity with dose, abundance, and duration of treatment. Chem Res Toxicol. 22:267-279.
    • (2009) Chem Res Toxicol , vol.22 , pp. 267-279
    • Smith, D.A.1    Obach, R.S.2
  • 23
    • 0032955464 scopus 로고    scopus 로고
    • Characterization of the human hepatic cytochromes P450 involved in the in vitro oxidation of clozapine
    • DOI 10.1016/S0009-2797(99)00006-X, PII S000927979900006X
    • Tugnait M, Hawes EM, McKay G, Eichelbaum M, and Midha KK (1999) Characterization of the human hepatic cytochromes P450 involved in the in vitro oxidation of clozapine. Chem-Biol Interact 118:171-189. (Pubitemid 29179541)
    • (1999) Chemico-Biological Interactions , vol.118 , Issue.2 , pp. 171-189
    • Tugnait, M.1    Hawes, E.M.2    McKay, G.3    Eichelbaum, M.4    Midha, K.K.5
  • 25
    • 80051550259 scopus 로고    scopus 로고
    • Role of residue 87 in substrate selectivity and regioselectivity of drug-metabolizing cytochrome P450 CYP102A1 M11
    • Vottero E, Rea V, Lastdrager J, Honing M, Vermeulen NP, and Commandeur JN (2011) Role of residue 87 in substrate selectivity and regioselectivity of drug-metabolizing cytochrome P450 CYP102A1 M11. J Biol Inorg Chem 16:899-912.
    • (2011) J Biol Inorg Chem , vol.16 , pp. 899-912
    • Vottero, E.1    Rea, V.2    Lastdrager, J.3    Honing, M.4    Vermeulen, N.P.5    Commandeur, J.N.6
  • 26
    • 0037243460 scopus 로고    scopus 로고
    • Clozapine: In prevention of suicide in patients with schizophrenia or schizoaffective disorder
    • DOI 10.2165/00023210-200317040-00004
    • Wagstaff A and Perry C (2003) Clozapine: in prevention of suicide in patients with schizophrenia or schizoaffective disorder. CNS Drugs 17:273-280 (Pubitemid 36390411)
    • (2003) CNS Drugs , vol.17 , Issue.4 , pp. 273-280
    • Wagstaff, A.J.1    Perry, C.M.2
  • 27
    • 34250215649 scopus 로고    scopus 로고
    • The bacterial P450 BM3: A prototype for a biocatalyst with human P450 activities
    • DOI 10.1016/j.tibtech.2007.05.003, PII S0167779907001321
    • Yun CH, Kim KH, Kim DH, Jung HC, and Pan JG (2007) The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol 25:289-298. (Pubitemid 46899248)
    • (2007) Trends in Biotechnology , vol.25 , Issue.7 , pp. 289-298
    • Yun, C.-H.1    Kim, K.-H.2    Kim, D.-H.3    Jung, H.-C.4    Pan, J.-G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.