메뉴 건너뛰기




Volumn 40, Issue 12, 2012, Pages 2256-2266

Inhibition of bupropion metabolism by selegiline: Mechanism-based inactivation of human CYP2B6 and characterization of glutathione and peptide adducts

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXY 4 (TRIFLUOROMETHYL)COUMARIN; AMFEBUTAMONE; ASPARTIC ACID 64; ASPARTYLVALYLPHENYLALANYLTHREONYLVALYLLEUCYLGLYCYLPROLYLARGININE; CARBON MONOXIDE; COUMARIN; CYTOCHROME P450; CYTOCHROME P450 2B6; GLUTATHIONE; KETENE DERIVATIVE; PEPTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SELEGILINE; UNCLASSIFIED DRUG;

EID: 84869127435     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.046979     Document Type: Article
Times cited : (22)

References (38)
  • 3
    • 18844433876 scopus 로고    scopus 로고
    • The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation
    • Bumpus NN, Sridar C, Kent UM, and Hollenberg PF (2005) The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos 33:795-802.
    • (2005) Drug Metab Dispos , vol.33 , pp. 795-802
    • Bumpus, N.N.1    Sridar, C.2    Kent, U.M.3    Hollenberg, P.F.4
  • 4
    • 0027374515 scopus 로고
    • A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4-trifluoromethylcoumarin
    • Buters JT, Schiller CD, and Chou RC (1993) A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4- trifluoromethylcoumarin. Biochem Pharmacol 46:1577-1584.
    • (1993) Biochem Pharmacol , vol.46 , pp. 1577-1584
    • Buters, J.T.1    Schiller, C.D.2    Chou, R.C.3
  • 5
    • 0027369366 scopus 로고
    • Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes
    • Chang TK, Weber GF, Crespi CL, and Waxman DJ (1993) Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Res 53:5629-5637.
    • (1993) Cancer Res , vol.53 , pp. 5629-5637
    • Chang, T.K.1    Weber, G.F.2    Crespi, C.L.3    Waxman, D.J.4
  • 6
    • 1242330313 scopus 로고    scopus 로고
    • Phe393 mutants of cytochrome P450 BM3 with modified heme redox potentials have altered heme vinyl and propionate conformations
    • Chen Z, Ost TW, and Schelvis JP (2004) Phe393 mutants of cytochrome P450 BM3 with modified heme redox potentials have altered heme vinyl and propionate conformations. Biochemistry 43:1798-1808.
    • (2004) Biochemistry , vol.43 , pp. 1798-1808
    • Chen, Z.1    Ost, T.W.2    Schelvis, J.P.3
  • 7
    • 0019298752 scopus 로고
    • Behavioral and biochemical effects of the antidepressant bupropion (Wellbutrin): Evidence for selective blockade of dopamine uptake in vivo
    • Cooper BR, Hester TJ, and Maxwell RA (1980) Behavioral and biochemical effects of the antidepressant bupropion (Wellbutrin): evidence for selective blockade of dopamine uptake in vivo. J Pharmacol Exp Ther 215:127-134.
    • (1980) J Pharmacol Exp Ther , vol.215 , pp. 127-134
    • Cooper, B.R.1    Hester, T.J.2    Maxwell, R.A.3
  • 8
    • 0026513381 scopus 로고
    • An estimate of the incidence of depression in idiopathic Parkinson's disease
    • Dooneief G, Mirabello E, Bell K, Marder K, Stern Y, and Mayeux R (1992) An estimate of the incidence of depression in idiopathic Parkinson's disease. Arch Neurol 49:305-307.
    • (1992) Arch Neurol , vol.49 , pp. 305-307
    • Dooneief, G.1    Mirabello, E.2    Bell, K.3    Marder, K.4    Stern, Y.5    Mayeux, R.6
  • 10
    • 33750071426 scopus 로고    scopus 로고
    • Bupropion: Pharmacology and therapeutic applications
    • Foley KF, DeSanty KP, and Kast RE (2006) Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother 6:1249-1265.
    • (2006) Expert Rev Neurother , vol.6 , pp. 1249-1265
    • Foley, K.F.1    DeSanty, K.P.2    Kast, R.E.3
  • 11
    • 0019798422 scopus 로고
    • The acetylenic monoamine oxidase inhibitors clorgyline, deprenyl, pargyline and J-508: Their properties and applications
    • Fowler CJ, Oreland L, and Callingham BA (1981) The acetylenic monoamine oxidase inhibitors clorgyline, deprenyl, pargyline and J-508: their properties and applications. J Pharm Pharmacol 33:341-347.
    • (1981) J Pharm Pharmacol , vol.33 , pp. 341-347
    • Fowler, C.J.1    Oreland, L.2    Callingham, B.A.3
  • 15
    • 0034177265 scopus 로고    scopus 로고
    • Expression of human cytochrome P450 2B6 in Escherichia coli: Characterization of catalytic activity and expression levels in human liver
    • Hanna IH, Reed JR, Guengerich FP, and Hollenberg PF (2000) Expression of human cytochrome P450 2B6 in Escherichia coli: characterization of catalytic activity and expression levels in human liver. Arch Biochem Biophys 376:206-216.
    • (2000) Arch Biochem Biophys , vol.376 , pp. 206-216
    • Hanna, I.H.1    Reed, J.R.2    Guengerich, F.P.3    Hollenberg, P.F.4
  • 16
    • 0031822496 scopus 로고    scopus 로고
    • Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- And hydroperoxide-supported activities
    • Hanna IH, Teiber JF, Kokones KL, and Hollenberg PF (1998) Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch Biochem Biophys 350:324-332.
    • (1998) Arch Biochem Biophys , vol.350 , pp. 324-332
    • Hanna, I.H.1    Teiber, J.F.2    Kokones, K.L.3    Hollenberg, P.F.4
  • 18
    • 0034772878 scopus 로고    scopus 로고
    • CYP2B6 and CYP2C19 as the major enzymes responsible for the metabolism of selegiline, a drug used in the treatment of Parkinson's disease, as revealed from experiments with recombinant enzymes
    • Hidestrand M, Oscarson M, Salonen JS, Nyman L, Pelkonen O, Turpeinen M, and Ingelman-Sundberg M (2001) CYP2B6 and CYP2C19 as the major enzymes responsible for the metabolism of selegiline, a drug used in the treatment of Parkinson's disease, as revealed from experiments with recombinant enzymes. Drug Metab Dispos 29:1480-1484.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1480-1484
    • Hidestrand, M.1    Oscarson, M.2    Salonen, J.S.3    Nyman, L.4    Pelkonen, O.5    Turpeinen, M.6    Ingelman-Sundberg, M.7
  • 19
    • 38949099990 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human cytochromes P450s: Experimental characterization, reactive intermediates, and clinical implications
    • Hollenberg PF, Kent UM, and Bumpus NN (2008) Mechanism-based inactivation of human cytochromes P450s: experimental characterization, reactive intermediates, and clinical implications. Chem Res Toxicol 21:189-205.
    • (2008) Chem Res Toxicol , vol.21 , pp. 189-205
    • Hollenberg, P.F.1    Kent, U.M.2    Bumpus, N.N.3
  • 20
    • 0015274536 scopus 로고
    • Some puzzling pharmacological effects of monoamine oxidase inhibitors
    • Knoll J and Magyar K (1972) Some puzzling pharmacological effects of monoamine oxidase inhibitors. Adv Biochem Psychopharmacol 5:393-408.
    • (1972) Adv Biochem Psychopharmacol , vol.5 , pp. 393-408
    • Knoll, J.1    Magyar, K.2
  • 22
    • 0030300160 scopus 로고    scopus 로고
    • The pharmacology of B-type selective monoamine oxidase inhibitors; milestones in (-)-deprenyl research
    • Magyar K, Szende B, Lengyel J, and Tekes K (1996) The pharmacology of B-type selective monoamine oxidase inhibitors; milestones in (-)-deprenyl research. J Neural Transm Suppl 48:29-43.
    • (1996) J Neural Transm Suppl , vol.48 , pp. 29-43
    • Magyar, K.1    Szende, B.2    Lengyel, J.3    Tekes, K.4
  • 23
    • 0038119910 scopus 로고    scopus 로고
    • Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain
    • Miksys S, Lerman C, Shields PG, Mash DC, and Tyndale RF (2003) Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain. Neuropharmacology 45:122-132.
    • (2003) Neuropharmacology , vol.45 , pp. 122-132
    • Miksys, S.1    Lerman, C.2    Shields, P.G.3    Mash, D.C.4    Tyndale, R.F.5
  • 24
    • 0036874345 scopus 로고    scopus 로고
    • Drug-metabolizing cytochrome P450s in the brain
    • Miksys SL and Tyndale RF (2002) Drug-metabolizing cytochrome P450s in the brain. J Psychiatry Neurosci 27:406-415.
    • (2002) J Psychiatry Neurosci , vol.27 , pp. 406-415
    • Miksys, S.L.1    Tyndale, R.F.2
  • 25
    • 0021946341 scopus 로고
    • Branchpoint for heme alkylation and metabolite formation in the oxidation of arylacetylenes by cytochrome P-450
    • Ortiz de Montellano PR and Komives EA (1985) Branchpoint for heme alkylation and metabolite formation in the oxidation of arylacetylenes by cytochrome P-450. J Biol Chem 260:3330-3336.
    • (1985) J Biol Chem , vol.260 , pp. 3330-3336
    • Ortiz De Montellano, P.R.1    Komives, E.A.2
  • 26
    • 0025647353 scopus 로고
    • 2-Phenylethylamine: A modulator of catecholamine transmission in the mammalian central nervous system?
    • Paterson IA, Juorio AV, and Boulton AA (1990) 2-Phenylethylamine: a modulator of catecholamine transmission in the mammalian central nervous system? J Neurochem 55:1827-1837.
    • (1990) J Neurochem , vol.55 , pp. 1827-1837
    • Paterson, I.A.1    Juorio, A.V.2    Boulton, A.A.3
  • 27
    • 0018068203 scopus 로고
    • Amphetamine and 2-phenylethylamine in post-mortem Parkinsonian brain after (-)deprenyl administration
    • Reynolds GP, Riederer P, Sandler M, Jellinger K, and Seemann D (1978) Amphetamine and 2-phenylethylamine in post-mortem Parkinsonian brain after (-)deprenyl administration. J Neural Transm 43:271-277.
    • (1978) J Neural Transm , vol.43 , pp. 271-277
    • Reynolds, G.P.1    Riederer, P.2    Sandler, M.3    Jellinger, K.4    Seemann, D.5
  • 28
    • 0030664249 scopus 로고    scopus 로고
    • A survey of antidepressant drug use in Parkinson's disease. Parkinson Study Group
    • Richard IH and Kurlan R (1997) A survey of antidepressant drug use in Parkinson's disease. Parkinson Study Group. Neurology 49:1168-1170.
    • (1997) Neurology , vol.49 , pp. 1168-1170
    • Richard, I.H.1    Kurlan, R.2
  • 29
    • 0022496317 scopus 로고
    • Monoamine oxidase activity and monoamine metabolism in brains of parkinsonian patients treated with l-deprenyl
    • Riederer P and Youdim MB (1986) Monoamine oxidase activity and monoamine metabolism in brains of parkinsonian patients treated with l-deprenyl. J Neurochem 46:1359-1365.
    • (1986) J Neurochem , vol.46 , pp. 1359-1365
    • Riederer, P.1    Youdim, M.B.2
  • 31
    • 0030807313 scopus 로고    scopus 로고
    • Retrospective study of selegiline-antidepressant drug interactions and a review of the literature
    • Ritter JL and Alexander B (1997) Retrospective study of selegiline-antidepressant drug interactions and a review of the literature. Ann Clin Psychiatry 9:7-13.
    • (1997) Ann Clin Psychiatry , vol.9 , pp. 7-13
    • Ritter, J.L.1    Alexander, B.2
  • 32
    • 3042553224 scopus 로고    scopus 로고
    • Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl)imidazole at 1.9-A resolution: Insight into the range of P450 conformations and the coordination of redox partner binding
    • Scott EE, White MA, He YA, Johnson EF, Stout CD, and Halpert JR (2004) Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl) imidazole at 1.9-A resolution: insight into the range of P450 conformations and the coordination of redox partner binding. J Biol Chem 279:27294-27301.
    • (2004) J Biol Chem , vol.279 , pp. 27294-27301
    • Scott, E.E.1    White, M.A.2    He, Y.A.3    Johnson, E.F.4    Stout, C.D.5    Halpert, J.R.6
  • 33
    • 0030068081 scopus 로고    scopus 로고
    • Inactivation of cytochrome P4502B1 by the monoamine oxidase inhibitors R-(-)-deprenyl and clorgyline
    • Sharma U, Roberts ES, and Hollenberg PF (1996) Inactivation of cytochrome P4502B1 by the monoamine oxidase inhibitors R-(-)-deprenyl and clorgyline. Drug Metab Dispos 24:669-675.
    • (1996) Drug Metab Dispos , vol.24 , pp. 669-675
    • Sharma, U.1    Roberts, E.S.2    Hollenberg, P.F.3
  • 34
    • 40849119970 scopus 로고    scopus 로고
    • Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice
    • Siu EC and Tyndale RF (2008) Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice. J Pharmacol Exp Ther 324:992-999.
    • (2008) J Pharmacol Exp Ther , vol.324 , pp. 992-999
    • Siu, E.C.1    Tyndale, R.F.2
  • 35
    • 0032926621 scopus 로고    scopus 로고
    • Monospecific antipeptide antibody to cytochrome P-450 2B6
    • Stresser DM and Kupfer D (1999) Monospecific antipeptide antibody to cytochrome P-450 2B6. Drug Metab Dispos 27:517-525.
    • (1999) Drug Metab Dispos , vol.27 , pp. 517-525
    • Stresser, D.M.1    Kupfer, D.2
  • 38
    • 70350028665 scopus 로고    scopus 로고
    • Effect of conformational dynamics on substrate recognition and specificity as probed by the introduction of a de novo disulfide bond into cytochrome P450 2B1
    • Zhang H, Kenaan C, Hamdane D, Hoa GH, and Hollenberg PF (2009) Effect of conformational dynamics on substrate recognition and specificity as probed by the introduction of a de novo disulfide bond into cytochrome P450 2B1. J Biol Chem 284:25678-25686.
    • (2009) J Biol Chem , vol.284 , pp. 25678-25686
    • Zhang, H.1    Kenaan, C.2    Hamdane, D.3    Hoa, G.H.4    Hollenberg, P.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.