메뉴 건너뛰기




Volumn 216, Issue 3, 2006, Pages 387-398

Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated β-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6

Author keywords

carbolines; 1 Methyl 4 phenyl 1,2,3,6 tetrahydropyridine; 1 Methyl 4 phenylpyridinium; CYP2D6; Cytochrome P450; Hydroxylation; Isoquinolines; MAO; Metabolism; Monoamine oxidase; MPTP neurotoxin; N demethylation; Parkinson's disease; Polymorphism; Tetrahydro carbolines

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 6 HYDROXY N2 METHYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE; BETA CARBOLINE; CARBOLINE DERIVATIVE; CYTOCHROME P450 2D6; ISOQUINOLINE ALKALOID; N2 METHYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE; NEUROTOXIN; UNCLASSIFIED DRUG;

EID: 33750079907     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2006.06.003     Document Type: Article
Times cited : (37)

References (87)
  • 1
    • 0030472746 scopus 로고    scopus 로고
    • Action of harman (1-methyl-beta-carboline) on the brain: body temperature and in vivo efflux of 5-HT from hippocampus of the rat
    • Adell A., Biggs T.A., and Myers R.D. Action of harman (1-methyl-beta-carboline) on the brain: body temperature and in vivo efflux of 5-HT from hippocampus of the rat. Neuropharmacology 35 (1996) 1101-1107
    • (1996) Neuropharmacology , vol.35 , pp. 1101-1107
    • Adell, A.1    Biggs, T.A.2    Myers, R.D.3
  • 2
    • 0019776320 scopus 로고
    • β-carbolines, psychoactive compounds in the mammalian body: Part 2. Effects
    • Airaksinen M.M., and Kari I. β-carbolines, psychoactive compounds in the mammalian body: Part 2. Effects. Med. Biol. 59 (1981) 190-211
    • (1981) Med. Biol. , vol.59 , pp. 190-211
    • Airaksinen, M.M.1    Kari, I.2
  • 3
    • 0025688141 scopus 로고
    • Mitochondrial respiratory inhibition by N-methylated beta-carboline derivatives structurally resembling N-methyl-4-phenylpyridine
    • Albores R., Neafsey E.J., Drucker G., Fields J.Z., and Collins M.A. Mitochondrial respiratory inhibition by N-methylated beta-carboline derivatives structurally resembling N-methyl-4-phenylpyridine. Proc. Natl. Acad. Sci. U. S. A. 87 (1990) 9368-9372
    • (1990) Proc. Natl. Acad. Sci. U. S. A. , vol.87 , pp. 9368-9372
    • Albores, R.1    Neafsey, E.J.2    Drucker, G.3    Fields, J.Z.4    Collins, M.A.5
  • 4
    • 0030600524 scopus 로고    scopus 로고
    • Harman-induced changes of extracellular concentrations of neurotransmitters in the nucleous accumbens of rats
    • Baum S.S., Hill R., and Rommelspacher H. Harman-induced changes of extracellular concentrations of neurotransmitters in the nucleous accumbens of rats. Eur. J. Pharmacol. 314 (1996) 75-82
    • (1996) Eur. J. Pharmacol. , vol.314 , pp. 75-82
    • Baum, S.S.1    Hill, R.2    Rommelspacher, H.3
  • 6
    • 3242703231 scopus 로고    scopus 로고
    • The strong inhibition of triosephosphate isomerase by the natural beta-carbolines may explain the neurotoxic actions
    • Bonnet R., Pavlovic S., Lehmann J., and Rommelspacher H. The strong inhibition of triosephosphate isomerase by the natural beta-carbolines may explain the neurotoxic actions. Neuroscience 127 (2004) 443-453
    • (2004) Neuroscience , vol.127 , pp. 443-453
    • Bonnet, R.1    Pavlovic, S.2    Lehmann, J.3    Rommelspacher, H.4
  • 7
    • 0022634053 scopus 로고
    • Contribution of N-oxygenation to the metabolism of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) by various liver preparations
    • Cashman J.R., and Ziegler D.M. Contribution of N-oxygenation to the metabolism of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) by various liver preparations. Mol. Pharmacol. 29 (1986) 163-167
    • (1986) Mol. Pharmacol. , vol.29 , pp. 163-167
    • Cashman, J.R.1    Ziegler, D.M.2
  • 8
    • 0021276089 scopus 로고
    • Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase
    • Chiba K., Trevor A., and Castagnoli Jr. N. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120 (1984) 574-578
    • (1984) Biochem. Biophys. Res. Commun. , vol.120 , pp. 574-578
    • Chiba, K.1    Trevor, A.2    Castagnoli Jr., N.3
  • 9
    • 0023687420 scopus 로고
    • Characterization of hepatic microsomal metabolism as an in vivo detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice
    • Chiba K., Kubota E., Miyakawa T., Kato Y., and Ishizaki T. Characterization of hepatic microsomal metabolism as an in vivo detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice. J. Pharmacol. Exp. Ther. 246 (1988) 1108-1115
    • (1988) J. Pharmacol. Exp. Ther. , vol.246 , pp. 1108-1115
    • Chiba, K.1    Kubota, E.2    Miyakawa, T.3    Kato, Y.4    Ishizaki, T.5
  • 10
    • 0037198965 scopus 로고    scopus 로고
    • Constitutive expression and localization of the major drug metabolizing enzyme, cytochrome P4502D in human brain
    • Chinta S.J., Pai H.V., Upadhya S.C., Boyd M.R., and Ravindranath V. Constitutive expression and localization of the major drug metabolizing enzyme, cytochrome P4502D in human brain. Mol. Brain Res. 103 (2002) 49-61
    • (2002) Mol. Brain Res. , vol.103 , pp. 49-61
    • Chinta, S.J.1    Pai, H.V.2    Upadhya, S.C.3    Boyd, M.R.4    Ravindranath, V.5
  • 11
    • 18044371666 scopus 로고    scopus 로고
    • Presence of splice variant forms of cytochrome P4502D1 in rat brain but not in liver
    • Chinta S.J., Pai H.V., and Ravindranath V. Presence of splice variant forms of cytochrome P4502D1 in rat brain but not in liver. Mol. Brain Res. 135 (2005) 81-92
    • (2005) Mol. Brain Res. , vol.135 , pp. 81-92
    • Chinta, S.J.1    Pai, H.V.2    Ravindranath, V.3
  • 12
    • 0028176878 scopus 로고
    • Differential cytotoxycities of N-methyl-β-carbolinium analogues of MPP+ in PC12 cells: insights into potential neurotoxicants in Parkinson's disease
    • Cobuzzi R.J., Neafsey E.J., and Collins M.A. Differential cytotoxycities of N-methyl-β-carbolinium analogues of MPP+ in PC12 cells: insights into potential neurotoxicants in Parkinson's disease. J. Neurochem. 62 (1994) 1503-1510
    • (1994) J. Neurochem. , vol.62 , pp. 1503-1510
    • Cobuzzi, R.J.1    Neafsey, E.J.2    Collins, M.A.3
  • 13
    • 0030436624 scopus 로고    scopus 로고
    • 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) is N-demethylated by cytochromes P450 2D6, 1A2 and 3A4. Implications for susceptibility to Parkinson's disease
    • Coleman T., Ellis S.W., Martin I.J., Lennard M.S., and Tucker G.T. 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) is N-demethylated by cytochromes P450 2D6, 1A2 and 3A4. Implications for susceptibility to Parkinson's disease. J. Pharmacol. Exp. Ther. 277 (1996) 685-690
    • (1996) J. Pharmacol. Exp. Ther. , vol.277 , pp. 685-690
    • Coleman, T.1    Ellis, S.W.2    Martin, I.J.3    Lennard, M.S.4    Tucker, G.T.5
  • 14
    • 0036767978 scopus 로고    scopus 로고
    • Alkaloids, alcohol and Parkinson's disease
    • Collins M.A. Alkaloids, alcohol and Parkinson's disease. Parkinsonism Relat. Disord. 8 (2002) 417-422
    • (2002) Parkinsonism Relat. Disord. , vol.8 , pp. 417-422
    • Collins, M.A.1
  • 15
    • 0021992979 scopus 로고
    • Beta-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): endogenous factors underlying parkinsonism?
    • Collins M.A., and Neafsey E.J. Beta-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): endogenous factors underlying parkinsonism?. Neurosci. Lett. 55 (1985) 179-184
    • (1985) Neurosci. Lett. , vol.55 , pp. 179-184
    • Collins, M.A.1    Neafsey, E.J.2
  • 16
    • 0036715374 scopus 로고    scopus 로고
    • Potential neurotoxic "agents provocateurs" in Parkinson's disease
    • Collins M.A., and Neafsey E.J. Potential neurotoxic "agents provocateurs" in Parkinson's disease. Neurotoxicol. Teratol. 24 (2002) 571-577
    • (2002) Neurotoxicol. Teratol. , vol.24 , pp. 571-577
    • Collins, M.A.1    Neafsey, E.J.2
  • 17
    • 2542513258 scopus 로고    scopus 로고
    • Further evidence that interactions between CYP2D6 and pesticide exposure increase risk for Parkinson's disease
    • Deng Y., Newman B., Dunne M.P., Silburn P.A., and Mellick G.D. Further evidence that interactions between CYP2D6 and pesticide exposure increase risk for Parkinson's disease. Ann. Neurol. 55 (2004) 897
    • (2004) Ann. Neurol. , vol.55 , pp. 897
    • Deng, Y.1    Newman, B.2    Dunne, M.P.3    Silburn, P.A.4    Mellick, G.D.5
  • 18
    • 0035367218 scopus 로고    scopus 로고
    • Human NADPH-P450 oxidoreductase modulates the level of cytochrome P450 CYP2D6 holoprotein via haem oxygenase-dependent and -independent pathways
    • Ding S., Yao D., Deeni Y.Y., Burchell B., Wolf C.R., and Friedberg T. Human NADPH-P450 oxidoreductase modulates the level of cytochrome P450 CYP2D6 holoprotein via haem oxygenase-dependent and -independent pathways. Biochem. J. 356 (2001) 613-619
    • (2001) Biochem. J. , vol.356 , pp. 613-619
    • Ding, S.1    Yao, D.2    Deeni, Y.Y.3    Burchell, B.4    Wolf, C.R.5    Friedberg, T.6
  • 20
    • 2642570170 scopus 로고    scopus 로고
    • Moving towards individualized medicine with pharmacogenomics
    • Evans W.E., and Relling M.V. Moving towards individualized medicine with pharmacogenomics. Nature 429 (2004) 464-468
    • (2004) Nature , vol.429 , pp. 464-468
    • Evans, W.E.1    Relling, M.V.2
  • 21
    • 0027235317 scopus 로고
    • Occurrence and partition of the β-carboline norharman in rat organs
    • Fekkes D., and Bode W.T. Occurrence and partition of the β-carboline norharman in rat organs. Life Sci. 52 (1993) 2045-2054
    • (1993) Life Sci. , vol.52 , pp. 2045-2054
    • Fekkes, D.1    Bode, W.T.2
  • 22
    • 0023568113 scopus 로고
    • MPTP, the neurotoxin inducing Parkinson's disease, is a potent competitive inhibitor of human and rat cytochrome P450 isozymes (P450bufI, P450db1) catalyzing debrisoquine-4-hydroxylation
    • Fonne-Pfister R., Bargetzi M.J., and Meyer U.A. MPTP, the neurotoxin inducing Parkinson's disease, is a potent competitive inhibitor of human and rat cytochrome P450 isozymes (P450bufI, P450db1) catalyzing debrisoquine-4-hydroxylation. Biochem. Biophys. Res. Commun. 148 (1987) 1144-1150
    • (1987) Biochem. Biophys. Res. Commun. , vol.148 , pp. 1144-1150
    • Fonne-Pfister, R.1    Bargetzi, M.J.2    Meyer, U.A.3
  • 23
    • 0034663081 scopus 로고    scopus 로고
    • The decreased in vivo clearance of CYP2D6 substrates by CYP2D6*10 might be caused not only by low-expression but also by low affinity of CYP2D6
    • Fukuda T., Nishida Y., Imaoka S., Hiroi T., Naohara M., Funae Y., and Azuma J. The decreased in vivo clearance of CYP2D6 substrates by CYP2D6*10 might be caused not only by low-expression but also by low affinity of CYP2D6. Arch. Biochem. Biophys. 380 (2000) 303-308
    • (2000) Arch. Biochem. Biophys. , vol.380 , pp. 303-308
    • Fukuda, T.1    Nishida, Y.2    Imaoka, S.3    Hiroi, T.4    Naohara, M.5    Funae, Y.6    Azuma, J.7
  • 24
    • 0034210323 scopus 로고    scopus 로고
    • Increased beta-carboline 9N-methyltransferase activity in the frontal cortex in Parkinson's disease
    • Gearhart D.A., Collins M.A., Lee J.M., and Neafsey E.J. Increased beta-carboline 9N-methyltransferase activity in the frontal cortex in Parkinson's disease. Neurobiol. Dis. 7 (2000) 201-211
    • (2000) Neurobiol. Dis. , vol.7 , pp. 201-211
    • Gearhart, D.A.1    Collins, M.A.2    Lee, J.M.3    Neafsey, E.J.4
  • 25
    • 0031014344 scopus 로고    scopus 로고
    • Metabolism of MPTP by cytochrome P450 2D6 and the demonstration of 2D6 mRNA in human foetal and adult brain by in situ hybridization
    • Gilham D.E., Cairns W., Paine M.J.I., Modi S., Poulsom R., Roberts G.C.K., and Wolf C.R. Metabolism of MPTP by cytochrome P450 2D6 and the demonstration of 2D6 mRNA in human foetal and adult brain by in situ hybridization. Xenobiotica 27 (1997) 111-125
    • (1997) Xenobiotica , vol.27 , pp. 111-125
    • Gilham, D.E.1    Cairns, W.2    Paine, M.J.I.3    Modi, S.4    Poulsom, R.5    Roberts, G.C.K.6    Wolf, C.R.7
  • 28
    • 0035955733 scopus 로고    scopus 로고
    • Diversity in mechanisms of substrate oxidation by Cytochrome P450 2D6. Lack of an allosteric role of NADPH-cytochrome P450 reductase in catalytic regioselectivity
    • Hanna I.H., Krauser J.A., Cai H., Kim M.-S., and Guengerich F.P. Diversity in mechanisms of substrate oxidation by Cytochrome P450 2D6. Lack of an allosteric role of NADPH-cytochrome P450 reductase in catalytic regioselectivity. J. Biol. Chem. 276 (2001) 39553-39561
    • (2001) J. Biol. Chem. , vol.276 , pp. 39553-39561
    • Hanna, I.H.1    Krauser, J.A.2    Cai, H.3    Kim, M.-S.4    Guengerich, F.P.5
  • 29
    • 0021224694 scopus 로고
    • Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors
    • Heikkila R.E., Manzino L., Cabbat F.S., and Duvoisin R.C. Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature 311 (1984) 467-469
    • (1984) Nature , vol.311 , pp. 467-469
    • Heikkila, R.E.1    Manzino, L.2    Cabbat, F.S.3    Duvoisin, R.C.4
  • 30
    • 0034625496 scopus 로고    scopus 로고
    • Analysis of the bioactive alkaloids tetrahydro-β-carboline and β-carboline in food
    • Herraiz T. Analysis of the bioactive alkaloids tetrahydro-β-carboline and β-carboline in food. J. Chromatogr. A 881 (2000) 483-499
    • (2000) J. Chromatogr. A , vol.881 , pp. 483-499
    • Herraiz, T.1
  • 31
    • 30544447525 scopus 로고    scopus 로고
    • Tetrahydro-β-carboline bioactive alkaloids in beverages and foods
    • Herraiz T. Tetrahydro-β-carboline bioactive alkaloids in beverages and foods. ACS Sympos. Ser. 871 (2004) 405-426
    • (2004) ACS Sympos. Ser. , vol.871 , pp. 405-426
    • Herraiz, T.1
  • 32
    • 11944275594 scopus 로고    scopus 로고
    • Relative exposure to β-carbolines norharman and harman from foods and tobacco smoke
    • Herraiz T. Relative exposure to β-carbolines norharman and harman from foods and tobacco smoke. Food Addit. Contamin. 21 (2004) 1041-1050
    • (2004) Food Addit. Contamin. , vol.21 , pp. 1041-1050
    • Herraiz, T.1
  • 33
    • 9944263390 scopus 로고    scopus 로고
    • Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors
    • Herraiz T., and Chaparro C. Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors. Biochem. Biophys. Res. Commun. 326 (2005) 378-386
    • (2005) Biochem. Biophys. Res. Commun. , vol.326 , pp. 378-386
    • Herraiz, T.1    Chaparro, C.2
  • 34
    • 30544432396 scopus 로고    scopus 로고
    • Human monoamine oxidase enzyme inhibition by coffee and β-carbolines norharman and harman isolated from coffee
    • Herraiz T., and Chaparro C. Human monoamine oxidase enzyme inhibition by coffee and β-carbolines norharman and harman isolated from coffee. Life Sci. 78 (2006) 795-802
    • (2006) Life Sci. , vol.78 , pp. 795-802
    • Herraiz, T.1    Chaparro, C.2
  • 35
    • 0036681598 scopus 로고    scopus 로고
    • Tetrahydro-β-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay
    • Herraiz T., and Galisteo J. Tetrahydro-β-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay. Free Radical Res. 36 (2002) 923-928
    • (2002) Free Radical Res. , vol.36 , pp. 923-928
    • Herraiz, T.1    Galisteo, J.2
  • 36
    • 1342347654 scopus 로고    scopus 로고
    • Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay
    • Herraiz T., and Galisteo J. Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. Free Radical Res. 38 (2004) 323-331
    • (2004) Free Radical Res. , vol.38 , pp. 323-331
    • Herraiz, T.1    Galisteo, J.2
  • 38
    • 24644445302 scopus 로고    scopus 로고
    • The human genome project and novel aspects of cytochrome P450 research
    • Ingelman-Sundberg M. The human genome project and novel aspects of cytochrome P450 research. Toxicol. Appl. Pharmacol. 207 (2005) S52-S56
    • (2005) Toxicol. Appl. Pharmacol. , vol.207
    • Ingelman-Sundberg, M.1
  • 39
    • 13544249943 scopus 로고    scopus 로고
    • Genetic polymorphisms of cytochrome P450 2D6 (CYP2D6): clinical consequences, evolutionary aspects and functional diversity
    • Ingelman-Sundberg M. Genetic polymorphisms of cytochrome P450 2D6 (CYP2D6): clinical consequences, evolutionary aspects and functional diversity. The Pharmacogenomics J. 5 (2005) 6-13
    • (2005) The Pharmacogenomics J. , vol.5 , pp. 6-13
    • Ingelman-Sundberg, M.1
  • 42
    • 0027965620 scopus 로고
    • Genetic analysis of the Chinese cytochrome P4502D locus: characterization of variant CYP2D6 genes present in subjects with diminished capacity for debrisoquine hydroxylation
    • Johansson I., Oscarson M., Yue Q.Y., Bertilsson L., Sjoqvist F., and Ingelman-Sundberg M. Genetic analysis of the Chinese cytochrome P4502D locus: characterization of variant CYP2D6 genes present in subjects with diminished capacity for debrisoquine hydroxylation. Mol. Pharmacol. 46 (1994) 452-459
    • (1994) Mol. Pharmacol. , vol.46 , pp. 452-459
    • Johansson, I.1    Oscarson, M.2    Yue, Q.Y.3    Bertilsson, L.4    Sjoqvist, F.5    Ingelman-Sundberg, M.6
  • 43
    • 0037404037 scopus 로고    scopus 로고
    • Influence of lipophilicity on the interactions of N-alkyl-4-phenyl-1,2,3,6-tetrahydropyridines and their positively charged N-alkyl-4-phenylpyridinium metabolites with cytochrome P450 2D6
    • Kalgutkar A.S., Zhou S., Fahmi O.A., and Taylor T.J. Influence of lipophilicity on the interactions of N-alkyl-4-phenyl-1,2,3,6-tetrahydropyridines and their positively charged N-alkyl-4-phenylpyridinium metabolites with cytochrome P450 2D6. Drug Metab. Dis. 31 (2003) 596-605
    • (2003) Drug Metab. Dis. , vol.31 , pp. 596-605
    • Kalgutkar, A.S.1    Zhou, S.2    Fahmi, O.A.3    Taylor, T.J.4
  • 44
    • 0020680904 scopus 로고
    • Chronic parkinsonism in humans due to a product of meperidine-analog synthesis
    • Langston J.W., Ballard P., Tertrud J.W., and Irwin I. Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219 (1983) 979-980
    • (1983) Science , vol.219 , pp. 979-980
    • Langston, J.W.1    Ballard, P.2    Tertrud, J.W.3    Irwin, I.4
  • 46
    • 0346102800 scopus 로고    scopus 로고
    • Disposition of 1,2,3,4-tetrahydroisoquinoline in the brain of male Wistar and Dark Agouti rats
    • Lorenc-Koci E., Wójcikowski J., Kot M., Haduch A., Boksa J., and Daniel W.A. Disposition of 1,2,3,4-tetrahydroisoquinoline in the brain of male Wistar and Dark Agouti rats. Brain Res. 996 (2004) 168-179
    • (2004) Brain Res. , vol.996 , pp. 168-179
    • Lorenc-Koci, E.1    Wójcikowski, J.2    Kot, M.3    Haduch, A.4    Boksa, J.5    Daniel, W.A.6
  • 50
    • 0027252719 scopus 로고
    • Potential bioactivated neurotoxicants, N-methylated β-carbolinium ions, are present in human brain
    • Matsubara K., Collins M.A., Akane A., Ikebuchi J., Neafsey E.J., Kagawa M., and Shiono H. Potential bioactivated neurotoxicants, N-methylated β-carbolinium ions, are present in human brain. Brain Res. 610 (1993) 90-96
    • (1993) Brain Res. , vol.610 , pp. 90-96
    • Matsubara, K.1    Collins, M.A.2    Akane, A.3    Ikebuchi, J.4    Neafsey, E.J.5    Kagawa, M.6    Shiono, H.7
  • 52
    • 0031472072 scopus 로고    scopus 로고
    • The association between polymorphisms in the cytochrome P-450 2D6 gene and Parkinson's disease: a case-control study and meta-analysis
    • McCann S.J., Pond S.M., James K.M., and Le Couteur D.G. The association between polymorphisms in the cytochrome P-450 2D6 gene and Parkinson's disease: a case-control study and meta-analysis. J. Neurol. Sci. 153 (1997) 50-53
    • (1997) J. Neurol. Sci. , vol.153 , pp. 50-53
    • McCann, S.J.1    Pond, S.M.2    James, K.M.3    Le Couteur, D.G.4
  • 53
    • 0242596021 scopus 로고
    • Piperidine derivatives: XXVII. The condensation of 4-piperidones and piperidinols with phenols
    • McElvain S.M., and Berger R.S. Piperidine derivatives: XXVII. The condensation of 4-piperidones and piperidinols with phenols. J. Am. Chem. Soc. 77 (1955) 2848-2850
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 2848-2850
    • McElvain, S.M.1    Berger, R.S.2
  • 54
    • 3042519581 scopus 로고    scopus 로고
    • The unique regulation of brain cytochrome P450 2 (CYP2) family enzymes by drugs and genetics
    • Miksys S., and Tyndale R.F. The unique regulation of brain cytochrome P450 2 (CYP2) family enzymes by drugs and genetics. Drug Metab. Rev. 36 (2004) 313-333
    • (2004) Drug Metab. Rev. , vol.36 , pp. 313-333
    • Miksys, S.1    Tyndale, R.F.2
  • 55
    • 0036736195 scopus 로고    scopus 로고
    • Regional and cellular expression of CYP2D6 in human brain: higher levels in alcoholics
    • Miksys S., Rao Y., Hoffmann E., Mash D.C., and Tyndale R.F. Regional and cellular expression of CYP2D6 in human brain: higher levels in alcoholics. J. Neurochem. 82 (2002) 1376-1387
    • (2002) J. Neurochem. , vol.82 , pp. 1376-1387
    • Miksys, S.1    Rao, Y.2    Hoffmann, E.3    Mash, D.C.4    Tyndale, R.F.5
  • 56
    • 0030963409 scopus 로고    scopus 로고
    • 1-Methyl-4-phenyl-1,2,3,4-tetrahydropyridine as a substrate of cytochrome P450 2D6: allosteric effects of NADPH-cytochrome P450 reductase
    • Modi S., Gilham D.E., Sutcliffe M.J., Lian L.Y., Primrose W.U., Wolf C.R., and Roberts G.C.K. 1-Methyl-4-phenyl-1,2,3,4-tetrahydropyridine as a substrate of cytochrome P450 2D6: allosteric effects of NADPH-cytochrome P450 reductase. Biochemistry 36 (1997) 4461-4470
    • (1997) Biochemistry , vol.36 , pp. 4461-4470
    • Modi, S.1    Gilham, D.E.2    Sutcliffe, M.J.3    Lian, L.Y.4    Primrose, W.U.5    Wolf, C.R.6    Roberts, G.C.K.7
  • 57
    • 0030840624 scopus 로고    scopus 로고
    • Isoquinoline neurotoxins in the brain and Parkinson's disease
    • Nagatsu T. Isoquinoline neurotoxins in the brain and Parkinson's disease. Neurosci. Res. 29 (1997) 99-111
    • (1997) Neurosci. Res. , vol.29 , pp. 99-111
    • Nagatsu, T.1
  • 58
    • 0036719858 scopus 로고    scopus 로고
    • Amine-related neurotoxins in Parkinson's disease. Past, present and future
    • Nagatsu T. Amine-related neurotoxins in Parkinson's disease. Past, present and future. Neurotoxicol. Teratol. 24 (2002) 565-569
    • (2002) Neurotoxicol. Teratol. , vol.24 , pp. 565-569
    • Nagatsu, T.1
  • 59
    • 0028182781 scopus 로고
    • Novel toxins and Parkinson's disease: N-methylation and oxidation as metabolic bioactivation of neurotoxin
    • Naoi M., Maruyama W., Niwa T., and Nagatsu T. Novel toxins and Parkinson's disease: N-methylation and oxidation as metabolic bioactivation of neurotoxin. J. Neural Transm. (supplement) 41 (1994) 197-205
    • (1994) J. Neural Transm. (supplement) , vol.41 , pp. 197-205
    • Naoi, M.1    Maruyama, W.2    Niwa, T.3    Nagatsu, T.4
  • 60
    • 0030032933 scopus 로고    scopus 로고
    • Cytochrome P4502D and -2C enzymes catalyze the oxidative N-demethylation of the Parkinsonism-inducing substance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyiridine in rat liver microsomes
    • Narimatsu S., Tachibana M., Masubuchi Y., and Suzuki T. Cytochrome P4502D and -2C enzymes catalyze the oxidative N-demethylation of the Parkinsonism-inducing substance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyiridine in rat liver microsomes. Chem. Res. Toxicol. 9 (1996) 93-98
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 93-98
    • Narimatsu, S.1    Tachibana, M.2    Masubuchi, Y.3    Suzuki, T.4
  • 61
    • 0024546491 scopus 로고
    • Determination of the absolute concentrations of monoamine oxidase A and B in human tissues
    • O'Carrol A.M., Anderson M.C., Tobbia I., Phillips J.P., and Tipton K.F. Determination of the absolute concentrations of monoamine oxidase A and B in human tissues. Biochem. Pharmacol. 38 (1989) 901-905
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 901-905
    • O'Carrol, A.M.1    Anderson, M.C.2    Tobbia, I.3    Phillips, J.P.4    Tipton, K.F.5
  • 62
    • 3042641834 scopus 로고    scopus 로고
    • A frameshift mutation and alternate splicing in human brain generate a functional form of pseudogene cytochrome P4502D7 that demethylates codeine to morphine
    • Pai H.V., Kommaddi R.P., Chinta S.J., Mori T., Boyd M.R., and Ravindranath V. A frameshift mutation and alternate splicing in human brain generate a functional form of pseudogene cytochrome P4502D7 that demethylates codeine to morphine. J. Biol. Chem. 279 (2004) 27383-27389
    • (2004) J. Biol. Chem. , vol.279 , pp. 27383-27389
    • Pai, H.V.1    Kommaddi, R.P.2    Chinta, S.J.3    Mori, T.4    Boyd, M.R.5    Ravindranath, V.6
  • 65
    • 0023148530 scopus 로고
    • 4-Phenylpyridine and three other analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lack dopaminergic nigrostriatal neurotoxicity in mice and marmosets
    • Perry T.L., Jones K., Hansen S., and Wall R.A. 4-Phenylpyridine and three other analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lack dopaminergic nigrostriatal neurotoxicity in mice and marmosets. Neurosci. Lett. 75 (1987) 65-70
    • (1987) Neurosci. Lett. , vol.75 , pp. 65-70
    • Perry, T.L.1    Jones, K.2    Hansen, S.3    Wall, R.A.4
  • 66
    • 0142089101 scopus 로고    scopus 로고
    • Parkinson's disease and CYP2D6 polymorphism in Asian populations: a meta analysis
    • Persad A.S., Stedeford T., Tanaka S., Chen L.P., and Banasik M. Parkinson's disease and CYP2D6 polymorphism in Asian populations: a meta analysis. Neuroepidemiology 22 (2003) 357-361
    • (2003) Neuroepidemiology , vol.22 , pp. 357-361
    • Persad, A.S.1    Stedeford, T.2    Tanaka, S.3    Chen, L.P.4    Banasik, M.5
  • 67
    • 0034888241 scopus 로고    scopus 로고
    • Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates
    • Ramamoorthy Y., Tyndale R.F., and Sellers E.M. Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. Pharmacogenetics 11 (2001) 477-487
    • (2001) Pharmacogenetics , vol.11 , pp. 477-487
    • Ramamoorthy, Y.1    Tyndale, R.F.2    Sellers, E.M.3
  • 68
    • 0031671444 scopus 로고    scopus 로고
    • Metabolism of xenobiotics in the central nervous system
    • Ravindranath V. Metabolism of xenobiotics in the central nervous system. Biochem. Pharmacol. 56 (1998) 547-551
    • (1998) Biochem. Pharmacol. , vol.56 , pp. 547-551
    • Ravindranath, V.1
  • 69
    • 0031907725 scopus 로고    scopus 로고
    • P450 enzymes and Parkinson's disease: the story so far
    • Riedl A.G., Watts P.M., Jenner P., and Marsden C.D. P450 enzymes and Parkinson's disease: the story so far. Mov. Disord. 13 (1998) 212-220
    • (1998) Mov. Disord. , vol.13 , pp. 212-220
    • Riedl, A.G.1    Watts, P.M.2    Jenner, P.3    Marsden, C.D.4
  • 71
    • 0035839156 scopus 로고    scopus 로고
    • Stimulatory effect of harmane and other beta-carbolines on locus coeruleus neurons in anaesthetized rats
    • Ruiz-Durantez E., Ruiz-Ortega J.A., Pineda J., and Ugedo L. Stimulatory effect of harmane and other beta-carbolines on locus coeruleus neurons in anaesthetized rats. Neurosci. Lett. 308 (2001) 197-200
    • (2001) Neurosci. Lett. , vol.308 , pp. 197-200
    • Ruiz-Durantez, E.1    Ruiz-Ortega, J.A.2    Pineda, J.3    Ugedo, L.4
  • 72
    • 0026550390 scopus 로고
    • 3H-Ro 19-6327 in vitro: localization and abundance of MAO-A and MAO-B in rat CNS, peripheral organs and human brain
    • 3H-Ro 19-6327 in vitro: localization and abundance of MAO-A and MAO-B in rat CNS, peripheral organs and human brain. J. Neurosci. 12 (1992) 1977-1999
    • (1992) J. Neurosci. , vol.12 , pp. 1977-1999
    • Saura, J.1    Kettler, R.2    Da Prada, M.3    Richards, J.G.4
  • 73
    • 0035049437 scopus 로고    scopus 로고
    • Cellular localization and regional distribution of CYP2D6 mRNA and protein expression in human brain
    • Siegle I., Fritz P., Eckhardt K., Zanger U.M., and Eichelbaum M. Cellular localization and regional distribution of CYP2D6 mRNA and protein expression in human brain. Pharmacogenetics 11 (2001) 237-245
    • (2001) Pharmacogenetics , vol.11 , pp. 237-245
    • Siegle, I.1    Fritz, P.2    Eckhardt, K.3    Zanger, U.M.4    Eichelbaum, M.5
  • 75
    • 2042423928 scopus 로고    scopus 로고
    • Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake
    • Storch A., Hwang Y.I., Gearhart D.A., Beach J.W., Neafsey E.J., Collins M.A., and Schwarz J. Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. J. Neurochem. 89 (2004) 685-694
    • (2004) J. Neurochem. , vol.89 , pp. 685-694
    • Storch, A.1    Hwang, Y.I.2    Gearhart, D.A.3    Beach, J.W.4    Neafsey, E.J.5    Collins, M.A.6    Schwarz, J.7
  • 76
    • 0026512229 scopus 로고
    • Cytochrome P450 isozymes catalysing the 4-hydroxylation of parkinsonism-related compound 1,2,3,4-tetrahydroisoquinoline in rat liver microsomes
    • Suzuki T., Fujita S., Narimatsu S., Masubuchi Y., Tachibana M., Ohta S., and Hirobe M. Cytochrome P450 isozymes catalysing the 4-hydroxylation of parkinsonism-related compound 1,2,3,4-tetrahydroisoquinoline in rat liver microsomes. FASEB J. 6 (1992) 771-776
    • (1992) FASEB J. , vol.6 , pp. 771-776
    • Suzuki, T.1    Fujita, S.2    Narimatsu, S.3    Masubuchi, Y.4    Tachibana, M.5    Ohta, S.6    Hirobe, M.7
  • 77
    • 0027534454 scopus 로고
    • Substrate-specific enhancement of the oxidative half-reaction of monoamine oxidase
    • Tan A.K., and Ramsay R.R. Substrate-specific enhancement of the oxidative half-reaction of monoamine oxidase. Biochemistry 32 (1993) 2137-2143
    • (1993) Biochemistry , vol.32 , pp. 2137-2143
    • Tan, A.K.1    Ramsay, R.R.2
  • 78
    • 0034681831 scopus 로고    scopus 로고
    • Gen expression in distinct regions of the heart
    • Thum T., and Borlak J. Gen expression in distinct regions of the heart. Lancet 355 (2000) 979-983
    • (2000) Lancet , vol.355 , pp. 979-983
    • Thum, T.1    Borlak, J.2
  • 79
    • 0032809128 scopus 로고    scopus 로고
    • Characterization of cytochrome P-450 2D1 activiy in rat brain: high-affinity kinetics for dextrome thorpan.
    • Tyndale R.F., Li Y., Li N.-Y., Messina E., Miksys S., and Sellers E.M. Characterization of cytochrome P-450 2D1 activiy in rat brain: high-affinity kinetics for dextrome thorpan. Drug. Metab. Dispos. 27 (1999) 924-930
    • (1999) Drug. Metab. Dispos. , vol.27 , pp. 924-930
    • Tyndale, R.F.1    Li, Y.2    Li, N.-Y.3    Messina, E.4    Miksys, S.5    Sellers, E.M.6
  • 80
    • 0035170851 scopus 로고    scopus 로고
    • Characterization and localization of cytochrome P450 mediated metabolism of MPTP to nor-MPTP in mouse brain: relevance to Parkinson's disease
    • Upadhya S.C., Boyd M.R., and Ravindranath V. Characterization and localization of cytochrome P450 mediated metabolism of MPTP to nor-MPTP in mouse brain: relevance to Parkinson's disease. Neurotoxycity Res. 3 (2001) 369-380
    • (2001) Neurotoxycity Res. , vol.3 , pp. 369-380
    • Upadhya, S.C.1    Boyd, M.R.2    Ravindranath, V.3
  • 81
    • 5444243967 scopus 로고    scopus 로고
    • Involvement of cytochrome P450 2E1 in the 1-methyl-4-phenyl-1,2,3-6-tetrahydropyridine-induced mouse model of Parkinson's disease
    • Vaglini F., Pardini C., Viaggi C., Bartoli C., Dinucci D., and Corsini G.U. Involvement of cytochrome P450 2E1 in the 1-methyl-4-phenyl-1,2,3-6-tetrahydropyridine-induced mouse model of Parkinson's disease. J. Neurochem. 91 (2004) 285-298
    • (2004) J. Neurochem. , vol.91 , pp. 285-298
    • Vaglini, F.1    Pardini, C.2    Viaggi, C.3    Bartoli, C.4    Dinucci, D.5    Corsini, G.U.6
  • 82
    • 0021819789 scopus 로고
    • Metabolism of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by liver homogenate fractions
    • Weissman J., Trevor A., Chiba K., Peterson L.A., Caldera P., Castagnoli N., and Baillie T. Metabolism of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by liver homogenate fractions. J. Med. Chem. 28 (1985) 997-1001
    • (1985) J. Med. Chem. , vol.28 , pp. 997-1001
    • Weissman, J.1    Trevor, A.2    Chiba, K.3    Peterson, L.A.4    Caldera, P.5    Castagnoli, N.6    Baillie, T.7
  • 83
    • 33645307953 scopus 로고    scopus 로고
    • The therapeutic potential of monoamine oxidase inhibitors
    • Youdim M.B.H., Edmondson D., and Tipton K.F. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev., Neurosci. 7 (2006) 295-309
    • (2006) Nat. Rev., Neurosci. , vol.7 , pp. 295-309
    • Youdim, M.B.H.1    Edmondson, D.2    Tipton, K.F.3
  • 84
    • 0036897469 scopus 로고    scopus 로고
    • Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms
    • Yu A., Kneller B.M., Rettie A.E., and Haining R.L. Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms. J. Pharmacol. Exp. Ther. 303 (2002) 1291-1300
    • (2002) J. Pharmacol. Exp. Ther. , vol.303 , pp. 1291-1300
    • Yu, A.1    Kneller, B.M.2    Rettie, A.E.3    Haining, R.L.4
  • 86
    • 0038240578 scopus 로고    scopus 로고
    • Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase
    • Yu A.M., Idle J.R., Herraiz T., Küpfer A., and Gonzalez F.J. Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. Pharmacogenetics 13 (2003) 307-319
    • (2003) Pharmacogenetics , vol.13 , pp. 307-319
    • Yu, A.M.1    Idle, J.R.2    Herraiz, T.3    Küpfer, A.4    Gonzalez, F.J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.