메뉴 건너뛰기




Volumn 356, Issue 1, 2007, Pages 118-123

N-Methyltetrahydro-β-carboline analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxin are oxidized to neurotoxic β-carbolinium cations by heme peroxidases

Author keywords

Carbolines; Carbolinium; 1 Methyl 4 phenyl 1,2,3,6 tetrahydropyridine; 1 Methyl 4 phenylpyridinium; CYP2D6; Cytochrome P450; Heme peroxidases; Horseradish peroxidase; Lactoperoxidase; Monoamine oxidase (MAO); MPP+; MPTP; Myeloperoxidase; N Methyltetrahydro carbolines; Neurotoxins; Parkinson's disease

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; 1,2,3,4 TETRAHYDRO 2 METHYL BETA CARBOLINE; 1,2,3,4 TETRAHYDRO 2,9 DIMETHYL BETA CARBOLINE; 1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; ASCORBIC ACID; BETA CARBOLINE DERIVATIVE; CYTOCHROME P450 2D6; HORSERADISH PEROXIDASE; HYDROXYLAMINE; LACTOPEROXIDASE; MYELOPEROXIDASE; NEUROTOXIN; PEROXIDASE; SODIUM AZIDE; UNCLASSIFIED DRUG;

EID: 33947141371     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2007.02.089     Document Type: Article
Times cited : (28)

References (34)
  • 2
    • 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
  • 3
    • 0021992979 scopus 로고
    • β-Carboline analogs of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP). Endogenous factors underlying idiopathic Parkinsonism
    • Collins M.A., and Neafsey E.J. β-Carboline analogs of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP). Endogenous factors underlying idiopathic Parkinsonism. Neurosci. Lett. 55 (1985) 179-184
    • (1985) Neurosci. Lett. , vol.55 , pp. 179-184
    • Collins, M.A.1    Neafsey, E.J.2
  • 6
    • 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
  • 7
    • 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
  • 8
    • 0019406904 scopus 로고
    • β-Carbolines, psychoactive compounds in the mammalian body. 1. Occurrence, origin and metabolism
    • Airaksinen M.M., and Kari I. β-Carbolines, psychoactive compounds in the mammalian body. 1. Occurrence, origin and metabolism. Med. Biol. 59 (1981) 21-34
    • (1981) Med. Biol. , vol.59 , pp. 21-34
    • Airaksinen, M.M.1    Kari, I.2
  • 9
    • 0242691743 scopus 로고    scopus 로고
    • Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers
    • Herraiz T., and Galisteo J. Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. J. Agric. Food Chem. 51 (2003) 7156-7161
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 7156-7161
    • Herraiz, T.1    Galisteo, J.2
  • 10
    • 0034210323 scopus 로고    scopus 로고
    • Increased β-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 β-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
  • 11
    • 2042423928 scopus 로고    scopus 로고
    • Dopamine transporter-mediated cytotoxicity of β-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 β-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
  • 12
    • 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
  • 14
    • 0031952527 scopus 로고    scopus 로고
    • Endogenously occurring β-carboline induces parkinsonism in nonprimate animals: a possible causative protoxin in idiopathic Parkinson's disease
    • Matsubara K., Gonda T., Sawada H., Uezono T., Kobayashi Y., Kawamura T., Ohtaki K., Kimura K., and Akaike A. Endogenously occurring β-carboline induces parkinsonism in nonprimate animals: a possible causative protoxin in idiopathic Parkinson's disease. J. Neurochem. 70 (1998) 727-735
    • (1998) J. Neurochem. , vol.70 , pp. 727-735
    • Matsubara, K.1    Gonda, T.2    Sawada, H.3    Uezono, T.4    Kobayashi, Y.5    Kawamura, T.6    Ohtaki, K.7    Kimura, K.8    Akaike, A.9
  • 15
    • 33750079907 scopus 로고    scopus 로고
    • Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated β-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6
    • Herraiz T., Guillén H., Arán V.J., Idle J.R., and Gonzalez F.J. Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated β-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6. Toxicol. Appl. Pharm. 216 (2006) 387-398
    • (2006) Toxicol. Appl. Pharm. , vol.216 , pp. 387-398
    • Herraiz, T.1    Guillén, H.2    Arán, V.J.3    Idle, J.R.4    Gonzalez, F.J.5
  • 16
    • 0024516540 scopus 로고
    • Studies on semirigid tricyclic analogs of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
    • Booth R.G., Trevor A., Singer T.P., and Castagnoli N. Studies on semirigid tricyclic analogs of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Med. Chem. 32 (1989) 473-477
    • (1989) J. Med. Chem. , vol.32 , pp. 473-477
    • Booth, R.G.1    Trevor, A.2    Singer, T.P.3    Castagnoli, N.4
  • 17
    • 0024492782 scopus 로고
    • Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methyl-isoquinolinium ion by monoamine oxidase
    • Naoi M., Matsuura S., Parvez H., Takahashi T., Hirata Y., Minami M., and Nagatsu T. Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methyl-isoquinolinium ion by monoamine oxidase. J. Neurochem. 52 (1989) 653-655
    • (1989) J. Neurochem. , vol.52 , pp. 653-655
    • Naoi, M.1    Matsuura, S.2    Parvez, H.3    Takahashi, T.4    Hirata, Y.5    Minami, M.6    Nagatsu, T.7
  • 18
    • 0031014344 scopus 로고    scopus 로고
    • Metabolism of MPTP by cytochrome P4502D6 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 P4502D6 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
  • 19
    • 0025134990 scopus 로고
    • Studies on the cytochrome-P-450 catalyzed ring alpha-carbon oxidation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
    • Ottoboni S., Carlson T.J., Trager W.F., Castagnoli K., and Castagnoli N. Studies on the cytochrome-P-450 catalyzed ring alpha-carbon oxidation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Chem. Res. Toxicol. 3 (1990) 423-427
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 423-427
    • Ottoboni, S.1    Carlson, T.J.2    Trager, W.F.3    Castagnoli, K.4    Castagnoli, N.5
  • 20
    • 18944406318 scopus 로고    scopus 로고
    • Peroxidases: a role in the metabolism and side effects of drugs
    • Tafazoli S., and O'Brien P.J. Peroxidases: a role in the metabolism and side effects of drugs. Drug Discov. Today 10 (2005) 617-625
    • (2005) Drug Discov. Today , vol.10 , pp. 617-625
    • Tafazoli, S.1    O'Brien, P.J.2
  • 23
    • 0032893232 scopus 로고    scopus 로고
    • A rat brain fraction and different purified peroxidases catalyzing the formation of dopaminochrome from dopamine
    • Galzigna L., Schiappelli M.P., Rigo A., and Scarpa M. A rat brain fraction and different purified peroxidases catalyzing the formation of dopaminochrome from dopamine. Biochem. Biophys. Acta 1427 (1999) 329-336
    • (1999) Biochem. Biophys. Acta , vol.1427 , pp. 329-336
    • Galzigna, L.1    Schiappelli, M.P.2    Rigo, A.3    Scarpa, M.4
  • 24
    • 18044388917 scopus 로고    scopus 로고
    • Role of peroxidases in Parkinson disease: a hypothesis
    • Everse J., and Coates P.W. Role of peroxidases in Parkinson disease: a hypothesis. Free Radic. Biol. Med. 38 (2005) 1296-1310
    • (2005) Free Radic. Biol. Med. , vol.38 , pp. 1296-1310
    • Everse, J.1    Coates, P.W.2
  • 25
    • 0026764244 scopus 로고
    • Mono-N-methylation of 1,2,3,4-tetrahydro-β-carbolines in brain cytosol: absence of indole methylation
    • Matsubara K., Collins M.A., and Neafsey E.J. Mono-N-methylation of 1,2,3,4-tetrahydro-β-carbolines in brain cytosol: absence of indole methylation. J. Neurochem. 59 (1992) 505-510
    • (1992) J. Neurochem. , vol.59 , pp. 505-510
    • Matsubara, K.1    Collins, M.A.2    Neafsey, E.J.3
  • 26
    • 0019377920 scopus 로고
    • Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland
    • Barker S.A., Harrison R.E.W., Monti J.A., Brown G.B., and Christian S.T. Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland. Biochem. Pharmacol. 30 (1981) 9-17
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 9-17
    • Barker, S.A.1    Harrison, R.E.W.2    Monti, J.A.3    Brown, G.B.4    Christian, S.T.5
  • 28
    • 33746398090 scopus 로고    scopus 로고
    • Neurotoxic mechanisms of 2,9-dimethyl-β-carbolinium ion in primary dopaminergic culture
    • Hamann J., Rommelspacher H., Storch A., Reichmann H., and Gille G. Neurotoxic mechanisms of 2,9-dimethyl-β-carbolinium ion in primary dopaminergic culture. J. Neurochem. 98 (2006) 1185-1199
    • (2006) J. Neurochem. , vol.98 , pp. 1185-1199
    • Hamann, J.1    Rommelspacher, H.2    Storch, A.3    Reichmann, H.4    Gille, G.5
  • 30
    • 33744968384 scopus 로고    scopus 로고
    • Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants
    • Herraiz T., and Chaparro C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants. J. Chromatogr. A 1120 (2006) 237-243
    • (2006) J. Chromatogr. A , vol.1120 , pp. 237-243
    • Herraiz, T.1    Chaparro, C.2
  • 31
    • 0036478818 scopus 로고    scopus 로고
    • Redox intermediates of plant and mammalian peroxidases: a comparative transient-kinetic study of their reactivity toward indole derivatives
    • Jantschko W., Furtmüller P.G., Allegra M., Livrea M.A., Jakopitsch C., Regelsberger G., and Obinger C. Redox intermediates of plant and mammalian peroxidases: a comparative transient-kinetic study of their reactivity toward indole derivatives. Arch. Biochem. Biophys. 398 (2002) 12-22
    • (2002) Arch. Biochem. Biophys. , vol.398 , pp. 12-22
    • Jantschko, W.1    Furtmüller, P.G.2    Allegra, M.3    Livrea, M.A.4    Jakopitsch, C.5    Regelsberger, G.6    Obinger, C.7
  • 32
    • 0030849619 scopus 로고    scopus 로고
    • Horseradish peroxidase oxidation of tyrosine-containing peptides and their subsequent polymerization: a kinetic study
    • Michon T., Chenu M., Kellershon N., Desmadril M., and Gueguen J. Horseradish peroxidase oxidation of tyrosine-containing peptides and their subsequent polymerization: a kinetic study. Biochemistry 36 (1997) 8504-8513
    • (1997) Biochemistry , vol.36 , pp. 8504-8513
    • Michon, T.1    Chenu, M.2    Kellershon, N.3    Desmadril, M.4    Gueguen, J.5
  • 33
    • 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 Radic. Res. 36 (2002) 923-928
    • (2002) Free Radic. Res. , vol.36 , pp. 923-928
    • Herraiz, T.1    Galisteo, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.