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Volumn 40, Issue 13, 1997, Pages 1982-1989

Probing the active sites of monoamine oxidase A and B with 1,4- disubstituted tetrahydropyridine substrates and inactivators

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 (2 PHENYLPHENYL)PYRIDINE OXALATE; 1,2,3,6 TETRAHYDRO 1 METHYL 4 (3 PHENYLPHENYL)PYRIDINE OXALATE; 1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING); UNCLASSIFIED DRUG;

EID: 0030968180     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970079r     Document Type: Article
Times cited : (18)

References (41)
  • 1
    • 0001624577 scopus 로고
    • Contributions of monoamine oxidase to the metabolism of xenobiotics
    • Strolin Benedetti, M.; Dostert, P.; Tipton, K. F. Contributions of monoamine oxidase to the metabolism of xenobiotics. Prog. Drug Metab. 1988, 11, 149-154.
    • (1988) Prog. Drug Metab. , vol.11 , pp. 149-154
    • Strolin Benedetti, M.1    Dostert, P.2    Tipton, K.F.3
  • 2
    • 0024534967 scopus 로고
    • Interactions of monoamine oxidase with substrates and inhibitors
    • Dostert, P.; Strolin Benedetti, M.; Tipton, K. F. Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 1989, 9, 45-89.
    • (1989) Med. Res. Rev. , vol.9 , pp. 45-89
    • Dostert, P.1    Strolin Benedetti, M.2    Tipton, K.F.3
  • 6
    • 0023081733 scopus 로고
    • Amine oxidases and their endogenous substrates (with special references to monoamine oxidase and the brain)
    • Waldmeier, P. C. Amine oxidases and their endogenous substrates (with special references to monoamine oxidase and the brain). J. Neural Transm. Suppl. 1987, 23, 55-72.
    • (1987) J. Neural Transm. Suppl. , vol.23 , pp. 55-72
    • Waldmeier, P.C.1
  • 7
    • 0026520063 scopus 로고
    • The new generation of monoamine oxidase inhibitors
    • Cesura, A. M.; Pletscher, A. The new generation of monoamine oxidase inhibitors. Prog. Drug Res. 1992, 38, 174-297.
    • (1992) Prog. Drug Res. , vol.38 , pp. 174-297
    • Cesura, A.M.1    Pletscher, A.2
  • 8
    • 0026733164 scopus 로고
    • Monoamine oxidase: From physiology and pathophysiology to the design and clinical application of reversible inhibitors
    • Strolin Benedetti, M.; Dostert, P. Monoamine oxidase: From physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv. Drug Res. 1992, 23, 65-125.
    • (1992) Adv. Drug Res. , vol.23 , pp. 65-125
    • Strolin Benedetti, M.1    Dostert, P.2
  • 9
    • 0029004089 scopus 로고
    • Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism
    • Kalgutkar, A. S.; Castagnoli, N., Jr.; Testa, B. Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism. Med. Res. Rev. 1995, 15, 325-389.
    • (1995) Med. Res. Rev. , vol.15 , pp. 325-389
    • Kalgutkar, A.S.1    Castagnoli Jr., N.2    Testa, B.3
  • 10
    • 0028997415 scopus 로고
    • Studies on the monoamine oxidase (MAO)-catalyzed oxidation of phenyl-substituted 1-methyl-4-phenoxy-1,2,3,6-tetrahydropyridine derivatives: Factors contributing to MAO-A and MAO-B selectivity
    • Wang, Y.-X.; Castagnoli, N., Jr. Studies on the monoamine oxidase (MAO)-catalyzed oxidation of phenyl-substituted 1-methyl-4-phenoxy-1,2,3,6-tetrahydropyridine derivatives: Factors contributing to MAO-A and MAO-B selectivity. J. Med. Chem. 1995, 38, 1904-1910.
    • (1995) J. Med. Chem. , vol.38 , pp. 1904-1910
    • Wang, Y.-X.1    Castagnoli Jr., N.2
  • 12
    • 0029001364 scopus 로고
    • Probing the mechanism of bioactivation of MPTP type analogs by monoamine oxidase B: Structure-activity studies on substituted 4-phenoxy-, 4-phenyl, and 4-thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridines
    • Rimoldi, J. M.; Wang, Y.-X.; Nimkar, S. K.; Kuttab, S. H.; Anderson, A. H.; Burch, H.; Castagnoli, N., Jr. Probing the mechanism of bioactivation of MPTP type analogs by monoamine oxidase B: Structure-activity studies on substituted 4-phenoxy-, 4-phenyl, and 4-thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridines. Chem. Res. Toxicol. 1995, 8, 703-710.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 703-710
    • Rimoldi, J.M.1    Wang, Y.-X.2    Nimkar, S.K.3    Kuttab, S.H.4    Anderson, A.H.5    Burch, H.6    Castagnoli Jr., N.7
  • 13
    • 0024498507 scopus 로고
    • Mechanisms underlaying neuronal degeneration in Parkinson's disease: An experimental and theoretical treatise
    • Langston, W. J. Mechanisms underlaying neuronal degeneration in Parkinson's disease: An experimental and theoretical treatise. Movement Disorders 1989, 4, S15-S25.
    • (1989) Movement Disorders , vol.4
    • Langston, W.J.1
  • 15
    • 0023127392 scopus 로고
    • Evaluation of the biological activity of several analogs of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
    • Youngster, S. K.; Sonsalla, P. K.; Heikkila, R. E. Evaluation of the biological activity of several analogs of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem. 1987, 929-934.
    • (1987) J. Neurochem. , pp. 929-934
    • Youngster, S.K.1    Sonsalla, P.K.2    Heikkila, R.E.3
  • 16
    • 0026709245 scopus 로고
    • Quantitative structure-metabolism relationship analyses of MAO-mediated toxication of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and analogues
    • Altomare, C.; Carrupt, P. A.; Gaillard, P.; El Tayar, N.; Testa, B.; Carotti, A. Quantitative structure-metabolism relationship analyses of MAO-mediated toxication of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and analogues. Chem. Res. Toxicol. 1992, 5, 366-375.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 366-375
    • Altomare, C.1    Carrupt, P.A.2    Gaillard, P.3    El Tayar, N.4    Testa, B.5    Carotti, A.6
  • 17
    • 0021236839 scopus 로고
    • The importance of 4′-5′ double bond for neurotoxicity in primates of the pyridine derivative MPTP
    • Langston, J. W.; Irwin, I.; Langston, E. B.; Forno, L. S. The importance of 4′-5′ double bond for neurotoxicity in primates of the pyridine derivative MPTP. Neurosci. Lett. 1984, 50, 289-294.
    • (1984) Neurosci. Lett. , vol.50 , pp. 289-294
    • Langston, J.W.1    Irwin, I.2    Langston, E.B.3    Forno, L.S.4
  • 18
    • 0022368214 scopus 로고
    • Further exploration of unnatural alkaloids
    • Brossi, A. Further exploration of unnatural alkaloids. J. Nat. Prod. 1985, 48, 878-893.
    • (1985) J. Nat. Prod. , vol.48 , pp. 878-893
    • Brossi, A.1
  • 19
    • 0022643083 scopus 로고
    • Synthesis and toxicity toward nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) analogues
    • Fries, D. S.; Vries, J.; Hazelhoff, B.; Horn, A. S. Synthesis and toxicity toward nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) analogues. J. Med. Chem. 1986, 29, 424-427.
    • (1986) J. Med. Chem. , vol.29 , pp. 424-427
    • Fries, D.S.1    Vries, J.2    Hazelhoff, B.3    Horn, A.S.4
  • 20
    • 0025147290 scopus 로고
    • The MPTP story: MAO activates tetrahydropyridine derivatives to toxins causing parkinsonism
    • Maret, G.; Testa, B.; Jenner, P.; El Tayar, N.; Carrupt, P. A. The MPTP story: MAO activates tetrahydropyridine derivatives to toxins causing parkinsonism. Drug Metab. Rev. 1990, 22, 291-332.
    • (1990) Drug Metab. Rev. , vol.22 , pp. 291-332
    • Maret, G.1    Testa, B.2    Jenner, P.3    El Tayar, N.4    Carrupt, P.A.5
  • 21
    • 0025088106 scopus 로고
    • Toxication of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and analogs by monoamine oxidase
    • Maret, G.; Tayar, N.; Carrupt, P.-A.; Testa, B.; Jenner, P.; Bairds, M. Toxication of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and analogs by monoamine oxidase. Biochem. Pharmacol. 1990, 40, 783-792.
    • (1990) Biochem. Pharmacol. , vol.40 , pp. 783-792
    • Maret, G.1    Tayar, N.2    Carrupt, P.-A.3    Testa, B.4    Jenner, P.5    Bairds, M.6
  • 22
    • 0024463565 scopus 로고
    • Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products
    • Youngster, S. K.; McKeon, K. A.; Jin, Y.-Z.; Ramsay, R. R.; Heikkila, R. E.; Singer, T. P. Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products. J. Neurochem. 1989, 53, 1837-1842.
    • (1989) J. Neurochem. , vol.53 , pp. 1837-1842
    • Youngster, S.K.1    McKeon, K.A.2    Jin, Y.-Z.3    Ramsay, R.R.4    Heikkila, R.E.5    Singer, T.P.6
  • 23
    • 0027504297 scopus 로고
    • Advances in our understanding of the mechanisms of the neurotoxicity of MPTP and related compounds
    • Tipton, K. F.; Singer, T. P. Advances in our understanding of the mechanisms of the neurotoxicity of MPTP and related compounds. J. Neurochem. 1993, 61, 1191-1206.
    • (1993) J. Neurochem. , vol.61 , pp. 1191-1206
    • Tipton, K.F.1    Singer, T.P.2
  • 24
    • 0026232589 scopus 로고
    • Molecular determinants in the bioactivation of the dopaminergic neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
    • Efange, S. M. N.; Boudreau, R. J. Molecular determinants in the bioactivation of the dopaminergic neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). J. Comput.-Aided Mol. Des. 1991, 5, 405-417.
    • (1991) J. Comput.-Aided Mol. Des. , vol.5 , pp. 405-417
    • Efange, S.M.N.1    Boudreau, R.J.2
  • 25
    • 0027270168 scopus 로고
    • Molecular size and flexibility as determinants of selectivity in the oxidation of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs by monoamine oxidase A and B
    • Efange, S. M. N.; Michelson, R. H.; Tan, A. K.; Krueger, M. J.; Singer, T. P. Molecular size and flexibility as determinants of selectivity in the oxidation of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs by monoamine oxidase A and B. J. Med. Chem. 1993, 36, 1278-1283.
    • (1993) J. Med. Chem. , vol.36 , pp. 1278-1283
    • Efange, S.M.N.1    Michelson, R.H.2    Tan, A.K.3    Krueger, M.J.4    Singer, T.P.5
  • 26
    • 0028294989 scopus 로고
    • Novel 4-(aryloxy)tetrahydropyridine analogs of MPTP as monoamine oxidase A and B substrates
    • Kalgutkar, A. S.; Castagnoli, K.; Hall, A.; Castagnoli, N., Jr. Novel 4-(aryloxy)tetrahydropyridine analogs of MPTP as monoamine oxidase A and B substrates. J. Med. Chem. 1994, 37, 944-949.
    • (1994) J. Med. Chem. , vol.37 , pp. 944-949
    • Kalgutkar, A.S.1    Castagnoli, K.2    Hall, A.3    Castagnoli Jr., N.4
  • 27
    • 0027771934 scopus 로고
    • Three dimensional quantitative structure-activity relationship of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: A comparison of the Hansch and CoMFA methods
    • Agarwal, A.; Pearson, P. P.; Taylor, E. W.; Li, H. B.; Dahlgren, T.; Herslof, M.; Yang, Y.; Lambert, G.; Nelson, D. L.; Regan, J. W.; Martin, A. R. Three dimensional quantitative structure-activity relationship of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: A comparison of the Hansch and CoMFA methods. J. Med. Chem. 1993, 36, 4006-4014.
    • (1993) J. Med. Chem. , vol.36 , pp. 4006-4014
    • Agarwal, A.1    Pearson, P.P.2    Taylor, E.W.3    Li, H.B.4    Dahlgren, T.5    Herslof, M.6    Yang, Y.7    Lambert, G.8    Nelson, D.L.9    Regan, J.W.10    Martin, A.R.11
  • 28
    • 0029837393 scopus 로고    scopus 로고
    • Assessment of structural requirements for the MAO-B catalyzed oxidation of 1,4-disubstituted tetrahydropyridine derivatives related to the neurotoxin MPTP
    • Mabic, S.; Castagnoli, N., Jr. Assessment of structural requirements for the MAO-B catalyzed oxidation of 1,4-disubstituted tetrahydropyridine derivatives related to the neurotoxin MPTP. J. Med. Chem. 1996, 39, 3694-3700.
    • (1996) J. Med. Chem. , vol.39 , pp. 3694-3700
    • Mabic, S.1    Castagnoli Jr., N.2
  • 29
    • 0026019304 scopus 로고
    • The kinetic mechanisms of monoamine oxidases A and B
    • Ramsay, R. R.; Singer, T. P. The kinetic mechanisms of monoamine oxidases A and B. Biochem. Soc. Trans. 1991, 19, 219-223.
    • (1991) Biochem. Soc. Trans. , vol.19 , pp. 219-223
    • Ramsay, R.R.1    Singer, T.P.2
  • 30
    • 0024321011 scopus 로고
    • Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs
    • Youngster, S. K.; Sonsalla, P. K.; Sieber, B.-A.; Heikkila, R. E. Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs. J. Pharmacol. Exp. Ther. 1989, 249, 820-828.
    • (1989) J. Pharmacol. Exp. Ther. , vol.249 , pp. 820-828
    • Youngster, S.K.1    Sonsalla, P.K.2    Sieber, B.-A.3    Heikkila, R.E.4
  • 31
    • 0025963728 scopus 로고
    • The interaction of monoamine oxidases with tertiary amines
    • Singer, T. P.; Ramsay, R. R. The interaction of monoamine oxidases with tertiary amines. Biochem. Soc. Trans. 1991, 19, 211-214.
    • (1991) Biochem. Soc. Trans. , vol.19 , pp. 211-214
    • Singer, T.P.1    Ramsay, R.R.2
  • 32
    • 0000897453 scopus 로고
    • Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl,N-arylalkylamines
    • Silverman, R. B.; Hoffman, S. J. Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl,N-arylalkylamines. J. Am. Chem. Soc. 1980, 102, 884-886.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 884-886
    • Silverman, R.B.1    Hoffman, S.J.2
  • 33
    • 0026774923 scopus 로고
    • Studies on 1,2,3,6-tetrahydropyridine derivatives as potential monoamine oxidase inactivator
    • Hall, L.; Murray, S.; Castagnoli, K.; Castagnoli, N., Jr. Studies on 1,2,3,6-tetrahydropyridine derivatives as potential monoamine oxidase inactivator. Chem. Res. Toxicol. 1992, 5, 625-633.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 625-633
    • Hall, L.1    Murray, S.2    Castagnoli, K.3    Castagnoli Jr., N.4
  • 34
    • 85050528342 scopus 로고
    • Semiempirical molecular orbital methods
    • Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: Weinheim
    • Stewart, J. J. P. Semiempirical molecular orbital methods. In Reviews in computational chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: Weinheim, 1990; Vol. 1, pp 45-81.
    • (1990) Reviews in Computational Chemistry , vol.1 , pp. 45-81
    • Stewart, J.J.P.1
  • 35
  • 36
    • 15644363455 scopus 로고    scopus 로고
    • note
    • A thorough discussion of the assumptions and limitations of this method will be proposed in a paper currently in preparation.
  • 37
    • 15644364736 scopus 로고    scopus 로고
    • note
    • The fate and binding properties of 37 in MAO-A and MAO-B active sites are discussed in details in reference 36. Briefly, the flexibility around the oxygen is the reason for the low SCA/B observed.
  • 39
    • 0028035231 scopus 로고
    • Mechanistic studies on the monoamine oxidase B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines
    • Kuttab, S.; Kalgutkar, A.; Castagnoli, N., Jr. Mechanistic studies on the monoamine oxidase B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines. Chem. Res. Toxicol. 1994, 7, 740-744.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 740-744
    • Kuttab, S.1    Kalgutkar, A.2    Castagnoli Jr., N.3
  • 40
    • 0023068687 scopus 로고
    • Preparation of the flavin-containing aromatic amine oxidases of human placenta and beef liver
    • Kaufman, S., Ed.; Academic Press: London
    • Salach, J. I.; Weyler, W. Preparation of the flavin-containing aromatic amine oxidases of human placenta and beef liver. In Methods in Enzymology; Kaufman, S., Ed.; Academic Press: London, 1987; Vol. 142, pp 627-637.
    • (1987) Methods in Enzymology , vol.142 , pp. 627-637
    • Salach, J.I.1    Weyler, W.2
  • 41
    • 0026450944 scopus 로고
    • Design, synthesis, and biological evaluation of novel 4-substituted-1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP
    • Zhao, Z.; Dalvie, D.; Naiman, N.; Castagnoli, K.; Castagnoli, N., Jr. Design, synthesis, and biological evaluation of novel 4-substituted-1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP. J. Med. Chem. 1992, 35, 4473-4478.
    • (1992) J. Med. Chem. , vol.35 , pp. 4473-4478
    • Zhao, Z.1    Dalvie, D.2    Naiman, N.3    Castagnoli, K.4    Castagnoli Jr., N.5


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