메뉴 건너뛰기




Volumn 8, Issue 5, 1995, Pages 703-710

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

Author keywords

[No Author keywords available]

Indexed keywords

1 CYCLOPROPYL 1,2,3,6 TETRAHYDRO 4 (2 METHYLPHENYL)PYRIDINE; 1 CYCLOPROPYL 1,2,3,6 TETRAHYDRO 4 PHENOXYPYRIDINE; 1 CYCLOPROPYL 1,2,3,6 TETRAHYDRO 4 PHENYLPYRIDINE; 1 CYCLOPROPYL 1,2,3,6 TETRAHYDRO 4 THIOPHENOXYPYRIDINE; 1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 4 BENZYL 1 CYCLOPROPYL 1,2,3,6 TETRAHYDROPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CATION; HYDROGEN; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029001364     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00047a010     Document Type: Article
Times cited : (28)

References (30)
  • 1
    • 0024534967 scopus 로고
    • Interactions of monoamine oxidase with substrates and inhibitors
    • Dosert, P., Strolin Benedetti, M., and Tipton, K. F. (1989) Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 9, 45–89.
    • (1989) Med. Res. Rev. , vol.9 , pp. 45-89
    • Dosert, P.1    Strolin Benedetti, M.2    Tipton, K.F.3
  • 2
    • 0027349946 scopus 로고
    • Biochemical mechanisms underlying MPTP-induced and idiopathic parkinsonism. New Vistas
    • Singer, T. P., Ramsay, R. R., Sonsalla, Pl. K., Nicklas, W. J., and Heikkila, R. E. (1993) Biochemical mechanisms underlying MPTP-induced and idiopathic parkinsonism. New Vistas. Adv. Neurol. 60, 300–305.
    • (1993) Adv. Neurol. , vol.60 , pp. 300-305
    • Singer, T.P.1    Ramsay, R.R.2    Sonsalla, P.K.3    Nicklas, W.J.4    Heikkila, R.E.5
  • 3
    • 0000480438 scopus 로고
    • Electron Transfer Chemistry of Monoamine Oxidase
    • (Mariano, P. S., Ed.) JAI Press, Greenwich, CT
    • Silverman, R. B. (1992) Electron Transfer Chemistry of Monoamine Oxidase. In Advances in Electron Transfer Chemistry (Mariano, P. S., Ed.) Vol. 2, pp 177–213, JAI Press, Greenwich, CT.
    • (1992) Advances in Electron Transfer Chemistry , vol.2 , pp. 177-213
    • Silverman, R.B.1
  • 4
    • 0001267540 scopus 로고
    • SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms
    • Kim, J. M., Bogdan, M. A., and Mariano, P. S. (1991) SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms. J. Am. Chem. Soc. 113, 9251–9257.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9251-9257
    • Kim, J.M.1    Bogdan, M.A.2    Mariano, P.S.3
  • 5
    • 0024498299 scopus 로고
    • Electron spin resonance studies of monoamine oxidase B. First direct evidence for a substrate radical intermediate
    • Yelekci, K., Lu., X., and Silverman, R. B. (1989) Electron spin resonance studies of monoamine oxidase B. First direct evidence for a substrate radical intermediate. J. Am. Chem. Soc. 111, 1138–1140.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1138-1140
    • Yelekci, K.1    Lu, X.2    Silverman, R.B.3
  • 6
    • 33751392486 scopus 로고
    • Evidence for a hydrogen atom transfer mechanism or a proton/fast electron transfer mechanism for monoamine oxidase
    • Silverman, R. B., and Zelechonok, Y. (1992) Evidence for a hydrogen atom transfer mechanism or a proton/fast electron transfer mechanism for monoamine oxidase. J. Org. Chem. 57, 6373–6374.
    • (1992) J. Org. Chem. , vol.57 , pp. 6373-6374
    • Silverman, R.B.1    Zelechonok, Y.2
  • 7
    • 0028278443 scopus 로고
    • Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoamine oxidase B
    • Walker, M. C., and Edmondson, D. E. (1994) Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoamine oxidase B. Biochemistry 33, 7088—7098.
    • (1994) Biochemistry , vol.33 , pp. 7088-7098
    • Walker, M.C.1    Edmondson, D.E.2
  • 8
    • 0028294989 scopus 로고
    • Novel 4-(aryloxy)tetrahydropyridine analogs of MPTP as monoamine oxidase A and B substrates
    • Castagnoli, Jr.
    • Kalgutkar, A. S., Castagnoli, K., Hall, A., and Castagnoli, Jr. (1994) Novel 4-(aryloxy)tetrahydropyridine analogs of MPTP as monoamine oxidase A and B substrates. J. Med. Chem. 37, 944–949.
    • (1994) J. Med. Chem. , vol.37 , pp. 944-949
    • Kalgutkar, A.S.1    Castagnoli, K.2    Hall, A.3
  • 9
    • 0026450944 scopus 로고
    • Design, synthesis and biological evaluation of novel 4-substituted 1-methyl-4-phenyl-1, 2, 3,6-tetrahydropyridine analogs of MPTP
    • Zhao, Z., Dalvie, D., Naiman, N., Castagnoli, K., and Castagnoli, N., Jr. (1992) Design, synthesis and biological evaluation of novel 4-substituted 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs of MPTP. J. Med. Chem. 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, N.5
  • 10
    • 0026591809 scopus 로고
    • Synthesis of novel MPTP analogs as potential monoamine oxidase B (MAO-B) inhibitors
    • Kalgutkar, A. S., and Castagnoli, N., Jr. (1992) Synthesis of novel MPTP analogs as potential monoamine oxidase B (MAO-B) inhibitors. J. Med. Chem. 35, 4165–4174.
    • (1992) J. Med. Chem. , vol.35 , pp. 4165-4174
    • Kalgutkar, A.S.1    Castagnoli, N.2
  • 11
    • 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., Sieberg, B.-A., and Heikkila, R. E. (1989) 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. 249, 820–828.
    • (1989) J. Pharmacol. Exp. Ther. , vol.249 , pp. 820-828
    • Youngster, S.K.1    Sonsalla, P.K.2    Sieberg, B.-A.3    Heikkila, R.E.4
  • 12
    • 0026691634 scopus 로고
    • Interaction of flexible analogs of N-methyl-4-phenyl-1, 2, 3,6-tetrahydropyridine and of N-methyl-4-phenylpyridinium with highly purified monoamine oxidase A and B
    • Krueger, M. J., Efange, S. M. N., Michelson, R. H., and Singer, T. P. (1992) Interaction of flexible analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and of N-methyl-4-phenylpyridinium with highly purified monoamine oxidase A and B. Biochemistry 31, 5611–5615.
    • (1992) Biochemistry , vol.31 , pp. 5611-5615
    • Krueger, M.J.1    Efange, S.M.N.2    Michelson, R.H.3    Singer, T.P.4
  • 13
    • 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., and Singer, T. P. (1993) 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. 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
  • 14
    • 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., and Carotti, A. (1992) Quantitative structure-metabolism relationship analyses of MAO-mediated toxication of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and analogues. Chem. Res. Toxicol. 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
  • 15
    • 0024516540 scopus 로고
    • Studies on semirigid tricyclic analogues of the nigrostriatal neurotoxin 1-methyl-4-phenyl-1, 2, 3,6-tetrahydropyridine
    • Booth, R. G., Trevor, A., Singer, T. P., and Castagnoli, N., Jr. (1989) Studies on semirigid tricyclic analogues of the nigrostriatal neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Med. Chem. 32, 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
  • 16
    • 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, K. P., and Heikkila, R. E. (1987) Evaluation of the biological activity of several analogs of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem. 48, 929–934.
    • (1987) J. Neurochem. , vol.48 , pp. 929-934
    • Youngster, S.K.1    Sonsalla, K.P.2    Heikkila, R.E.3
  • 17
    • 0026774923 scopus 로고
    • Studies on 1, 2, 3,6-tetrahydropyridine derivatives as potential monoamine oxidase inactivators
    • Hall, L., Murray, S., Castagnoli, K., and Castagnoli, N., Jr. (1992) Studies on 1,2,3,6-tetrahydropyridine derivatives as potential monoamine oxidase inactivators. Chem. Res. Toxicol., 5, 625–633.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 625-633
    • Hall, L.1    Murray, S.2    Castagnoli, K.3    Castagnoli, N.4
  • 18
    • 0000611561 scopus 로고
    • Kinetic applications of electron paramagnetic resonance spectroscopy. 35. The search for a dialkylaminyl rearrangement. Ring opening of N-cyclobutyl-N-n-propylaminyl
    • Maeda, Y., and Ingold, K. U. (1980) Kinetic applications of electron paramagnetic resonance spectroscopy. 35. The search for a dialkylaminyl rearrangement. Ring opening of N-cyclobutyl-N-n-propylaminyl. J. Am. Chem. Soc. 102, 328–331.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 328-331
    • Maeda, Y.1    Ingold, K.U.2
  • 19
    • 0021761512 scopus 로고
    • Mechanism-based inactivation of mitochondrial monoamine oxidase by N-(1-meth-ylcyclopropyl)benzylamine
    • Silverman, R. B., and Yamasaki, R. B. (1984) Mechanism-based inactivation of mitochondrial monoamine oxidase by N-(1-meth-ylcyclopropyl)benzylamine. Biochemistry 23, 1322–1332.
    • (1984) Biochemistry , vol.23 , pp. 1322-1332
    • Silverman, R.B.1    Yamasaki, R.B.2
  • 20
    • 0022514969 scopus 로고
    • 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate
    • Silverman, R. B., and Zieske, P. A. (1986) 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate. Biochemistry 25, 341–346.
    • (1986) Biochemistry , vol.25 , pp. 341-346
    • Silverman, R.B.1    Zieske, P.A.2
  • 21
    • 0024463565 scopus 로고
    • Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidase A and B and the inhibition of monoamine oxidases by the oxidation products
    • Youngster, S. K., McKeown, K. A., Jin, Y.-Z., and Ramsay, R. R. (1989) Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidase A and B and the inhibition of monoamine oxidases by the oxidation products. J. Neurochem. 53, 1837–1842.
    • (1989) J. Neurochem. , vol.53 , pp. 1837-1842
    • Youngster, S.K.1    McKeown, K.A.2    Jin, Y.-Z.3    Ramsay, R.R.4
  • 22
    • 0028035231 scopus 로고
    • Mechanistic studies on the monoamine oxidase-B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines
    • Kuttab, S., Kalgutkar, A., and Castagnoli, N., Jr. (1994) Mechanistic studies on the monoamine oxidase-B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines. J. Chem. Res. 7, 740–744.
    • (1994) J. Chem. Res. , vol.7 , pp. 740-744
    • Kuttab, S.1    Kalgutkar, A.2    Castagnoli, N.3
  • 23
    • 0002600682 scopus 로고    scopus 로고
    • Recommended practices for the safe handling of MPTP
    • (Markey, S. P., Castagnoli, N., Jr., Trevor, A. J., and Kopin, I. J., Eds.) Academic Press, New York
    • Pitts, S. M., Markey, S. P., Murphy, D. L., and Weisz, A. (1996) Recommended practices for the safe handling of MPTP. In MPTP—A Neurotoxin Producing a Parkinsonian Syndrome (Markey, S. P., Castagnoli, N., Jr., Trevor, A. J., and Kopin, I. J., Eds.) pp 703–716, Academic Press, New York.
    • (1996) MPTP—A Neurotoxin Producing a Parkinsonian Syndrome , pp. 703-716
    • Pitts, S.M.1    Markey, S.P.2    Murphy, D.L.3    Weisz, A.4
  • 24
    • 0023068687 scopus 로고
    • Preparation of the flavincontaining aromatic amine oxidases of human placenta and beef liver
    • (Kaufman, S., Ed.) Academic Press, London
    • Salach, J. I., and Weyler, W. (1987) Preparation of the flavincontaining aromatic amine oxidases of human placenta and beef liver. In Methods in Enzymology (Kaufman, S., Ed.) Vol. 142, pp 627–637, Academic Press, London.
    • (1987) Methods in Enzymology , vol.142 , pp. 627-637
    • Salach, J.I.1    Weyler, W.2
  • 25
    • 84918635941 scopus 로고
    • Nucleophilic substitution reactions of cyclopropane derivatives
    • Aksenov, V. S., Terent'eva, G. A., and Savinykh, Yu. V. (1980) Nucleophilic substitution reactions of cyclopropane derivatives. Russ. Chem. Rev. 49, 549–557.
    • (1980) Russ. Chem. Rev. , vol.49 , pp. 549-557
    • Aksenov, V.S.1    Terent'eva, G.A.2    Savinykh, Y.V.3
  • 26
    • 85022271918 scopus 로고
    • Synthesis and isolation of chelidonic acid
    • Gagan, J. M. F., and Herbert, R. B. (1976) Synthesis and isolation of chelidonic acid. Ed. Chem. 13, 140–141.
    • (1976) Ed. Chem. , vol.13 , pp. 140-141
    • Gagan, J.M.F.1    Herbert, R.B.2
  • 27
    • 0344192806 scopus 로고
    • Ultraviolet absorption of a series of eight organic substances of the γ-pyridone type, in water solution
    • Reigel, E. R., and Reinhard, M. C. (1926) Ultraviolet absorption of a series of eight organic substances of the γ-pyridone type, in water solution. J. Am. Chem. Soc. 48, 1334–1345.
    • (1926) J. Am. Chem. Soc. , vol.48 , pp. 1334-1345
    • Reigel, E.R.1    Reinhard, M.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.