Studies on the monoamine oxidase-B-catalyzed biotransformation of 4- azaaryl-1-methyl-1,2,3,6-tetrahydropyridine derivatives

Journal of Medicinal Chemistry

Volumn 42, Issue 10, 1999, Pages 1828-1835

  Nimkar, Sandeep K ^a   Mabic, Stéphane ^a   Anderson, Andrea H ^a   Palmer, Sonya L ^a   Graham, Thomas H ^a   De Jonge, Milly ^a   Hazelwood, Lisa ^a   Hislop, Sean J ^a   Castagnoli Jr , Neal ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 3 PIPERIDEINE DERIVATIVE; 4 AZAARYL 1 METHYL 1,2,3,6 TETRAHYDROPYRIDINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENZYME ACTIVE SITE; ENZYME SUBSTRATE COMPLEX; MICHAELIS CONSTANT; STRUCTURE ACTIVITY RELATION;

ANIMALS; AZA COMPOUNDS; CATALYSIS; CATTLE; KINETICS; LIVER; MONOAMINE OXIDASE; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 0033587029     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9900319     Document Type: Article

References (41)

1. Weyler, W.; Hsu, Y.-P. P.; Breakefield, X. O. Biochemistry and genetics of monoamine oxidase. Pharmacol. Ther. 1990, 47, 391-417.
2. Powell, J. F. Amine oxidases: Structure, function and expression. Biochem. Soc. Trans. 1991, 19, 199-214.
3. Dostert, P.; Strolin Benedetti, M.; Tipton, K. F. Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 1989, 9, 45-89.
4. Castagnoli, N., Jr.; Rimoldi, J. M.; Bloomquist, J.; Castagnoli, K. P. Potential metabolic bioactivation pathways involving cyclic tertiary amines and azaarenes. Chem. Res. Toxicol. 1997, 10, 924-940.
5. Anderson, A.; Kuttab, S.; Castagnoli, N., Jr. Deuterium isotope effect studies on the MAO-B catalyzed oxidation of 4-benzyl-1-cyclopropyl-1,2,3,6-tetrahydropyridine. Biochemistry 1996, 35, 3335-3340.
6. Ottoboni, S.; Caldera, P.; Trevor, A.; Castagnoli, N., Jr. Deuterium isotope effect measurements on the interactions of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine with monoamine oxidase B. J. Biol. Chem. 1989, 264, 13684-13688.
7. Walker, M. C.; Edmonson, D. E. Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoaamine oxidase B. Biochemistry 1994, 33, 7088-7098.
8. Silverman, R. B.; Yamasaki, R. B. Mechanism-based inactivation of mitochondrial monoamine oxidase by N-(1-methylcyclopropyl)benzylamine. Biochemistry 1984, 23, 1322-1332.
9. Silverman, R. B. Mechanism based enzyme inactivators. Methods in Enzymology; Academic Press: New York, 1995; Vol. 249, pp 240-263.
10. Zhong, B. Y.; Silverman, R. B. Identification of the active site cysteine in bovine liver monoamine oxidase B. J. Am. Chem. Soc. 1997, 119, 6690-6691.
11. Silverman, R. B. Radical ideas about monoamine oxidase. Acc. Chem. Res. 1995, 28, 335-342.
12. Hall, L.; Murray, S.; Castagnoli, K.; Castagnoli, N., Jr. Studies on 1,2,3,6-tetrahydropyridine derivatives as potential monoamine oxidase inactivators. Chem. Res. Toxicol. 1992, 5, 625-633.
13. Palmer, S.; Mabic, S.; Castagnoli, N., Jr. Design, synthesis, and biological evaluation of MAO-A selective substrates and inactivators. J. Med. Chem. 1997, 40, 1982-1989.
14. 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 analogues 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. 1996, 8, 703-710.
15. Nimkar, S. K.; Anderson, A.; Rimoldi, J. M.; Stanton, M.; Castagnoli, K. P.; Mabic, S.; Wang, X.-Y.; Castagnoli, N., Jr. Synthesis and MAO-B catalyzed oxidation of C-4 heteroaromatic substituted MPTP analogues. Chem. Res. Toxicol. 1996, 9, 1013-1022.
16. Franot, C.; Mabic, S.; Castagnoli, N., Jr. Chemical model studies on the monoamine oxidase-B catalyzed oxidation of 4-substituted 1-cyclopropyl-1,2,3,6-tetrahydropyridines. Bioorg. Med. Chem. 1998, 6, 283-291.
17. Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. Akinetic scale for dialkylaminyl radical reactions. J. Am. Chem. Soc. 1996, 118, 3862-3868.
18. Abell, C. W.; Stewart, R.; Andrews, P.; Kwan, S. W. Molecular and functional properties of the monoamine oxidases. Heterocycles 1994, 39, 933-955.
19. Hsu, Y.-P. P.; Weyler, W.; Chen, S.; Sims, K. B.; Rinehart, W. B.; Utterback, M.; Powell, J. F.; Breakfield, X. O. Structural features of human monoamine oxidase A elucidated from cDNA and peptide sequences. J. Neurochem. 1988, 51, 1321-1324.
20. Bach, A. J. W.; Lan, N. C.; Johnson, D. L.; Abell, C. W.; Bembenek, M. E.; Kwan, S. W.; Seeburg, P.; Shin, J. C. cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4934-4938.
21. 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.
22. 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.
23. Mabic, S.; Castagnoli, N., Jr. Assessment of structural requirements for the MAO-B catalyzed oxidation of C4-substitued tetrahydropyridine derivatives related to the neurotoxin MPTP. J. Med. Chem. 1996, 39, 3694-3700.
24. Youngster, S. K.; Sonsalla, P. K.; Heikkila, R. E. Evaluation of the biological activity of several analogues of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem. 1987, 929-934.
25. 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.
26. 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 analogues by monoamine oxidase. Biochem. Pharmacol. 1990, 40, 783-792.
27. Markey, S. P.; Schmiff, N. R. The pharmacology of the parkinsonian syndrome producing neurotoxin MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and structurally related compounds. Med. Res. Rev. 1986, 6, 389-429.
28. Lyle, R. E.; Nelson, D. A.; Anderson, P. S. The mechanism of the reduction of pyridinium ions with sodium borohydride. Tetrahedron Lett. 1962, 4, 553-557.
29. Porter, Q. N. In Mass spectrometry of heterocyclic compounds; Taylor, E. C., Weissgerger, A., Eds.; John Wiley & Sons: New York, 1985.
30. Seki, K.; Ohkura, K.; Terashima, M.; Kanaoka, Y. A facile synthesis of N-(2- and 4-pyridyl)indoles. Heterocycles 1994, 37, 993-996.
31. Thurkauf, A.; Yuan, J.; Chen, X.; Wasley, J. W. F.; Meade, R.; Woodruff, K. H.; Huston, K.; Ross, P. C. 1-Phenyl-3-(amino-methyl)pyrroles as potential antipsychotic agents. Synthesis and dopamine receptor binding. J. Med. Chem. 1995, 38, 4950-4952.
32. Kalgutkar, A. S.; Castagnoli, N., Jr. Synthesis of novel MPTP analogues as potential monoamine oxidase B (MAO-B) inhibitors. J. Med. Chem. 1992, 35, 4165-4174.
33. Mabic, S.; Rimoldi, J. M.; Castagnoli, N., Jr. Regioselective deuterium labeling of 1,4-disubstituted-1,2,3,6-tetrahydropyridines. J. Labeled Compd. Radiopharm. 1997, 39, 409-423.
34. Wang, X.-Y.; Castagnoli, N., Jr. Studies on 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.
35. Naiman, N.; Rollema, H.; Johnson, E.; Castagnoli, N., Jr. Studies on benzyl-1-methyl-1,2,3,6-tetrahydropyridine, a nonneurotoxic analogue of the parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Chem. Res. Toxicol. 1990, 3, 133-138.
36. Boudakian, M. M. New developments in the synthesis of lower fluorinated pyridines via diazotation-fluorination of aminopyridines in anhydrous hydrogen fluoride. J. Fluorine Chem. 1981, 18, 497-506.
37. Roe, A.; Hawkins, G. F. The preparation of heterocyclic fluorine compounds by the Schiemann reaction. I. The monofluoropyridines. J. Am. Chem. Soc. 1947, 69, 2443-2444.
38. Sprague, R. H.; Brooker, L. G. S. Studies in the cyanine dyes series. IX. 4,4′-Pyridocyanines and 4-pyrido-4′-cyanines. J. Am. Chem. Soc. 1937, 59, 2697-2699.
39. de Jonge, M.; Mabic, S.; Castagnoli, N., Jr. Synthesis of 4-(1H- and 2H-indazolyl)pyridine. Manuscript in preparation.
40. Salach, J. I.; Weyler, W. Preparation of the flavin-containing aromatic amine oxidases of human placenta and beef liver. Methods Enzymol. 1987, 142, 627-637.
41. Kalgutkar, A. S.; Castagnoli, K.; Hall, A.; Castagnoli, N., Jr. Novel 4-(aryloxy)tetrahydropyridine analogues of MPTP as monoamine oxidase A and B substrates. J. Med. Chem. 1994, 37, 944-949.