Studies on 1,2,3,6-Tetrahydropyridine Derivatives as Potential Monoamine Oxidase Inactivators

Chemical Research in Toxicology

Volumn 5, Issue 5, 1992, Pages 625-633

  Hall, Larry ^a   Murray, Sam ^a   Castagnoli, Kay ^a   Castagnoli, Neal ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

3 PIPERIDEINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; NEUROTOXIN; PROTECTIVE AGENT; PYRIDINE DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INACTIVATION; ENZYME INHIBITION; INTRAPERITONEAL DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; ANIMAL; BUTANES; CYCLOPROPANES; DOPAMINE; MICE; MICE, INBRED C57BL; MONOAMINE OXIDASE INHIBITORS; NEOSTRIATUM; SELEGILINE; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

ANIMALIA;

EID: 0026774923     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00029a006     Document Type: Article

References (52)

1. Singer, T. P., Trevor, A. J., and Castagnoli, N., Jr. (1987) Biochemistry of the neurotoxic action of MPTP—Or how a faulty batch of a “designer drug” led to Parkinsonism in drug abusers. Trends Biochem. Sci. 12, 266-271.
2. Dostert, P. L., Strolin Benedetti, M., and Tipton, K. F. (1989) Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 9, 45-89.
3. Johnston, J. P. (1968) Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. 17, 1285-1297.
4. Knoll, J., and Magyar, K. (1972) Some puzzling pharmacological effects of monoamine oxidase inhibitors. In Adv. Biochem. Psychopharmacol. (Costa, E., and Sandler, M., Eds.) Vol. V, pp 393- 408, Raven Press, New York
5. Bach, A. W. J., Lan, N. C., Johnson, D. L., Abell, C. W., Bembenek, M. E., Kwan, S.-W., Seeburg, P. H., and Shih, J. C. (1988) cDNA cloning of human liver monoamine oxidase A and B: Molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. U.S.A. 85, 4934-4938
6. Hsu, Y.-P. P., Powell, J. F., Sims, K. B., and Breakefield, X. O. (1989) Molecular genetics of the monoamine oxidases. J. Neurochem. 53, 12-18
7. Silverman, R. B. (1991) The use of mechanism-based inactivators to probe the mechanism of monoamine oxidase. Biochem. Soc. Trans. 19, 201-206.
8. Silverman, R. B., and Yamasaki, R. B. (1984) Mechanism-based inactivation of mitochondrial monoamine oxidase by N-(1-methylcyclopropyl)benzylamine. Biochemistry 23, 1322-1332
9. Silverman, R. B., and Zieske, P. A. (1985) Mechanism of inactivation of monoamine oxidase by 1-phenylcyclopropylamine. Biochemistry 24, 2128-2138
10. 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.
11. Gates, K. S., and Silverman, R. B. (1989) Model studies for the mechanism of inactivation of monoamine oxidase by 5-(aminomethyl)- 3-aryl-2-oxazolidinones. J. Am. Chem. Soc. 111, 8891-8895
12. Silverman, R. B., and Banik, G. M. (1987) (Aminoalkyl)trimethylsilanes. A new class of monoamine oxidase inactivators. J. Am. Chem. Soc. 109, 2219-2220.
13. 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.
14. 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. III, 1138-1140.
15. Youngster, S. K., McKeown, K. A., Jin, Y.-Z., Ramsay, R. R., Heikkila, R. E., and Singer, T. P. (1989) 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. 53, 1837-1842.
16. Singer, T. P., Salach, J. I., and Crabtree, D. (1985) Reversible inhibition and mechanism-based irreversible inactivation of monoamine oxidases by l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Biochem. Biophys. Res. Commun. 127, 707-712
17. Kopin, I. J., and Markey, S. P. (1989) MPTP toxicity: Implications for research in Parkinson's Disease. Annu. Rev. Neurosci. 11, 81- 96
18. Langston, J. W., Irwin, I., Langston, E. B., and Forno, L. S. (1984) 1-Methyl-4-phenylpyridinium ion (MPP+): Identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci. Lett. 48, 87-92.
19. Heikkila, R. E., Manzino, L., Cabbat, R. S., and Duvoisin, R. C. (1984) Protection against the dopaminergic neurotoxicity of 1-methyl- 4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature 311, 467-469
20. Langston, J. W., Irwin, I., Langston, E. B., and Forno, L. S. (1984) Pargyline prevents MPTP-induced parkinsonism in primates. Science 225, 1480-1482.
21. Cohen, G., Pasik, P., Cohen, B., Leist, A., Mytilineou, C., and Yahr, M. D. (1984) Pargyline and deprenyl prevent the neurotoxicity of 1- methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in monkeys. Eur. J. Pharmacol. 106, 209-210.
22. Collins, M. A., and Neafsey, E. J. (1985) β-Carboline analogues of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP): endogenous factors underlying idiopathic parkinsonism? Neurosci. Lett. 55, 179-184.
23. Tanner, C. M., and Langston, J. W. (1990) Do environmental toxins cause Parkinson's disease?—A critical review. Neurology 40 (Suppl. 3), 17-30.
24. The Parkinson Study Group. (1989) Effect of deprenyl on the progression of disability in early Parkinson's disease. N. Engl. J. Med. 321, 1364-1371
25. Tetrud, J. W., and Langston, J. W. (1989) The effect of deprenyl (selegiline) on the natural history of Parkinson's disease. Science 245, 519-522.
26. Birkmayer, W., Knoll, J., Reiderer, P., Youdim, M. B. H., Hars, V., and Marton, J. (1985) Increased life expectancy resulting from addition of L-deprenyl to Madopar treatment in Parkinson's diseases long-term study. J. Neural Transm. 64, 113-127.
27. Pitts, S. M., Markey, S. P., Murphy, D. L., and Weisz, A. (1986) 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
28. Salach, J. I. (1979) Monoamine oxidase from beef liver mitochondria: simplified isolation procedure, properties, and determination of its cysteinyl flavin content. Arch. Biochem. Biophys. 192, 128-137.
29. Weyler, W., and Salach, J. I. (1981) Iron content and spectral properties of highly purified bovine liver monoamine oxidase. Arch. Biochem. Biophys. 212, 147-153.
30. Salach, J. I., and Weyler, W. (1987) Preparation of the flavincontaining aromatic amine oxidases of human placenta and beef liver. Methods Enzymol. 142, 627-637
31. Ricaurte, G. A., Langston, J. W., Delanney, L. E., Irwin, I.,Peroutka, S. J., and Forno, L. S. (1986) Fate of nigrostriatal neurons in young mature mice given l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A neurochemical and morphological reassessment. Brain Res. 376, 117-124.
32. Schmidle, C. J., and Mansfield, R. C. (1956) The aminomethylation of olefins. V. A new synthesis of 4-phenylpyridine and related compounds. J. Am. Chem. Soc. 78, 1702-1705.
33. Hanzlik, R. P., Tullman, R. H., and Kishore, V. (1980) Inactivation of cytochrome P-450 enzymes by cyclopropylamines. In Microsomes, Drug Oxidations and Chemical Carcinogenesis (Coon, M. J., Conney, A. H., Estabrook, W., Gelboin, H. V., Gillette, J. R., and O'Brien, P. J., Eds.) pp 327-330, Academic Press, New York.
34. Subramanyam, B., Woolf, T., and Castagnoli, N., Jr. (1991) Studies on the in vitro conversion of haloperidol to a potentially neurotoxic pyridinium metabolite. Chem. Res. Toxicol. 4, 123-128.
35. Gessner, W., and Brossi, A. (1985) Reduction of phenyl-substituted pyridinium methiodides with sodium borohydride. Formation of amine-borane complexes in water. Synth. Commun. 15, 911-916
36. Crisp, G. T., and Flynn, B. L. (1990) Palladium-catalyzed coupling of uridine inflate with organostannanes. Tetrahedron Lett. 31,1347- 1350.
37. Pelter, A., Rowlands, M., and Clements, G. (1987) Cross-coupling reactions for the preparation of 2-arylfurans, 2-benzylfuran and 2- cinnamylfuran. Synthesis, 51-53.
38. Heikkila, R. E., Manzino, L., Cabbat, F. S., and Duvoisin, R. C. (1985) Studies on the oxidation of the dopaminergic neurotoxin l-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase B. J. Neurochem. 45, 1049-1054
39. Brossi, A., Gessner, W. P., Fritz, R. R., Bembenek, M. E., and Abell, C. W. (1986) Interaction of monoamine oxidase B with analogues of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine derived from prodinetype analgesics. J. Med. Chem. 29, 444-445.
40. Hiebert, C.K., and Silverman, R. B. (1988) 1-Methyl-4-phenyl-1,2,3,6- tetrahydropyridine analogues. Inactivation of monoamine oxidase by conformationally rigid analogues of N,N-dimethylcinnamylamine. J. Med. Chem. 31, 1566-1570.
41. Fries, D. S., de Vries, J., Hazelhoff, B., and Horn, A. S. (1986) Synthesis and toxicity toward nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) analogues. J. Med. Chem. 29, 424-427.
42. Barwell, C. J., Basma, A. N., Lafi, M. A. K., and Leake, L. D. (1989) Deamination of hordenine by monoamine oxidase and its action on vasa deferentia of the rat. J. Pharm. Pharmacol. 41, 421-423.
43. Fowler, C. J., and Ross, S. B. (1984) Selective inhibitors of monoamine oxidase A and B: biochemical, pharmacological, and clinical properties. Med. Res. Rev. 4, 323-358
44. Silverman, R. B., and Hoffman, S. J. (1984) The organic chemistry of mechanism-based enzyme inhibition: a chemical approach to drug design. Med. Res. Rev. 4, 415-457.
45. Tipton, K. F., McCrodden, J. M., Kalir, A. S., and Youdim, M. B. H. (1982) Inhibition of rat liver monoamine oxidase by α-methyl and N-propargyl-amine derivatives. Biochem. Pharmacol. 31, 1251-1255
46. Silverman, R. B., and Hoffman, S. J. (1981) N-(1-methyl)- cyclopropylbenzylamine: a novel inactivator of mitochondrial monoamine oxidase. Biochem. Res. Commun. 101, 1396-1401.
47. Ottoboni, S., Caldera, P., Trevor, A., and Castagnoli, N., Jr. (1989) 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. 264, 13684-13688
48. Singer, T.P., and Ramsay, R. R. (1991) The interaction of monoamine oxidases and tertiary amines. Biochem. Soc. Trans. 19, 211-215.
49. Hiebert, C. K., Sayre, L. M., and Silverman, R. B. (1989) Inactivation of monoamine oxidase by 3,3-dimethyl analogues of 1-methyl-4- phenyl-1,2,3,6-tetrahydropyridine and 1-methyl-4-phenyl-2,3-dihydropyridinium ion. J. Biol. Chem. 264, 21516-21521.
50. Peterson, L. A., Caldera, P. S., Trevor, A., Chiba, K., and Castagnoli, N., Jr. (1985) Studies on the 1-methyl-4-phenyl-2,3-dihydropyridinium species 2,3-MPDP+, the monoamine oxidase catalyzed oxidation product of the nigrostriatal toxin 1-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine (MPTP). J. Med. Chem. 28, 1432-1436.
51. Heikkila, R. E., Hess, A., and Duvoisin, R. C. (1984) Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine in mice. Science 224, 1451-1453
52. Rollema, H., Johnson, E. A., Booth, R. G., Caldera, P., Lampen, P., Youngster, S. K., Trevor, A. J., Naiman, N. A., and Castagnoli, N., Jr. (1990) In vivo intracerebral microdialysis studies in rats of MPP+ analogues and related charged species. J. Med. Chem. 33, 2221- 2230