Relevance of benzyloxy group in 2-indolyl methylamines in the selective MAO-B inhibition

British Journal of Pharmacology

Volumn 127, Issue 4, 1999, Pages 869-876

  Pérez, Virgili ^a   Marco, José Luis ^b   Fernández Álvarez, Eldiberto ^b   Unzeta, Mercedes ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Benzyloxy tryptamine derivatives; MAO B inhibitors

Indexed keywords

2 INDOLYL METHYLAMINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; BRAIN ENZYME; METHYLAMINE; MONOAMINE OXIDASE B INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BRAIN SYNAPTOSOME; CAUDATE NUCLEUS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DOPAMINE UPTAKE; DRUG SELECTIVITY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; DOPAMINE; HUMANS; MALE; MICE; MICE, INBRED C57BL; MITOCHONDRIA, LIVER; MONOAMINE OXIDASE INHIBITORS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPTAMINES;

EID: 0033023543     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0702600     Document Type: Article

References (40)

1. AVILA, M., BALSA, M.D., FERNÁNDEZ-ÁLVAREZ, E., TIPTON, K.F. & UNZETA, M. (1993). The effect of side-chain substitution at Positions 2 and 3 of the heterocyclic ring of N-acctylenic analogues of tryptamine as monoamine oxidase inhibitors. Biochem. Pharmacol., 45, 2231-2237.
2. BACK, A.W., LAN, N.C., JOHNSON, D.L., ABELL, C.W., BEMBENEK, M.E., KWAN, S.W., SEEBURG, P.H. & SHIH, J.C. (1988). c-DNA cloning of human liver monoamine oxidases A and B. Molecular basis of differences in enzymalic properties. Proc. Natl. Acad. Sci. U.S.A., 85, 4934-4938.
3. BALSA, D., FERNÁNDEZ-ÁLVAREZ, E.,TIPTON, K.F. & UNZETA, M. (1990). Inhibition oF MAO by substituted tryptamine analogues. J. Neural. Transm. [Suppl.], 32, 103-105.
4. BALSA, D., FERNÁNDEZ-ÁLVAREZ, E., TIPTON, K.F. & UNZETA, M. (1991). Monoamine oxidase inhibitory potencies and selectivities of 2-[N-(2-propynyl)-aminomethyl]-1-methyl indole derivatives. Bicchem. Soc. Trans., 19, 215-218.
5. BALSA, D., FERNÁNDEZ-ÁLVAREZ, E., & UNZETA, M. (1992). Structure-activity relationship studies on some indolealkylamine acetylenic derivatives as selective MAO-A inhibitors. Behav. Pharmacol. [Suppl 1], 3, 40.
6. BALSA, D., PÉREZ, V., FERNÁNDEZ-ÁLVAREZ, E. & UNZETA, M. (1994). Kinetic behaviour of some acetylenic indolalkylamine derivatives and their corresponding parent amines. J. Neural. Transm. [Suppl.], 41, 281-285.
7. CRUCES, M.A., ELORRIAGA, C., FERNÁNDEZ-ÁLVAREZ, E., LÓPEZ, M.T. & NIETO, O. (1988). Acetylenic and allenic derivatives of 2-(1-mBthylindolyl)methylamine as selective inhibitors of the monoamine oxidases A and B. Il Farmaco De Sci., 43, 567-573.
8. CRUCES, M.A., ELORRIAGA, C., FERNÁNDEZ-ÁLAVAREZ, E. & NIETO, O. (1990). Acetylenic and allenic derivatives of 2-(5-methoxyindolyl)methylamine synthesis and evaluation as selective inhibitors of monoarnine oxidases A and B. Eur. J. Med. Chem., 25, 251-265.
9. CRUCES, M.A., ELORRIAGA, C. & FERNÁNDEZ-ÁLVAREZ, E. (1991). Acetylenic and allenic derivatives of 2-(5-methoxyindo-lyl) and 2-(5-hydroxyindolyl)methylamines: synthesis and in vitro evaluation as monoamine oxidase inhibitors. Eur. J. Med. Chem., 26, 33-41.
10. DODD, P.R., HARDY, J.A., OAKLEY, A.E., EDWARDSON, J.A., PERRY, E.K. & DELAUNOY, J.P. (1981). A rapid method for preparing synaptosomes: Comparison with alternative procedures. Br. Res., 226, 107-118.
11. DOSTERT, P., STROLIN-BENEDETTI, M. & TIPTON, K.F. (1989). Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev., 9, 45-48.
12. FOWLER, C.J. & TIPTON, K.F. (1981). Concentration dependence of the oxidation of tyramine by the two forms of rat liver mitochondrial monoamine oxidase. Biochem. Pharmacol., 30, 3329-3332.
13. FOWLFR, C.J., MANTLE, T.J. & TIPTON, K.F. (1982). The nature of inhibition of rat liver monoamine oxidase types A and B by the acetylenic inhibitors clorgyline. 1-deprenil and pargyline. Biochem, Pharmacol., 31, 3555-3561.
14. GOMEZ, N., BALSA, M.D. & UNZETA, M. (1988). A comparative study of some kinetic and molecular properties of microsomal and mitochondrial monoamine oxidases. Biochem. Pharmarnl., 37, 3407-3413.
15. HARFENIST, M., HEUSER, D.J., JOYNER, C.T., BATCHELOR, J.F. & WHITE, H.L. (1996). Selective inhibitors of monoamine oxidase. Structure-activity relationship of tricyclics bearing imidazoline, oxadiazole, or tetrazole groups. J. Med. Chem., 39, 1857-1863.
16. HEIKKILA, R.E. (1984). Behavioral properties of GBR-12909, GBR-13069 and GBR-13098: specific inhibitors of dopamine uptake. Eur. J. Pharmacol., 103, 241-248.
17. HEIKKILA, R.E., MANZINO, L., CABBAT, F.S. & DUVOISIN, R.C. (1984). Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature, 311, 467-469.
18. HEINONEN, E., MYLLYLA, V., SOTANIEMI, K., LAMINTAUSTA, R., SALONFN, J., ANTTILA, M., SAVIJARVI, M., KOTILA, M. & RONNE, U. (1989). Pharmacokinetics and metabolism of selegiline. Act. Neurol. Scand., 126, 93-99.
19. JAVITCH, J.A., D'AMATO, R.J., STRITTMATTER, S.M. & SYNDER, S.H. (1985). Parkinsonism-inducing neurotoxin, N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine: uptake of the metabolite N-methyl-4-phenylpyridine by dopamine neurons explains selective toxicity. Proc. Natl. Acad. Sci. U.S.A., 82, 2173-2177.
20. JOHNSTON, J.P. (1968). Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol., 17, 1285-1297.
21. KALGUTKAR, A.S. & CASTAGNOLI, JR, N. (1995). Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism. Medicinal Res. Rev., 15, 325-388.
22. KNEUBUHLER, S., THULL, U., ALTOMARE, C., CARTA, V., GAILLARD, P., CARRUPT, P.A., CAROTTI, A. & TESTA, B. (1995). Inhibition of monoamine oxidase B by 5H-indenol[1,2-c]pyridazines: Biological activities, quantitative structure-activity relationships (QSARs) and 3D-QSARs. J. Med. Chem., 38, 3874-3883.
23. MAZOUZ, F., GUEDDARl, S., BURSTEIN, C., MANSUY, D. & MILCENT, R. (1993). 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogues: new reversible, highly potent, and selective monoamine oxidase type B inhibitors. J. Med. Chem., 36, 1157-1167.
24. MCDONALD, I.A., BEY, P., ZREIKA, M. & PALPREYMAN, M.G. (1991). MDL 72,974A. Drugs Future, 16, 428-431.
25. MYLLYLÄ, V.V., HEINONEN, E.H., VUORINEN, J.A., KIKKU, O.I. & SOTANIEMI, K.A. (1995). Early selegiline therapy reduces levodopa dose requirement in Parkinson's disease. Acta Neurol. Scand., 91, 177-182.
26. NAOI, M. & YAGI, K. (1980). Effects of phospholipids on beef heart mitochondrial monoamine oxidase. Arch. Biochem. Biophys., 205, 18-26.
27. NIKOI, A. & SILVERMAN, R.B. (1993). New analogues of N-(2-aminoethyl)-4-chlorobenzamide (Ro-16-6491). Some of the most potent monoaminc oxidase-B inaetivators. J. Med. Chem., 36, 3968-3970.
28. O'BRIEN, E.M., TIPTON, K.F., MERONl, M. & DOSTERT, P. (1994). Inhibition of monoaminc oxidase by clorgyline analogues. J. Neural Transm. [Suppl.], 41, 295-305.
29. PALMER, S.L., MABIC, S. & CASTAGNOLI, JR, N. (1997). Probing the active sites of monoamine oxidases A and B with 1,4-Disubstiluted tetrahydropyridine substrates and inactivators. J. Med. Chem., 40, 1982-1989.
30. PÉREZ, V., MARCO, J.L., FERNÁNDEZ-ÁLVAREZ, E. & UNZETA, M. (1996). Kinectic studies of N-allenic analogues of tryptaminc as monoamine oxidase inhibitors. J. Pharm. Pharmacol., 48, 718-722.
31. SANCHEZ-RAMOS, J.R., SONG, S., MASH, D.C. & WEINER, W.J. (1992). 21-Aminosteroides interact with the dopamine transporter to protect against 1-methyl-4-phenytpyridinium-induced neurotoxicily. J. Neurochem., 58, 328-334.
32. SINGER, T.P. & RAMSAY, R.R. (1993). New aspects of the substrate specificities, kinetic mechanisms and inhibition of monoamine oxidases. In Monoumine Oxidase: basic and clinical aspects. Yasuhara H, Parvez S.H., Oguchi K, Sandler M and Nagatsu T. (eds). pp 23-43, Utrecht, Holland: VSP.
33. SPRAGUE, J.F., & NICHOLS, D.E. (1995). Inhibition of MAO-B protects against MDMA-induced neurotoxicity in the striatum. Psychopharmacology, 118, 357-359.
34. TETRUD, J.W. & LANGSTON, J.W. (1989). The effect of deprenyl (selegiline) on the natural history of Parkinson's disease. Science. 245, 519-522.
35. TIPTON, K.F., BALSA, D. & UNZETA, M. (1993). Newer approaches to the study of monoamine oxidase inhibition. In Monoamine oxidase: basic and clinical aspects. Yasuhara H, Parvez S.H., Oguchi K, Sandler M and Nagatsu T. (eds). pp 1-13, Utrech, Holland: VSP.
36. WALDEMEIR, P.C., PELNER, A.E. & TIPTON, K.F. (1983). The monoaminE oxidase inhibitory properties of CGP 1135A. Euro. J. Pharmacol., 94, 73-83.
37. YOUDIM, M.B.H. & FINBERG, J.M.P. (1983), Monoamine oxidase inhibitors. In Psychopharmacology, Preclinical Psychopharmacology. Grahame-Smith D.G. and Cowen P.E. (eds). pp 37-51, Amsterdam: Elsevier Science.
38. YOUDIM, M.B.H., HINBERG, J.P.M. & TIPTON, K.F. (1988). Monoamine oxidase. In Handbook of experimental pharmacology. Catecholamines, I. Trendelenburg U and Weiner N. (eds). pp 119-192. Berlin: Springer-Verlag.
39. YU, P.H., DAVIS, B.A. & BOULTON, A.A. (1992). Aliphatic propargylamines: potent, selective, irreversible monoamine oxidase B inhibitors. J. Metl. Chem., 35, 3705-3713.
40. YU, P.H., DAVIS, B.A., FANG, J. & BOULTON, A.A. (1994). Neuroprotective effects of some monoamine oxidase-B inhibitors against DSP-4 induced noradrenaline depletion in the mouse hippocampus. J. Neurochem., 63, 1820-1828.