Structural aspects of monoamine oxidase and its reversible inhibition

Current Medicinal Chemistry

Volumn 5, Issue 2, 1998, Pages 137-162

  Wouters, Johan ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

3 (6 CYCLOPROPYLMETHOXY 2 NAPHTHYL) 5 METHOXYMETHYL 2 OXAZOLIDONE; 3 [2 (3 CYANO 1 HYDROXYPROPYL) 6 BENZOTHIAZOLYL] 5 METHOXYMETHYL 2 OXAZOLIDINONE; 3 [2 (3 CYANO 1 HYDROXYPROPYL)BENZOTHIAZOL 6 YL]METHOXY OXAZILIDIN 2 ONE; 3 [6 (CYCLOPROPYLMETHOXY) 2 NAPHTALENYL] 5 METHOXYMETHYL OXAZOLIDIN 2 ONE; 4 (4 CYANOANILINO) 6,7 DIHYDRO 5H CYCLOPENTA[D]PYRIMIDINE; 4 (4 CYANOPHENYL)AMINO 6,7 DIHYDRO 5H CYCLOPENTA)PYRIDINE; AMIFLAMINE; BAZINAPRINE; BEFLOXATONE; BROFAROMINE; CIMOXATONE; HYDROXYAMPHETAMINE; LAZABEMIDE; MOCLOBEMIDE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; MONOAMINE OXIDASE INHIBITOR; RO 6327; TOLOXATONE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; DEPRESSION; DRUG EFFECT; DRUG PROTEIN BINDING; ENZYME INHIBITION; PARKINSON DISEASE; SITE DIRECTED MUTAGENESIS; THREE DIMENSIONAL IMAGING;

EID: 0031898408     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (152)

1. Dostert, P.; Strolin Benedetti, M.; Tipton, K. Medicinal Research Reviews 1989, 9, 45.
2. Kalgutkar, A.; Castagnoli, N. Medicinal Research Reviews 1995, 15, 325.
3. Dostert, P.; Strolin Benedetti, M.; Jafre, M. Monoamine oxidase: basic and clinical frontiers.: Amsterdam, 1982.
4. Singer, T. P. In Chemistry and Biochemistry of Flavoenzymes; Muller, F, Ed.; CRC Press, 1991; Vol. II; pp 437.
5. Strolin Benedetti, M. L'Encéphale 1982, 8, 545.
6. Monoamine oxidase: from physiology and pathophysiology to the design and clinical application of reversible inhibitors.; Strolin Benedetti, M.; Dostert, P., Ed.; Academic Press: London, 1992; Vol. 23, pp 67-125.
7. Weyler, W.; Hsu, Y.-P.; Breakefield, X. Pharmac. Ther. 1990, 47, 391
8. Cesura, A.; Pletscher, A. In Progress in Drug Research; Birkhauser Verlag. Basel, 1992; Vol. 38; pp 171.
9. Youdim, M. B.; Finberg, J. P. Psychopharmacology 1985, 2, 35.
10. Youdim, M.; Finberg, J.; Tipton, K. In Cathecolamine I; Trendelenburg, U., Weiner, N., Ed.; Springer-Verlag: Berlin, 1988; Vol. 90; pp 119.
11. Fowler, C.; Ross, S. Medicinal Research Reviews 1984, 4, 323
12. Hare Biochem. J. 1928, 22, 968.
13. Singer, T. P. The colorful past and bright future of monoamine oxidase research.; Elsevier: Amsterdam, 1995; Vol. 106.
14. Zeller, E. Classification and nomenclature of monoamine oxidases and other amine oxidases : structure, function and altered functions.; Academic Press: New York, 1979.
15. Berry, M.; Juorio, A.; Paterson, I. Progress in Neurobiology. 1994, 42, 375.
16. Tipton, K. Br. Med. Bull. 1973, 29, 116.
17. Tipton, K. Cell Biochemistry and Function. 1986, 4, 79.
18. Johnston, J. Biochem. Pharmacol. 1968, 17, 1285-.
19. Knoll, J.; Mayar, K. Adv. Biochem. Psychopharmacol. 1972, 5, 393.
20. Blaschko, H. J. Pharm. Pharmacol. 1989, 41, 664.
21. Shih, J. Neuropsychopharmacology 1991, 4, 1.
22. Bach, A.; Lan, N.; Johnson, D.; Abell, C.; Bembenek, M.; Kwan, S.-W.; Seeburg, P.; Shih, J. Proc. Natl, Acad. Sci, USA 1988, 85, 4934.
23. Shih, J.; Chen, K.; Zhu, Q. S.; Grimsby, J. In 6th Amine oxidase workshop and 5th trace amine conference.: Saskatoon, 1994; pp L-14.
24. Kearney, E.; Salach, J.; Walker, W.; Seng, R.; Kenney, W.; Zeszotek, E.; Singer, T. P. Eur. J. Biochem. 1971, 24, 321.
25. Walker, W.; Kearney, E.; Seng, R.; Singer, T. P. Eur. J. Biochem. 1971, 24, 328.
26. Weyler, W.; Titlow, C.; Salach, J. Biochem. Biophys. Res. Commun. 1990, 173, 1205.
27. Lan, N.; Chen, C.; Shih, J. J. Neurochem. 1989, 52, 1652-.
28. Woo, J. C.; Silverman, R. Biochem. Biophys. Res. Commun. 1994, 202, 1574.
29. DeRose, V.; Woo, J.; Hawe, W.; Hoffman, B.; Silverman, R.; Yelekci, K. Biochemistry 1996, 35, 11085.
30. Yue, K.; Bhattacharyya, A.; Zhelyaskov, V.; Edmondson, D. Arch. Biochem. Biophys. 1993, 300, 178
31. Weyler, W.; Salach, J. J. Biol. Chem. 1985, 260, 13199.
32. Gomes, B.; Kloepfer, H.; Oi, S.; Yasunobu, K. Biochem. Biophys. Acta. 1976, 438, 347.
33. Yasunobu, K.; Tan, A. Advances in monoamine oxidase enzymology.; CRC Press: Boca Raton, FL, 1985.
34. Zhong, B.; Silverman, R. J. Am. Chem. Soc. 1997, 119, 6690.
35. Hiramatsu, A.; Tsurushiin, S.; Yasunobu, K. Eur. J. Biochem. 1975, 57, 587.
36. Tesson, F.; Limon-Boulez, I.; Urban, P.; Puype, M.; Vandekerckhove, J.; Coupry, I.; Pompon, D.; Parini, A. J. Biol. Chem. 1995, 270, 9856.
37. Limon-Boulez, I.; Tesson, F.; Gargalidis-Moudanos, C.; Parini, A. The Journal of Pharmacology and Experimental Therapeutics. 1996, 276, 359.
38. Oreland, L. Arch. Biochem. Biophys. 1971, 146, 410.
39. Akopyan, Z.; Stesina, L.; Gorkin, V. J. Biol. Chem. 1971, 246, 4610.
40. Salach, J. I. Archives of Biochemistry and Biophysics 1979, 192, 128.
41. Huang, R. Molec. Pharmac. 1980, 17, 192.
42. Huang, R.; Faulkner, R. J. Biol. Chem. 1981, 256, 9211.
43. Zhuang, Z.; McCauley, R. J. Biol. Chem. 1989, 264, 14594.
44. Zhuang, Z.; Marks, B.; McCauley, R. J. Biol. Chem. 1992, 267, 591.
45. Mitoma, J.-Y.; Ito, A. J. Biochem. 1992, 111, 20.
46. Weyler, W. J. Neural Transm.[Suppl] 1992, 41, 3.
47. Hsu, Y.-P.; Weyler, W.; Chen, S.; Sims, K.; Rinehart, W.; Utterback, M.; Powell, J.; Breakfield, X. J. Neurochem. 1988, 51, 1321.
48. Powell, J.; Hsu, Y.-P.; Weyler, W.; Chen, S.; Salach, J.; Andrikopoulos, K.; Mallet, J.; Breakefield, X. Biochem. J. 1989, 259, 407.
49. Kuwahara, T.; Takamoto, S.; Ito, A. Agric. Biol. 1990, 54, 253.
50. Kwan, S.-W.; Abell, C. Comp. Biochem. Physiol. 1991, 102B, 143.
51. Chen, K.; Wu, H.-F.; Shih, J. J. Neurochem. 1993, 61, 187.
52. Ito, A.; Kuwahara, T.; Inadome, S.; Sagara, Y. Biochem. Biophys. Res. Commun. 1988, 157, 970.
53. Chen, S.; Weyler, W. Biochem. Biophys. Res. Commun. 1988, 156, 445.
54. Kwan, S.-W.; Lewis, D.; Zhou, B.; Kirksey, T.; Abell, C. Arch. Biochem. Biophys. 1995, 316, 385.
55. Grimsby, J.; Zentner, M.; Shih, J. Life Sciences 1996, 58, 777.
56. Wouters, J.; Ramsay, R.; Goormaghtigh, E.; Ruysschaert, J.; Brasseur, R.; Durant, F. Biochem. Biophys. Res. Commun. 1995, 208, 773.
57. Brunner, H.; Nelen, M.; Breakefield, X. Science 1993, 262, 578.
58. Lim, L.; Powell, J.; Sham, P.; Castle, D.; Hunt, N.; Murray, R.; Gill, M. American Journal of Medical Genetics 1995, 60, 325.
59. Wouters, J. PhD Thesis, 1995, Fac. Uni. ND de la Paix, Belgium.
60. Wu, H.-F.; Chen, K.; Shih, J. Molecular Pharmacology 1993, 43, 888.
61. Hiro, I.; Tsugeno, Y.; Hirashiki, I.; Ogata, F.; Ito, A. In 6th Amine oxidase workshop and 5th trace amine conference.: Saskatoon, 1994; pp A.06.
62. Gottowik, J.; Cesura, A.; Malherbe, P.; Lang, G.; Da Prada, M. FEBS 1993, 317, 152.
63. Tsugeno, Y.; Ito, A. J. Biol. Chem. 1997, 272, 14033.
64. Chen, K.; Wu, H.; Shih, J. C. J. Neurochem. 1996, 66, 797.
65. Tsugeno, Y.; Hairashiki, I.; Ogata, F.; Ito, A. J. Biochem. 1995, 118, 974.
66. Wouters, J.; Baudoux, G. manuscript in preparation.
67. Rost, B.; Casadio, R.; Fariselli, P.; Sander, C. Protein Science 1995, 4, 521.
68. Jones, D. T. Curr. Opin. Stru. Biol. 1997, 7[3], 377.
69. Palmer, S.; Mabic, S.; Castagnoli, N. J. Med. Chem. 1997, 40, 1982.
70. Mabic, S.; Castagnoli, N. J. Med. Chem. 1996, 39, 3694.
71. Efrange, S.; Boudreau, R. J. Comput-Aided Mol. Design 1991, 5, 405.
72. Edmondson, D. Biochimie 1995, 77, 643.
73. Youdim, M.; Finberg, J. In Adv. Neurology, Yatir, M., Bergmann, K., Ed; Raven Press: New York, 1986; Vol. 45; pp 127.
74. Altomare, C.; Carrupt, P.-A.; Gaillard, P.; Tayar, N.; Testa, B.; Carotti, A. Chem. Res. Toxicol. 1992, 5, 366.
75. Medvedev, A.; Ivanov, A.; Kamyshanskaya, N.; Kirkel, A.; Moskvitina, T.; Gorkin, V.; Marshakov, V. Biochem. Mol. Biol. Int. 1995, 36, 113.
76. Medvedev, A.; Ivanov, A.; Veselovsky, A.; Skvortsov, V.; Archakov, A. J. Chem. Inf. Comput. Sci. 1996, 36, 664.
77. Thull, U.; Kneubühler, S.; Gaillard, P.; Carrupt, P. A.; Testa, B.; Altomare, C.; Carotti, A.; Jenner, P.; McNaught, K. Biochem. Pharmacol. 1995, 50, 869.
78. Silverman, R. B. Acc. Chem. Res. 1995, 28, 335.
79. Silverman, R. Mechanism-based inactivators:, CRC Press, Inc., Boca Raton: Florida; Vol. vol I & II.
80. Dostert, P.; Strolin Benedetti, M. Actual. Chim. Ther. 1986, 13, 269.
81. Kan, J. P.; Malone, A.; Strolin-benedetti, M. J. Pharm. Pharmac. 1978, 30, 190.
82. Fowler, C.; Strolin Benedetti, M. J. Neurochem. 1983, 40, 510.
83. Raynaud, G.; Gouret, C. Chim. Ther. 1973, 3, 328.
84. Provost, J.; Funk-Brentano, C.; Rovei, V.; d'Estanque, J.; Ego, D.; Jaillon, P. Clin. Pharmacol. 1992, 52, 384.
85. Curet, O.; Damioseau, G.; Aubin, N.; Sontag, N.; Rovei, V.; Jarrea, F.X. J. Pharmacol. Exp. Ther. 1996, 227, 253.
86. Gates, K.; Silverman, R. J. Am. Chem. Soc. 1989, 111, 8891.
87. Gates, K.; Silverman, R. J. Am. Chem. Soc. 1990, 112, 9364.
88. Ding, C.; Lu, X.; Nishimura, K.; Silverman, R. J. Med. Chem. 1993, 36, 3606.
89. Ding, C., Lu, X.; Nishimura, K.; Silerman, R. J. Med. Chem. 1993, 36, 1711.
90. Ding, C.; Silverman, R. Bioorg. Med. Chem. Lett. 1993, 3, 2077.
91. Kagaka, T.; Kajiwara, A.; Nagato, S.; Akasaka, K.; Kubota, A. J. Pharmacol. Exp. Ther. 1996, 278, 243.
92. Naitoh, T.; Horie, T.; Nagato, S.; Kagaya, T.; Kubota, A.; Akasaka, K. Xenobiotica 1994, 24, 819.
93. Kato, M.; Iwata, H.; Katakama, T.; Asai, H.; Narita, H.; Endo, T. Biol. Pharm. Bull. 1997, 20[4], 349.
94. Mazouz, F.; Lebreton, L.; Milcent, R.; Burstein, C. Eur. J. Med. Chem. 1990, 25, 659.
95. Mazouz, F.; Gueddari, S.; Burstein, C.; Mansuy, D.; Milcent, R. J. Med. Chem. 1993, 36, 1157.
96. Lebreton, L.; Curet, O.; Gueddari, S.; Mazouz, F.; Bernard, S.; Burstein, C.; Milcent, R. J. Med. Chem. 1995, 38, 4786.
97. Wouters, J.; Ooms, F.; Jegham, S.; Koenig, J.; George, P.; Durant, F. Eur. J. Med. Chem. 1997, 32, 721.
98. Bernard, S.; Fuseau, C.; Schmid, L.; Milcent, R.; Crouzel, C. European Journal of Nuclear Medecine 1996, 23, 150.
99. Kneubuhler, S.; Carta, V.; Altomare, C.; Carotti, A.; Testa, B. Helv. Chim. Acta 1993, 76, 1956.
100. Kneubühler, S.; Thull, U.; Altomare, C.; Carta, V.; Gaillard, P.; Carrupt, P. A.; Carotti, A.; Testa, B. J. Med. Chem. 1995, 38, 3874.
101. Kan, J.-P.; Steinberg, R.; Leclercq, J.; Worms, P.; Biziere, K. J. Neurochem. 1989, 50, 1137.
102. Da Prada, M.; Kettler, R. Mod. Prob. Pharmacopsychiat. 1983, 19, 231.
103. Morreti, A.; Caccia, C. Biochem. Pharmacol. 1981, 30, 2728.
104. Kim; Sablin, S.; Ramsay, R. Arch. Biochem. Biophys. 1997.
105. Kojima, T.; Naoi, M.; Wakabayashi, K.; Sugimura, T.; Nagatsu, T. Neurochem. Int. 1990, 16, 51.
106. Harfenist, M.; Joyner, C.; Mize, P.; White, H. J. Med. Chem. 1994, 37, 2085.
107. Harfenist, M.; Heuser, D.; Joyner, C.; Batchelor, J.; White, H. J. Med. Chem. 1996, 39, 1857.
108. Harfenist, M.; Joseph, D.; Spence, S.; Mcgee, D.; Reeves, M.; White, H. J. Med. Chem. 1997, 40, 2466.
109. Dingemanse, J. Int. Clinic. Psychopharmacology 1993, 7, 167.
110. Fitton, A.; Faulds, D.; Goa, K. Drugs 1992, 43, 561.
111. Haefely, W.; Burkard, W.; Cesura, A.; Kettler, R.; Lorez, H.; Martin, J.; Richards, J.; Scherschlicht, R.; Da Prada, M. Psychopharmacology 1992, 106, S6.
112. Da Prada, M.; Kettler, R.; Keller, H.; Cesura, A.; Richards, J.; Saura Marti, J.; Muggli Maniglio, D.; Wyss, P. C.; Kyburz, E.; Imhof, R. J. Neural. Transm.[Suppl.] 1990, 29, 279.
113. Da Prada, M.; Kettler, R.; Keller, H.; Bonetti, E.; Imhof, R. Adv. Neurology 1986, 45, 175.
114. Waldmeier, P.; Baumann, P.; Delini-Stula, A.; Bernasconi, R.; Sigg, K.; Buech, O., A. Mod. Probl. Pharmacopsychiat. 1983, 19, 31.
115. Waldmeier, P.; Felner, A.; Tipton, K. Eur. J. Pharmacol. 1983, 94, 73.
116. Waldmeier, P.; Glatt, A.; Jackel, J. Clin. Neuropharmacol. 1993, 16[2 Suppl.], S19.
117. Steiger, A.; Holsboer, F.; Benkert, O. Psychopharmacology 1987, 92, 110.
118. Schiwy, W.; Heath, W.; Delini-Stula, A. J. Neura Transm.[Σuppl.] 1989, 28, 33.
119. Volz, H.-P.; Gleiter, C.; Struck, M.; H-J., M. CNS Drugs 1995 3[1], 1.
120. Rendenbach-Müller, B.; Schlecker, R.; Traut, M.; Weifenbach, H. Bioorg. Med. Chem. Lett. 1994, 4, 1195.
121. Hossain, C.; Okuyama, E.; Yamazaki, M. Chem. Pharm. Bull 1996, 44, 1535.
122. Renaut, P.; Bellamy, F.; Boucher, T. WO 90/11997 October 18,1990.
123. Schoofs, A.; Langlois, M.; Jeanpetit, C.; Masson, M. US Patent 4,971,995 November 20, 1990.
124. Arvanitis, A.; Scholfield, E.; Grigoriadis, D.; Heytler, P.; Bowdle, J.; Chorvat, R. Bioorg, Med. Chem. Lett. 1996, 6, 115.
125. Ask, A. L.; Hellström, W.; Norrman, S.; Ögren, S. O.; Ross, S. Neuropharmacology 1982, 21, 299.
126. Arai, Y.; Toyoshima, Y.; Kinemuchi, H. Japan J. Pharmacol. 1986, 41, 191.
127. Kinemuchi, H.; Arai, Y.; Toyoshima, Y.; Tadano, T.; Kisara, K. Japan J. Pharmacol. 1988, 46, 197.
128. Mahmoudian, M. Acta Pharm. Suec. 1988, 25, 151.
129. Hasegawa, K.; Kimura, T.; Miyashita, Y.; Fanatsu, K. J. Chem. Inf. Comput. Sci. 1996, 36, 1025.
130. Florvall, L.; Fagervall, I.; Ask, A.-L.; Ross, S. J. Med. Chem. 1986, 29, 2250.
131. Kai, M.; Noda, A.; Noda, H.; Goto, S. Chem. Pharm. Bull. 1988, 36, 3604.
132. Naoi, M.; Nagatsu, T. Life Sciences 1987, 40, 1075.
133. Kai, M.; Noda, A.; Noda, H.; Goto, S. Chem. Pharm. Bull. 1985, 33, 5585.
134. Dvoryantseva, G.; Pol'shakov, V.; Sheinker, Y.; Shvedov, V.; Grynev, A.; Mashkovsky, M. Eur. J. Med. Chem. 1985, 20, 414.
135. Karapetyan, H.; Struchkov, Y.; Dvoryantseva, G. Cryst. Struct. Comm. 1982, 11, 1441.
136. Bruhwyler, J.; Liegeois, J. F.; Geczy, J. Pharmacol. Research, 1997, in the press.
137. Bruhwyler, J.; Monseu, M.; Vandekerkhove, K.; Geczy, J. Eur. J. Clinical. Res. 1997, 9, 225.
138. Yokoyama, T.; Kamioka, T.; Iwata, N.; Kobayashi, T. Japan. J. Pharmacol. 1987, 44, 413.
139. Yokoyama, T.; Karube, T.; Iwata, N. J. Pharm. Pharmacol. 1989, 41, 32.
140. Palaska, E.; Erol, D.; Demirdamar, R. Eur. J. Med. Chem. 1996, 31, 43.
141. Rocha, L.; Marston, A.; Kaplan, M.; Stoeckli-Evans, H.; Thull, U.; Testa, B.; Hostettmann, K. Phytochemistry 1994, 36, 1381.
142. Moureau, F.; Wouters, J.; Vercauteren, D.P.; Collin, S.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J.J.; Jarreau, F.X. Eur.J.Med.Chem 1992, 27, 939.
143. Moureau, F.; Wouters, J.; Vercauteren, D.P.; Collin, S.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J.J.; Jarreau, F.X. Eur.J.Med.Chem 1994, 29, 269.
144. Moureau, F.; Wouters, J.; Vercauteren, D.P.; Depas, M.; Durant, F.; Ducrey, F.; Koenig, J.J.; Jarreau, F.X. Eur.J.Med.Chem 1995, 30, 823.
145. Wouters, J.; Moureau, F.; Vercauteren, D.P.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J.J.; Jarreau, F.X. J. Neural Transm.[Suppl] 1994, 41, 313.
146. Wouters, J.; Moureau, F.; Dory, M.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J.J.; Jarreau, F.X. In Trends in QSAR and molecular modelling 92.; Wermuth, C. Ed.; ESCOM; Leiden; 1993, pp. 291.
147. Wouters, J. Biochem. Psychiatry 1997, 42, 1263
148. Bernard, S.; Paillat, C.; Oddos, T.; Seman, M.; Milcent, R. Eur J Med Chem. 1995, 30, 471.
149. Concil, N. Am. J. Psychiatry 1993, 150, 1447.
150. Narabayashi, H.; Nagatsu, T.; Yanagisawa, N.; Mizuno, Y. Advances in Neurology, Parkinson's Disease 1993, 60, Raven Press, New York.
151. Youdim, M. Biochem. Psychiatry 1997, 42, 126S.
152. Artigas, F.; Romero, L.; de Montigny, C.; Blier, P. Trends Neurosci. 1996, 19, 378.