Natural and synthetic xanthones as monoamine oxidase inhibitors: Biological assay and 3D-QSAR

Helvetica Chimica Acta

Volumn 84, Issue 3, 2001, Pages 552-570

  Guerre, Carmela ^a   Thull, Ulrike ^a   Gaillard, Patrick ^a   Carrupt, Pierre Alain ^a   Testa, Bernard ^a   Fernandes, Eduarda ^b   Silva, Francisco ^b   Pinto, Manuela ^b   Pinto, Madalena M M ^b   Wolfender, Jean Luc ^a   Hostettmann, Kurt ^a   Cruciani, Gabriele ^c  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PORTO   (Portugal)

^c UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CHARGE TRANSFER; ELECTRIC FIELDS; ELECTRON ABSORPTION; ENZYME INHIBITION; ENZYMES;

TOPOGRAPHICAL INFORMATION;

BIOASSAY;

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; LUMIFLAVINE; MONOAMINE OXIDASE INHIBITOR; XANTHONE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; DRUG ACTIVITY; DRUG SELECTIVITY; ELECTRIC FIELD; ENZYME INHIBITION; IC 50; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY;

EID: 0035048669     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010321)84:3<552::AID-HLCA552>3.0.CO;2-X     Document Type: Article

References (57)

1. C. Altomare, P. A. Carrupt, P. Gaillard, N. El Tayar, B. Testa, A. Carotti, Chem. Res. Toxicol. 1992, 5, 366.
2. Y. Tsugeno, A. Ito, J. Biol. Chem. 1997, 272, 14033.
3. J. A. Moron, M. Campillo, V. Perez, M. Unzeta, L. Pardo, J. Med. Chem. 2000, 43, 1684.
4. E. Kyburz, Drug News Persp. 1990, 3, 592.
5. M. E. Bembenek, C. W. Abell, L. A. Chrisey, M. D. Rozwadowska, W. Gessner, A. Brossi, J. Med. Chem. 1990, 33, 147.
6. M. Strolin Benedetti, P. L. Dostert, J. Neural Transm. 1987, 23, 103.
7. F. Mazouz, S. Gueddari, C. Burstein, D. Mansuy, R. Milcent, J. Med. Chem. 1993, 36, 1157.
8. H. L. White, P. Scates, Drug Dev. Res. 1992, 25, 191.
9. O. Suzuki, Y. Katsumata, M. Oya, V. M. Chari, B. Vermes, H. Wagner, K. Hostettmann, Planta Med. 1981, 42, 17.
10. K. Hostettmann, M. Hostettmann, in 'Methods In Plant Biochemistry', Ed. Y. B. Harborne, Academic Press, New York, 1989, pp. 493-508.
11. B. Shearer, J. Sullivan, J. Carter, R. Mathew, P. Waid, J. Connor, R. Patch, J. Burch, J. Med. Chem. 1991, 34, 2931.
12. V. Rovei, D. Caille, O. Curet, D. Ego, F. X. Jarreau, J. Neural Transm. 1994, 41, 339.
13. F. Moureau, J. Wouters, D. P. Vercauteren, S. Collin, G. Evrard, F. Durant, F. Ducrey, J. J. Koenig, F. X. Jarreau, Eur. J. Med. Chem. 1994, 29, 269.
14. M. J. Laughton, P. J. Evans, M. A. Moroney, J. R. S. Hoult, B. Halliwell, Biochem. Pharmacol. 1991, 42, 1673.
15. T. A. Halgren, J. Comput. Chem. 1996, 17, 520.
16. GAUSSIAN 98 software (Revision A.1). M. J. Frish, G. W. Trucks, H. B. Schelgel, M. A. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zahrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople. Pittsburgh PA, Copyright(©) 1998, Gaussian, Inc., 1998.
17. P. Gaillard, P. A. Carrupt, B. Testa, A. Boudon, J. Comput.-Aided Mol. Design 1994, 8, 83.
18. Almond 2.0. Multivariate Infometric Analysis, Perugia, Italy, 1999.
19. Grid1.7. Molecular Discovery Ltd, West Way House, Elms Parade, Oxford OX29LL, 1999.
20. GOLPE 4.5. Multivariate Infometric Analysis, Perugia, Italy, 1999.
21. Tsar 3.0. Oxford Molecular Ltd., Oxford, UK, 1997.
22. H. Weissbach, T. E. Smith, J. W. Daly, B. Witkop, S. Udenfriend, J. Biol. Chem. 1960, 235, 1160.
23. S. Kneubühler, U. Thull, C. Altomare, V. Carta, P. Gaillard, P. A. Carrupt, A. Carotti, B. Testa, J. Med. Chem. 1995, 38, 3874.
24. P. J. F. Henderson, in 'Techniques in the Life Sciences, B1/II Supplement, Protein and Enzyme Biochemistry', Ed. K. F. Tipton, Elsevier, Dublin, 1985, pp. 1-48.
25. U. Thull, S. Kneubühler, B. Testa, M. F. M. Borges, M. M. M. Pinto, Pharm. Res. 1993, 10, 1187.
26. V. Glover, J. Liebowitz, I. Armando, M. Sandler, J. Neural Transm. 1982, 54, 209.
27. P. L. Dostert, E. M. O'Brien, K. F. Tipton, M. Meroni, P. Melloni, M. Strolin Benedetti, Eur. J. Med. Chem. 1992, 27, 45.
28. A. Codoner, I. S. Monzo, C. Ortiz, A. Olba, J. Chem. Soc., Perkin Trans. 2 1989, 107.
29. M. Baroni, G. Costantino, G. Cruciani, D. Riganelli, R. Valigi, S. Clementi, Quant. Struct.-Act. Relat. 1993, 12, 9.
30. J. L. Wolfender, M. Hamburger, J. D. Msonthi, K. Hostettmann, Phytochemistry 1991, 30, 3625.
31. L. Rocha, A. Marston, M. A. C. Kaplan, H. Stoeckli-Evans, U. Thull, B. Testa, K. Hostettmann, Phytochemistry 1994, 36, 1381.
32. I. Sordat-Diserens, C. Rogers, B. Sordat, K. Hostettmann, Phytochemistry 1992, 31, 313.
33. I. Sordat-Diserens, M. Hamburger, C. Rogers, K. Hostettmann, Phytochemistry 1992, 31, 3589.
34. D. Schaufelberger, K. Hostettmann, Planta Med. 1987, 54, 219.
35. I. Sordat-Diserens, A. Marston, M. Hamburger, C. Rogers, K. Hostettmann, Helv. Chim. Acta 1989, 72, 1001.
36. A. Bashir, M. Hamburger, J. D. Msonthi, K. Hostettmann, Phytochemistry 1992, 31, 309.
37. A. Bashir, M. Hamburger, M. P. Gupta, P. Solis, K. Hostettmann, Phytochemistry 1992, 31, 3203.
38. M. C. Recio-Iglesias, A. Marston, K. Hostettmann, Phytochemistry 1992, 31, 1387.
39. W. G. Ma, N. Fuzzati, Q. S. Li, C. R. Yang, K. Hostettmann, H. Stoeckli-Evans, Photochemistry 1995, 39, 1049.
40. A. J. Quillinan, F. Scheinmann, J. Chem. Soc., Perkin Trans. 1 1973, 1329.
41. C. N. Lin, S. S. Liou, F. N. Ko, C. M. Teng, J. Pharm. Sci. 1993, 82, 11.
42. R. A. Finnegan, P. L. Bachmann, J. Pharm. Sci. 1965, 54, 633.
43. J. E. Atkinson, J. R. Lewis, J. Chem. Soc. (C) 1969, 281.
44. F. D. Monache, M. M. Mac-Quhae, G. D. Monache, G. B. M. Bettolo, R. A. Lima, Phytochemistry 1983, 22, 227.
45. P. W. Westerman, S. P. Gunasekera, M. Uvais, S. Sultanbawa, R. Kazlauskas, Org. Magn. Reson. 1977, 9, 631.
46. A. W. Frahm, R. K. Chaudhuri, Tetrahedron 1979, 35, 2035.
47. D. B. Boyd, in 'Reviews in Computational Chemistry', Eds. K. B. Lipkowitz and D. B. Boyd, VCH Publishers, New York, 1995, Vol. 6, pp. 317-382.
48. R. K. Chaudhuri, F. Zymalkowski, A. W. Frahm, Tetrahedron 1978, 34, 1837.
49. R. A. Finnegan, J. K. Patel, J. Chem. Soc., Perkin Trans. 1 1972, 1896.
50. J. L. Okogun, J. Chem. Soc., Perkin Trans, 1 1976, 21, 2241.
51. R. C. Young, R. C. Mitchell, T. H. Brown, C R. Ganellin, R. Griffiths, M. Jones, K. K. Rana, D. Saunders, I. R. Smith, N. E. Sore, T. J. Wilks, J. Med. Chem. 1988, 31, 656.
52. R. Royer, J. Lechartier, P. Demerseman, Bull. Soc. Chim. Fr. 1971, 1707.
53. P. K. Grover, G. D. Shah, R. C. Shah, J. Chem. Soc. 1955, 3982.
54. T. Sargi, Tetrahedron 1996, 52, 13623.
55. O. R. Gottlieb, A. A. L. Mesquita, G. G. Oliveira, M. T. Melo, Phytochemistry 1970, 9, 2535.
56. S. P. Gunasekera, S. Ramachandran, S. Selliah, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1975, 1, 2447.
57. M. M. M. Pinto, J. Polonia, Helv. Chim. Acta 1974, 57, 2613.