Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 4829-4840

  Manley King, Clarina I ^a   Bergh, Jacobus J ^a   Petzer, Jacobus P ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Isatin; Molecular docking; Monoamine oxidase; Phthalimide; Reversible inhibition

Indexed keywords

5 (2 PHENYLETHOXY)PHTHALIMIDE DERIVATIVE; 5 (3 PHENYLPROP 2 EN 1 YL)PHTHALIMIDE DERIVATIVE; 5 (3 PHENYPROPOXY)PHTHALIMIDE DERIVATIVE; 5 (4 BROMOBENZYLOXY)PHTHALIMIDE DERIVATIVE; 5 (4 BROMOPHENYL)PHTHALIMIDE DERIVATIVE; 5 (NAPHTHALEN 2 YLOXY)PHTHALIMIDE DERIVATIVE; 5 [2 (4 BROMOPHENYL)ETHOXY]PHTHALIMIDE DERIVATIVE; 5 ALKYLOXYPHTHALIMIDE DERIVATIVE; 5 ARYLOXYPHTHALIMIDE DERIVATIVE; 5 BENZYLOXYISATIN; 5 BENZYLOXYPHTHALIMIDE DERIVATIVE; 5 PHENOXYPHTHALIMIDE DERIVATIVE; 6 BENZYLOXYISATIN; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; HARMINE; ISATIN; MONOAMINE OXIDASE INHIBITOR; PHTHALIMIDE DERIVATIVE; SAFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; NONHUMAN;

ANIMALS; DRUG EVALUATION, PRECLINICAL; HUMANS; INSECTS; ISATIN; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PHTHALIMIDES; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 79961170657     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.070     Document Type: Article

References (47)

1. C. Binda, P. Newton-Vinson, F. Hubálek, D.E. Edmondson, and A. Mattevi Nat. Struct. Biol. 9 2002 22
2. D.E. Edmondson, A. Mattevi, C. Binda, M. Li, and F. Hubálek Curr. Med. Chem. 11 2004 1983
3. J.C. Shih, K. Chen, and M.J. Ridd Annu. Rev. Neurosci. 22 1999 197
4. W. Weyler, Y.P. Hsu, and X.O. Breakefield Pharmacol. Ther. 47 1990 391
5. K. Chen, H.F. Wu, and J.C. Shih J. Neurochem. 61 1993 187
6. W. Weyler, and J.I. Salach J. Biol. Chem. 260 1985 13199
7. J. Saura, Z. Bleuel, J. Ulrich, A. Mendelowitsch, K. Chen, J.C. Shih, P. Malherbe, M. Da Prada, and J.G. Richards Neuroscience 70 1996 755
8. H. Inoue, K. Castagnoli, C.J. Van der Schyff, S. Mabic, K. Igarashi, and N. Castagnoli Jr. J. Pharmacol. Exp. Ther. 291 1999 856
9. K.N. Westlund, R.M. Denney, R.M. Rose, and C.W. Abell Neuroscience 25 1988 439
10. J.C. Fowler, A. Wiberg, L. Oreland, J. Marcusson, and B. Winblad J. Neural Transm. Gen. Sect. 49 1980 1
11. R.N. Kalaria, M.J. Mitchell, and S.I. Harik Brain 111 1988 1441
12. G.G.S. Collins, M. Sandler, E.D. Williams, and M.B.H. Youdim Nature 225 1970 817
13. P.C. Waldmeier J. Neural Transm. Suppl. 23 1987 55
14. M.B.H. Youdim, D. Edmondson, and K.F. Tipton Nat. Rev. Neurosci. 7 2006 295
15. M.B.H. Youdim, and Y.S. Bakhle Br. J. Pharmacol. 147 2006 S287
16. T.P. Singer, R.R. Ramsay, K. McKeown, A. Trevor, and N. Castagnoli Jr. Toxicology 49 1988 17
17. S.E. Zisook Psychosomatics 26 1985 240
18. M.B.H. Youdim, G.G.S. Collins, M. Sandler, A.B. Bevan-Jones, C.M. Pare, and W.J. Nicholson Nature 236 1972 225
19. D.A. Di Monte, L.E. DeLanney, I. Irwin, J.E. Royland, P. Chan, M.W. Jakowec, and J.W. Langston Brain Res. 738 1996 53
20. J.P. Finberg, J. Wang, K. Bankiewich, J. Harvey-White, I.J. Kopin, and D.S. Goldstein J. Neural Transm. Suppl. 52 1998 279
21. H.H. Fernandez, and J.J. Chen Pharmacotherapy 27 2007 174S
22. A. Nicotra, F. Pierucci, H. Parvez, and O. Senatori Neurotoxicology 25 2004 155
23. J.S. Fowler, N.D. Volkow, G.J. Wang, J. Logan, N. Pappas, C. Shea, and R. MacGregor Neurobiol. Aging 18 1997 431
24. M.B. Youdim, and M. Weinstock Neurotoxicology 25 2004 243
25. J.S. Fowler, N.D. Volkow, J. Logan, G.J. Wang, R.R. MacGregor, D. Schyler, A.P. Wolf, N. Pappas, D. Alexoff, and C. Shea Synapse B 18 1994 86
26. F. Hubálek, C. Binda, A. Khalil, M. Li, A. Mattevi, N. Castagnoli Jr., and D.E. Edmondson J. Biol. Chem. 280 2005 15761
27. C. Binda, M. Li, F. Hubálek, N. Restelli, D.E. Edmondson, and A. Mattevi Proc. Natl. Acad. Sci. U.S.A. 100 2003 9750
28. E.M. Van der Walt, E.M. Milczek, S.F. Malan, D.E. Edmondson, N. Castagnoli Jr., J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. Lett 19 2009 2509
29. C.I. Manley-King, J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 19 2011 261
30. N.E. Galanin, E.V. Kudrik, and G.P. Shaposhnikov Russ. J. Org. Chem. 42 2006 603
31. P. Tau, and T. Nyokong Electrochim. Acta 52 2007 3641
32. W. Pluempanupat, S. Adisakwattana, S. Yibchok-Anun, and W. Chavasiri Arch. Pharm. Res. 30 2007 1501
33. L. Novaroli, M. Reist, E. Favre, A. Carotti, M. Catto, and P.A. Carrupt Bioorg. Med. Chem. 13 2005 6212
34. B. Strydom, S.F. Malan, N. Castagnoli, J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 18 2010 1018
35. L.H.A. Prins, J.P. Petzer, and S.F. Malan Eur. J. Med. Chem. 45 2010 4458
36. Y.C. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
37. J.P. Pretorius, S.F. Malan, N. Castagnoli Jr., J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 16 2008 8676
38. N. Vlok, S.F. Malan, N. Castagnoli Jr., J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 14 2006 3512
39. J.P. Petzer, S. Steyn, K.P. Castagnoli, J.F. Chen, M.A. Schwarzschild, C.J. Van der Schyf, and N. Castagnoli Jr. Bioorg. Med. Chem. 11 2003 1299
40. J. Iley, T. Calheiros, and R. Moreira Bioorg. Med. Chem. Lett. 8 1998 955
41. S.-Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Proc. Natl. Acad. Sci. U.S.A. 105 2008 5739
42. C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi J. Med. Chem. 50 2007 5848
43. C. Binda, R. Angelini, R. Federico, A. Ascenzi, and A. Mattevi Biochemistry 40 2001 2766
44. C. Binda, A. Mattevi, and D.E. Edmondson J. Biol. Chem. 277 2002 23973
45. L. Novaroli, A. Daina, E. Favre, J. Bravo, A. Carotti, F. Leonetti, M. Catto, P.A. Carrupt, and M. Reist J. Med. Chem. 49 2006 6264
46. S. Sou, S. Mayumi, H. Takahashi, R. Yamasaki, S. Kadoya, M. Sodeoka, and Y. Hashimoto Bioorg. Med. Chem. 10 2000 1081
47. W.L. DeLano The PyMOL Molecular Graphics System 2002 DeLano Scientific San Carlos, USA