Structure-activity relationships for inhibition of human cholinesterases by alkyl amide phenothiazine derivatives

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 1, 2005, Pages 211-222

  Darvesh, Sultan ^a,b,c   McDonald, Robert S ^b   Penwell, Andrea ^b   Conrad, Sarah ^b   Darvesh, Katherine V ^b   Mataija, Diane ^b   Gomez, Geraldine ^b   Caines, Angela ^b   Walsh, Ryan ^a   Martin, Earl ^b  

^a DALHOUSIE UNIVERSITY   (Canada)

^b MOUNT SAINT VINCENT UNIVERSITY   (Canada)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYLBUTANOYLPHENOTHIAZINE; 3 METHYLBUTANOYLPHENOTHIAZINE; 3,3 DIMETHYLBUTANOYLPHENOTHIAZINE; ACETYLPHENOTHIAZINE; BUTANOYLPHENOTHIAZINE; CHLOROACETYLPHENOTHIAZINE; CHLORPROMAZINE; CHOLINESTERASE; CYCLOBUTYLCARBONYLPHENOTHIAZINE; CYCLOHEPTYLCARBONYLPHENOTHIAZINE; CYCLOHEXYLACETYLPHENOTHIAZINE; CYCLOHEXYLCARBONYLPHENOTHIAZINE; CYCLOPENTYLACETYLPHENOTHIAZINE; CYCLOPENTYLCARBONYLPHENOTHIAZINE; CYCLOPROPYLCARBONYLPHENOTHIAZINE; DIMETHYLPROPANOYLPHENOTHIAZINE; HEPTANOYLPHENOTHIAZINE; HEXANOYLPHENOTHIAZINE; METHOXYACETYLPHENOTHIAZINE; METHYLPROPANOYLPHENOTHIAZINE; N METHYLPHENOTHIAZINE; PENTANOYLPHENOTHIAZINE; PHENOTHIAZINE DERIVATIVE; PROFENAMINE; PROPANOYLPHENOTHIAZINE; UNCLASSIFIED DRUG;

ARTICLE; CHOLINESTERASE INHIBITION; DRUG BINDING; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; MOLECULAR INTERACTION; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PHENOTHIAZINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9644259049     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.09.059     Document Type: Article

References (56)

1. P.J. Whitehouse, D.L. Price, A.W. Clark, J.T. Coyle, and M.R. DeLong Ann. Neurol. 10 1981 122
2. R.T. Bartus, R.L.I. Dean, B. Beer, and A.S. Lippa Science 217 1982 408
3. J.T. Coyle, D.L. Price, and M.R. DeLong Science 219 1983 1184
4. E.K. Perry, R.H. Perry, G. Blessed, and E. Tomlinson Neuropathol. Appl. Neurobiol. 4 1978 273
5. R.S. Doody J. Clin. Psychiatry 64 2003 11
6. K. Rockwood, and S. Darvesh J. Gray Drug Advances 2003 Remedica Publishing London, UK 159 177
7. C.G. Ballard Eur. Neurol. 47 2002 64
8. N.H. Greig, D.K. Lahiri, and K. Sambamurti Int. Psychogeriatr. 14 2002 77
9. E. Giacobini Butyrylcholinesterase: Its function and Inhibitors 2003 Martin Dunitz London and New York
10. K.K. O'Brien, B.K. Saxby, C.G. Ballard, J. Grace, F. Harrington, G.A. Ford, J.T. O'Brien, A.G. Swan, A.F. Fairbairn, K. Wesnes, T. del Ser, J.A. Edwardson, C.M. Morris, and I.G. McKeith Pharmacogenetics 13 2003 231
11. S. Darvesh, D.A. Hopkins, and C. Geula Nat. Rev. Neurosci. 4 2003 131
12. E. Giacobini E. Giacobini Cholinesterases and Cholinesterase Inhibitors 2000 Martin Dunitz London and New York 181 226
13. M.-M. Mesulam, and C. Geula Ann. Neurol. 36 1994 722
14. A.L. Guillozet, J.F. Smiley, D.C. Mash, and M.-M. Mesulam Ann. Neurol. 42 1997 909
15. D.J. Lehmann, Z. Nagy, S. Litchfield, M.C. Borja, and A.D. Smith Hum. Genet. 106 2000 447
16. S. Darvesh, D.L. Grantham, and D.A. Hopkins J. Comp. Neurol. 393 1998 374
17. S. Darvesh, and D.A. Hopkins J. Comp. Neurol. 463 2003 25
18. M.-M. Mesulam, A. Guillozet, P. Shaw, A. Levey, E.G. Duysen, and O. Lockridge Neuroscience 110 2002 627
19. S. Darvesh, R. Walsh, R. Kumar, A. Caines, S. Roberts, D. Magee, K. Rockwood, and E. Martin Alzheimer Dis. Assoc. Disord. 17 2003 117
20. Q. Yu, H.W. Holloway, T. Utsuki, A. Brossi, and N.H. Greig J. Med. Chem. 42 1999 1855
21. N.H. Greig, K. Sambamurti, Q.-S. Yu, A.P. Tracy, H.W. Holloway, F. Haberman, A. Brossi, D. Ingram, and D. Lahiri E. Giacobini Butyrylcholinesterase: Its Function and Inhibitors 2003 Martin Dunitz London and New York 69 90
22. L. Savini, A. Gaeta, C. Fattorusso, B. Catalanotti, G. Campiani, L. Chiasserini, C. Pellerano, E. Novellino, D. McKissic, and A. Saxena J. Med. Chem. 46 2003 1
23. A. Saxena, A.M. Redman, X. Jiang, O. Lockridge, and B.P. Doctor Biochemistry 36 1997 14642
24. J. Debord, L. Merle, J.C. Bollinger, and T. Dantoine J. Enzyme Inhib. Med. Chem. 17 2002 197
25. R.J. Baldessarini, and F.I. Tarazi J.G. Hardman L.E. Limbird A.G. Gilman Goodman and Gilman's the Pharmacological Basis of Therapeutics 10th ed. 2001 McGraw-Hill Companies Inc. New York 485 520
26. G. Chouinard, L. Annable, A. Ross-Chouinard, and M.L. Kropsky J. Clin. Psychiatry 40 1979 147
27. G. Gardos, I. Samu, M. Kallos, and J.O. Cole Psychopharmacology 71 1980 29
28. S. Fahn Can. J. Neural Sci. 14 1987 528
29. Fischer, H.; Buergin, W. Patent number CH 653 675 AD. 1986
30. S. Darvesh, R. Kumar, S. Roberts, R. Walsh, and E. Martin Cell. Mol. Neurobiol. 21 2001 285
31. G.L. Ellman, K.D. Courtney, V.J. Andres, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88
32. E. Ragg, G. Fronza, and R. Mondelli J. Chem. Soc., Perkin Trans. 2 9 1983 1289
33. A.D. Becke J. Chem. Phys. 98 1993 1372
34. A.D. Becke J. Chem. Phys. 98 1993 5648
35. C. Lee, W. Yang, and G. Parr Phys. Rev. B 37 1988 785
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11.2. Gaussian, Inc., Pittsburgh PA, 2001
37. M.A. Palafox, M. Gil, J.L. Nunez, and G. Tardajos Int. J. Quantum Chem. 89 2002 147
38. J.J.H. McDowell Acta Crystallogr., Sect. B 32 1976 5
39. J.D. Bell, J.F. Blount, O.V. Briscoe, and H.C. Freeman Chem. Commun. 1968 1656
40. Æ. Frisch, and M.J. Frisch Gaussian 98 User's Reference 2nd ed. 1999 Gaussian Inc. Pittsburg, PA
41. J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Science 253 1991 872
42. A. Shafferman, B. Velan, A. Ordentlich, C. Kronman, H. Grosfeld, M. Leitner, Y. Flashner, S. Cohen, D. Barak, and N. Ariel EMBO J. 11 1992 3561
43. D.C. Vellom, Z. Radić, Y. Li, N.A. Pickering, S. Camp, and P. Taylor Biochemistry 32 1993 12
44. Z. Radić, N.A. Pickering, D.C. Vellom, S. Camp, and P. Taylor Biochemistry 32 1993 12074
45. A. Gnatt, Y. Loewenstein, A. Yaron, M. Schwarz, and H. Soreq J. Neurochem. 62 1994 749
46. Y. Nicolet, O. Lockridge, P. Masson, J.C. Fontecilla-Camps, and F. Nachon J. Biol. Chem. 278 2003 41141 PDB ID: 1POP
47. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne The protein data bank Nucleic Acids Res. 28 2000 235 (http://www.pdb.org/)
48. G. Kryger, M. Harel, K. Giles, L. Toker, B. Velan, A. Lazar, C. Kronman, D. Barak, N. Ariel, A. Shafferman, I. Silman, and J.L. Sussman Acta Crystallogr., Sect. D 56 2000 1385 PDB ID: 1B41
49. DeLano, W. L. The PyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA. 2002. (http://www.pymol.org)
50. P. Masson, M.T. Froment, C.F. Bartels, and O. Lockridge Eur. J. Biochem. 235 1996 36
51. S. Darvesh, C. MacKnight, and K. Rockwood Int. Psychogeriatr. 13 2001 461
52. H. Roseboom, and A.D. Forch J. Pharm. Sci. 68 1979 515
53. M. Siska, L. Szporny, and O. Clauder Acta Pharm. Hung. 31 1961 91
54. G. Cauquil, and A. Casadevall Compt. Rend. 236 1953 1569
55. P. Stoss, and G. Satzinger Chem. Ber. 111 1978 1453
56. H. Gilman, and R.D. Nelson J. Amer. Chem. Soc. 75 1953 5422