Homo- and hetero-bivalent edrophonium-like ammonium salts as highly potent, dual binding site AChE inhibitors

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 15, 2008, Pages 7450-7456

  Leonetti, Francesco ^a   Catto, Marco ^a   Nicolotti, Orazio ^a   Pisani, Leonardo ^a   Cappa, Anna ^a   Stefanachi, Angela ^a   Carotti, Angelo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Butyrylcholinesterase inhibition; Edrophonium like ammonium salts; Molecular docking; Selective acetylcholinesterase inhibitors

Indexed keywords

1,4 BIS (3 NITROPHENOXY)BUTANE; 3,3' (BUTANE 1,4 DIYLBIS (OXY)BIS(N,N,N TRIMETHYLBENZENAMINIUM IODIDE); 3,3' (BUTANE 1,4 DIYLBIS(OXY))DIBENZENAMINE; AMMONIUM DERIVATIVE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; COUMARIN; EDROPHONIUM LIKE AMMONIUM SALT DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MOLECULAR DOCKING;

ACETYLCHOLINESTERASE; ANIMALS; BUTYRYLCHOLINESTERASE; CATTLE; CHOLINESTERASE INHIBITORS; COMPUTER SIMULATION; DRUG DESIGN; EDROPHONIUM; HORSES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 48449093461     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.06.022     Document Type: Article

References (39)

1. Lane R.M., Potkin S.G., and Enz A. Int. J. Neuropsychopharmacol. 9 (2006) 101
2. Zimmerman G., and Soreq H. Cell Tissue Res. 326 (2006) 655
3. Abraham D.J. Anticholinergic Drugs in Burger's Medicinal Chemistry and Drug Discovery. 6th ed. Vol. 6 (2003), Wiley, New York ch 4
4. Giacobini E. Pharmacol. Res. 50 (2004) 433
5. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker I., and Silman I. Science 253 (1991) 872
6. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235
7. Du D.M., and Carlier P.R. Curr. Pharm. Des. 10 (2004) 3141
8. Li W.M., Kan K.K., Carlier P.R., Pang Y.P., and Han Y.F. Cur. Alzheimer Res. 4 (2007) 386
9. Camps P., and Munoz-Torrero D. Mini-Rev. Med. Chem. 1 (2001) 163
10. Pang Y.P., Quiram P., Jelacic T., Hong F., and Brimijoin S. J. Biol. Chem. 271 (1996) 23646
11. Carlier P.R., Han Y.F., Chow E.S.H., Li C.P.L., Wang H., Lieu T.X., Wong H.S., and Pang Y.P. Bioorg. Med. Chem. 7 (1999) 351
12. Hu M.K., Wu L.J., Hsiao G., and Yen M.H. J. Med. Chem. 45 (2002) 2277
13. Rydberg E.H., Brumshtein B., Greenblatt H.M., Wong D.M., Shaya D., Williams L.D., Carlier P.R., Pang Y.P., Silman I., and Sussman J.L. J. Med. Chem. 49 (2006) 5491
14. Campiani G., Fattorusso C., Butini S., Gaeta A., Agnusdei M., Gemma S., Persico M., Catalanotti B., Savini L., Nacci V., Novellino E., Holloway H.W., Greig N.H., Belinskaya T., Fedorko J.M., and Saxena A. J. Med. Chem. 48 (2005) 1919
15. Carlier P.R., Du D.M., Han Y.F., Liu J., Perola E., William I.D., and Pang Y.P. Angew. Chem., Int. Ed. 39 (2000) 1775
16. Carlier P.R., Chow E.S., Han Y., Liu J., Ek Yazal J., and Pang Y.P. J. Med. Chem. 42 (1999) 4225
17. Gemma S., Gabellieri E., Huleatt P., Fattorusso C., Borriello M., Catalanotti B., Butini S., De Angelis M., Novellino E., Nacci V., Belinskaya T., Saxena A., and Campiani G. J. Med. Chem. 49 (2006) 3421
18. Elisinghorst P.W., Tanarro C.M., and Gutschow M. J. Med. Chem. 49 (2006) 7540
19. Kryger G., Silman I., and Sussman J.L. Struct. Fold Des. 7 (1999) 297
20. Seltzer B. Expert Opin. Pharmacother. 8 (2007) 1011
21. Brühlmann C., Ooms F., Carrupt P.A., Testa B., Catto M., Leonetti F., Altomare C., and Carotti A. J. Med. Chem. 44 (2001) 3195
22. Hajduk P.J., and Greer J. Nat. Rev. Drug Disc. 6 (2007) 211
23. Leonetti F., Cappa A., Maccallini C., and Carotti A. Arkivoc 5 (2004) 272
24. Ellman G.L., Courtney K.D., Andres Jr. V., and Featherstone R.M.A. Biochem. Pharmacol. 7 (1961) 88
25. Hodge A.S., Humphrey D.R., and Rosenberry T.L. Mol. Pharmacol. 41 (1992) 931
26. Atack J.R., Yu Q.S., Soncrant T.T., Brossi V., and Rapoport S.I. J. Pharmacol. Exp. Ther. 249 (1989) 194
27. Camps P., Gómez E., Muñoz-Torrero D., Badia V., Clos M.V., Curutchet C., Muñoz-Muriedas V., and Luque F.G. J. Med. Chem. 49 (2006) 6833
28. Ravelli R.B., Raves M.L., Ren Z., Bourgeois D., Roth M., Kroon J., Silman I., and Sussman J.L. Acta Crystallogr. 4 (1998) 1359
29. Barril X., Orzoco M., and Luque F.J. J. Med. Chem. 42 (1999) 5110
30. Verdonk M.L., Cole J.C., Hartshorn M.J., Murray C.W., and Taylor R.D. Proteins 52 (2003) 609
31. Warren G.L., Andrews C.W., Capelli A.M., Clarke B., La Londe J., Lambert M.H., Lindvall M., Nevins N., Semus S.F., Senger S., Tedesco G., and Wall I.D. J. Med. Chem. 49 (2006) 5912
32. Kalyanaraman C., Bernacki K., and Jacobson M.P. Biochemistry 44 (2005) 2059
33. Maestro7.5, Schrödinger Inc., Portland, OR 97201, USA.
34. Piazzi L., Rampa A., Bisi A., Gobbi S., Belluti F., Cavalli A., Bartolini M., Andrisano V., Valenti P., and Recanatini M. J. Med. Chem. 46 (2003) 2279
35. Bartolini M., Bertucci C., Cavrini V., and Andrisano V. Biochem. Pharmacol. 65 (2003) 407
36. Zacharias N., and Dougherty D.A. Trends Pharmacol. Sci 23 (2002) 281
37. Imai Y.N., Inoue Y., and Yamamoto Y. J. Med. Chem. 50 (2007) 1189
38. SYBYL7.2 Tripos Inc., St. Louis, MO 63144.
39. The PyMOL Molecular Graphics System; DeLano Scientific: San Carlos, CA, USA.