Design of novel α7-subtype-preferring nicotinic acetylcholine receptor agonists: Application of docking and MM-PBSA computational approaches, synthetic and pharmacological studies

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 22, 2009, Pages 6353-6357

  Grazioso, Giovanni ^a   Pomè, Diego Yuri ^a   Matera, Carlo ^a   Frigerio, Fabio ^a   Pucci, Luca ^a   Gotti, Cecilia ^a   Dallanoce, Clelia ^a   Amici, Marco De ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

7 Selective nicotinic agonists; Binding affinity; MM PBSA; Neuronal nicotinic acetylcholine receptors

Indexed keywords

ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONIST; AMMONIUM DERIVATIVE; EPIBATIDINE; MORPHOLINE; NICOTINIC ACID DERIVATIVE; NICOTINIC AGENT; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR ALPHA4BETA2; UNCLASSIFIED DRUG; ADIPIC ACID DERIVATIVE; LIGAND; POLY(TETRAMETHYLENE SUCCINATE CO TETRAMETHYLENE ADIPATE); POLY(TETRAMETHYLENE SUCCINATE-CO-TETRAMETHYLENE ADIPATE); SUCCINIC ACID DERIVATIVE;

ARTICLE; BINDING AFFINITY; BIOLOGY; CALCULATION; DIAGNOSTIC ACCURACY; DRUG BINDING; DRUG SYNTHESIS; ENERGY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; NERVE CELL; PHARMACOLOGICAL PARAMETERS; SCREENING TEST; BINDING COMPETITION; BINDING SITE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; METABOLISM; MOLECULAR GENETICS; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

ADIPIC ACIDS; BINDING SITES; BINDING, COMPETITIVE; COMPUTATIONAL BIOLOGY; COMPUTER SIMULATION; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NICOTINIC AGONISTS; PROTEIN BINDING; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; SUCCINATES;

EID: 71249158877     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.09.073     Document Type: Article

References (32)

1. Romanelli M.N., Gratteri P., Guandalini L., Martini E., Bonaccini C., and Gualtieri F. ChemMedChem 2 (2007) 746
2. Lippiello P.M., Bencherif M., Hauser T.A., Jordan K.G., Letchworth S.R., and Mazurov A.A. Exp. Opin. Drug Discovery 2 (2007) 1185
3. Gotti C., Zoli M., and Clementi F. Trends Pharmacol. Sci. 27 (2006) 482
4. Dajas-Bailador F., and Wonnacott S. Trends Pharmacol Sci. 25 (2004) 317
5. Gotti C., and Clementi F. Prog. Neurobiol. 74 (2004) 363
6. Cincotta S.L., Yorek M.S., Moschak T.M., Lewis S.R., and Rodefer J.S. Curr. Opin. Invest. Drugs 9 (2008) 47
7. Bertrand D., and Gopalakrishnan M. Biochem. Pharmacol. 74 (2007) 1155
8. Faghih F., Gopalakrishnan M., and Briggs C.A. J. Med. Chem. 51 (2008) 701
9. Grazioso G., Cavalli A., De Amici M., Recanatini M., and De Micheli C. J. Comput. Chem. 29 (2008) 2593
10. Borea P.A., Varani K., Gessi S., Merighi S., Dal Piaz A., Gilli P., and Gilli G. Curr. Top. Med. Chem. 4 (2004) 361
11. Ferrari A.M., Degliesposti G., Sgobba M., and Rastelli G. Bioorg. Med. Chem. 15 (2007) 7865
12. Jones G., Willett P., Glen R.C., Leach A.R., and Taylor R. J. Mol. Biol. 267 (1997) 727
13. Hopkins B. Ann. Bot. (Oxford, UK) 18 (1954) 213
14. Bottegoni G., Cavalli A., and Recanatini M. J. Chem. Inf. Model. 46 (2006) 852
15. Bottegoni G., Rocchia W., Recanatini M., and Cavalli A. Bioinformatics 22 14 (2006) e58
16. Celie P.H.N., Van Rossum-Fikkert S.E., Van Dijk W.J., Brejc K., Smit A.B., and Sixma T.K. Neuron 41 (2004) 907
17. Huang X., Zheng F., Chen X., Crooks P.A., Dwoskin L.P., and Zhan C.G. J. Med. Chem. 49 (2006) 7661
18. Guandalini L., Martini E., Dei S., Manetti D., Scapecchi S., Teodori E., Romanelli M.N., Varani K., Greco G., Spadola L., and Novellino E. Bioorg. Med. Chem. 13 (2005) 799
19. Seifert S., Gündisch D., Tilotta M.C., and Seitz G. Pharmazie 58 (2003) 353
20. Nicolaou C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
21. Yin L., and Liebscher J. Chem. Rev. 107 (2007) 133
22. Doucet H. Eur. J. Org. Chem. 12 (2008) 2013
23. Carroll F.I., Liang F., Navarro H.A., Brieaddy L.E., Abraham P., Damaj M.I., and Martin B.R. J. Med. Chem. 44 (2001) 2229
24. Rizzi L., Dallanoce C., Matera C., Magrone P., Pucci L., Gotti C., Clementi F., and De Amici M. Bioorg. Med. Chem. Lett. 18 (2008) 4651
25. Gohlke H., Gündisch D., Schwarz S., Seitz G., Tilotta M.C., and Wegge T. J. Med. Chem. 45 (2002) 1064
26. 3O (271.36): C, 70.82, H, 7.80, N, 15.49. Found: C, 70.43; H, 7.61; N, 15.72.
27. 3O (413.30): C, 49.40; H, 5.85; N, 10.17. Found: C, 49.73; H, 5.72; N, 9.87.
28. Fletcher S.R., Baker R., Chambers M.S., Herbert R.H., Hobbs S.C., Thomas S.R., Verrier H.M., Watt A.P., and Ball G.R. J. Org. Chem. 59 (1994) 1771
29. Zhang C., and Trudell M.L. J. Org. Chem. 61 (1996) 7189
30. Dallanoce C., Bazza P., Grazioso G., De Amici M., Gotti C., Riganti L., Clementi F., and De Micheli C. Eur. J. Org. Chem. (2006) 3746
31. Munson P.J., and Rodbard D. Ann. Biochem. 107 (1980) 220
32. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099