Design of novel nicotinic ligands through 3D database searching

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 3, 2005, Pages 799-807

  Guandalini, Luca ^a   Martini, Elisabetta ^a   Dei, Silvia ^a   Manetti, Dina ^a   Scapecchi, Serena ^a   Teodori, Elisabetta ^a   Romanelli, M Novella ^a   Varani, Katia ^b   Greco, Giovanni ^c   Spadola, Loredana ^c   Novellino, Ettore ^c  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

3D database search; Molecular modeling; Nicotinic receptor

Indexed keywords

1,1 DIMETHYL 2 (QUINOLIN 6 YL)PYRROLIDINIUM IODIDE; 5 (DIMETHYLAMINO)METHYLQUINOLINE; 6 (1 METHYLPYRROLIDIN 2 YL)QUINOLINE; 6 (DIMETHYLAMINO)METHYLQUINOLINE; 6 (METHYLAMINO)METHYLQUINOLINE; 6 (PYRROLIDIN 2 YL)QUINOLINE; 6 [2 (DIMETHYLAMINO)ETHYL]QUINOLINE; 7 (DIMETHYLAMINO)METHYLQUINOLINE; LIGAND; N,N,N TRIMETHYL 2 (QUINOLIN 7 YL)METHANAMINIUM IODIDE; N,N,N TRIMETHYL(QUINOLIN 5 YL)METHANAMINIUM IODIDE; N,N,N TRIMETHYL(QUINOLIN 6 YL)METHANAMINIUM IODIDE; N,N,N TRIMETHYL(QUINOLIN 7 YL)METHANAMINIUM IODIDE; NICOTINIC AGENT; NICOTINIC RECEPTOR; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN CORTEX; CONTROLLED STUDY; DATA BASE; DRUG DESIGN; DRUG RECEPTOR BINDING; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; RAT; STRUCTURE ANALYSIS; THREE DIMENSIONAL IMAGING;

GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INFORMATION STORAGE AND RETRIEVAL; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUINOLINES; RECEPTORS, NICOTINIC;

EID: 19944429188     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.10.039     Document Type: Article

References (44)

1. F. Hucho, and C. Weise Angew. Chem., Int. Ed. 40 2001 3100 3116
2. P.-J. Corringer, N. Le Novère, and J.-P. Changeux Annu. Rev. Pharmacol. Toxicol. 40 2000 431 458
3. M. Cordero-Erausquin, L.M. Marubio, R. Klink, and J.-P. Changeux Trends Pharmacol. Sci. 21 2000 211 217
4. S. Mihailescu, and R. Drucker-Colìn Arch. Med. Res. 31 2000 131 144
5. M. Lee, C. Martin-Ruiz, A. Graham, J. Court, E. Jaros, R. Perry, P. Iversen, M. Bauman, and E. Perry Brain 125 2002 1483 1495
6. C. Gotti, D. Fornasari, and F. Clementi Prog. Neurobiol. 53 1997 199 237
7. F. Clementi, D. Fornasari, and C. Gotti Eur. J. Pharmacol. 393 2000 3 10
8. Y.C. Martin J. Med. Chem. 35 1992 2145 2154
9. S. Wang, D.W. Zaharevitz, R. Sharma, V.E. Marquez, N.E. Lewin, L. Du, P.M. Blumberg, and G.W.A. Milne J. Med. Chem. 37 1994 4479 4489
10. K. Gohda, D. Ohta, A. Kozaki, K. Fujimori, I. Mori, and T. Kikuchi Quant. Struct.-Act. Relat. 20 2001 143 147
11. I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, and S. Wang Bioorg. Med. Chem. Lett. 13 2003 513 517
12. R.A. Glennon, and M. Dukat Bioorg. Med. Chem. Lett. 14 2004 1841 1844 and references cited therein
13. Cambridge Structural Database. Version 5.25, November 2003
14. R.P. Sheridan, and R. Venkataraghavan J. Comput. Aid. Mol. Des. 1 1987 243 256
15. A.B. Smit, N.I. Syed, D. Schaap, J. van Minnen, J. Klumperman, K.S. Kits, H. Lodder, R.C. van der Schors, R. van Elk, B. Sorgedrager, K. Brejc, T.K. Sixma, and W.P.M. Geraerts Nature 411 2001 261 268
16. P.H.N. Celie, S.E. van Rossum-Fikkert, W.J. van Dijk, K. Brejc, A.B. Smit, and T.K. Sixma Neuron 41 2004 907 914
17. K. Brejc, W.J. van Dijk, R.V. Klaassen, M. Schuurmans, J. van der Oost, A.B. Smit, and T.K. Sixma Nature 411 2001 269 276
18. N. Le Novère, T. Grutter, and J.-P. Changeux Proc. Natl. Acad. Sci. U.S.A. 99 2002 3210 3215
19. M. Schapira, R. Abagyan, and M. Totrov BMC Struct. Biol. 2 2002 1 8
20. C. Fruchart-Gaillard, B. Gilquin, S. Antil-Delbeke, N. Le Novère, T. Tamiya, P.-J. Corringer, J.-P. Changeux, A. Menez, and D. Servent Proc. Natl. Acad. Sci. U.S.A. 99 2002 3216 3221
21. V. Costa, A. Nistri, A. Cavalli, and P. Carloni Br. J. Pharmacol. 140 2003 912 931
22. I.J. Bruno, J.C. Cole, P.R. Edgington, M. Kessler, C.F. Macrae, P. McCabe, J. Pearson, and R. Taylor Acta Crystallogr., Sect. B B58 2000 389 397
23. D.B. Kanne, and L.G. Abood J. Med. Chem. 31 1988 506 509
24. U. Hacksell, and C. Mellin Progress in Brain Research 1989 Elsevier Science Publisher B.V.
25. InsightII2000, Accelrys Inc., http://www.accelrys.com
26. A. Rericha, I. Seidal, and G. Robisch Cryst. Res. Technol. 25 1990 1049
27. B.P. Lugowkin Zhurnal Obshchei Khimii 29 1959 1350 1353 CA 1354:44654 (41960)
28. H. Steinberg, and F.L.J. Sixma Recl. Trav. Chim. Pays-Bas 79 1960 679 686
29. R.G. Jones, Q.F. Soper, O.K. Behrens, and J.W. Corse J. Am. Chem. Soc. 70 1948 2843 2848
30. M.H. Palmer J. Chem. Soc., Perkin Trans. 1 1962 3645 3652
31. W. La Coste Chem. Ber. 15 1882 557 563
32. Y. Fukuda, S. Matsubara, and K. Utimoto J. Org. Chem. 56 1991 5812 5816
33. C. Ghelardini, N. Galeotti, F. Gualtieri, C. Bellucci, D. Manetti, P.A. Borea, and A. Bartolini Drug Dev. Res. 41 1997 1 9
34. C.M. Flores, S.W. Rogers, L.A. Pabreza, B.B. Wolfe, and K.J. Kellar Mol. Pharmacol. 41 1991 31 37
35. Y. Koide, T. Hasegawa, A. Takahashi, A. Endo, N. Mochizuki, M. Nakagawa, and A. Nishida J. Med. Chem. 45 2002 4629 4638
36. Y. Iwata, M. Arisawa, R. Hamada, Y. Kita, M.Y. Mizutani, N. Tomioka, A. Itai, and S. Miyamoto J. Med. Chem. 44 2001 1718 1728
37. R.A. Glennon, A. Maarouf, S. Fahmy, B. Martin, F. Fan, M. Yousif, R.M. Shafik, and M. Dukat Med. Chem. Res. 2 1993 546 551
38. M. Dukat, W. Fiedler, D. Dumas, M.I. Damaj, B.R. Martin, J.A. Rosecrans, J.R. James, and R.A. Glennon Eur. J. Med. Chem. 31 1996 875 888
39. R.A. Glennon, J.L. Herndon, and M. Dukat Med. Chem. Res. 4 1994 461 473
40. J.D. Schmitt Curr. Med. Chem. 7 2000 749 800
41. S. Wonnacott, S. Jackman, K.L. Swanson, H. Rapoport, and E.X. Albuquerque J. Pharmacol. Exp. Ther. 259 1991 387 391
42. M.N. Romanelli, D. Manetti, S. Scapecchi, P.A. Borea, S. Dei, A. Bartolini, C. Ghelardini, F. Gualtieri, L. Guandalini, and K. Varani J. Med. Chem. 44 2001 3946 3955
43. R. Simsek, J. Chang-Fong, M. Lee, M. Dukat, M.I. Damaj, B.R. Martin, and R.A. Glennon Bioorg. Med. Chem. Lett. 13 2003 2917 2920
44. D.L. Beene, G.S. Brandt, W. Zhong, N.M. Zacharias, H.A. Lester, and D.A. Dougherty Biochemistry 41 2002 10262 10269