QSAR study on maximal inhibition (Imax) of quaternary ammonium antagonists for S-(-)-nicotine-evoked dopamine release from dopaminergic nerve terminals in rat striatum

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 13, 2009, Pages 4477-4485

  Zheng, Fang ^a   McConnell, Matthew J ^a   Zhan, Chang Guo ^a   Dwoskin, Linda P ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

Author keywords

Antagonists; Maximal inhibition; Nicotinic receptors; QSAR study

Indexed keywords

DOPAMINE; NICOTINE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR BLOCKING AGENT; QUATERNARY AMMONIUM DERIVATIVE; RECEPTOR SUBTYPE;

ARTICLE; ARTIFICIAL NEURAL NETWORK; CIGARETTE SMOKING; CORPUS STRIATUM; DOPAMINE RELEASE; DOPAMINERGIC NERVE CELL; DRUG STRUCTURE; MOLECULAR MODEL; MULTIPLE LINEAR REGRESSION ANALYSIS; NONHUMAN; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SMOKING CESSATION; STATISTICAL MODEL; SYNTHESIS; TOBACCO DEPENDENCE;

ANIMALS; CORPUS STRIATUM; DOPAMINE; LINEAR MODELS; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; NEURAL NETWORKS (COMPUTER); NICOTINE; NICOTINIC ANTAGONISTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUATERNARY AMMONIUM COMPOUNDS; RATS; RECEPTORS, NICOTINIC;

RATTUS;

EID: 66449132134     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.010     Document Type: Article

References (45)

1. Ericon, N., U.S. Department of Justice, 2001 May #17.
2. Lam C.Y., Minnix J.A., Robinson J.D., and Cinciripini P.M. J. Natl. Compr. Canc. Netw. 4 (2006) 583
3. Glover E.D., and Rath J.M. Expert Opin. Pharmacother. 8 (2007) 1757
4. Potts L.A., and Garwood C.L. Am. J. Health-Syst. Pharm 64 (2007) 1381
5. Hurt R.D., Sachs D.P.L., Glover E.D., Offord K.P., Johnston J.A., Dale L.C., Khayrallah M.A., Schroeder D.R., Glover P.N., Sullivan C.R., Croghan I.T., and Sullivan P.M. N. Eng. J. Med. 337 (1997) 1195
6. Jorenby D.E., Leischow S.J., Nides M.A., Rennard S.I., Johnston J.A., Hughes A.R., Smith S.S., Muramoto J.L., Daughton D.M., Doan K., Fiore M.C., and Baker T.B.A. N. Eng. J. Med. 340 (1999) 685
7. Shiffman S., Johnston J.A., Khayrallah M., Elash C.A., Gwaltney C.J., Paty J.A., Gnys M., and Evoniuk G. DeVeaugh-Geiss Psychopharmacol. (Berl.) 148 (2000) 33
8. Rose J.E., Behm F.M., Westman E.C., Levin E.D., Stein R.M., and Ripka G.V. Clin. Pharmacol. Ther. 56 (1994) 86
9. Rose J.E., Westman E.C., Behm F.M., Johnson M.P., and Goldberg J.S. Pharmacol. Biochem. Behav. 62 (1999) 165
10. Crooks P.A., Ayers J.T., Xu R., Sumithran S.P., Grinevich V.P., Wilkins Jr. L.H., Deaciuc A.G., Allen D.D., and Dwoskin L.P. Bioorg. Med. Chem. Lett. 14 (2004) 1869
11. Dwoskin L.P., Sumithran S.P., Zhu J., Deaciuc A.G., Ayers J.T., and Crooks P.A. Bioorg. Med. Chem. Lett. 14 (2004) 1863
12. Xu R., Dwoskin L.P., Grinevich V.P., Sumithran S.P., and Crooks P.A. Drug Dev. Res. 55 (2002) 173
13. Wilkins Jr. L.H., Grinevich V.P., Ayers J.T., Crooks P.A., and Dwoskin L.P. J. Pharmacol. Exp. Ther. 304 (2003) 400
14. Dwoskin L.P., Wilkins Jr. L.H., Pauly J.R., and Crooks P.A. Ann. N.Y. Acad. Sci. 868 (1999) 617
15. Wilkins Jr. L.H., Haubner A., Ayers J.T., Crooks P.A., and Dwoskin L.P. J. Pharmacol. Exp. Ther. 301 (2002) 1088
16. Crooks P.A., Ravard A., Wilkins Jr. L.H., Teng L.H., Buxton S.T., and Dwoskin L.P. Drug Dev. Res. 36 (1995) 91
17. Dwoskin L.P., and Crooks P.A. J. Pharmacol. Exp. Ther 298 (2001) 395
18. Albayati Z.A.F., Dwoskin L.P., and Crooks P.A. Drug Metab. Dispos. 36 (2008) 2024
19. Huang X.Q., Zheng F., Crooks P.A., Dwoskin L.P., and Zhan C.-G. J. Am. Chem. Soc. 127 (2005) 14401
20. Huang X., Zheng F., Chen X., Crooks P.A., Dwoskin L.P., and Zhan C.-G. J. Med. Chem. 49 (2006) 7661
21. Huang X., Zheng F., Stokes C., Papke R.L., and Zhan C.-G. J. Med. Chem. 51 (2008) 6293
22. Huang X., Zheng F., and Zhan C.-G. J. Am. Chem. Soc. 130 (2008) 16691
23. Zheng F., Bayram E., Sumithran S.P., Ayers J.T., Zhan C.-G., Schmitt J.D., Dwoskin L.P., and Crooks P.A. Bioorg. Med. Chem. 14 (2006) 3017
24. Ayers J.T., Clauset A., Schmitt J.D., Dwoskin L.P., and Crooks P.A. AAPS J. 7 (2005) E678
25. Zheng F., Zheng G.R., Deaciuc A.G., Zhan C.-G., Dwoskin L.P., and Crooks P.A. J. Enzym. Inhib. Med. Chem. 24 (2009) 157
26. Salminen O., Murphy K.L., McIntosh J.M., Drago J., Marks M.J., Collins A.C., and Grady S.R. Mol. Pharmacol. 65 (2004) 1526
27. Gotti C., Zoli M., and Clemente F. Trends Pharmacol. Sci. 27 (2006) 482
28. Grady S.R., Salminen O., Laverty D.C., Whiteaker P., McIntosh J.M., Collins A.C., and Marks M.J. Biochem. Pharmacol. 74 (2007) 1235
29. Salminen O., Drapeau J.A., McIntosh J.M., Drago J., Marks M.J., Collins A.C., and Grady S.R. Mol. Pharmacol. 71 (2007) 1563
30. Teng L., Crooks P.A., Buxton S.T., and Dwoskin L.P. J. Pharmacol. Exp. Ther. 283 (1997) 778
31. Champtiaux N., Han Z.Y., Bessis A., Rossi F.M., Zoli M., Marubio L., McIntosh J.M., and Changeux J.P. J. Neurosci. 22 (2002) 1208
32. Whiteaker P., Peterson C.G., Xu W., McIntosh J.M., Paylor R., Beaudet A.L., Collins A.C., and Marks M.J. J. Neurosci. 22 (2002) 2522
33. McIntosh J.M., Azam L., Staheli S., Dowell C., Lindstrom J.M., Kuryatov A., Garrett J.E., Marks M.J., and Whiteaker P. Mol. Pharmacol. 65 (2004) 944
34. Dwoskin L.P., Wooters T.E., Sumithran S.P., Siripurapu K.B., Joyce B.M., Lockman P.R., Manda V.K., Ayers J.T., Zhang Z., Deaciuc A.G., Mclntonsh J.M., Crooks P.A., and Bardo M.T. J. Pharmacol. Exp. Ther. 326 (2008) 563
35. Katritzky A.R., Pacureanu L.M., Slavov S., Dobchev D.A., and Karelson M. Bioorg. Med. Chem. 14 (2006) 7490
36. dragon software version 3.0, 2003, developed by Milano Chemometrics and QSAR Research Group (http://www.disat.nimib.it/chm/Dragon.htm).
37. Katritzky A.R., Pacureanu L.M., Dobchev D.A., Fara D.C., Duchowicz P.R., and Karelson M. Bioorg. Med. Chem. 14 (2006) 4987
38. Zheng F., Zheng G., Deaciuc A.G., Zhan C.-G., Dwoskin L.P., and Crooks P.A. Bioorg. Med. Chem. 15 (2007) 2975
39. Duch W., Swaminathan K., and Meller J. Curr. Pharm. Des. 13 (2007) 1497
40. Khan M.T.H., and Sylte I. Curr. Drug Discovery Techcnol. 4 (2007) 141
41. Fabry-Asztalos L., Andonie R., Collar C.J., Abdul-Wahid S., and Salim N. Bioorg. Med. Chem. 16 (2008) 2903
42. Vasilakos A.V., and Spyrou G. J. Comput. Theor. Nanosci. 5 (2008) 2365
43. Tripos discovery software package with sybyl 6.8.1, Tripos Inc., 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
44. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; 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.; Gonzalez, C.; Pople, J. A. gaussian 03, Revision A.1, Gaussian, Pittsburgh, PA, 2003.
45. Todeschini R., and Consonni V. Handbook of Molecular Descriptors (2002), Wiley-VCH, Weinheim (Germany)