Using physical chemistry to differentiate nicotinic from cholinergic agonists at the nicotinic acetylcholine receptor

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 350-356

  Cashin, Amanda L ^a   James Petersson, E ^a   Lester, Henry A ^b   Dougherty, Dennis A ^a  

^a California Institute of Technology   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; DRUG PRODUCTS; HYDROGEN BONDS; MATHEMATICAL MODELS; MEMBRANES; MUTAGENESIS;

AGONIST BINDING SITE; BACKBONE CARBONYL; MEMBRANE RECEPTORS; STRUCTURAL MODEL;

AMINO ACIDS;

CHOLINERGIC RECEPTOR STIMULATING AGENT; EPIBATIDINE; NICOTINIC ACID; NICOTINIC RECEPTOR;

AMINO ACID METABOLISM; ARTICLE; BINDING AFFINITY; CATION EXCHANGE; CHEMICAL MUTAGENESIS; CHEMICAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR MODEL; PHYSICAL CHEMISTRY; SIGNAL TRANSDUCTION;

ACETYLCHOLINE; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CHEMISTRY, PHYSICAL; CHOLINERGIC AGONISTS; CRYSTALLOGRAPHY, X-RAY; ELECTROSTATICS; HYDROGEN BONDING; KINETICS; MODELS, MOLECULAR; NICOTINE; NICOTINIC AGONISTS; PYRIDINES; RECEPTORS, NICOTINIC; SURFACE PROPERTIES; THREONINE; TRYPTOPHAN; XENOPUS LAEVIS;

EID: 11844286949     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0461771     Document Type: Article

References (56)

1. Beene, D. L.; Dougherty, D. A.; Lester, H. A. Curr. Opin. Neurobiol. 2003, 13, 264-270.
2. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652.
3. Paterson, D.; Nordberg, A. Prog. Neurobiol. 2000, 61, 75-111.
4. Miyazawa, A.; Fujiyoshi, Y.; Stowell, M.; Unwin, N. J. Mol. Biol. 1999, 288, 765-786.
5. Grutter, T.; Changeux, J. P. Trends Biochem. Sci. 2001, 26, 459-463.
6. Karlin, A. Nat. Rev. Neurosci. 2002, 3, 102-114.
7. Corringer, P.-J.; Le Novère, N.; Changeux, J.-P. Annu. Rev. Pharmacol. Toxicol. 2000, 40, 431-458.
8. Brejc, K.; van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van Der Oost, J.; Smit, A. B.; Sixma, T. K. Nature 2001, 411, 269-276.
9. Dougherty, D. A. Science 1996, 271, 163-168.
10. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
11. Zacharias, N.; Dougherty, D. A. Trends Pharmacol. Sci. 2002, 23, 281-287.
12. Zhong, W.; Gallivan, J. P.; Zhang, Y.; Li, L.; Lester, H. A.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12088-12093.
13. Beene, D. L.; Brandt, G. S.; Zhong, W.; Zacharias, N. M.; Lester, H. A.; Dougherty, D. A. Biochemistry 2002, 41, 10262-10269.
14. Schapira, M.; Abagyan, R.; Totrov, M. BMC Struct. Biol. 2002, 2, 1.
15. Le Novere, N.; Grutter, T.; Changeux, J. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 3210-3215.
16. Celie, P. H. N.; van Rossum-Fikkert, S. E.; van Dijk, W. J.; Brejc, K.; Smit, A. B.; Sixma, T. K. Neuron 2004, 41, 907-914.
17. Akk, G.; Auerbach, A. Br. J. Pharmacol. 1999, 128, 1467-1476.
18. Gerzanich, V.; Peng, X.; Wang, F.; Wells, G.; Anand, R.; Fletcher, S.; Lindstrom, J. Mol. Pharmacol. 1995, 48, 774-782.
19. Prince, R. J.; Sine, S. M. Biophys. J. 1998, 75, 1817-1827.
20. Badio, B.; Daly, J. W. Mol. Pharmacol. 1994, 45, 563-569.
21. Dukat, M.; Glennon, R. A. Cell Mol. Neurobiol. 2003, 23, 365-378.
22. Servi, S. J. Org. Chem. 1985, 50, 5865-5867.
23. England, P. M.; Lester, H. A.; Dougherty, D. A. Tetrahedron Lett. 1999, 40, 6189-6192.
24. Nowak, M. W.; Gallivan, J. P.; Silverman, S. K.; Labarca, C. G.; Dougherty, D. A.; Lester, H. A. Methods Enzymol. 1998, 293, 504-529.
25. Li, L. T.; Zhong, W. G.; Zacharias, N.; Gibbs, C.; Lester, H. A.; Dougherty, D. A. Chem. Biol. 2001, 8, 47-58.
26. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
27. Foresman, J. B.; Frisch, E. Exploring Chemistry with Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
29. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
30. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. Molekel; Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
31. Filatov, G. N.; White, M. M. Mol. Pharmacol. 1995, 48, 379-384.
32. Revah, F.; Bertrand, D.; Galzi, J. L.; Devillers-Theiry, A.; Mulle, C. Nature 1991, 353, 846-849.
33. Labarca, C.; Nowak, M. W.; Zhang, H.; Tang, L.; Deshpande, P.; Lester, H. A. Nature 1995, 376, 514-516.
34. Kearney, P. C.; Nowak, M. W.; Zhong, W.; Silverman, S. K.; Lester, H. A.; Dougherty, D. A. Mol. Pharmacol. 1996, 50, 1401-1412.
35. Mu, T. W.; Lester, H. A.; Dougherty, D. A. J. Am. Chem. Soc. 2003, 125, 6850-6851.
36. Petersson, E. J.; Choi, A.; Dahan, D. S.; Lester, H. A.; Dougherty, D. A. J. Am. Chem. Soc. 2002, 124, 12662-12663.
37. Deechongkit, S.; Nguyen, H.; Powers, E. T.; Dawson, P. E.; Gruebele, M.; Kelly, J. W. Nature 2004, 430, 101-105.
38. Koh, J. T.; Cornish, V. W.; Schultz, P. G. Biochemistry 1997, 36, 11314-11322.
39. Elmore, D. E.; Dougherty, D. A. J. Org. Chem. 2000, 65, 742-747.
40. Vistoli, G.; Pedretti, A.; Villa, L.; Testa, B. J. Am. Chem. Soc. 2002, 124, 7472-7480.
41. Partington, P.; Feeney, J.; Burgen, A. S. Mol. Pharmacol. 1972, 8, 269-277.
42. Biot, C.; Buisine, E.; Rooman, M. J. Am. Chem. Soc. 2003, 125, 13988-13994.
43. Biot, C.; Wintjens, R.; Rooman, M. J. Am. Chem. Soc. 2004, 126, 6220-6221.
44. Sponer, J. E.; Sychrovsky, V.; Hobza, P.; Sponer, J. Phys. Chem. Chem. Phys. 2004, 6, 2772-2780.
45. Sponer, J.; Leszczynski, J.; Hobza, P. Biopolymers 2001, 61, 3-31.
46. Siu, F. M.; Ma, N. L.; Tsang, C. W. Chem. Eur. J. 2004, 10, 1966-1976.
47. Graton, J.; Berthelot, M.; Gal, J. F.; Laurence, C.; Lebreton, J.; Le Questel, J. Y.; Maria, P. C.; Richard, R. J. Org. Chan. 2003, 68, 8208-8221.
48. Graton, J.; van Mourik, T.; Price, S. L. J. Am. Chem. Soc. 2003, 125, 5988-5997.
49. Cannizzaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163-7169.
50. Thomas, K. A.; Smith, G. M.; Thomas, T. B.; Feldmann, R. J. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 4843-4847.
51. Duan, G.; Smith, V. H.; Weaver, D. F. J. Phys. Chem. A 2000, 104, 4521-4532.
52. Schmitt, J. D. Curr. Med. Chem. 2000, 7, 749-800.
53. Bouzat, C.; Gumilar, F.; Spitzmaul, G.; Wang, H. L.; Rayes, D.; Hansen, S. B.; Taylor, P.; Sine, S. M. Nature 2004, 430, 896-900.
54. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475-3478.
55. Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308.
56. Lee, W. Y.; Sine, S. M. J. Gen. Physiol. 2004, 124, 555-567.