Interaction of 18-methoxycoronaridine with nicotinic acetylcholine receptors in different conformational states

Biochimica et Biophysica Acta - Biomembranes

Volumn 1798, Issue 6, 2010, Pages 1153-1163

  Arias, Hugo R ^a   Rosenberg, Avraham ^b   Feuerbach, Dominik ^c   Targowska Duda, Katarzyna M ^d   Maciejewski, Ryszard ^d   Jozwiak, Krzysztof ^d   Moaddel, Ruin ^b   Glick, Stanley D ^e   Wainer, Irving W ^b  

^a MIDWESTERN UNIVERSITY   (United States)

^b NATIONAL INSTITUTE ON AGING   (United States)

^c NOVARTIS PHARMA AG   (Switzerland)

^d MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^e ALBANY MEDICAL COLLEGE   (United States)

Author keywords

18 Methoxycoronaridine; Conformational state; Ibogaine analog; Nicotinic acetylcholine receptor; Noncompetitive antagonist

Indexed keywords

18 METHOXYCORONARIDINE; CALCIUM ION; CYTISINE; IBOGAINE; NICOTINIC RECEPTOR; PHENCYCLIDINE;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; CALCIUM TRANSPORT; CANCER CELL CULTURE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG POTENCY; DRUG RECEPTOR BINDING; ENTHALPY; ENTROPY; HUMAN; HUMAN CELL; INCUBATION TIME; INHIBITION KINETICS; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN DOMAIN; RECEPTOR DOWN REGULATION; RHABDOMYOSARCOMA;

ANIMALS; BINDING SITES; CHOLINERGIC ANTAGONISTS; ELECTRIC ORGAN; FISH PROTEINS; IBOGAINE; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, CHOLINERGIC; TORPEDO;

EID: 77952583243     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2010.03.013     Document Type: Article

References (39)

1. Arias H.R. Thermodynamics of nicotinic receptor interactions. Drug-Receptor Thermodynamics: Introduction and Applications 2001, 293-358. John Wiley & Sons, Ltd., USA. R.B. Raffa (Ed.).
2. Arias H.R. Ligand-gated ion channel receptor superfamilies. Biological and Biophysical Aspects of Ligand-Gated Ion Channel Receptor Superfamilies 2006, 1-25. Research Signpost, Kerala, India. H.R. Arias (Ed.).
3. Arias H.R., Bhumireddy P., Bouzat C. Molecular mechanisms and binding site locations for noncompetitive antagonists of nicotinic acetylcholine receptors. Int. J. Biochem. Cell Biol. 2006, 38:1254-1276.
4. Albuquerque E.X., Pereira E.F.R., Alkondon A., Rogers S.W. Mammalian nicotinic acetylcholine receptors: From structure to function. Physiol. Rev. 2009, 89:73-120.
5. Sine S.M., Engel A.G. Recent advances in Cys-loop receptor structure and function. Nature 2006, 440:448-455.
6. Badio B., Padgett W.L., Daly J.W. Ibogaine: a potent noncompetitive blocker of ganglionic/neuronal nicotinic receptors. Mol. Pharmacol. 1997, 51:1-5.
7. Fryer J.D., Lukas R.J. Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J. Pharmacol. Exp. Ther. 1999, 288:88-92.
8. Glick S.D., Maisonneuve I.M., Kitchen B.A., Fleck M.W. Antagonism of α3β4 nicotinic receptors as a strategy to reduce opioid and stimulant self-administration. Eur. J. Pharmacol. 2002, 438:99-105.
9. Pace C.J., Glick S.D., Maisonneuve I.M., He L.W., Jokiel P.A., Kuehne M.E., Fleck M.W. Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration. Eur. J. Pharmacol. 2004, 492:159-167.
10. Maisonneuve I.M., Glick S.D. Anti-addictive actions of an iboga alkaloid congener: a novel mechanism for a novel treatment. Pharmacol. Biochem. Behav. 2003, 75:607-618.
11. Glick S.D., Ramirez R.L., Livi J.M., Maisonneuve I.M. 18-Methoxycoronaridine acts in the medial habenula and/or interpeduncular nucleus to decrease morphine self-administration in rats. Eur. J. Pharmacol. 2006, 537:94-98.
12. Kuehne M.E., He L., Jokiel P.A., Pace C.J., Fleck M.W., Maisonneuve I.M., Glick S.D., Bidlack J.M. Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents. J. Med. Chem. 2003, 46:2716-2730.
13. Arias H.R. Is the inhibition of nicotinic acetylcholine receptors by bupropion involved in its clinical actions?. Int. J. Biochem. Cell Biol. 2009, 41:2098-2108.
14. Arias H.R., McCardy E.A., Bayer E.Z., Gallagher M.J., Blanton M.P. Allosterically linked noncompetitive antagonist binding sites in the resting nicotinic acetylcholine receptor ion channel. Arch. Biochem. Biophys. 2002, 403:121-131.
15. Arias H.R., Trudell J.R., Bayer E.Z., Hester B., McCardy E.A., Blanton M.P. Noncompetitive antagonist binding sites in the Torpedo nicotinic acetylcholine receptor ion channel. Structure-activity relationship studies using adamantane derivatives. Biochemistry 2003, 42:7358-7370.
16. Arias H.R., Bhumireddy P., Spitzmaul G., Trudell J.R., Bouzat C. Molecular mechanisms and binding site location for the noncompetitive antagonist crystal violet on nicotinic acetylcholine receptors. Biochemistry 2006, 45:2014-2026.
17. Sanghvi M., Hamouda A.K., Jozwiak K., Blanton M.P., Trudell J.R., Arias H.R. Identifying the binding site(s) for antidepressants on the Torpedo nicotinic acetylcholine receptor: [3H]2-Azidoimipramine photolabeling and molecular dynamics studies. Biochem. Biophys. Acta 2008, 1778:2690-2699.
18. Hamouda A.K., Chiara D.C., Blanton M.P., Cohen J.B. Probing the structure of the affinity-purified and lipid-reconstituted Torpedo nicotinic acetylcholine receptor. Biochemistry 2008, 47:12787-12794.
19. Eaton M.J., Labarca C., Eterovi? V.A. M2 Mutations of the nicotinic acetylcholine receptor increase the potency of the non-competitive inhibitor phencyclidine. J. Neurosci. Res. 2000, 61:44-51.
20. Pedersen S.E., Dreyer E.B., Cohen J.B. Location of ligand-binding sites on the nicotinic acetylcholine receptor α-subunit. J. Biol. Chem. 1986, 261:13735-13743.
21. Moaddel R., Jozwiak K., Whittington K., Wainer I.W. Conformational mobility of immobilized α3β2, α3β4, α4β2, α4β4 nicotinic acetylcholine receptors. Anal. Chem. 2005, 77:895-901.
22. Arias H.R., Gumilar F., Rosenberg A., Targowska-Duda K.M., Feuerbach D., Jozwiak K., Moaddel R., Weiner I.W., Bouzat C. Interaction of bupropion with muscle-type nicotinic acetylcholine receptors in different conformational states. Biochemistry 2009, 48:4506-4518.
23. Michelmore S., Croskery K., Nozulak J., Hoyer D., Longato R., Weber A., Bouhelal R., Feuerbach D. Study of the calcium dynamics of the human α4β2, α3β4 and α1β1γδ nicotinic acetylcholine receptors. Naunyn-Schmiedebergs Arch. Pharmacol. 2002, 366:235-245.
24. Arias H.R., Feuerbach D., Bhumireddy P., Ortells M.O. Inhibitory mechanisms and binding site locations for serotonin selective reuptake inhibitors on nicotinic acetylcholine receptors. Int. J. Biochem. Cell Biol. 2010, 42:712-724.
25. Scatchard G. The attraction of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 1949, 51:660-672.
26. Moore M.A., McCarthy M.P. Snake venom toxins, unlike smaller antagonists, appear to stabilize a resting state conformation of the nicotinic acetylcholine receptor. Biochim. Biophys. Acta 1995, 1235:336-342.
27. Cheng Y., Prusoff W.H. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 percent inhibition (IC50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22:3099-3108.
28. Pagán O.R., Eterovi? V.A., García M., Vergne D., Basilio C.M., Rodríguez A.D., Hann R.M. Cembranoid and long-chain alkanol sites on the nicotinic acetylcholine receptor and their allosteric interaction. Biochemistry 2001, 40:11121-11130.
29. Malone J., Jozwiak K., Arias H.R. Interaction of ibogaine analogs with the Torpedo nicotinic receptor. 48th Annual Meeting of the American Society for Cell Biology (ASCB), San Francisco, CA, USA December 13-17 2008.
30. Schild H.O. pAx and competitive drug antagonism. Br. J. Pharmacol. 1949, 4:277-280.
31. Wade J.L., Bergold A.F., Carr P.W. Theoretical description of nonlinear chromatography, with applications to physicochemical measurements in affinity chromatography and implications for preparative-scale separations. Anal. Chem. 1987, 59:1286-1295.
32. Jozwiak K., Ravichandran S., Collins J.S., Wainer I.W. Interaction of noncompetitive inhibitors with an immobilized α3β4 nicotinic acetylcholine receptor investigated by affinity chromatography, quantitative-structure activity relationship analysis, and molecular docking. J. Med. Chem. 2004, 47:4008-4021.
33. Moaddel R., Jozwiak K., Wainer I.W. Allosteric modifiers of neuronal nicotinic receptors: New methods, new opportunities. Med. Res. Rev. 2007, 27:723-753.
34. Miyazawa A., Fujiyoshi Y., Unwin N. Structure and gating mechanism of the acetylcholine receptor pore. Nature 2003, 423:949-955.
35. Unwin N. Refined structure of the nicotinic acetylcholine receptor at 4 Å resolution. J. Mol. Biol. 2005, 346:967-989.
36. Jozwiak K., Hernandez S., Kellar K.J., Wainer I.W. The enantioselective interactions of dextromethorphan and levomethorphan with the α3β4-nicotinic acetylcholine receptor: comparison of chromatographic and functional data. J. Chromatogr. B 2003, 797:373-379.
37. Jozwiak K., Haginaka J., Moaddel R., Wainer I.W. Displacement and nonlinear chromatographic techniques in the investigation of interaction of noncompetitive inhibitors with an immobilized α3β4 nicotinic acetylcholine receptor liquid chromatographic stationary phase. Anal. Chem. 2002, 74:4618-4624.
38. Pratt M.B., Pedersen S.E., Cohen J.B. Identification of the sites of incorporation of [3H]ethidium diazide within the Torpedo nicotinic acetylcholine receptor ion channel. Biochemistry 2000, 39:11452-11462.
39. Oswald R.E., Bamberger M.J., McLaughlin J.T. Mechanism of phencyclidine binding to the acetylcholine receptor from Torpedo electroplaque. Mol. Pharmacol. 1984, 25:360-368.