The minimal pharmacophore for silent agonism of the α7 nicotinic acetylcholine receptor

Journal of Pharmacology and Experimental Therapeutics

Volumn 350, Issue 3, 2014, Pages 665-680

  Papke, Roger L ^a   Chojnacka, Kinga ^b   Horenstein, Nicole A ^b  

^a UNIVERSITY OF FLORIDA   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL QUINUCLIDINE; ALKYL GROUP; BUNGAROTOXIN RECEPTOR; CATION; CHOLINERGIC RECEPTOR STIMULATING AGENT; DIETHYLDIMETHYLAMMONIUM; ION CHANNEL; NITROGEN; QUATERNARY AMMONIUM DERIVATIVE; TETRAMETHYLAMMONIUM; UNCLASSIFIED DRUG; NICOTINIC AGENT;

ALLOSTERISM; ANIMAL CELL; ARTICLE; BINDING SITE; CONFORMATIONAL TRANSITION; DENSITY; DOWNSTREAM PROCESSING; HUMAN; MOLECULAR INTERACTION; NONHUMAN; PARTICLE SIZE; PHARMACOPHORE; PRIORITY JOURNAL; PROBABILITY; REGULATORY MECHANISM; SYNTHESIS; ANIMAL; DRUG EFFECT; DRUG POTENTIATION; FEMALE; METABOLISM; PHYSIOLOGY; XENOPUS LAEVIS;

ALLOSTERIC REGULATION; ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR; ANIMALS; BINDING SITES; FEMALE; HUMANS; NICOTINIC AGONISTS; QUATERNARY AMMONIUM COMPOUNDS; XENOPUS LAEVIS;

EID: 84907285600     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.114.215236     Document Type: Article

References (50)

1. Armstrong CM and Hille B (1972) The inner quaternary ammonium ion receptor in potassium channels of the node of Ranvier. J Gen Physiol 59:388-400.
2. Auerbach A and Akk G (1998) Desensitization of mouse nicotinic acetylcholine receptor channels. A two-gate mechanism. J Gen Physiol 112:181-197.
3. Borovikova LV, Ivanova S, ZhangM, YangH, Botchkina GI, Watkins LR, Wang H, Abumrad N, Eaton JW, and Tracey KJ (2000) Vagus nerve stimulation attenuates the systemic inflammatory response to endotoxin. Nature 405:458-462.
4. Calas M, Ancelin ML, Cordina G, Portefaix P, Piquet G, Vidal-Sailhan V, and Vial H (2000) Antimalarial activity of compounds interfering with Plasmodium falciparum phospholipid metabolism: comparison between mono- and bisquaternary ammonium salts. J Med Chem 43:505-516.
5. Carter AA and Oswald RE (1993) Channel blocking properties of a series of nicotinic cholinergic agonists. Biophys J 65:840-851.
6. Chen G, Portman R, and Wickel A (1951) Pharmacology of 1,1-dimethyl-4-phenylpiperazinium iodide, a ganglion stimulating agent. J Pharmacol Exp Ther 103:330-336.
7. Chojnacka K, Papke RL, and Horenstein NA (2013) Synthesis and evaluation of a conditionally-silent agonist for the α7 nicotinic acetylcholine receptor. Bioorg Med Chem Lett 23:4145-4149.
8. Clark RB, Lamppu D, Libertine L, McDonough A, Kumar A, LaRosa G, Rush R, and Elbaum D (2014) Discovery of novel 2-((pyridin-3-yloxy)methyl)piperazines as α7 nicotinic acetylcholine receptor modulators for the treatment of inflammatory disorders. J Med Chem 57:3966-3983.
9. Clarke HT, Gillespie HB, and Weisshaus SZ (1933) Action of formaldehyde on amines and amino acids. J Am Chem Soc 55:4571-4587.
10. de Jonge WJ and Ulloa L (2007) The alpha7 nicotinic acetylcholine receptor as a pharmacological target for inflammation. Br J Pharmacol 151:915-929.
11. Eschweiler W (1905) Ersatz von an Stickstoff gebundenen Wasserstoffatomen durch die Methylgruppe mit Hulfe von formaldehyde. Ber Dtsch Chem Ges 38:880-882.
12. Freitas K, Carroll FI, and Damaj MI (2013) The antinociceptive effects of nicotinic receptors α7-positive allosteric modulators in murine acute and tonic pain models. J Pharmacol Exp Ther 344:264-275.
13. Gamal-Eldin MA and Macartney DH (2013) Cucurbit[7]uril host-guest complexes and [2]pseudorotaxanes with N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution. Org Biomol Chem 11:1234-1241.
14. Green KD, Fridman M, and Garneau-Tsodikova S (2009) hChAT: a tool for the chemoenzymatic generation of potential acetyl/butyrylcholinesterase inhibitors. ChemBioChem 10:2191-2194.
15. Halevi S, Yassin L, Eshel M, Sala F, Sala S, Criado M, and Treinin M (2003) Conservation within the RIC-3 gene family. Effectors of mammalian nicotinic acetylcholine receptor expression. J Biol Chem 278:34411-34417.
16. Hibbs RE, Sulzenbacher G, Shi J, Talley TT, Conrod S, Kem WR, Taylor P, Marchot P, and Bourne Y (2009) Structural determinants for interaction of partial agonists with acetylcholine binding protein and neuronal alpha7 nicotinic acetylcholine receptor. EMBO J 28:3040-3051.
17. Horenstein NA, Leonik FM, and Papke RL (2008) Multiple pharmacophores for the selective activation of nicotinic alpha7-type acetylcholine receptors. Mol Pharmacol 74:1496-1511.
18. Hünig S and Baron W (1957) Abbau Quartarer Ammoniumsalze mit Athanolamin. Chem Ber 90:395-402.
19. Ito K, Nagase K, Morohashi N, and Ohba Y (2005) Interaction between quaternary ammonium ions and dipeptides: positive anion allosteric effect. Chem Pharm Bull (Tokyo) 53:90-94.
20. Kabbani N, Nordman JC, Corgiat BA, Veltri DP, Shehu A, Seymour VA, and Adams DJ (2013) Are nicotinic acetylcholine receptors coupled to G proteins? BioEssays 35:1025-1034.
21. Kasuga K, Kato T, Kabata N, and Handa M (1969) Cycloaddition of carbon dioxide to 1,2-epoxypropane catalyzed by tetra-t-butylphthalocyaninatoaluminium(III) hydroxide. Bull Chem Soc Jpn 69:2885-2888.
22. Lowe BM and Rendall HM (1971) Dilute aqueous solutions of unsymmetrical quaternary ammonium iodides. Part 1. - Viscosity and density measurements. Trans Faraday Soc 67:2318-2327.
23. MacFarlane DR, Meakin P, Sun J, Amini N, and Forsyth M (1999) Pyrrolidinium imides: a new family of molten salts and conductive plastic crystal phases. J Phys Chem B 103:4164-4170.
24. Papke RL (2006) Estimation of both the potency and efficacy of alpha7 nAChR agonists from single-concentration responses. Life Sci 78:2812-2819.
25. Papke RL (2010) Tricks of perspective: insights and limitations to the study of macroscopic currents for the analysis of nAChR activation and desensitization. J Mol Neurosci 40:77-86.
26. Papke RL (2014) Merging old and new perspectives on nicotinic acetylcholine receptors. Biochem Pharmacol 89:1-11.
27. Papke RL, Bencherif M, and Lippiello P (1996) An evaluation of neuronal nicotinic acetylcholine receptor activation by quaternary nitrogen compounds indicates that choline is selective for the α 7 subtype. Neurosci Lett 213:201-204.
28. Papke RL, Kem WR, Soti F, López-Hernández GY, and Horenstein NA (2009) Activation and desensitization of nicotinic alpha7-type acetylcholine receptors by benzylidene anabaseines and nicotine. J Pharmacol Exp Ther 329:791-807.
29. Papke RL, Millhauser G, Lieberman Z, and Oswald RE (1988) Relationships of agonist properties to the single channel kinetics of nicotinic acetylcholine receptors. Biophys J 53:1-10.
30. Papke RL and Porter Papke JK (2002) Comparative pharmacology of rat and human alpha7 nAChR conducted with net charge analysis. Br J Pharmacol 137:49-61.
31. Papke RL and Stokes C (2010) Working with OpusXpress: methods for high volume oocyte experiments. Methods 51:121-133.
32. Paulo JA, Brucker WJ, and Hawrot E (2009) Proteomic analysis of an alpha7 nicotinic acetylcholine receptor interactome. J Proteome Res 8:1849-1858.
33. Pavlov VA, Ochani M, Yang LH, Gallowitsch-Puerta M, Ochani K, Lin X, Levi J, Parrish WR, Rosas-Ballina M, and Czura CJ, et al. (2007) Selective alpha7-nicotinic acetylcholine receptor agonist GTS-21 improves survival in murine endotoxemia and severe sepsis. Crit Care Med 35:1139-1144.
34. Pesti K, Szabo AK, Mike A, and Vizi ES (2014) Kinetic properties and open probability of α7 nicotinic acetylcholine receptors. Neuropharmacology 81:101-115.
35. Rosas-Ballina M, Goldstein RS, Gallowitsch-Puerta M, Yang L, Valdés-Ferrer SI, Patel NB, Chavan S, Al-Abed Y, Yang H, and Tracey KJ (2009) The selective alpha7 agonist GTS-21 attenuates cytokine production in human whole blood and human monocytes activated by ligands for TLR2, TLR3, TLR4, TLR9, and RAGE. Mol Med 15:195-202.
36. Rosas-Ballina M and Tracey KJ (2009) Cholinergic control of inflammation. J Intern Med 265:663-679.
37. Short JH and Biermacher U (1962) Sympathetic nervous system blocking agents. Investigation of ethyl-, hydroxyethyl-, vinyloxyethyl-, and propargyl-benzyldimethylammonium halides and related compounds. JPharmSci51:881-884.
38. Skok MV (2009) Editorial: To channel or not to channel? Functioning of nicotinic acetylcholine receptors in leukocytes. J Leukoc Biol 86:1-3.
39. Stokes C and Papke RL (2012) Use of an α3β4 nicotinic acetylcholine receptor subunit concatamer to characterize ganglionic receptor subtypes with specific subunit composition reveals species-specific pharmacologic properties. Neuropharmacology 63:538-546.
40. Thomsen MS and Mikkelsen JD (2012) The α7 nicotinic acetylcholine receptor ligands methyllycaconitine, NS6740 and GTS-21 reduce lipopolysaccharide-induced TNF-α release from microglia. J Neuroimmunol 251:65-72.
41. van Maanen MA, Papke RL, Koepke J, Bevaart L, Clark R, Lamppu D, Vervoordeldonk MJ, LaRosa GJ, and Tak PP (2009) Therapeutic effect of stimulating the nicotinic acetylcholine receptor in the collagen-induced model of rheumatoid arthritis: a role for ion channel activity and penetration of the central nervous system, in Cholinergic Nervous System as Therapeutic Approach for the Treatment of Arthritis. pp 77-97. Doctoral dissertation, University of Amsterdam, Amsterdam, The Netherlands.
42. van Westerloo DJ, Giebelen IA, Florquin S, Bruno MJ, Larosa GJ, Ulloa L, Tracey KJ, and van der Poll T (2006) The vagus nerve and nicotinic receptors modulate experimental pancreatitis severity in mice. Gastroenterology 130:1822-1830.
43. von Braun J and Buchman ER (1931) Über den Zerfall quartärer Ammoniumhydroxyde (V. Mitteil.). Chem Ber 64:2610-2617.
44. + ions. J Mol Struct 562:63-78.
45. Williams DK, Peng C, Kimbrell MR, and Papke RL (2012) Intrinsically low open probability of α7 nicotinic acetylcholine receptors can be overcome by positive allosteric modulation and serum factors leading to the generation of excitotoxic currents at physiological temperatures. Mol Pharmacol 82:746-759.
46. Williams DK, Wang J, and Papke RL (2011a) Investigation of the molecular mechanism of the α7 nicotinic acetylcholine receptor positive allosteric modulator PNU-120596 provides evidence for two distinct desensitized states. Mol Pharmacol 80:1013-1032.
47. Williams DK, Wang J, and Papke RL (2011b) Positive allosteric modulators as an approach to nicotinic acetylcholine receptor-targeted therapeutics: advantages and limitations. Biochem Pharmacol 82:915-930.
48. Young GT, Zwart R, Walker AS, Sher E, and Millar NS (2008) Potentiation of alpha7 nicotinic acetylcholine receptors via an allosteric transmembrane site. Proc Natl Acad Sci USA 105:14686-14691.
49. Zhang J, Xue F, Liu Y, Yang H, and Wang X (2013) The structural mechanism of the Cys-loop receptor desensitization. Mol Neurobiol 48:97-108.
50. Zhong W, Gallivan JP, Zhang Y, Li L, Lester HA, and Dougherty DA (1998) From ab initio quantum mechanics to molecular neurobiology: a cation-pi binding site in the nicotinic receptor. Proc Natl Acad Sci USA 95:12088-12093.