Anabaseine is a potent agonist on muscle and neuronal alpha- bungarotoxin-sensitive nicotinic receptors

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 3, 1997, Pages 979-992

  Kem, William R ^a   Mahnir, Vladimir M ^a   Papke, Roger L ^a   Lingle, Christopher J ^b  

^a UNIVERSITY OF FLORIDA COLLEGE OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINE; ANABASEINE; ANABASINE; NICOTINIC AGENT; NICOTINIC RECEPTOR; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONCENTRATION RESPONSE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; MUSCLE CONTRACTILITY; NEUROMUSCULAR SYSTEM; NONHUMAN; OOCYTE; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR DENSITY; XENOPUS;

ANABASINE; ANIMALS; BRAIN; BUNGAROTOXINS; INJECTIONS, INTRAVENTRICULAR; MICE; MUSCLES; NEUROMUSCULAR JUNCTION; NICOTINIC AGONISTS; RADIOLIGAND ASSAY; RANA PIPIENS; RATS; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; TORPEDO; XENOPUS;

EID: 0031459933     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (84)

1. ABOOD, L. G., REYNOLDS, D. T., BOOTH, H. AND BIDLACK, J. M.: Sites and mechanisms for nicotine's action in the brain. Neurosci. Behav. Rev. 5: 479-486, 1981.
2. ANAND, R., PENG, X. AND LINDSTROM, J.: Homomeric and native alpha7 acetylcholine receptors exhibit remarkably similar but nonidentical pharmacolgical properties suggesting that the native receptor is a heteromeric protein complex. FEBS Lett. 327: 241-246, 1993.
3. ALBUQUERQUE, E. X., ALKONDON, M., PEREIRA, E. F. R., CASTRO, N. B., SCHRATTENHOLZ, A., BARBOSA, C. T. F., BONFANTE-CABARCAS, R., ARACAVA, Y., EISENBERG, H. M. AND MAELICKE, A.: Properties of neuronal nicotinic acetylcholine receptors: Pharmacological characterization and modulation of synaptic function. J. Pharmacol. Exp. Ther. 280: 1117-1136, 1997.
4. ALKONDON, M. AND ALBUQUERQUE, E. X.: Diversity of nicotinic acetylcholine receptors in rat hippocampal neurons. III. Agonist actions of the novel alkaloid epibatidine and analysis of type II current. J. Pharmacol. Exp. Ther. 274: 771-782, 1995.
5. ARAUJO D. M., LAPCHAK, P. A., ROBITAILLE, Y., GAUTHIER, S. AND QUIRION, R.: Differential alteration of various cholinergic markers in cortical and subcortical regions of human brain in Alzheimer's disease. J. Neurochem. 50: 1914-1923, 1988.
6. ARENDASH G. W., SANBERG, P. R. AND SENGSTOCK, G. J.: Nicotine enhances the learning and memory of aged rats. Pharmacol. Biochem. Behavior 52: 517-523, 1995a.
7. ARENDASH G. W., SENGSTOCK, G. J., SANBERG, P. R. AND KEM, W. R.: Improved learning and memory in aged rats with chronic administration of the nicotinic receptor agonist GTS-21. Brain Res. 674: 252-259, 1995b.
8. AUERBACH, A. AND LINGLE, C. J.: Activation of the primary kinetic modes of large- and small-conductance cholinergic ion channels in Xenopus myocytes. J. Physiol. 393: 437-466, 1987.
9. BADIO, B. AND DALY, J. W.: Epibatidine, a potent analgetic and nicotinic agonist. Mol. Pharmacol. 45: 563-569, 1994.
10. BARLOW, R. B. AND HAMILTON, J. T.: The effects of pH on the activity of nicotine and nicotine monomethiodide on the rat diaphragm preparation. Br. J. Pharmacol. 18: 543-549, 1962.
11. BARLOW, R. B. AND MCLEOD, L. J.: Some studies on cytisine and its methylated derivatives. Br. J. Pharmacol. 35: 161-174, 1969.
12. BARLOW, R. B., THOMPSON, G. M. AND SCOTT, N. C.: The affinity and activity of compounds related to nicotine on the rectus abdominis muscle of the frog (Rana pipiens). Br. J. Pharmacol. 37: 555-584, 1969.
13. BARTELS, E. AND PODLESKI, T. R.: Action of nicotine on the electroplax and difference of potency between ionized and unionized forms. Biochim. Biophys. Acta 79: 11-520, 1964.
14. BENCHERIF, M., LOVETTE, M. E., FOWLER, K. W., ARRINGTON, S., REEVES, L., CALDWELL, W. S. AND LIPPIELLO, P. M.: RJR-2403: A nicotinic agonist with CNS selectivity I. In vitro characterization. J. Pharm. Exp. Ther. 279: 1413-1421, 1996.
15. BJUGSTAD, K. B., MAHNIR, V. M., KEM, W. R. AND ARENDASH, G. W.: Long-term treatment with GTS-21 or nicotine enhances water maze performance in aged rats without affecting the density of nicotinic receptor subtypes in neocortex. Drug Dev. Res. 39: 19-28, 1996.
16. BLATZ, A. L. AND MAGLEBY, K. L.: Correcting single channel data for missed evens. Biophys. J. 49: 967-980, 1986.
17. BLOOM, L. B.: Influence of solvent on the ring-chain hydrolysis equilibrium of anabaseine and syntheses of anabaseine and nicotine analogues. Ph.D. Dissertation, Gainesville, University of Florida, pp. 1-206, 1990.
18. BONHAUS, D. W., BLEY, K. R., BROKA, C. A., FONTANA, D. J., LEUNG, E., LEWIS, R., SHIEH, A. AND WONG, E. H. F.: Characterization of the electrophysiological, biochemical and behavioral actions of epibatidine. J. Pharmacol. Exp. Ther. 272: 1199-1203, 1995.
19. 3H]N-methyl-carbamylcholine, a new radioligand specific for nicotinic acetylcholine receptors in brain. Eur. J. Pharmacol. 139: 323-333, 1987.
20. 50) of an enzymatic reaction. Biochem. Pharmacol. 22: 3099-3108, 1973.
21. COVARRUBIAS, M., KOPTA, C. AND STEINBACH, J. H.: Inhibitors of asparagine-linked oligosaccharide processing alter the kinetics of the nicotinic acetylcholine receptor. J. Gen. Physiol. 93: 765-783, 1989.
22. COLQUHOUN, D. AND SAKMANN, B.: Fast events in single-channel currents activated by acetylcholine and its analogues at the frog muscle end-plate. J. Physiol. 369: 501-557, 1985.
23. DECKER, M., BRIONI, J., BANNON, A. AND ARNERIC, S.: Diversity of neuronal nicotinic acetylcholine receptors: Lessons from behavior and implications for CNS therapeutics. Life Sci. 56: 545-570, 1995.
24. 125I-a-bungarotoxin receptor subtypes. Mol. Pharmacol. 47: 164-171, 1995.
25. ELDEFRAWI, M. E., ARONSTAM, R. S., BAKRY, N. M., ELDEFRAWI, A. T. AND ALBUQUERQUE, E. X.: Activation, inactivation, and desensitization of acetylcholine receptor channel complex detected by binding of perhydrohistrionicotoxin. Proc. Natl. Acad. Sci. U.S.A. 77: 2309-2313, 1980.
26. ERSPAMER, V.: Isolation of leptodactyline (m-hydroxyphenylethyltrimethyl-ammonium) from extracts of Leptodactylus skin. Arch. Biochem. Biophys. 82: 431-438, 1959.
27. FLORES, C. M., ROGERS, S. W., PABREZA, L. A., WOLFE, B. AND KELLAR, K. J.: A subtype of nicotinic cholinergic receptor is composed of alpha4 and beta2 subunits and is up-regulated by chronic nicotine treatment. Mol. Pharmacol. 41: 11-37, 1992.
28. GUND, T. M. AND SPIVAK, C. E.: Pharmacophore for nicotinic agonists. Methods Enzymol. 203: 677-695, 1991.
29. HAEFELY, W.: The effects of various "nicotine-like" agents in the cat superior cervical ganglion in situ. N. S. Arch. Pharmacol. Pathol. 281: 93-117, 1974.
30. KELLAR, K. J., WHITEHOUSE, P. J., MARTINO-BARROWS, A. M., MARCUS, K. AND PRICE, D. L.: Muscarinic and nicotinic cholinergic binding sites in Alzheimer's disease cerebral cortex. Brain Res. 435: 62-68, 1987.
31. KEM, W. R.: A study of the occurrence of anabaseine in Paranemertes and other nemertines. Toxicon 9: 23-32, 1971.
32. KEM, W. R. AND PAPKE, R. L.: Actions of anabaseine and DMAB-anabaseine upon neuronal alpha4-beta2 and PC12 cell nicotinic receptors (Abstract). Soc. Neurosci. 18: 1358, 1992.
33. KEM, W. R., ABBOTT, B. C. AND COATES, R. M.: Isolation and structure of a hoplonemertine toxin. Toxicon 9: 15-22, 1971.
34. KEM, W. R., MAHNIR, V. M., BLOOM, L. B. AND GABRIELSON, B. J.: The active form of the nicotinic receptor agonist anabaseine is the cyclic iminium cation. In Eleventh World Congress on Animal, Plant, and Microbial Toxins, Tel Aviv, p. 157, 1994b (Abstract).
35. KEM, W. R., MAHNIR, V. M. AND LIN, B.: Interaction of DMXBA (GTS-21), a cognition-enhancing compound, with cholinergic receptors. Soc. Neurosci. Abstr. 20: 1134, 1994c (Abstract 467.2).
36. KEM, W. R., MAHNIR, V. M., LIN, B., LINGLE, C. J., PAPKE, R. L. AND PROKAI-TATRAI, K.: The marine toxin anabaseine is a potent nicotinic agonist. In Proceedings of the International Symposium on Nicotine, Montreal, p. 22, 1994a (Abstract).
37. KEM, W. R., MAHNIR, V. M., LIN, B. AND PROKAI-TARTRAI, K.: Two primary GTS-21 metabolites are potent partial agonists at alpha7 nicotinic receptors expressed in the Xenopus oocyte. Soc. Neurosci. Abstr. 22: 268, 1996 (Abstract 110.7).
38. KEM, W. R., SCOTT, K. N. AND DUNCAN, J. H.: Hoplonemertine worms - a new source of pyridine neurotoxins. Experientia 32: 684-686, 1976.
39. KEMP, G. AND EDGE, M.: Cholinergic function and a-bungarotoxin binding in PC12 cells. Mol. Pharmacol. 32: 356-363, 1987.
40. LINDSTROM, J.: Neuronal nicotinic acetylcholine receptors. In Ion Channels, ed. by T. Narahashi, pp. 377-450, Plenum Press, New York, 1996.
41. LINGLE, C. J., MACONOCHIE, D. AND STEINBACH, J. H.: Activation of skeletal muscle nicotinic acetylcholine receptors. J. Membrane Biol. 126: 195-217, 1992.
42. LUETJE, C. W., WADA, K., ROGERS, S., ABRAMSON, S. N., HEINEMANN, S. AND PATRICK, J: Neurotoxins distinguish between different neuronal nicotinic acetylcholine receptors. J. Neurochem. 55: 632-640, 1990.
43. LUKAS, R. J.: Pharmacological distinctions between functional nicotinic acetylcholine receptors on the PC12 rat pheochromocytoma and the TE671 human medulloblastoma. J. Pharmacol. Exp. Ther. 251: 175-182.
44. LUKAS, R. J. AND CULLEN, M. J.: An isotopic rubidium ion efflux assay for the functional characterization of nicotinic acethylcholine receptors on clonal cell lines. Anal. Biochem. 175: 212-218, 1988.
45. LUNTZ-LEYBMAN, V., BICKFORD, P. C. AND FREEDMAN, R.: Cholinergic gating of response to auditory stimuli in rat hippocampus. Brain Res. 587: 130-136, 1992.
46. MACHU, T. K., STRAHLENDORF, J. AND KEM, W. R.: Nicotinic receptor ligands antagonize 5-HT3 receptors expressed in Xenopus oocytes. Soc. Neurosci. 22: 1780, 1996 (Abstr. 700.5).
47. 3H]nicotine binding to a nicotinic cholinergic receptor on PC12 cells. Endocrinology 130: 825-830, 1992.
48. MARKS, M. J., AND COLLINS, A. C.: Characterization of nicotine binding in mouse brain and comparison with the binding of alpha-bungarotoxin and quinuclidinyl benzilate. Mol. Pharmacol. 22: 554-564, 1982.
49. MARSHALL, C. G., OGDEN, D. AND COLQUHOUN, D.: Activation of ion channels in the frog endplate by several analogues of acetylcholine. J. Physiol. 433: 73-93, 1991.
50. MCGEHEE, D. S. AND ROLE, L. W.: Physiological diversity of nicotinic acetylcholine receptors expressed by vertebrate neurons. Ann. Rev. Physiol. 57: 521-546, 1995.
51. 3H]acetylcholine release in the rat cerebral cortex. J. Neurochem. 49: 1758-1762, 1987.
52. MEYER, E. M., DE FIEBRE, C. M., HUNTER, B. E., SIMPKINS, C. E., FRAUWORTH, N. AND DE FIEBRE, N. E.: Effects of anabaseine-related analogs on rat brain nicotinic receptor binding and on avoidance behaviors. Drug Dev. Res. 31: 127-134, 1994.
53. NEWHOUSE, P. A., POTTER, A. AND LENOX, R. H.: The effects of nicotinic agents on human cognition: possible therapeutic applications in Alzheimer's and Parkinson's diseases. Med. Chem. Res. 2: 628-642, 1993.
54. OGDEN, D. C. AND COLQUHOUN, D.: Ion channel block by acetylcholine, carbachol, and suberyldicholine at the frog neuromuscular junction. Proc. Roy. Soc. B 225: 329-355, 1985.
55. PAPKE, R. L.: The kinetic properties of neuronal nicotinic receptors: genetic basis of functional diversity. Prog. Neurobiol. 41: 509-531, 1993.
56. PAPKE, R. L. AND HEINEMANN, S. F.: Partial agonist properties of cytisine on neuronal nicotinic receptors containing the B2 subunit. Mol. Pharmacol. 45: 142-149, 1994.
57. PAPKE, R. L., MILLHAUSER, G., LIEBERMAN, Z. AND OSWALD, R.: E. Relationships of agonist properties to the single channel kinetics of nicotinic acetylcholine receptors. Biophys. J. 53: 1-10, 1988.
58. PAPKE, R. L., DE FIEBRE, C. M., KEM, W. R. AND MEYER, E. M.: The subunit specific effects of novel anabaseine-derived nicotinic agents. In Alzheimer Disease: Therapeutic Strategies, ed. by E. Giacobini and R. Becker, eds., pp. 206-211, Birkhauser, Boston, 1994.
59. PAPKE, R. L., FRANCIS, M. M. AND THINSCHMIDT, J. S.: Techniques for improved resolution of kinetic data from macroscopic currents. Biophys. J. 72: Abstr. M-Pos86, 1997.
60. PAPKE, R. L., THINSCHMIDT, J. S., MOUTON, B. A., MEYER, E. M. AND POIRIER, A.: Activation and inhibition of rat neuronal nicotinic receptors by ABT-418. Br. J. Pharmacol. 120: 429-438, 1997.
61. QUIK, M., CHOREMIS, J., KOMOURIAN, J., LUKAS, R. J. AND PUCHACZ, E.: Similarity between rat brain nicotinic alpha-bungarotoxin receptors and stably expressed alpha-bungarotoxin binding sites. J. Neurochem. 67: 145-154, 1996.
62. ROGERS, S. W., GAHRING, L. C., PAPKE, R. L. AND HEINEMANN, S.: Identification of cultured cells expressing ligand-gated cationic channels. Prot. Exp. Purif. 2: 108-116, 1991.
63. ROGERS, S. W., MANDELZYS, A., DENERIS, E. S., COOPER, E. AND HEINEMANN, S.: The expression of nicotinic acetylcholine receptors by PC12 cells treated with NGF. J Neurosci. 12: 4611-1623, 1992.
64. ROMANO, C.: Nicotine action on rat colon. J. Pharmacol. Exp. Ther. 217: 828-833, 1981.
65. SAKMANN, B., PATLAK, J. AND NEHER, E.: Single acetylcholine-activated channels show burst-kinetics in presence of desensitizing concentrations of agonist. Nature 287: 447-449, 1980.
66. SEEMAN, J. I.: Recent studies in nicotine chemistry. Conformational analysis, chemical reactivity studies, and theoretical modeling. Heterocycles 22: 165-193, 1984.
67. SIGWORTH, F. J. AND SINE, S. M.: Data transformations for improved display and fitting of single-channel dwell time histograms. Biophys. J. 52: 1047-1054, 1987.
68. SINE, S. M. AND STEINBACH, J. H.: Agonists block currents through acetylcholine receptor channels. Biophys. J. 46: 277-284, 1984.
69. 3H-l cells by low concentrations of agonist. J. Physiol. 373: 129-162, 1986.
70. 3H-1 cells by high concentrations of agonist. J. Physiol. 385: 325-359, 1987.
71. STAUFFER, D. A. AND KARLIN, A.: Electrostatic potential of the acetylcholine binding sites in the nicotinic receptor probed by reactions of binding-site cysteines with charged methanethiosulfonates. Biochemistry 33: 6840-6849, 1994.
72. SUMMERS, K. L., KEM, W. R. AND GIACOBINI, E.: Nicotinic agonist modulation of neurotransmitter levels in the rat frontoparietal cortex. Jpn. J. Pharmacol. 74: 139-146, 1997.
73. SWANSON, K. L. AND ALBUQUERQUE, E. X.: Nicotinic acetylcholine receptors and low molecular weight toxins. Handb. Exp. Pharmacol. 102: 611-658, 1992.
74. TAKAYAMA, H., MAJEWSKA, M. D. AND LONDON, E. D.: Interactions of noncompetitive inhibitors with nicotinic receptors in the rat brain. J. Pharmacol. Exp. Ther. 253: 1083-1089, 1989.
75. TOROCSIK, A., OBERFRANK, F., SERSHEN, H., LAJTHA, A., NEMESY, K. AND VIZI, E. S.: Characterization of somatodendritic neuronal nicotinic receptors located on the myenteric plexus. Eur. J. Pharmacol. 202: 297-302, 1991.
76. WARD, J. M., COCKCROFT, V. B., LUNT, G. G., SMILLIE, F. S. AND WONNACOTT, S.: Methyllycaconitine: A selective probe for neuronal alpha-bungarotoxin binding sites. FEBS Lett. 270: 45-48, 1990.
77. WHEELER, J. W., OLUBAJO, O., STORM, C. B. AND DUFFIELD, R. M.: Anabaseine: venom alkaloid of Aphaenogaster ants. Science 211: 1051-1052, 1981.
78. WHIDBY, J. F. AND SEEMAN, J. I.: The configuration of nicotine. A nuclear magnetic resonance study. J. Org. Chem. 41: 1585-1590, 1976.
79. WONG, E. T., HOLSTAD, S. G., MENNERICK, S. J., HONG, S. E., ZORUMSKI, C. F. AND ISENBERG, K. E.: Pharmacological and physiological properties of a putative ganglionic nicotinic receptor, alpha3-beta4, expressed in transfected eucaryotic cells. Mol. Brain Res. 28: 101-109, 1995.
80. WONNACOTT, S.: Alpha-Bungarotoxin binds to low-affinity nicotine binding sites in rat brain. J. Neurochem. 47: 1706-1712, 1986.
81. WOODRUFF-PAK, D. S., LI, Y-T. AND KEM, W. R.: A nicotinic receptor agonist (GTS-21), eyeblink classical conditioning, and nicotinic receptor binding in rabbit brain. Brain Res. 645: 309-317, 1994.
82. YAMAMOTO, I., KAMIMURA, H., YAMAMOTO, R., SKAI, S., GODA, M.: Studies on nicotinoids as insecticides. I. Relation of structure to toxicity. Agr. Biol. Chem.(Tokyo) 26: 709-716, 1962.
83. ZHANG, Y., CHEN, J. AND AUERBACH, A.: Activation of recombinant mouse acetylcholine receptors by acetylcholine, carbamylcholine, or tetramethylammonium. J. Physiol. 486: 189-206, 1995.
84. ZOLTEWICZ, J. A., BLOOM, L. B. AND KEM, W. R.: Quantitative determination of the ring-chain hydrolysis equilibrium constant for anabaseine and related tobacco alkaloids. J. Org. Chem. 54: 4462-4468, 1989.