The interaction of the enantiomers of aceclidine with subtypes of the muscarinic receptor

Journal of Pharmacology and Experimental Therapeutics

Volumn 279, Issue 3, 1996, Pages 1335-1344

  Ehlert, Frederick J ^a   Griffin, Michael T ^b   Glidden, Paul F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CHAPMAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACECLIDINE; ADENYLATE CYCLASE; CYCLIC AMP; MUSCARINIC M1 RECEPTOR; MUSCARINIC M2 RECEPTOR; MUSCARINIC M3 RECEPTOR; MUSCARINIC M4 RECEPTOR; MUSCARINIC M5 RECEPTOR; MUSCARINIC RECEPTOR; PHOSPHATIDYLINOSITIDE; RECEPTOR SUBTYPE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHO CELL; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; ENANTIOMER; ENZYME ACTIVITY; GENETIC TRANSFECTION; GUINEA PIG; HEART; ILEUM; INTESTINE CONTRACTION; NONHUMAN; PAROTID GLAND; PRIORITY JOURNAL; RAT; RECEPTOR OCCUPANCY; SECOND MESSENGER; STEREOISOMERISM;

ADENYLATE CYCLASE; ANIMALS; CHO CELLS; CRICETINAE; CYCLIC AMP; FORSKOLIN; HYDROLYSIS; MALE; MUSCARINIC AGONISTS; MYOCARDIUM; PAROTID GLAND; PHOSPHATIDYLINOSITOLS; PROTEIN BINDING; QUINUCLIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, MUSCARINIC; RECOMBINANT PROTEINS; STEREOISOMERISM;

EID: 0030441045     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. BARLOW, R. B. AND CASY, A. F.: Inversion of stereospecificity by methylation of compounds acting at acetylcholine receptors. Mol. Pharmacol. 11: 690-693, 1975.
2. BERRIDGE, M. J., DOWNES, C. P. AND HANLEY, M. R.: Lithium amplifies agonist-dependent phosphatidylinositol responses in brain and salivary glands. Biochem. J. 206: 587-595, 1982,
3. BIRDSALL, N. J., HULME, E. C. AND BURGEN, A.: The character of the muscarinic receptors in different regions of the rat brain. Proc. R. Soc. Lond. B. Biol. Sci. 207: 1-12, 1980.
4. BONNER, T. I., YOUNG, A. C., BRANN, M. R. AND BUCKLEY, N. J.: Cloning and expression of the human and rat m5 muscarinic acetylcholine receptor genes. Neuron 1: 403-410, 1988.
5. BRAUNER-OSBORNE, H. AND BRANN, M. R.: Pharmacology of muscarinic acetylcholine receptor subtypes (m1-m5): High throughout assays in mammalian cells. Eur. J. Pharmacol. 296: 93-102, 1996.
6. BUCKLEY, N. J., BONNER, T. I., BUCKLEY, C. M. AND BRANN, M. R.: Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells. Mol. Pharmacol. 36: 469-476, 1989.
7. CANDELL, L. M., YUN, S. H., TRAN, L. L. AND EHLERT, F. J.: Differential coupling of subtypes of the muscarinic receptor to adenylate cyclase and phosphoinositide hydrolysis in the longitudinal muscle of the rat ileum. Mol. Pharmacol. 38: 689-697, 1990.
8. CHO, A K., JENDEN, D. J. AND LAMB, S. I.: Rates of alkaline hydrolysis and muscarinic activity of some aminoacetates and their Quaternary ammonium analogs. J. Med. Chem. 15: 391-394, 1972.
9. EHLERT, F. J.: The relationship between muscarinic receptor occupancy and adenylate cyclase inhibition in the rabbit myocardium. Mol. Pharmacol. 28: 410-421, 1985.
10. EHLERT, F. J.: Gallamine allosterically antagonizes muscarinic receptor-mediated inhibition of adenylate cyclase activity in the rat myocardium. J. Pharmacol. Exp. Ther. 247: 596-602, 1988.
11. EHLERT, F. J., DELEN, F. M., YUN, S. H., FRIEDMAN, D. J. AND SELF, D. W.: Coupling of subtypes of the muscarinic receptor to adenylate cyclase in the corpus striatum and heart. J. Pharmacol. Exp. Ther. 251: 660-671, 1989.
12. EHLERT, F. J. AND YAMAMURA, H. I.: Pharmacological analysis of muscarinic receptor-mediated inhibition of adenylate cyclase and stimulation of phosphoinositide hydrolysis. In Molecular Mechanisms of Muscarinic Acetylcholine Receptor Function, ed. by J. Wess, pp. 47-69, R. Landes Company, Austin, 1995.
13. ELTZE, M., ULLRICH, B., MUTSCHLER, E., MOSER, U., BUNGARDT, E., FRIEBE, T., GUBITZ, C., TACKE, R. AND LAMBRECHT, G.: Characterization of muscarinic receptors mediating vasodilation in rat perfused kidney. Eur. J. Pharmacol. 238: 343-355, 1993.
14. FISHER, A., BRANDEIS, R., PITTEL, Z., KARTON, I., SAPIR, M., DACHIR, S., LEVY, A. AND HELDMAN, E.: (±)-cis-2-methyl-spiro(1,3-oxathiolane-5,3′)quinuclidine (AF102B): A new M1 agonist attenuates cognitive dysfunctions in AF64A-treated rats. Neurosci. Lett. 102: 325-331, 1989.
15. FISHER, A., WEINSTOCK, M., GITTER, S. AND COHEN, S.: A new probe for heterogeneity in muscarinic receptors: 2-Methyl-spiro-(1,3-dioxolane-4,3′)-quinuclidine. Eur. J. Pharmacol. 37: 329-338, 1976.
16. FREEDMAN, S. B., HARLEY, E. A., PATEL, S., NEWBERRY, N. R., GILBERT, M. J., MCKNIGHT, A. T., TANG, J. K., MAGUIRE, J. J., MUDUNKOTUWA, N. T. AND BAKER, R.: A novel series of non-Quaternary oxadiazoles acting as full agonists at muscarinic receptors. Br. J. Pharmacol. 101: 575-580, 1990.
17. FURCHGOTT, R. F. AND BURSZTYN, P.: Comparison of dissociation constants and of relative efficacies of selected agonists acting on parasympathetic receptors. Ann. N.Y. Acad. Sci. 144: 882-899, 1967.
18. GIACHETTI, A., MICHELETTI, R. AND MONTAGNA, E.: Cardioselective profile of AF-DX 116, a muscarine M2 receptor antagonist. Life Sci. 38: 1663-1672, 1986.
19. GIL, D. W. AND WOLFE, B. B.: Pirenzepine distinguishes between muscarinic receptor-mediated phosphoinositide breakdown and inhibition of adenylate cyclase. J. Pharmacol. Exp. Ther. 232: 608-616, 1985.
20. LAMBRECHT, G.: Struktur und konformations-wirkungs-beziehungen heterocyclischer acetylcholinanaloga. 1. Muscariniwirkung enantiomerer 3-acetoxychinuclidine und 3-acetoxypiperidine. Eur. J. Med. Chem. 11: 461-466, 1976.
21. LAZARENO, S., FARRIES, T. AND BIHDSALL, N. J.: Pharmacological characterization of guanine nucleotide exchange reactions in membranes from CHO cells stably transfected with human muscarinic receptors m1-m4. Life Sci. 82: 449-456, 1993.
22. LEFKOWITZ, R. J., HOFFMAN, B. B. AND TAYLOR, P.: Neurohumoral transmission: The autonomic and somatic motor nervous systems. In Goodman and Gilman's the Phamacological Basis of Therapeutics, ed. by A. G. Gilman, T. W. Rall, A. S. Nies and P. Taylor, 8th ed., pp. 84-121, Pergamon Press, New York, 1990.
23. MASHKOVSKY, M. D. AND YAKHONTOV, L. N.: Relationships between the chemical structure and pharmacological activity in a series of synthetic quinuclidine derivatives. Prog. Drug Res. 18: 293-339, 1969.
24. MCKINNEY, M., MILLER, J. H., GIBSON, V. A., NICKELSON, L. AND AKSOY, S.: Interactions of agonists with M2 and M4 muscarinic receptor subtypes mediating cyclic AMP inhibition. Mol. Pharmacol. 40: 1014-22, 1991.
25. MEI, L., LAI, J., YAMAMURA, H. I. AND ROESKE, W. R.: Pharmacologic comparison of selected agonists for the M1 muscarinic receptor in transfected murine fibroblast cells (B82). J. Pharmacol. Exp. Ther. 256: 689-694, 1991.
26. MEYERHOFFER, A.: Absolute configuration of 3-quinuclidinyl benzilate and the behavioral effect in the dog of the optical isomers. J. Med. Chem. 15: 994-995, 1972.
27. PERALTA, E. G., ASHKENAZI, A., WINSLOW, J. W., RAMACHANDRAN, J. AND CAPON, D. J.: Differential regulation of PI hydrolysis and adenylyl cyclase by muscarinic receptor subtypes. Nature (Lond.) 334: 434-437, 1988.
28. PYTTEL, R. AND ROBINSON, J. B.: Interaction of 3-quinuclidinol and its derivatives with acetylcholinesterase. J. Pharmaceut. Sci. 62: 684-685, 1973.
29. RICHARDS, M. H. AND VAN GIERSBERGEN, P. L.: Human muscarinic receptors expressed in A9L and CHO cells: Activation by full and partial agonists. Br. J. Pharmacol. 114: 1241-1249, 1995.
30. RINGDAHL, B., EHLERT, F. J. AND JENDEN, D. J.: Muscarinic activity and receptor binding of the enantiomers of aceclidine and its methiodide. Mol. Pharmacol. 21: 594-599, 1982.
31. RINGDAHL, B., RESUL, B. AND DAHLBOM, R.: Facile preparation of the enantiomers of 3-acetoxyquinuclidine and 3-quinuclidinol. Acta Pharmaceut. Suecica 16: 281-283, 1979.
32. ROBINSON, J. B., BELLEAU, B. AND COX, B.: 3-Acetoxyquinuclidine methiodide. Resolution, absolute configuration, and stereospecificity of interaction with the acetylcholine binding sites. J. Med. Chem. 12: 848-851, 1969.
33. SALOMON, Y., LONDOS, C. AND RODBELL, M.: A highly sensitive adenylate cyclase assay. Anal. Biochem. 58: 541-548, 1974.
34. SAUNDERS, J., CASSIDY, M., FREEDMAN, S. B., HARLEY, E. A., IVERSEN, L. L., KNEEN, C., MACLEOD, A. M., MERCHANT, K. J., SNOW, R. J. AND BAKER, R.: Novel quinuclidine-based ligands for the muscarinic cholinergic receptor. J. Med. Chem. 33: 1128-1138, 1990.
35. SCHULTZ, J., HAMPRECHT, B. AND DALY, J. W.: Accumulation of adenosine 3′:5′-cyclic monophosphate in clonal glial cells: Labeling of intracellular adenine nucleotides with radioactive adenine. Proc. Natl. Acad. Sci. U.S.A. 69:1266-1270, 1972.
36. SCHWARZ, R. D., DAVIS, R. E., JAEN, J. C., SPENCER, C. J., TECLE, H. AND THOMAS, A. J.: Characterization of muscarinic agonists in recombinant cell lines. Life Sci. 52: 465-472, 1993.
37. WAELBROECK, M., GILLARD, M., ROBBERECHT, P. AND CHRISTOPHE, J.: Muscarinic receptor heterogeneity in rat central nervous system. I. Binding of four selective antagonists to three muscarinic receptor subclasses: A comparison with M2 cardiac muscarinic receptors of the C type. Mol. Pharmacol. 32: 91-99, 1987.
38. WEINSTEIN, H., MAAYANI, S., SREBRENIK, S., COHEN, S. AND SOKOLOVSKY, M.: A theoretical and experimental study of the semirigid cholinergic agonist 3-acetoxyquinuclidine. Mol. Pharmacol. 11: 671-689, 1975.
39. JPET 279:1345-1356, 1996