Stereoselective recognition of the enantiomers of phenglutarimide and of six related compounds by four muscarinic receptor subtypes

British Journal of Pharmacology

Volumn 119, Issue 7, 1996, Pages 1319-1330

  Waelbroeck, M ^c   Lazareno, S ^a   Pfaff, O ^b   Friebe, T ^b   Tastenoy, M ^c   Mutschler, E ^b   Lambrecht, G ^b  

^a MEDICAL RESEARCH COUNCIL   (United Kingdom)

^b GOETHE UNIVERSITY   (Germany)

^c FREE UNIVERSITY OF BRUSSELS   (Belgium)

Author keywords

Binding functional correlations; Muscarinic receptor antagonists; Muscarinic receptor subtypes; Phenglutarimide derivatives; Stereoselectivity; Structure affinity relationships

Indexed keywords

METHYLSCOPOLAMINE; MUSCARINIC M1 RECEPTOR; MUSCARINIC M2 RECEPTOR; MUSCARINIC M3 RECEPTOR; MUSCARINIC M4 RECEPTOR; PHENGLUTARIMIDE;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHO CELL; CORPUS STRIATUM; DRUG RECEPTOR BINDING; ENANTIOMER; HEART; HEART ATRIUM; ILEUM; MALE; NONHUMAN; PANCREAS; PRIORITY JOURNAL; RABBIT; RAT; STEREOCHEMISTRY; VAS DEFERENS;

EID: 0029841440     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1476-5381.1996.tb16041.x     Document Type: Article

References (44)

1. ARUNLAKSHANA, O. & SCHILD, H.O. (1959). Some quantitative uses of drug antagonists. Br. J. Pharmacol. Chemother., 14, 48-58.
2. BARLOW, R.B. & WESTON-SMITH, P. (1985). The relative potencies of some agonists at M2 muscarinic receptors in guinea-pig ileum, atria and bronchi. Br. J. Pharmacol., 85, 437-440.
3. BRANN, M.R., ELLIS, J., JORGENSEN, H., HILL-EUBANKS, D. & JONES, S.V.P. (1993). Muscarinic acetylcholine receptor subtypes: localization and structure/function. Prog. Brain Res., 98, 121-127.
4. CAULFIELD, M.P. (1993). Muscarinic receptors-characterization, coupling and function. Pharmacol. Ther., 58, 319-379.
5. CHOO, L.K. & MITCHELSON, F. (1990). Selective inhibition of responses to carbachol and McN-A-343 in the rabbit vas deferens. Clin. Exp. Pharmacol. Physiol., 17, 601-611.
6. DÖRJE, F., LEVEY, A.I. & BRANN, M.R. (1991a). Immunological detection of muscarinic receptor subtype proteins (m1-m5) in rabbit peripheral tissues. Mol. Pharmacol., 40, 459-462.
7. DÖRJE, F., WESS, J., LAMBRECHT, G., TACKE, R., MUTSCHLER, E. & BRANN, M.R. (1991b). Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J. Pharmacol. Exp. Ther., 256, 727-733.
8. ELTZE, M. (1988). Muscarinic M1- and M2-receptors mediating opposite effects on neuromuscular transmission in rabbit vas deferens. Eur. J. Pharmacol., 158, 11-19.
9. 2 receptor stimulation in rabbit vas deferens. Eur. J. Pharmacol., 263, 31-37.
10. ELTZE, M., GMELIN, G., WESS, J., STROHMANN, C., TACKE, R., MUTSCHLER, E. & LAMBRECHT, G. (1988). Presynaptic muscarinic receptors mediating inhibition of neurogenic contractions in rabbit vas deferens are of the ganglionic M1-type. Eur. J. Pharmacol., 158, 233-242.
11. ELTZE, M., ULLRICH, B., MUTSCHLER, E., MOSER, U., BUNGARDT, E., FRIEBE, T., GUBITZ, C., TACKE, R. & LAMBRECHT, G. (1993). Characterization of muscarinic receptors mediating vasodilation in rat perfused kidney. Eur. J. Pharmacol., 238, 343-355.
12. FEIFEL, R., RODRIGUES DE MIRANDA, J.F., STROHMANN, C., TACKE, R., AASEN, A.J., MUTSCHLER, E. & LAMBRECHT, G. (1991). Selective labelling of muscarinic M1 receptors in calf superior cervical ganglia by (3H)(+)-telenzepine. Eur. J. Pharmacol., 195, 115-123.
13. FEIFEL, R., WAGNER-RÖDER, M., STROHMANN, C., TACKE, R., WAELBROECK, M., CHRISTOPHE, J., MUTSCHLER, E. & LAMBRECHT, G. (1990). Stereoselective inhibition of muscarinic receptor subtypes by the enantiomers of hexahydro-difenidol and acetylenic analogues. Br. J. Pharmacol., 99, 455-460.
14. GRIMM, U., FUDER, H., MOSER, U., BÄUMERT, H.G., MUTSCHLER, E & LAMBRECHT, G. (1994). Characterization of the prejunctional muscarinic receptors mediating inhibition of evoked release of endogenous noradrenaline in rabbit isolated vas deferens. Naunyn-Schmiedeberg's Arch. Pharmacol., 349, 1-10.
15. GROSS, J., WAELBROECK, M., MUTSCHLER, E. & LAMBRECHT, G. (1995). Functional characterization of neuronal muscarinic receptors in rabbit anococcygeus muscle. Life Sci., 56, 1038.
16. HULME, E.C., BIRDSALL, N.J.M. & BUCKLEY, N.J. (1990). Muscarinic receptor subtypes. Annu. Rev. Pharmacol. Toxicol., 30, 633-673.
17. LAMBRECHT, G., FEIFEL, R., MOSER, U., AASEN, A.J., WAELBROECK, M., CHRISTOPHE, J. & MUTSCHLER, E. (1988). Stereoselectivity of the enantiomers of trihexyphenidyl and its methiodide at muscarinic receptor subtypes. Eur. J. Pharmacol., 155, 167-170.
18. LAMBRECHT, G., FEIFEL, R. & MUTSCHLER, E. (1989a). Stereoselectivity at muscarinic receptor subtypes: Observations with the enantiomers of phenglutarimide. Chirality, 1, 170-173.
19. LAMBRECHT, G., FEIFEL, R., WAGNER-RÖDER, M., STROHMANN, C., ZILCH, H., TACKE, R., WAELBROECK, M., CHRISTOPHE, J., BODDEKE, H. & MUTSCHLER, E. (1989b). Affinity profiles of hexahydro-sila-difenidol analogues at muscarinic receptor subtypes. Eur. J. Pharmacol., 168, 71-80.
20. LAMBRECHT, G., MOSER, U., GRIMM, U., PFAFF, O., HERMANNI, U., HILDEBRANDT, C., WAELBROECK, M., CHRISTOPHE, J. & MUTSCHLER, E. (1993). New functionally selective muscarinic agonists. Life Sci., 52, 481-488.
21. LAZARENO, S. & BIRDSALL, N.J.M. (1995). Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: Interactions of strychnine and acetylcholine at muscarinic receptors. Mol. Pharmacol., 48, 362-378.
22. 4 binding sites in rabbit lung, chicken heart, and NG 108-15 cells. Mol. Pharmacol., 38, 805-815.
23. LEHMANN, F.P.A. (1986). Stereoisomerism and drug action. Trends Pharmacol. Sci., 7, 281-285.
24. LEVINE, R.R. & BIRDSALL, N.J.M. (eds.) (1993). Subtypes of muscarinic receptors V. Life Sci., 52, 405-597.
25. LOWRY, O.H., ROSEBROUGH, N.J., FARR, A.L. & RANDALL, R.J. (1951). Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275.
26. 1 muscarinic receptors. Br. J. Pharmacol., 100, 395-397.
27. MITCHELSON, F. (1988). Muscarinic receptor differentiation. Pharmacol. Ther., 37, 357-423.
28. MUTSCHLER, E. & HULTZSCH, K. (1973). Über Struktur-Wirkungs-Beziehungen von ungesättigten Estern des Arecaidins und Dihydroarecaidins. Arzneim.-Forsch., 23, 732-737.
29. MUTSCHLER, E. & LAMBRECHT, G. (1984). Selective muscarinic agonists and antagonists in functional tests. Trends Pharmacol. Sci., Suppl., 5, 39-44.
30. NELSON, W.L. FREEMAN, D.S. & VINCENZI, F.F. (1976). Stereochemical analogs of a muscarinic, ganglionic stimulant. 2. Cis and trans olefinic, epoxide, and cyclopropane analogs related to 4-[N-(3-chlorophenyl)carbamoyloxy]-2-butynyltrimethylammonium chloride (McN-A-343). J. Med. Chem. 19, 153-158.
31. PATON, W.D.M. & ZAR, M.A. (1968). The origin of acetylcholine release from guinea-pig intestine and longitudinal muscle strips. J. Physiol., 194, 13-33.
32. PFAFF, O., FRIEBE, T.P., WAELBROECK, M., CHRISTOPHE, J., CAMUS, J., MUTSCHLER, E. & LAMBRECHT, G. (1993). Stereoselective interaction of phenglutarimide and of related antagonists, with four muscarinic receptor suybtypes. Naunyn-Schmiedeberg's Arch. Pharmacol., 347, (Suppl.), R116.
33. PFEIFFER, C.C. (1956). Optical isomerism and pharmacological action, a generalization. Science, 124, 29-31.
34. ROBERT, T.A., HAGARDORN, A.N. & DAIGNEAULT, E.A. (1982). Differential stereoselectivity of methotrimepazine enantiomers for selected central nervous system receptor types. Mol. Pharmacol., 21, 315-319.
35. 1 receptor-mediated responses. Life Sci., 52, 574.
36. TALLARIDA, R.J., COWAN, A. & ADLER, M.W. (1979). pA2 and receptor differentiation: a statistical analysis of competitive antagonism. Life Sci., 25, 637-654.
37. VAN ROSSUM, J.M. (1963). Cumulative dose-response curves. II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters. Arch. Int. Pharmacodyn., 143, 299-330.
38. WAELBROECK, M. (1994). Identification of drugs competing with d-tubocurarine for an allosteric site on cardiac muscarinic receptors. Mol. Pharmacol., 46, 685-692.
39. WAELBROECK, M., CAMUS, J., TASTENOY, M. & CHRISTOPHE, J. (1988). 80% of muscarinic receptors expressed by the NB-OK 1 human neuroblastoma cell line show high affinity for pirenzepine and are comparable to rat hippocampus M1 receptors. FEBS Lett., 226, 287-290.
40. 4. Eur. J. Pharmacol., 189, 135-142.
41. 4 muscarinic receptors. Chirality, 3, 118-123.
42. WAELBROECK, M., CAMUS, J., TASTENOY, M., MUTSCHLER, E., STROHMANN, C., TACKE, R., SCHJELDERUP, L., AASEN, A., LAMBRECHT, G. & CHRISTOPHE, J. (1992). Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur. J. Pharmacol., 221, 33-42.
43. WAELBROECK, M., TASTENOY, M., CAMUS, J. & CHRISTOPHE, J. (1990b). Binding of selective antagonists to four muscarinic receptors (M1 to M4) in rat forebrain. Mol. Pharmacol., 38, 267-273.
44. WAELBROECK, M., TASTENOY, M., CAMUS, J., FEIFEL, R., MUTSCHLER, E., STROHMANN, C., TACKE, R., LAMBRECHT, G. & CHRISTOPHE, J. (1989). Stereoselectivity of the interaction of muscarinic antagonists with their receptors. Trends Pharmacol. Sci., 10, Suppl., 65-69.