Pharmacological characterisation of the enantiomers of BM-5, a muscarinic partial agonist with opposed enantioselectivity between affinity and efficacy

Pharmacology and Toxicology

Volumn 86, Issue 1, 2000, Pages 44-50

  Sundquist, Staffan ^a,d   Modiri, Ali Reza ^a   Nilsson, Björn M ^b   Hacksell, Uli ^b   Gillberg, Per Göran ^a   Nilvebrant, Lisbeth ^c  

^a PFIZER INC   (United States)

^b UPPSALA UNIVERSITY   (Sweden)

^c P U AB   (Sweden)

^d Dept of Pharmacol Pharmacia/U AB ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPINE; BENZYLSULFONYL FLUORIDE; CARBACHOL; MUSCARINIC AGENT; N METHYL N (1 METHYL 4 PYRROLIDINO 2 BUTYNYL)ACETAMIDE; PARTIAL AGONIST; QUINUCLIDINYL BENZILATE; RADIOLIGAND;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLADDER CONTRACTION; CAT; CHIRALITY; CHO CELL; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; ENANTIOMER; FEMALE; GUINEA PIG; ILEUM CONTRACTION; LIGAND BINDING; MALE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR AFFINITY; SALIVATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALIA; CAVIA PORCELLUS; FELIS CATUS; SUS SCROFA;

EID: 0033961289     PISSN: 09019928     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-0773.2000.pto860108.x     Document Type: Article

References (35)

1. Baumgold, J. & A. Drobnick: An agonist that is selective for adenylate cyclase coupled muscarinic receptors. Mol. Pharmacol. 1989, 34, 2297-2301.
2. Best, L., K. J. Brooks & T. B. Bolton: Relationship between stimulated inositol lipid hydrolysis and contractility in guinea-pig visceral longitudinal smooth muscle. Biochem. Pharmacol. 1985, 34, 2297-2301.
3. Birdsall, N. J. M., A. S. V. Burgen & E. C. Hulme: The binding of agonists to brain muscarinic receptors. Mol. Pharmacol. 1978, 14, 723-736.
4. Bradford, M. M.: A rapid and sensitive method for the quantification of microgram quantities of protein utilising the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
5. Buckley, N. J., T. I. Bonner, C. M. Buckley & M. R. Brann: Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells. Mol. Pharmacol. 1989, 35, 469-476.
6. Casamenti, F., C. Cosi & G. Pepeu: Effect of BM-5, a presynaptic antagonist-postsynaptic agonist, on cortical acetylcholine release. Eur. J. Pharmacol. 1986, 122, 288-290.
7. Dahlbom, R., D. J. Jenden, B. Resul & B. Ringdahl: Stereochemical requirements for central and peripheral muscarinic and antimuscarinic activity of some acetylenic compounds related to oxotremorine. Brit. J. Pharmacol. 1982, 76, 299-304.
8. 3, muscarinic receptors in rat parotid gland couple to two second messenger systems. Amer. J. Physiol. 1991, 261, c1063-c1073.
9. Dörje, F., A. I. Levey & M. R Brann: Immunological detection of muscarinic receptor subtype proteins (m1-m5) in rabbit peripheral tissues. Mol. Pharmacol. 1991, 40, 459-462.
10. Engström, C., A. Undén, H. Ladinsky, S. Consolo & T. Bartfai: BM-5, a centrally active partial muscarinic agonist with low tremorgenic activity. In vitro and in vivo studies. Psychopharmacology 1987, 91, 161-167.
11. Glowinski, J. & L. L. Iversen: Regional studies of catecholamines in the rat brain. J. Neurochem. 1966, 13, 655-669.
12. Jacobs, S., K.-J. Chang & P. Cuatrecasas: Estimation of hormone receptor affinity by competitive displacement of labelled ligand. Effect of concentration of receptor and of labelled ligand. Biochem. Biophys. Res. Commun. 1975, 66, 687-692.
13. Lefkowitz, R. J., M. G. Caron, T. Michel & J. M. Stadel: Mechanisms of hormone receptor-effector coupling: The β-adrenergic receptor and adenylate cyclase. Fed. Proc. 1982, 41, 2664-2670.
14. Levey, A. I., C. H. Kitt, W. F. Simonds, D. L. Price & M. R. Brann:. Identification and localisation of muscarinic acetylcholine receptor proteins with subtype-specific antibodies. J. Neurosci. 1991, 11, 3218-3226.
15. Lowry, O. H., N. J. Rosenbrough, A. L. Farr & R. J. Randall: Protein measurement with the Folin phenol reagent. Biol. Chem. 1951, 193, 265-275.
16. Messer, W. S., D. O. Ngur, Y. F. Abuh, L. A. Dokas, S.-M. Ting, U. Hacksell, B. M. Nilsson, P. G. Dunbar & W. Hoss: Stereoselective binding and activity of oxotremorine analogs at muscarinic receptors in rat brain. Chirality 1992, 4, 463-468.
17. 3H]4-diphenylacetoxy-N-methylpiperidine methiodide to longitudinal ileal smooth muscle receptors. Eur. J. Pharmacol. 1990, 176, 197-205.
18. Munson, P. J. & D. Rodbard: Ligand: a versatile computerised approach for characterisation of ligand-binding systems. Anal. Biochem. 1980, 107, 220-239.
19. Nilsson, B. M., P. De Boer, C. J. Grol & U. Hacksell: An improved synthesis of the enantiomers of BM-5 and their effects on the central in vivo release of acetylcholine. Chirality 1992, 4, 367-376.
20. Nilvebrant, L. & B. Sparf: Muscarinic receptor binding in the parotid gland. Different affinities of some anticholinergic drugs between the parotid gland and ileum. Scand. J. Gastroenterol. 1982, 17 (Suppl. 72), 69-77.
21. Nilvebrant, L. & B. Sparf: Muscarinic receptor binding in the guinea pig urinary bladder. Acta pharmacol. et toxicol. 1983, 52, 30-38.
22. Nilvebrant, L. & B. Sparf: Dicyclomine, benzhexol and oxybutynin distinguish between subclasses of muscarinic binding site. Eur. J. Pharmacol. 1986, 123, 133-143.
23. Nilvebrant, L., K.-E. Andersson, P.-G. Gillberg, M. Stahl & B. Sparf: Tolterodine - a new bladder-selective antimuscarinic agent. Eur. J. Pharmacol. 1997, 327, 195-207.
24. Nordström, Ö., P. Alberts, A. Westlind, A. Undén & T. Bartfai: Presynaptic antagonist- postsynaptic agonist at muscarinic cholinergic synapses. (N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide). Mol. Pharmacol. 1983, 24, 1-5.
25. Noronha-Blob, L., V. C. Lowe & R. C. Hanson: Heterogeneity of muscarinic receptors coupled to phosphoinositide breakdown in guinea pig brain and peripheral tissues. Life Sci. 1987, 41, 967-975.
26. Paton, W. D. M. & E. S. Vizi: The inhibitory action of noradrenaline and adrenaline on acetylcholine output by guinea-pig ileum longitudinal muscle strip. Brit. J. Pharmacol. 1969, 35, 10-28.
27. Peralta, E. G., A. Ashkenazi, J. W. Winslow, D. H. Smith, J. Ramachandran & D. J. Capon: Distinct primary structure, ligand-binding properties and tissue-specific expression of four human muscarinic acetylcholine receptors. EMBO J. 1987, 6, 3923-3929.
28. Resul, B., R. Dahlbom, B. Ringdahl & D. J Jenden: N-alkyl-N-(4-tert-amino-1-methyl-2-butynyl) carboxamides, a new class of potent oxotremorine antagonists. Eur. J. Med. Chem. 1982, 17, 317-322.
29. Ringdahl, B.: Determination of dissociation constants and relative efficacies of oxotremorine analogs at muscarinic receptors in the guinea pig ileum by pharmacological procedures. J. Pharmacol. Exp. Therap. 1984, 229, 199-206.
30. Ringdahl, B.: Tissue selectivity of oxotremorine analogs based on differences in muscarinic receptor reserve. Proc. West. Pharmacol. Soc. 1986, 29, 413-417.
31. Ringdahl, B.: Selectivity of partial agonists related to oxotremorine based on differences in muscarinic receptor reserve between the guinea pig ileum and urinary bladder. Mol. Pharmacol. 1987, 31, 351-356.
32. Ringdahl, B., M. Roch & D. J. Jenden: Regional differences in receptor reserve for analogs of oxotremorine in vivo: implications for development of selective muscarinic agonists. J. Pharmacol. Exp. Therap. 1987, 242, 464-471.
33. 3H)-acetylcholine from the rat hippocampal slices. Neuropharmacology 1988, 27, 1191-1195.
34. Wang, P., G. R. Luthin & M. R. Ruggieri: Muscarinic acetylcholine receptors mediating urinary bladder contractility and coupling to GTP binding proteins. J. Pharmacol. Exp. Therap. 1995, 273, 959-966.
35. Wolfe, B. B. & R. P. Yasuda: Development of selective antisera for muscarinic cholinergic receptor subtypes. Ann. N. Y. Acad. Sci. 1995, 151, 186-193.