Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors.
作者： Magali Waelbroeck , Jean Camus , Michèle Tastenoy , Ernst Mutschler , Carsten Strohmann
DOI: 10.1016/0922-4106(92)90139-M
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摘要: We investigated the binding properties of (R)- and (S)-enantiomers muscarinic antagonists trihexyphenidyl, procyclidine, hexahydro-difenidol, p-fluoro-hexahydro-difenidol, hexbutinol, p-fluoro-hexbutinol, their corresponding methiodides at M1, M2, M3 M4 receptor subtypes. In addition, oxyphencyclimine were studied. The enantiomers (eutomers) all compounds had a greater affinity than (S)-isomers for four patterns generally different. did not observe any general correlation between potency high-affinity enantiomer ratio (eudismic ratio) two enantiomers. results are discussed in terms 'four subsites' model.
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Magali Waelbroeck, Jean Camus, Michèle Tastenoy, Günter Lambrecht, Ernst Mutschler, Reinhold Tacke, Jean Christophe, Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. European Journal of Pharmacology. ,vol. 189, pp. 135- 142 ,(1990) , 10.1016/0922-4106(90)90017-R
Günter Lambrecht, Roland Feifel, Monika Wagner-Röder, Carsten Strohmann, Harald Zilch, Reinhold Tacke, Magali Waelbroeck, Jean Christophe, Hendrikus Boddeke, Ernst Mutschler, Affinity profiles of hexahydro-sila-difenidol analogues at muscarinic receptor subtypes European Journal of Pharmacology. ,vol. 168, pp. 71- 80 ,(1989) , 10.1016/0014-2999(89)90634-1
R. TACKE, H. LINOH, D. SCHOMBURG, L. ERNST, U. MOSER, E. MUTSCHLER, G. LAMBRECHT, Absolute Configuration of the Enantiomers of the Antimuscarinic Agents Procyclidine and Tricyclamol Iodide: X-Ray Structural Analysis of (R)-1-[3-Cyclohexyl-3-hydroxy-3-phenylpropyl]-1-methylpyrrolidinium Iodide ChemInform. ,vol. 17, ,(1986) , 10.1002/CHIN.198622059
R. TACKE, C. STROHMANN, S. SARGE, H. K. CAMMENGA, D. SCHOMBURG, E. MUTSCHLER, G. LAMBRECHT, Preparation and Properties of the Enantiomers of the Selective Antimuscarinic Agent 1-Cyclohexyl-1-phenyl-4-piperidino-1-butanol (Hexahydro-Difenidol). ChemInform. ,vol. 20, ,(1989) , 10.1002/CHIN.198918213
P. Eveleigh, N. J. M. Birdsall, E. C. Hulme, C. Schudt, The existence of stable enantiomers of telenzepine and their stereoselective interaction with muscarinic receptor subtypes. Molecular Pharmacology. ,vol. 35, pp. 477- 483 ,(1989)
Carsten Strohmann, Sigurd Bauerecker, Heiko K. Cammenga, Peter G. Jones, Ernst Mutschler, Günter Lambrecht, Reinhold Tacke, Enantiomers of the muscarinic antagonist 1‐cyclohexyl‐1‐(4‐fluorophenyl)‐4‐piperidino‐1‐butanol (p‐fluoro‐hexahydro‐difenidol): Synthesis, absolute configuration, and enantiomeric purity European Journal of Organic Chemistry. ,vol. 1991, pp. 523- 527 ,(1991) , 10.1002/JLAC.199119910196
Lise Schjelderup, Michael R. Kozlowski, Albert Weissman, Arne J. Aasen, Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharmaceutical Research. ,vol. 5, pp. 236- 237 ,(1988) , 10.1023/A:1015945830309
R.B. BARLOW, K.J. BERRY, P.A.M. GLENTON, N.M. NIKOLAOU, K.S. SOH, A comparison of affinity constants for muscarine-sensitive acetylcholine receptors in guinea-pig atrial pacemaker cells at 29 degrees C and in ileum at 29 degrees C and 37 degrees C. British Journal of Pharmacology. ,vol. 58, pp. 613- 620 ,(1976) , 10.1111/J.1476-5381.1976.TB08631.X
N J Buckley, S Lazareno, F F Roberts, Characterization of muscarinic M4 binding sites in rabbit lung, chicken heart, and NG108-15 cells. Molecular Pharmacology. ,vol. 38, pp. 805- 815 ,(1990)
A. Lewis Farr, Oliver H. Lowry, Rose J. Randall, Nira J. Rosebrough, Protein Measurement with the Folin Phenol Reagent Journal of Biological Chemistry. ,vol. 193, pp. 265- 275 ,(1951)