The stereoselectivity of the interaction with muscarinic receptors of enantiomers of a series of chiral antagonists is receptor subtype dependent. There is no overall relationship between stereoselectivity and receptor affinity. Depending on the antagonist studied, receptor stereoselectivity may indeed reflect: (1) the weakening or loss of a single interaction involving one of the four groups bound to the asymmetric carbon; (2) steric hindrance preventing optimum interaction of the low affinity steroisomer with the receptor; and/or (3) the inversion of the relative positions of two moieties of the ligand with similar structural and electronic properties i.e. comparable affinities for the two corresponding subsites in the receptor.
        
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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 in Pharmacological SciencesSuppl: 65-9
Waelbroeck M, Tastenoy M, Camus J, Feifel R, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J (1989) Trends in Pharmacological SciencesSuppl: 65-9