Opposite effects of enantiomers of clofibric acid derivative on rat skeletal muscle chloride conductance: antagonism studies and theoretical modeling of two different receptor site interactions

J Pharmacol Exp Ther. 1992 Jan;260(1):364-8.

Abstract

The R-(+) enantiomer of 2-(p-chlorophenoxy) propionic acid (CPP) produces a biphasic effect on chloride channel conductance (GCl) of rat skeletal muscle, increasing GCl at low concentrations and decreasing it at concentrations greater than 10 microM; on the other hand, the S-(-) isomer mostly blocks GCl in a concentration-dependent manner. To explain the peculiar behavior of these compounds, a theoretical model based on the presence of two opposing receptor populations controlling chloride channel conductance has been used to fit the experimental data of the concentration-response curves of both S-(-) and R-(+) CPP. An analysis performed by means of the algebraic summation of two logistic terms suggests a reasonable merit of the proposed model and explains the resultant effect of each optical form as follows: S-(-) acts as a full agonist on an inhibitory sites, whereas R-(+) acts as a full agonist at both the inhibitory and excitatory sites. Antagonism studies appear to be consistent with the proposed model. Dose-response curves in which the block of GCl by the S-(-) isomer was evaluated in the presence of the R-(+) isomer (3-10 microM) clearly showed an antagonistic interaction between the two enantiomers, with an increase in the S-(-) concentration for half-maximal block. The antagonism was overcome by high concentrations of S-(-), and this might be consistent with the hypothesis that the block of GCl is modulated by an inhibitory site at which the two enantiomers compete.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Methyl-4-chlorophenoxyacetic Acid / analogs & derivatives
  • 2-Methyl-4-chlorophenoxyacetic Acid / antagonists & inhibitors
  • 2-Methyl-4-chlorophenoxyacetic Acid / metabolism
  • 2-Methyl-4-chlorophenoxyacetic Acid / pharmacology
  • Animals
  • Binding Sites
  • Chloride Channels
  • Chlorides / physiology*
  • Clofibric Acid / analogs & derivatives*
  • In Vitro Techniques
  • Kinetics
  • Male
  • Membrane Proteins / drug effects*
  • Membrane Proteins / metabolism
  • Models, Biological
  • Muscles / drug effects*
  • Muscles / physiology
  • Muscles / ultrastructure
  • Rats
  • Rats, Inbred Strains
  • Stereoisomerism

Substances

  • Chloride Channels
  • Chlorides
  • Membrane Proteins
  • 2-(4-chlorophenoxy)propionic acid
  • Clofibric Acid
  • 2-Methyl-4-chlorophenoxyacetic Acid