Kinetic studies on stereospecific recognition by the thromboxane A2/prostaglandin H2 receptor of the antagonist, S-145

Br J Pharmacol. 1991 Aug;103(4):1883-8. doi: 10.1111/j.1476-5381.1991.tb12346.x.

Abstract

1. The mechanism for the stereospecific recognition of the antagonist S-145 by the thromboxane A2 (TXA2)/prostaglandin H2 (PGH2) receptor was examined by ligand-binding techniques in rat vascular smooth muscle cells (VSMCs) and in human platelet membranes. 2. Scatchard analysis revealed the existence of a single class of binding sites with the same maximum number for both [3H]-(+)-S-145 and [3H]-(-)-S-145 in both cell types. The dissociation constants (Kd) for the binding of the (+)-isomer in rat VSMCs and human platelet membranes were, respectively, 0.40 +/- 0.03 and 0.20 +/- 0.02 nM, each value being lower than that for the (-)-isomer (3.57 +/- 0.74 and 2.87 +/- 0.08 nM, respectively). 3. The rank orders of potency (Ki) for a series of TXA2/PGH2 ligands at inhibiting [3H]-(+)-S-145 binding were highly correlated with those determined for [3H]-(-)-S-145 binding in both cell preparations. 4. Kinetic analysis of the binding of both radioligands revealed a much lower dissociation rate constant (k-1) and a slightly greater association rate constant (k1) for the (+)-isomer compared to those for the (-)-isomer. 5. These results suggest that it is at the stage of dissociation from the TXA2/PGH2 receptor that the stereochemistry of the optical isomers of S-145 confers their difference in affinity for these receptors in rat VSMCs and human platelet membranes.

MeSH terms

  • Animals
  • Blood Platelets / chemistry
  • Bridged Bicyclo Compounds / metabolism*
  • Cell Membrane / chemistry
  • Cells, Cultured
  • Fatty Acids, Monounsaturated / metabolism*
  • Humans
  • Male
  • Muscle, Smooth, Vascular / chemistry
  • Prostaglandins H / metabolism*
  • Rats
  • Rats, Inbred Strains
  • Receptors, Prostaglandin / metabolism*
  • Receptors, Thromboxane
  • Receptors, Thromboxane A2, Prostaglandin H2
  • Stereoisomerism
  • Thromboxane A2 / metabolism*

Substances

  • Bridged Bicyclo Compounds
  • Fatty Acids, Monounsaturated
  • Prostaglandins H
  • Receptors, Prostaglandin
  • Receptors, Thromboxane
  • Receptors, Thromboxane A2, Prostaglandin H2
  • S 145
  • Thromboxane A2