Binding and function of a potent new thromboxane receptor antagonist, BMS 180,291, in human platelets

J Pharmacol Exp Ther. 1993 Mar;264(3):1387-94.

Abstract

Binding and function of BMS 180,291 ([(+)1S-(1 alpha,2 alpha,3 alpha,4 alpha)]-2-[[3-[4-[(n-pentylamino)carbonyl]-2-oxazolyl]-7- oxabicyclo[2.2.1] hept-2-yl]methyl]benzenepropanoic acid]) in human platelets was examined. Kinetic determination of [3H]BMS 180,291 binding produced ligand-receptor association and dissociation rates of 1.4 x 10(7) +/- 0.2 M-1 x min-1 (n = 5) and 0.04 +/- 0.005 min-1 (n = 5), respectively. The resultant Kd was 3.1 +/- 1.1 nM (n = 5). Saturation binding analysis in platelet membranes was consistent with a single class of [3H]BMS 180,291 binding sites with a Kd of 3.6 +/- 0.19 nM (n = 4) and a binding site maxima (Bmax) of 2099.1 +/- 70.3 fmol/mg of protein (n = 4). Specific [3H]BMS 180,291 binding was inhibited by thromboxane A2/endoperoxide receptor antagonists and agonists with a rank order of potency of: BMS 180,291 > or = SQ 29,548 = I-BOP race 15-(1 alpha,2 beta(5Z), 3 alpha(1E,3S),4 alpha) d7-[3-(3-hydroxy-4-(p-iodophenoxy)-1-butenyl)-7- oxabicyclo[2.2.1]hept-2-yl]5-heptenoic acid) > or = BM 13,505 > or = SQ 30,741 = U 44,609 > U 46,619 >> BM 13,177. Prostaglandin E2 and prostacyclin did not appreciably inhibit the specific binding of [3H]BMS 180,291. BMS 180,291 (10 nM-5 microM) shifted the I-BOP-induced platelet shape change curve to the right in a parallel manner without reduction of the maximal response (KB = 13 +/- 3.5 nM; pA2 = 8 +/- 0.2; slope = -1.0 +/- 0.05), whereas 30 nM drug decreased the maximal I-BOP-induced platelet aggregation.(ABSTRACT TRUNCATED AT 250 WORDS)

MeSH terms

  • Biphenyl Compounds / metabolism
  • Biphenyl Compounds / pharmacology
  • Blood Platelets / drug effects
  • Blood Platelets / metabolism*
  • Bridged Bicyclo Compounds / pharmacology
  • Bridged Bicyclo Compounds, Heterocyclic*
  • Fatty Acids, Unsaturated / pharmacology
  • Heptanoic Acids / metabolism
  • Heptanoic Acids / pharmacology
  • Humans
  • Hydrazines / metabolism
  • Hydrazines / pharmacology
  • In Vitro Techniques
  • Kinetics
  • Oxazoles / metabolism*
  • Oxazoles / pharmacology
  • Platelet Aggregation / drug effects
  • Propionates / metabolism*
  • Propionates / pharmacology
  • Receptors, Thromboxane / antagonists & inhibitors*

Substances

  • Biphenyl Compounds
  • Bridged Bicyclo Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Fatty Acids, Unsaturated
  • Heptanoic Acids
  • Hydrazines
  • Oxazoles
  • Propionates
  • Receptors, Thromboxane
  • 7-(3-(3-hydroxy-4-(4'-iodophenoxy)-1-butenyl)-7-oxabicyclo(2.2.1)heptan-2-yl)-5-heptenoic acid
  • SQ 29548
  • ifetroban
  • vapiprost