Na+-dependent high affinity binding of [3H]LY515300, a 3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid receptor inverse agonist

Eur J Pharmacol. 2003 Dec 15;482(1-3):139-50. doi: 10.1016/j.ejphar.2003.09.043.

Abstract

Analogues of 3,4-dimethyl-4-(3-hydroxyphenyl)piperidines are high affinity inverse agonists for micro-, delta- and kappa-opioid receptors. To characterize inverse agonist binding, we synthesized a high specific activity radioligand from this series, [3H]LY515300 (3-[1-((3-cyclohexyl-[3,4-3H(2)])-3(R,S)-hydroxypropyl)-3(R),4(R)-dimethylpiperidin-4-yl]phenol). In membranes expressing cloned human opioid receptors, [3H]LY515300 binding was saturable and exhibited low nonspecific binding. [3H]LY515300 bound with high affinity to the micro- (K(d)=0.07 nM), delta- (K(d)=0.92 nM) and kappa-(K(d)=0.45 nM) opioid receptors. High affinity [3H]LY515300 binding to all opioid receptors was Na(+)-dependent, a characteristic of inverse agonists. Displacement by standard opioid compounds yielded K(i) values consistent with their known opioid receptor affinities. Autoradiographic localization of specific [3H]LY515300 binding in rat and guinea pig brain was high in areas known to express high levels of opioid (particularly micro-opioid receptor) binding sites including the caudate, nucleus accumbens, and nucleus tractus solitarius. Thus, [3H]LY515300 is the first radiolabeled opioid receptor inverse agonist useful for the study of opioid receptors in cell lines and native tissues.

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • CHO Cells
  • Cricetinae
  • Dose-Response Relationship, Drug
  • Guinea Pigs
  • Humans
  • Male
  • Piperidines / chemistry
  • Piperidines / metabolism*
  • Piperidines / pharmacology
  • Protein Binding / drug effects
  • Protein Binding / physiology
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Opioid / agonists*
  • Receptors, Opioid / metabolism*
  • Sodium / metabolism*
  • Sodium / pharmacology
  • Tritium / metabolism

Substances

  • 3,4-dimethyl-4-(3-hydroxyphenyl)piperidine
  • Piperidines
  • Receptors, Opioid
  • Tritium
  • Sodium