Highly Selective and Potent α4β2 nAChR Antagonist Inhibits Nicotine Self-Administration and Reinstatement in Rats

J Med Chem. 2017 Dec 28;60(24):10092-10104. doi: 10.1021/acs.jmedchem.7b01250. Epub 2017 Dec 13.

Abstract

The α4β2 nAChR is the most predominant subtype in the brain and is a well-known culprit for nicotine addiction. Previously we presented a series of α4β2 nAChR selective compounds that were discovered from a mixture-based positional-scanning combinatorial library. Here we report further optimization identified highly potent and selective α4β2 nAChR antagonists 5 (AP-202) and 13 (AP-211). Both compounds are devoid of in vitro agonist activity and are potent inhibitors of epibatidine-induced changes in membrane potential in cells containing α4β2 nAChR, with IC50 values of approximately 10 nM, but are weak agonists in cells containing α3β4 nAChR. In vivo studies show that 5 can significantly reduce operant nicotine self-administration and nicotine relapse-like behavior in rats at doses of 0.3 and 1 mg/kg. The pharmacokinetic data also indicate that 5, via sc administration, is rapidly absorbed into the blood, reaching maximal concentration within 10 min with a half-life of less than 1 h.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood-Brain Barrier / drug effects
  • Drug Evaluation, Preclinical / methods
  • Drug-Seeking Behavior / drug effects
  • Male
  • Nicotine / administration & dosage*
  • Nicotinic Antagonists / chemistry*
  • Nicotinic Antagonists / pharmacokinetics
  • Nicotinic Antagonists / pharmacology*
  • Rats, Sprague-Dawley
  • Receptors, Nicotinic* / metabolism
  • Reinforcement, Psychology
  • Self Administration
  • Structure-Activity Relationship

Substances

  • Nicotinic Antagonists
  • Receptors, Nicotinic
  • nicotinic receptor alpha4beta2
  • Nicotine