Novel Functionalized Cannabinoid Receptor Probes: Development of Exceptionally Potent Agonists

J Med Chem. 2021 Apr 8;64(7):3870-3884. doi: 10.1021/acs.jmedchem.0c02053. Epub 2021 Mar 24.

Abstract

We report the development of novel cannabinergic probes that can stabilize the cannabinoid receptors (CBRs) through tight binding interactions. Ligand design involves the introduction of select groups at a judiciously chosen position within the classical hexahydrocannabinol template (monofunctionalized probes). Such groups include the electrophilic isothiocyanato, the photoactivatable azido, and the polar cyano moieties. These groups can also be combined to produce bifunctionalized probes potentially capable of interacting at two distinct sites within the CBR-binding domains. These novel compounds display remarkably high binding affinities for CBRs and are exceptionally potent agonists. A key ligand (27a, AM11245) exhibits exceptionally high potency in both in vitro and in vivo assays and was designated as "megagonist," a property attributed to its tight binding profile. By acting both centrally and peripherally, 27a distinguishes itself from our previously reported "megagonist" AM841, whose functions are restricted to the periphery.

Publication types

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

MeSH terms

  • Analgesics / chemical synthesis
  • Analgesics / metabolism
  • Analgesics / pharmacology
  • Animals
  • Body Temperature Regulation / drug effects
  • CHO Cells
  • Cannabinoid Receptor Agonists / chemical synthesis
  • Cannabinoid Receptor Agonists / metabolism
  • Cannabinoid Receptor Agonists / pharmacology*
  • Cannabinoids / chemical synthesis
  • Cannabinoids / metabolism
  • Cannabinoids / pharmacology*
  • Cricetulus
  • Humans
  • Ligands
  • Locomotion / drug effects
  • Male
  • Mice
  • Molecular Docking Simulation
  • Rats
  • Receptor, Cannabinoid, CB1 / metabolism*
  • Receptor, Cannabinoid, CB2 / metabolism*

Substances

  • Analgesics
  • Cannabinoid Receptor Agonists
  • Cannabinoids
  • Ligands
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2

Grants and funding