The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis

Eur J Med Chem. 2020 Dec 15:208:112858. doi: 10.1016/j.ejmech.2020.112858. Epub 2020 Sep 29.

Abstract

Multiple sclerosis is a chronic inflammatory demyelinating disorder of the central nervous system that eventually leads to progressive neurodegeneration and disability. Recent findings highlighted the emerging role of each target of the endocannabinoid system in controlling the symptoms and disease progression of multiple sclerosis. Therefore, multi-target modulators of the endocannabinoid system could provide a more effective pharmacological strategy as compared to the single target modulation. In this work, N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide (B2) was identified as the most promising compound with dual agonism at cannabinoid receptors type-1 and cannabinoid receptors type-2 and good drug-like properties. In in vitro assays, B2 reduced glutamate release from rat synaptosomes through interaction with cannabinoid receptors type-1 and modulated the production of the pro- and anti-inflammatory cytokines (interleukins IL-1β and IL-6 and interleukin IL-10 respectively) via cannabinoid receptors type-2 activation. Furthermore, B2 demonstrated antinociceptive effects in an animal model of neuropathic pain and efficacy in an experimental autoimmune encephalomyelitis model of multiple sclerosis.

Keywords: 1,2-Dihydropyridine-2-oxo-3-carboxamides; EAE mouse Model multiple sclerosis; Endocannabinoid system; Glutamate release; Microglial cell; Neuropathic pain.

MeSH terms

  • Analgesics / chemical synthesis
  • Analgesics / metabolism
  • Analgesics / therapeutic use*
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / metabolism
  • Anti-Inflammatory Agents / therapeutic use*
  • Female
  • Ligands
  • Male
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Molecular Structure
  • Multiple Sclerosis / drug therapy*
  • Protein Binding
  • Pyridones / chemical synthesis
  • Pyridones / metabolism
  • Pyridones / therapeutic use*
  • Rats, Sprague-Dawley
  • Receptor, Cannabinoid, CB1 / agonists
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / agonists
  • Receptor, Cannabinoid, CB2 / metabolism
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Ligands
  • Pyridones
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2