The novel therapeutic strategy of vilazodone-donepezil chimeras as potent triple-target ligands for the potential treatment of Alzheimer's disease with comorbid depression

Eur J Med Chem. 2022 Feb 5:229:114045. doi: 10.1016/j.ejmech.2021.114045. Epub 2021 Dec 7.

Abstract

Depression is one of the most frequent comorbid psychiatric symptoms of Alzheimer's disease (AD), and no efficacious drugs have been approved specifically for this purpose thus far. Herein, we proposed a novel therapeutic strategy that merged the key pharmacophores of the antidepressant vilazodone (5-HT1A receptor partial agonist and serotonin transporter inhibitor) and the anti-AD drug donepezil (acetylcholinesterase inhibitor) together to develop a series of multi-target-directed ligands for potential therapy of the comorbidity of AD and depression. Accordingly, 55 vilazodone-donepezil chimeric derivatives were designed and synthesized, and their triple-target activities against acetylcholinesterase, 5-HT1A receptor, and serotonin transporter were systematically evaluated. Among them, compound 5 displayed strong triple-target bioactivities in vitro, low hERG potassium channel inhibition and acceptable brain distribution. Importantly, oral intake of 5 mg/kg of the compound 5 dihydrochloride significantly alleviated the depressive symptoms and ameliorated cognitive dysfunction in mouse models. In brief, these results highlight vilazodone-donepezil chimeras as a prospective therapeutic approach for the treatment of the comorbidity of AD and depression.

Keywords: Alzheimer's disease; Comorbidity; Depression; Multi-target-directed ligands.

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / complications
  • Alzheimer Disease / drug therapy*
  • Animals
  • Antidepressive Agents / chemistry
  • Antidepressive Agents / metabolism
  • Antidepressive Agents / therapeutic use
  • Binding Sites
  • Brain / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / metabolism
  • Cholinesterase Inhibitors / therapeutic use
  • Depression / complications
  • Depression / drug therapy*
  • Donepezil / chemistry*
  • Drug Design
  • Half-Life
  • Humans
  • Ligands
  • Mice
  • Molecular Docking Simulation
  • Rats
  • Rats, Sprague-Dawley
  • Serotonin Plasma Membrane Transport Proteins / chemistry
  • Serotonin Plasma Membrane Transport Proteins / metabolism
  • Structure-Activity Relationship
  • Vilazodone Hydrochloride / chemistry*

Substances

  • Antidepressive Agents
  • Cholinesterase Inhibitors
  • Ligands
  • Serotonin Plasma Membrane Transport Proteins
  • Donepezil
  • Acetylcholinesterase
  • Vilazodone Hydrochloride