Scaffold Hopping Toward Agomelatine: Novel 3, 4-Dihydroisoquinoline Compounds as Potential Antidepressant Agents

Sci Rep. 2016 Oct 4:6:34711. doi: 10.1038/srep34711.

Abstract

A scaffold-hopping strategy toward Agomelatine based on in silico screening and knowledge analysis was employed to design novel antidepressant agents. A series of 3, 4-dihydroisoquinoline compounds were selected for chemical synthesis and biological assessment. Three compounds (6a-1, 6a-2, 6a-9) demonstrated protective effects on corticosterone-induced lesion of PC12 cells. Compound 6a-1 also displayed low inhibitory effects on the growth of HEK293 and L02 normal cells and it was further evaluated for its potential antidepressant effects in vivo. The forced swim test (FST) results revealed that compound 6a-1 remarkably reduced the immobility time of rats and the open field test (OFT) results indicated a better general locomotor activity of the rats treated with compound 6a-1 than those with Agomelatine or Fluoxetine. Mechanism studies implied that compound 6a-1 can significantly reduce PC12 cell apoptosis by up-regulation of GSH and down-regulation of ROS in corticosterone-induced lesion of PC12 cells. Meanwhile, the down-regulation of calcium ion concentration and up-regulation of BDNF level in PC12 cells may account for the neuroprotective effects. Furthermore, compound 6a-1 can increase cell survival and cell proliferation, promote cell maturation in the rat hippocampus after chronic treatment. The acute toxicity data in vivo indicated compound 6a-1 exhibited less hepatotoxicity than Agomelatine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemical synthesis
  • Acetamides / pharmacology*
  • Animals
  • Antidepressive Agents / chemical synthesis
  • Antidepressive Agents / pharmacology*
  • Apoptosis / drug effects
  • Blood-Brain Barrier / drug effects
  • Blood-Brain Barrier / metabolism*
  • Brain-Derived Neurotrophic Factor / genetics
  • Brain-Derived Neurotrophic Factor / metabolism
  • Calcium / metabolism
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Corticosterone / antagonists & inhibitors
  • Corticosterone / pharmacology
  • Drug Design
  • Exploratory Behavior / drug effects
  • Gene Expression
  • Hippocampus / cytology
  • Hippocampus / drug effects*
  • Hippocampus / physiology
  • Humans
  • Isoquinolines / chemical synthesis
  • Isoquinolines / pharmacology*
  • Locomotion / drug effects
  • Male
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / pharmacology*
  • PC12 Cells
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Swimming

Substances

  • Acetamides
  • Antidepressive Agents
  • Brain-Derived Neurotrophic Factor
  • Isoquinolines
  • Neuroprotective Agents
  • agomelatine
  • BDNF protein, human
  • Calcium
  • Corticosterone