Synthesis and biological evaluation of strained unusual amino acid containing tetrapeptides as potential antidepressant agents

Bioorg Chem. 2015 Dec:63:53-7. doi: 10.1016/j.bioorg.2015.09.007. Epub 2015 Sep 30.

Abstract

Strained unusual amino acid derived tetrapeptides were synthesized as mimics of GLYX-13, a clinical candidate for neuroprotective and anti-depressant properties, were studied. The synthesized compounds were screened for neurite growth and anti-depressant properties in vitro and in vivo respectively comparing with the parent GLYX-13 compound. Neurite growth property was assessed by neurite length and anti-depressant property by percentage of immobility in forced swim test, a behavioural assay. Mechanistic insights about protein-ligand interactions were obtained using molecular docking study. Based on the in vitro and in vivo screening data and molecular docking study, a new analogue of GLYX-13, Compound 11a has been found to be as good as the parent compound in all respects.

Keywords: GRIN2B; NMDA receptor; Neurotrophic; Norbornane amino acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / pharmacology*
  • Animals
  • Antidepressive Agents / chemical synthesis
  • Antidepressive Agents / chemistry*
  • Antidepressive Agents / pharmacology*
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Mice
  • Molecular Docking Simulation
  • Molecular Structure
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry*
  • Neuroprotective Agents / pharmacology*
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Antidepressive Agents
  • Neuroprotective Agents
  • Oligopeptides
  • GLYX-13 peptide