The extracellular entrance provides selectivity to serotonin 5-HT7 receptor antagonists with antidepressant-like behavior in vivo

J Med Chem. 2014 Aug 14;57(15):6879-84. doi: 10.1021/jm500880c. Epub 2014 Aug 5.

Abstract

The finding that ergotamine binds serotonin receptors in a less conserved extended binding pocket close to the extracellular entrance, in addition to the orthosteric site, allowed us to obtain 5-HT7R antagonist 6 endowed with high affinity (Ki=0.7 nM) and significant 5-HT1AR selectivity (ratio>1428). Compound 6 exhibits in vivo antidepressant-like effect (1 mg/kg, ip) mediated by the 5-HT7R, which reveals its interest as a putative research tool or pharmaceutical in depression disorders.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antidepressive Agents / chemical synthesis
  • Antidepressive Agents / chemistry*
  • Antidepressive Agents / pharmacology
  • Body Temperature / drug effects
  • Female
  • Hypothermia / chemically induced
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Isoquinolines / pharmacology
  • Male
  • Mice, Inbred C57BL
  • Molecular Dynamics Simulation
  • Motor Activity / drug effects
  • Receptors, Serotonin / metabolism*
  • Serotonin Antagonists / chemical synthesis
  • Serotonin Antagonists / chemistry*
  • Serotonin Antagonists / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 1-(6-(3,4-dihydroisoquinolin-2(1H)-yl)hex-3-en-1-yl)-1,3-dihydro-2H-indol-2-one
  • Antidepressive Agents
  • Indoles
  • Isoquinolines
  • Receptors, Serotonin
  • Serotonin Antagonists
  • serotonin 7 receptor