Discovery of G Protein-Biased Antagonists against 5-HT7R

J Med Chem. 2021 Sep 23;64(18):13766-13779. doi: 10.1021/acs.jmedchem.1c01093. Epub 2021 Sep 14.

Abstract

5-HT7R belongs to a family of G protein-coupled receptors and is associated with a variety of physiological processes in the central nervous system via the activation of the neurotransmitter serotonin (5-HT). To develop selective and biased 5-HT7R ligands, we designed and synthesized a series of pyrazolyl-diazepanes 2 and pyrazolyl-piperazines 3, which were evaluated for binding affinities to 5-HTR subtypes and functional selectivity for G protein and β-arrestin signaling pathways of 5-HT7R. Among them, 1-(3-(3-chlorophenyl)-1H-pyrazol-4-yl)-1,4-diazepane 2c showed the best binding affinity for 5-HT7R and selectivity over other 5-HTR subtypes. It was also revealed as a G protein-biased antagonist. The self-grooming behavior test was performed with 2c in vivo with Shank3-/- transgenic (TG) mice, wherein 2c significantly reduced self-grooming duration time to the level of wild-type mice. The results suggest that 5-HT7R could be a potential therapeutic target for treating autism spectrum disorder stereotypy.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Autistic Disorder / drug therapy*
  • Drug Design
  • Grooming / drug effects
  • Male
  • Mice, Transgenic
  • Microfilament Proteins / deficiency
  • Microfilament Proteins / genetics
  • Molecular Docking Simulation
  • Nerve Tissue Proteins / deficiency
  • Nerve Tissue Proteins / genetics
  • Pyrazoles / chemical synthesis
  • Pyrazoles / metabolism
  • Pyrazoles / therapeutic use*
  • Receptors, Serotonin / chemistry
  • Receptors, Serotonin / metabolism*
  • Serotonin Antagonists / chemical synthesis
  • Serotonin Antagonists / metabolism
  • Serotonin Antagonists / therapeutic use*

Substances

  • Microfilament Proteins
  • Nerve Tissue Proteins
  • Pyrazoles
  • Receptors, Serotonin
  • Serotonin Antagonists
  • Shank3 protein, mouse
  • serotonin 7 receptor