Deciphering Specificity Determinants for FR900359-Derived Gq α Inhibitors Based on Computational and Structure-Activity Studies

ChemMedChem. 2018 Aug 20;13(16):1634-1643. doi: 10.1002/cmdc.201800304. Epub 2018 Jul 3.

Abstract

Direct targeting of intracellular Gα subunits of G protein-coupled receptors by chemical tools is a challenging task in current pharmacological studies and in the development of novel therapeutic approaches. In this study we analyzed novel FR900359-based analogs from natural sources, synthetic cyclic peptides, as well as all so-far known Gq α inhibitors in a comprehensive study to devise a strategy for the elucidation of characteristics that determine interactions with and inhibition of Gq in the specific FR/YM-binding pocket. Using 2D NMR spectroscopy and molecular docking we identified unique features in the macrocyclic structures responsible for binding to the target protein correlating with inhibitory activity. While all novel compounds were devoid of effects on Gi and Gs proteins, no inhibitor surpassed the biological activity of FR. This raises the question of whether depsipeptides such as FR already represent valuable chemical tools for specific inhibition of Gq and, at the same time, are suitable natural lead structures for the development of novel compounds to target Gα subunits other than Gq .

Keywords: Gα protein inhibitors; Gα proteins; NMR spectroscopy; depsipeptides; macrocyclic peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • CHO Cells
  • Cattle
  • Cricetulus
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry
  • Depsipeptides / metabolism
  • Depsipeptides / pharmacology*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology*
  • GTP-Binding Protein alpha Subunits, Gq-G11 / antagonists & inhibitors*
  • GTP-Binding Protein alpha Subunits, Gq-G11 / chemistry
  • GTP-Binding Protein alpha Subunits, Gq-G11 / metabolism
  • HEK293 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Binding
  • Rats
  • Structure-Activity Relationship

Substances

  • Depsipeptides
  • Enzyme Inhibitors
  • FR900359
  • GTP-Binding Protein alpha Subunits, Gq-G11