A Versatile Sub-Nanomolar Fluorescent Ligand Enables NanoBRET Binding Studies and Single-Molecule Microscopy at the Histamine H3 Receptor

J Med Chem. 2021 Aug 12;64(15):11695-11708. doi: 10.1021/acs.jmedchem.1c01089. Epub 2021 Jul 26.

Abstract

The histamine H3 receptor (H3R) is considered an attractive drug target for various neurological diseases. We here report the synthesis of UR-NR266, a novel fluorescent H3R ligand. Broad pharmacological characterization revealed UR-NR266 as a sub-nanomolar compound at the H3R with an exceptional selectivity profile within the histamine receptor family. The presented neutral antagonist showed fast association to its target and complete dissociation in kinetic binding studies. Detailed characterization of standard H3R ligands in NanoBRET competition binding using UR-NR266 highlights its value as a versatile pharmacological tool to analyze future H3R ligands. The low nonspecific binding observed in all experiments could also be verified in TIRF and confocal microscopy. This fluorescent probe allows the highly specific analysis of native H3R in various assays ranging from optical high throughput technologies to biophysical analyses and single-molecule studies in its natural environment. An off-target screening at 14 receptors revealed UR-NR266 as a selective compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites / drug effects
  • Bioluminescence Resonance Energy Transfer Techniques*
  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • HEK293 Cells
  • Histamine H3 Antagonists / chemical synthesis
  • Histamine H3 Antagonists / chemistry
  • Histamine H3 Antagonists / pharmacology*
  • Humans
  • Ligands
  • Molecular Structure
  • Receptors, Histamine H3 / metabolism*
  • Single Molecule Imaging*
  • Structure-Activity Relationship

Substances

  • Fluorescent Dyes
  • Histamine H3 Antagonists
  • Ligands
  • Receptors, Histamine H3