BOPPY-based novel fluorescent dopamine D2 and D3 receptor ligands

Bioorg Med Chem Lett. 2022 Mar 1:59:128573. doi: 10.1016/j.bmcl.2022.128573. Epub 2022 Jan 19.

Abstract

Dopamine is one of the crucial neurotransmitters in the human brain. Its out-of-range concentration can lead to various neurological diseases with special interest for dopamine D2 and D3 receptor subtypes. Although BODIPY is a highly versatile structural moiety for fluorescence labeling, we have looked out for structurally related pyridine-based moieties. We used BOPPY labelling of well-described D2R/D3R pharmacophores to obtain ligands with moderate to low nanomolar binding affinities as well as low to excellent quantum yields for bright fluorescence ligands. To best of our knowledge, this is the first report on the application of BOPPY fluorophores to GPCR ligands. This approach offers a general applicable way for fluorescence labelling via primary aliphatic amine elements.

Keywords: BOPPY; D(2)R; D(3)R; Dopamine; Fluorescence; Ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Fluorescent Dyes / chemistry*
  • Humans
  • Ligands
  • Molecular Structure
  • Receptors, Dopamine D2 / chemistry*
  • Receptors, Dopamine D3 / chemistry*

Substances

  • Amines
  • Fluorescent Dyes
  • Ligands
  • Receptors, Dopamine D2
  • Receptors, Dopamine D3