New coumarin-based fluorescent melatonin ligands. Design, synthesis and pharmacological characterization

Eur J Med Chem. 2015 Oct 20:103:370-3. doi: 10.1016/j.ejmech.2015.09.003. Epub 2015 Sep 8.

Abstract

The design and synthesis of a series of new fluorescent coumarin-containing melatonin analogues is presented. The combination of high-binding affinities for human melatonergic receptors (h-MT₁R and h-MT₂R) and fluorescent properties, derived from the inclusion of melatonin pharmacophoric elements in the coumarin scaffold, yielded suitable candidates for the development of MT₁R and MT₂R fluorescent probes for imaging in biological media.

Keywords: Bioisosterism; Coumarins; GPCRs fluorescent probes; Melatonin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry*
  • Humans
  • Ligands
  • Melatonin / chemistry*
  • Melatonin / metabolism
  • Molecular Imaging / methods
  • Molecular Structure
  • Receptor, Melatonin, MT1 / chemistry
  • Receptor, Melatonin, MT1 / metabolism*
  • Receptor, Melatonin, MT2 / chemistry
  • Receptor, Melatonin, MT2 / metabolism*
  • Structure-Activity Relationship

Substances

  • Coumarins
  • Fluorescent Dyes
  • Ligands
  • Receptor, Melatonin, MT1
  • Receptor, Melatonin, MT2
  • coumarin
  • Melatonin