Design, synthesis and cellular dynamics studies in membranes of a new coumarin-based "turn-off" fluorescent probe selective for Fe2+

Eur J Med Chem. 2013 Sep:67:60-3. doi: 10.1016/j.ejmech.2013.06.022. Epub 2013 Jun 19.

Abstract

A new coumarin-based 'turn-off' fluorescent probe, 7-(diethylamino)-N-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)-2-oxo-2H-chromene-3-carboxamide (AGD) was synthesized. This compound is highly selective for ferrous ions (Fe(2+)) and can reversibly detect them in aqueous medium. The probe localizes to the cell membrane in living cells, where it can detect changes in Fe(2+) concentration. Molecular dynamics (MD) simulations indicate that AGD interacts with the lipid bilayer at the level of the glycerol moieties.

Keywords: Fe(2+) ion; Fluorescent sensor; Molecular dynamics; Turn-off probes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Membrane / chemistry*
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacokinetics*
  • Drug Design*
  • Ferrous Compounds / analysis*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacokinetics*
  • Humans
  • Models, Molecular
  • Molecular Dynamics Simulation*
  • Molecular Structure
  • Spectrometry, Fluorescence
  • Tissue Distribution

Substances

  • Coumarins
  • Ferrous Compounds
  • Fluorescent Dyes
  • coumarin