Coumarin-based fluorescent probes for dual recognition of copper(II) and iron(III) ions and their application in bio-imaging

Sensors (Basel). 2014 Jan 13;14(1):1358-71. doi: 10.3390/s140101358.

Abstract

Two new coumarin-based "turn-off" fluorescent probes, (E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu²⁺ and Fe³⁺ ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin (3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10⁻⁵ M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu²⁺ and Fe³⁺ ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Tracking
  • Copper / chemistry
  • Coumarins / chemistry*
  • Fluorescence*
  • Fluorescent Dyes
  • Humans
  • Hydrogen Peroxide
  • Ions / chemistry
  • Iron / chemistry
  • Molecular Imaging / methods*

Substances

  • Coumarins
  • Fluorescent Dyes
  • Ions
  • Copper
  • coumarin
  • Hydrogen Peroxide
  • Iron