Facile synthesis, cytotoxicity and bioimaging of Fe(3+) selective fluorescent chemosensor

Bioorg Med Chem. 2014 Apr 1;22(7):2045-51. doi: 10.1016/j.bmc.2014.02.045. Epub 2014 Mar 5.

Abstract

The designing and development of fluorescent chemosensors have recently been intensively explored for sensitive and specific detection of environmentally and biologically relevant metal ions in aqueous solution and living cells. Herein, we report the photophysical results of alanine substituted rhodamine B derivative 3 having specific binding affinity toward Fe(3+) with micro molar concentration level. Through fluorescence titration at 599nm, we were confirmed that ligand 3 exhibited ratiometric fluorescence response with remarkable enhancement in emission intensity by complexation between 3 and Fe(3+) while it appeared no emission in case of the competitive ions (Sc(3+), Yb(3+), In(3+), Ce(3+), Sm(3+), Cr(3+), Sn(2+), Pb(2+), Ni(2+), Co(2+), Cu(2+), Ba(2+), Ca(2+), Mg(2+), Ag(+), Cs(+), Cu(+), K(+)) in aqueous/methanol (60:40, v/v) at neutral pH. However, the fluorescence as well as colorimetric response of ligand-iron complex solution was quenched by addition of KCN which snatches the Fe(3+) from complex and turn off the sensor confirming the recognition process was reversible. Furthermore, bioimaging studies against L-929 cells (mouse fibroblast cells) and BHK-21 (hamster kidney fibroblast), through confocal fluorescence microscopic experiment indicated that ligand showed good permeability and minimum toxicity against the tested cell lines.

Keywords: Bioimaging; Cell permeability; KCN induced fluorescence quenching; Toxicity assay; Turn on fluorescent chemosensor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cell Survival / drug effects
  • Cricetinae
  • Dose-Response Relationship, Drug
  • Ferric Compounds / chemical synthesis
  • Ferric Compounds / chemistry
  • Ferric Compounds / pharmacology*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Hydrogen-Ion Concentration
  • Mice
  • Microscopy, Fluorescence
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Ferric Compounds
  • Fluorescent Dyes