New turn-on fluorescent and colorimetric probe for cyanide detection based on BODIPY-salicylaldehyde and its application in cell imaging

J Hazard Mater. 2016 Aug 15:314:277-285. doi: 10.1016/j.jhazmat.2016.04.001. Epub 2016 Apr 4.

Abstract

Development of cyanide sensor is important as the anion is harmful to human health and the environment. Herein, a new colorimetric and fluorescent probe GSB based on boron dipyrrole-methene (BODIPY) containing salicylaldehyde group for cyanide detection has been reported. GSB undergoes exclusive colorimetric change from orange to colorless and exhibits selective fluorescence turn-on at 504nm upon the addition of cyanide. Other 13 anions give almost no interference under physiological condition. Detection limit of the new cyanide-sensing GSB is 0.88μM, which is below World Health Organization (WHO) recommended level in drinking water. A calculation by density functional theory (DFT) shows suppression of photoinduced electron transfer (PET) mechanism along with the interruption of π-conjugation between salicylaldehyde and BODIPY core by cyanide anion. Cell imaging studies demonstrated that GSB is compatible and capable of sensing cyanide anion in living cells.

Keywords: BODIPY; Colorimetry; Cyanide; Fluorescence; Living cell.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Boron Compounds / chemistry*
  • Colorimetry / instrumentation*
  • Cyanides / chemistry*
  • Fluorescent Dyes
  • Hep G2 Cells
  • Humans

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Aldehydes
  • Boron Compounds
  • Cyanides
  • Fluorescent Dyes
  • salicylaldehyde