Fluorescent push-pull pH-responsive probes for ratiometric detection of intracellular pH

Org Biomol Chem. 2014 Jun 14;12(22):3641-8. doi: 10.1039/c4ob00147h. Epub 2014 Apr 23.

Abstract

A family of fluorescent push-pull pH-responsive probes based on 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran as a strong electron acceptor group is described. Small structural variations allow obtaining pK(a) ranging from 4.8 to 8.6, underlining the role of the substituent in modulating the acidic properties. Remarkable changes in the optical properties (in particular the fluorescence intensity ratios) were observed as a function of pH. The most interesting probes with pK(a) close to neutrality were used for ratiometric imaging of intracellular pH.

MeSH terms

  • Fluorescent Dyes / metabolism*
  • HeLa Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Intracellular Space / metabolism*
  • Microscopy, Confocal
  • Molecular Probe Techniques*
  • Spectrometry, Fluorescence

Substances

  • Fluorescent Dyes