Issue 22, 2014

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

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 pKa 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 pKa close to neutrality were used for ratiometric imaging of intracellular pH.

Graphical abstract: Fluorescent push–pull pH-responsive probes for ratiometric detection of intracellular pH

Supplementary files

Article information

Article type
Paper
Submitted
20 Jan 2014
Accepted
31 Mar 2014
First published
31 Mar 2014

Org. Biomol. Chem., 2014,12, 3641-3648

Author version available

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

M. Ipuy, C. Billon, G. Micouin, J. Samarut, C. Andraud and Y. Bretonnière, Org. Biomol. Chem., 2014, 12, 3641 DOI: 10.1039/C4OB00147H

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