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SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc
Author(s) -
RiveraFuentes Pablo,
Lippard Stephen J.
Publication year - 2014
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201400014
Subject(s) - cyanine , zinc , fluorophore , fluorescence , chemistry , photochemistry , biocompatibility , aqueous solution , hela , organic chemistry , optics , biochemistry , physics , cell
A reversible, reaction‐based sensor for biological mobile zinc was designed, prepared, and characterized. The sensing mechanism of this probe is based on the zinc‐induced, ring‐opening reaction of spirobenzopyran to give a cyanine fluorophore that emits in the deep‐red region of the electromagnetic spectrum. This probe is not activated by protons and operates efficiently in aqueous solution at pH 7 and high ionic strength. The mechanism of this reaction was studied by using a combination of kinetics experiments and DFT calculations. The biocompatibility of the probe was demonstrated in live HeLa cells.