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Design of a Phosphinate‐Based Fluorescent Probe for Superoxide Detection in Mouse Peritoneal Macrophages
Author(s) -
Xu Kehua,
Liu Xia,
Tang Bo,
Yang Guiwen,
Yang Yong,
An Liguo
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600497
Subject(s) - phosphinate , fluorescence , chemistry , selectivity , superoxide , fluorescein , reactive oxygen species , biophysics , reagent , chemiluminescence , confocal microscopy , biochemistry , chromatography , microbiology and biotechnology , biology , organic chemistry , catalysis , physics , fire retardant , quantum mechanics , enzyme
3′,6′‐Bis(diphenylphosphinyl)fluorescein (PF‐1) was synthesized as a highly selective and sensitive fluorescent probe for imaging O 2 .− in living cells. The design strategy for the probe was based on the nucleophilic mechanism of O 2 .− to mediate deprotection of this probe to give fluorescein. Upon reaction with O 2 .− , the probe exhibits a strong fluorescence response and high selectivity for O 2 .− over other reactive oxygen species and some biological compounds. The phosphinate‐based probe, as a new fluorescent reagent, is cell‐permeable and can detect micromolar changes of O 2 .− concentrations by using confocal microscopy in living cells. The unique combination of good selectivity, high sensitivity, good water solubility, and rapid reactivity establishes the potential value of the probe for facilitating investigations of the generation, metabolism, and mechanisms of superoxide‐mediated cellular homeostasis and injury.