A mitochondria-targeted turn-on fluorescent probe for the detection of glutathione in living cells

A novel turn-on red fluorescent BODIPY-based probe (Probe 1) for the detection of glutathione was developed. Such a probe carries a para-dinitrophenoxy benzyl pyridinium moiety at the meso position of a BODIPY dye as self-immolative linker. Probe 1 responds selectively to glutathione with the detection limit of 109nM over other amino acids, common metal ions, reactive oxygen species, reactive nitrogen species, and reactive sulfur species. A novel electrostatic interaction to modulate the SNAr attack of glutathione was believed to play significant role for the observed selective response to glutathione. The cleavage of dinitrophenyl ether by glutathione leads to the production of para-hydroxybenzyl moiety which is able to self-immolate through an intramolecular 1,4-elimination reaction to release the fluorescent BODIPY dye. The low toxic probe has been successfully used to detect mitochondrial glutathione in living cells. A novel turn-on red fluorescent BODIPY-based probe (Probe 1) for the detection of GSH wes developed. Such a probe carrys a para-dinitrophenoxy benzyl pyridinium moiety at meso position as self-immolative linker. A novel electrostatic interaction to modulate the SNAr attack of GSH was believed to play significant role for the observed selective response to GSH. Such a probe is low toxic and has been successfully used to detect mitochondrial GSH in living cells. [Display omitted] •A novel turn-on red fluorescent BODIPY-based probe for the detection of GSH was developed.•The probe carries a para-dinitrophenoxy benzyl pyridinium moiety at the meso position of a BODIPY dye as self-immolative linker.•The probe displayed sensitivity and selectivity for GSH.•The probe have been used to detect mitochondrial GSH in living cells.