A BODIPY disulfonate near-infrared fluorescence-enhanced probe: synthesis, high selectivity to endogenous glutathione and two-photon fluorescent turn-on through thiol-induced SNAr substitution

Xiang Xia, Ying Qian, Baoxing Shen

Index: 10.1039/C7TB03321D

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Abstract

A novel BODIPY disulfonate BODIPY-diONs with two-photon fluorescent turn-on effect has been developed as fluorescence probe for selective detection of glutathione over cysteine and homocysteine. BODIPY-diONs is weakly fluorescent due to the 2, 4-dinitrobenzenesulfonyl quencher group. When GSH was added, a SNAr substitution had been triggered. The red emission of the BODIPY fluorophore at 675 nm is switched on. with an emission enhancement of 27.0 -fold. the color of the solution changed from blue to green together with the fluorescence appeared among 5 s. The absorbance and emission wavelengh of the probe BODIPY-diONs are achieved 650 nm and 675 nm (quantum yield is 0.11). Interestingly, under the sapphire pulsed laser’s 800 nm irradiation, in presence of GSH the two-photon excited fluorescence (TPEF) of probe BODIPY-diONs was turn on, affording an OFF–ON response signal and a strong emssion band at 682 nm. Besides, for detection of GSH, the chemodosimeter BODIPY-diONs exhibits high sensitivity and excellent anti-interference with low detection limit of 0.17 μM, works excellently within a wide pH range. Furthermore, the imaging studies proved that the probe BODIPY-diONs is suitable for the detection of GSH in biological systems for endogenous GSH.