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Issue 19, 2018
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Synthesis of a BODIPY disulfonate near-infrared fluorescence-enhanced probe with high selectivity to endogenous glutathione and two-photon fluorescent turn-on through thiol-induced SNAr substitution

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Abstract

A BODIPY disulfonate BODIPY-diONs with two-photon fluorescent turn-on effect was 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 reaction was triggered. The red emission of the BODIPY fluorophore at 675 nm was switched on, with a 27-fold emission enhancement in fluorescence intensity. The color of the solution changed from blue to green together with fluorescence appeared within 5 s. The absorbance and emission maxima of the probe BODIPY-diONs were achieved at 650 nm and 675 nm, respectively (quantum yield: 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 turned on, affording an OFF–ON response signal and a strong emission band at 682 nm. Furthermore, for detection of GSH, the chemodosimeter BODIPY-diONs exhibits high sensitivity and excellent anti-interference with low detection limit of 0.17 μM, and it works effectively within a wide pH range. Furthermore, the imaging studies proved that the probe BODIPY-diONs is suitable for the detection of GSH in complete physiological media.

Graphical abstract: Synthesis of a BODIPY disulfonate near-infrared fluorescence-enhanced probe with high selectivity to endogenous glutathione and two-photon fluorescent turn-on through thiol-induced SNAr substitution

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Publication details

The article was received on 26 Dec 2017, accepted on 09 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C7TB03321D
Citation: J. Mater. Chem. B, 2018,6, 3023-3029
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    Synthesis of a BODIPY disulfonate near-infrared fluorescence-enhanced probe with high selectivity to endogenous glutathione and two-photon fluorescent turn-on through thiol-induced SNAr substitution

    X. Xia, Y. Qian and B. Shen, J. Mater. Chem. B, 2018, 6, 3023
    DOI: 10.1039/C7TB03321D

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