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. 2024 Nov;416(28):6485-6495.
doi: 10.1007/s00216-024-05537-w. Epub 2024 Sep 26.

A near-infrared fluorescent probe with a large Stokes shift for the detection and imaging of biothiols in vitro and in vivo

Zhengjun Wu #  1 , Taotao Zhao #  1 , Xingyue Jiang  1 , Dan Zhang  1 , Feiyi Wang  1 , Xiaoming Ren  1 , Zhao Wang  2 , Erfei Wang  3 , Jun Ren  4
Affiliations

A near-infrared fluorescent probe with a large Stokes shift for the detection and imaging of biothiols in vitro and in vivo

Zhengjun Wu et al. Anal Bioanal Chem. 2024 Nov.

Abstract

In this study, a new near-infrared (NIR) fluorescent turn-on probe featuring a large Stokes shift (198 nm) was developed for the detection of biothiols. The probe was based on a dicyanoisophorone derivative serving as the fluorophore and a 2,4-dinitrobenzenesulfonyl (DNBS) group functioning as both a recognition site and a fluorescence quencher. In the absence of biothiols, the fluorescence of the probe was low due to the photoinduced electron transfer (PET) effect between the fluorophore and DNBS. Upon the presence of biothiols, the DNBS group underwent a nucleophilic aromatic substitution reaction with the sulfhydryl group of biothiols, leading to the release of the fluorophore and a notable emission peak at 668 nm. This developed probe exhibited exceptional selectivity and sensitivity to biothiols in solution, with an impressive detection limit of 28 nM for cysteine (Cys), 22 nM for homocysteine (Hcy), and 24 nM for glutathione (GSH). Furthermore, the probe demonstrated its applicability by successfully visualizing both endogenous and exogenous biothiols in living systems.

Keywords: Bioimaging; Biothiols; Large Stokes shift; Near-infrared fluorescent probe; Oxidative stress.

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References

    1. Chen XQ, Zhou Y, Peng XJ, Yoon J. Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev. 2010;39:2120–35. - PubMed - DOI
    1. Niu LY, Chen YZ, Zheng HR, Wu LZ, Tung CH, Yang QZ. Design strategies of fluorescent probes for selective detection among biothiols. Chem Soc Rev. 2015;44:6143–60. - PubMed - DOI
    1. Chen H, Tang YH, Liu WY. Recent progress in the fluorescent probes for the specific imaging of small molecular weight thiols in living cells. TrAC Trends Anal Chem. 2016;76:166–81. - DOI
    1. Dai JN, Ma CG, Zhang P, Fu YQ, Shen BX. Recent progress in the development of fluorescent probes for detection of biothiols. Dyes Pigm. 2020;177: 108321. - DOI
    1. Yin GX, Niu TT, Yu T, Gan YB, Sun XY, Yin P, Chen HM, Zhang YY, Li HT, Yao SZ. Simultaneous visualization of endogenous homocysteine, cysteine, glutathione, and their transformation through different fluorescence channels. Angew Chem Int Ed. 2019;58:4557–61. - DOI

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