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Target-activated and ratiometric photochromic probe for “double-check” detection of toxic thiols in live cells

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Abstract

Photochromic molecules can achieve reversible isomerization upon alternate light irradiations, which offers a great opportunity to improve the precision of analytes detection and imaging in complicated biological environments. Previous reported photochromic probe exhibited only mono-color switching and an initially fluorescence-ON state that may cause high background signal and impose an adverse impact on the desired sensing precision. To overcome this set-back, we developed a novel photochromic probe with an analyte-activation mode for ratiometric sensing of toxic thiols in both real water samples and live cells. The dynamic dual-fluorescence signal is released only after the fast and selective cleavage of the 2,4-dinitrophenyl sulfonate by the targeted thiophenol derivatives. Consequently, a “double-check” with synchronized dual-fluorescence blinking for analyte detection is successfully employed upon alternate light triggers with rapid response (k=7.2×10−2 s−1), high sensitivity (LOD=6.1 nM) as well as selectivity of thiophenol derivatives over other common thiol species (e.g., GSH, Cys and Hcy). The photochromic probe was successfully introduced to the fast and on-site detection of highly toxic thiophenols in real waste water samples. Moreover, by using confocal laser-scanning microscopy (CLSM) and flow cytometric analysis, the potential applications of this ratiometric photochromic probe for trace toxic thiol sensing in live cells are examined.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21788102, 21420102004, 21878086), the Shanghai Rising-Star Program (19QA1402500), Shanghai Municipal Science and Technology Major Project (2018SHZDZX03) and the Program of Introducing Talents of Discipline to Universities (B16017). X. Zhang was financially supported by an award from China Scholarship Council. The authors acknowledged the facilities and assistance of the Queensland Node of the Australian National Fabrication Facility (ANFF-Q), the University of Queensland.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai, 200237, China

    Youxin Fu, Wenhui Wang & Junji Zhang

  2. SHU Center of Green Urban Mining & Industry Ecology, School of Environmental and Chemical Engineering, Shanghai University, Shanghai, 200444, China

    Xing Zhang & Guangren Qian

  3. Australian Institute for Bioengineering and Nanotechnology, The University of Queensland, Brisbane, 4072, Australia

    Xing Zhang

  4. Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, Nijmegen, 6525AJ, the Netherlands

    Feng Cao

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  1. Youxin Fu
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  2. Xing Zhang
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  3. Feng Cao
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  4. Wenhui Wang
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  5. Guangren Qian
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  6. Junji Zhang
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Correspondence to Junji Zhang.

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Conflict of interest The authors declare that they have no conflict of interest.

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Fu, Y., Zhang, X., Cao, F. et al. Target-activated and ratiometric photochromic probe for “double-check” detection of toxic thiols in live cells. Sci. China Chem. 62, 1204–1212 (2019). https://doi.org/10.1007/s11426-019-9490-x

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