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A novel colorimetric and ratiometric NIR fluorescent sensor for glutathione based on dicyanomethylene-4H-pyran in living cells

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  • SPECIAL TOPIC · Fluorescent Chemical/Biological Sensors and Imaging
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Abstract

Glutathione (GSH) plays a critical role in maintaining oxidation-reduction homeostasis in biological systems. Considering the detection of GSH by fluorescence sensors is limited by either the short wavelength emission or the poor photostability, a highly stable colorimetric and ratiometric NIR fluorescent sensor (DCM-S) for GSH detection has been constructed on the basis of dicyanomethylene-4H-pyran (DCM) chromophore. The specific disulfide bond is incorporated via a carbamate linker as the GSH responsive group, which simultaneously blue-shifts and quenches the fluorescence. Upon addition of GSH, DCM-S exhibits outstanding colorimetric (from yellow to red) and ratiometric fluorescent response with the 6-fold enhancement of NIR fluorescence at 665 nm in quantum yield. More importantly, the GSH-treated DCM-S (DCM-NH2 actually) possesses 20-fold longer fluorescence half-life period as well as much better photostability than the FDA-approved ICG. Finally, the ratiometric detection of GSH is also successfully operated in the living cell imaging, exhibiting NIR fluorescence and large Stokes shift (215 nm) with nearly no background fluorescence interference. As a consequence, DCM-S can be utilized as colorimetric and ratiometric NIR fluorescent sensor for GSH, with a great potential in the development of GSH-induced drug delivery system.

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Authors and Affiliations

  1. Shanghai Key Laboratory of Functional Materials Chemistry, Shanghai, 200237, China

    Xumeng Wu, Andong Shao, Shiqin Zhu, Zhiqian Guo & Weihong Zhu

  2. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai, 200237, China

    Xumeng Wu, Andong Shao, Shiqin Zhu, Zhiqian Guo & Weihong Zhu

  3. East China University of Science and Technology, Shanghai, 200237, China

    Xumeng Wu, Andong Shao, Shiqin Zhu, Zhiqian Guo & Weihong Zhu

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  1. Xumeng Wu
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  2. Andong Shao
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  3. Shiqin Zhu
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  4. Zhiqian Guo
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  5. Weihong Zhu
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Correspondence to Weihong Zhu.

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Wu, X., Shao, A., Zhu, S. et al. A novel colorimetric and ratiometric NIR fluorescent sensor for glutathione based on dicyanomethylene-4H-pyran in living cells. Sci. China Chem. 59, 62–69 (2016). https://doi.org/10.1007/s11426-015-5490-y

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  • DOI: https://doi.org/10.1007/s11426-015-5490-y

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