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A near-infrared fluorescent probe based on chloroacetate modified naphthofluorescein for selectively detecting cysteine/homocysteine and its application in living cells

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Abstract

We have prepared a near-infrared (NIR) turn-on fluorescent probe (NFC) based on chloroacetate modified naphthofluorescein for specific detection of cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids (AAs) with the detection limits of 0.30 μM and 0.42 μM, respectively. The fluorescence intensity of the naphthofluorescein (NF) chromophore is modulated by an internal charge transfer (ICT) process. The probe NFC is readily available and weakly fluorescent, but of observably enhanced fluorescence after reacting with Cys or Hcy. We assumed and then demonstrated that the fluorescence off—on process involves a conjugate nucleophilic substitution/cyclization sequence. Furthermore, the probe has been successfully applied for detecting the total content of Cys and Hcy in human plasma and imaging in living cells with low toxicity.

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Authors and Affiliations

  1. Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China

    Jianxi Wang, Wei Liu, Jianjian Zhang, Xinyue Zhu, Xiaoyan Liu & Haixia Zhang

  2. Department of Cell Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000, P. R. China

    Cheng Zhou & Qin Wang

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  1. Jianxi Wang
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  2. Cheng Zhou
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  3. Wei Liu
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  4. Jianjian Zhang
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  5. Xinyue Zhu
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  7. Qin Wang
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  8. Haixia Zhang
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Correspondence to Haixia Zhang.

Additional information

Electronic supplementary information (ESI) available: Detailed procedures, characterization data and additional plots. See DOI: 10.1039/c6pp00219f

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Wang, J., Zhou, C., Liu, W. et al. A near-infrared fluorescent probe based on chloroacetate modified naphthofluorescein for selectively detecting cysteine/homocysteine and its application in living cells. Photochem Photobiol Sci 15, 1393–1399 (2016). https://doi.org/10.1039/c6pp00219f

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