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A Pyrene-Based Fluorescent Probe for Specific Detection of Cysteine and its Application in Living Cell

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Abstract

Cysteine (Cys) is an essential amino acid in organism, which is transformed from methionine in vivo and participates in protein synthesis and cell redox process. Therefore, the detection of Cys is of great significance. In this work, a novel fluorescent probe, (E)-3-(2-chloroquinolin-3-yl)-1-(pyren-3-yl) prop-2-en-1-one (PAQ) was designed and synthesized to specifically detect Cys. The response mechanism of the reaction between PAQ and Cys was due to the addition reaction of Cys to α,β-unsaturated ketone of PAQ. Interestingly, the addition of Cys induced significant fluorescence intensity enhancement at 462 nm. PAQ exhibited favorable sensing properties towards Cys such as the low limit of detection (0.27 μM) and fast response speed (2 min). In addition, PAQ displayed high selectivity and anti-interference ability toward Cys among various analytes. Notably, PAQ has been successfully used to image exogenous and endogenous Cys in HeLa cells.

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Availability of Data and Materials

The data and materials used or analysed during the current study are available from the corresponding author on reasonable request.

Funding

The work was supported by the National Natural Science Foundation of China (No. 21472118, 21672131), the Program for the Top Young and Middle-aged Innovative Talents of Higher Learning Institutions of Shanxi (No. 2013802), Talents Support Program of Shanxi Province (No. 2014401), Shanxi Province Outstanding Youth Fund (No. 2014021002), Natural Science Foundation of Shanxi Province of China (No. 201701D121018).

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Authors and Affiliations

  1. Scientific Instrument Center, Shanxi University, Taiyuan, 030006, China

    Jianbin Chao, Zhuo Wang, Ming Li & Yuexiang Duan

  2. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, China

    Zhuo Wang, Ming Li & Yuexiang Duan

  3. Research Institute of Applied Chemistry, Shanxi University, Taiyuan, 030006, China

    Yongbin Zhang & Fangjun Huo

  4. Institute of Molecular Science, Shanxi University, Taiyuan, 030006, China

    Caixia Yin

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  1. Jianbin Chao
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  2. Zhuo Wang
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  6. Ming Li
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Contributions

Jianbin Chao,Yongbin Zhang: contributed to the conception of the study;

Zhuo Wang: performed the experiment;

Jianbin Chao, Zhuo Wang: contributed significantly to analysis and manuscript preparation;

Zhuo Wang: performed the data analyses and wrote the manuscript;

Fangjun Huo, Caixia Yin, Ming Li, Yuexiang Duan: helped perform the analysis with constructive discussions.

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Correspondence to Jianbin Chao.

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Chao, J., Wang, Z., Zhang, Y. et al. A Pyrene-Based Fluorescent Probe for Specific Detection of Cysteine and its Application in Living Cell. J Fluoresc 31, 727–732 (2021). https://doi.org/10.1007/s10895-021-02703-6

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  • DOI: https://doi.org/10.1007/s10895-021-02703-6

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