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De Novo Design of Chemical Stability Near-Infrared Molecular Probes for High-Fidelity Hepatotoxicity Evaluation In Vivo

  • Dan Cheng
    Dan Cheng
    State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
    More by Dan Cheng
  • Juanjuan Peng
    Juanjuan Peng
    State Key Laboratory of Natural Medicines, School of Basic Medical Sciences and Clinical Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 211198, P. R. China
  • Yun Lv
    Yun Lv
    State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
    More by Yun Lv
  • Dongdong Su
    Dongdong Su
    Department of Chemistry and Chemical Engineering, Beijing University of Technology, Beijing 100124, P. R. China
    More by Dongdong Su
  • Dongjie Liu
    Dongjie Liu
    College of Materials Science and Engineering, Hunan University, Changsha 410082, P. R. China
    More by Dongjie Liu
  • Mei Chen
    Mei Chen
    College of Materials Science and Engineering, Hunan University, Changsha 410082, P. R. China
    More by Mei Chen
  • Lin Yuan*
    Lin Yuan
    State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
    *[email protected]
    More by Lin Yuan
  • , and 
  • Xiaobing Zhang
    Xiaobing Zhang
    State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
Cite this: J. Am. Chem. Soc. 2019, 141, 15, 6352–6361
Publication Date (Web):March 22, 2019
https://doi.org/10.1021/jacs.9b01374
Copyright © 2019 American Chemical Society

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    Abstract

    Abstract Image

    Near-infrared (NIR) fluorescence imaging technique is garnering increasing research attention due to various advantages. However, most NIR fluorescent probes still suffer from a false signals problem owing to their instability in real application. Especially in a pathological environment, many NIR probes can be easily destroyed due to the excessive generation of highly reactive species and causing a distorted false signal. Herein, we proposed an approach for developing a new stable NIR dye platform with an optically tunable group to eliminate false signals using the combination of dyes screening and rational design strategy. The conception is validated by the construction of two high-fidelity NIR fluorescent probes (NIR-LAP and NIR-ONOO) sensing leucine aminopeptidase (LAP) and peroxynitrite (ONOO), the markers of hepatotoxicity. These probes (NIR-LAP and NIR-ONOO) were demonstrated to sensitively and accurately monitor LAP and ONOO (detection limit: 80 mU/L for LAP and 90 nM for ONOO), thereby allowing one to precisely evaluate drug-induced hepatotoxicity. In addition, based on the fluctuation of LAP, the therapeutic efficacy of six hepatoprotective medicines for acetaminophen-induced hepatotoxicity was analyzed in vivo. We anticipate the high-fidelity NIR dye platform with an optically tunable group could provide a convenient and efficient tool for the development of future probes applied in the pathological environment.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b01374.

    • Experimental details for experimental methods, dyes/probes synthesis, additional optical spectrum and imaging data (PDF)

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