高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

基于模块化设计的香豆素-查尔酮探针用于谷胱甘肽的可逆比率检测

王超,曾令涛,张文青,代方方,陈光   

  1. 陕西科技大学 化学与化工学院
  • 收稿日期:2026-01-10 修回日期:2026-03-20 出版日期:2026-04-22 发布日期:2026-04-22
  • 通讯作者: 王超 E-mail:wangchao@sust.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 22174090)、陕西省自然科学基础研究计划项目（批准号: 2024JC-YBMS-138）资助

Coumarin-Chalcone Probes with Modular Design for Reversible Ratiometric Detection of Glutathione

WANG Chao, ZENG Lingtao, ZHANG Wenqing, CAO Xinhui, DAI Fangfang, LIU Yuxia, CHEN Guang   

  1. College of Chemistry and Chemical Engineering, Shaanxi University of Science & Technology
  • Received:2026-01-10 Revised:2026-03-20 Online:2026-04-22 Published:2026-04-22
  • Supported by:
    Supported by the National Natural Science Foundation of China (No.22174090), Natural Science Basic Research Plan in Shaanxi Province (NO. 2024JC-YBMS-138)

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摘要： 本研究基于模块化设计策略，以7-氨基香豆素为荧光母核，2’-羟基查尔酮为GSH的反应中心，并通过在查尔酮苯环5号位引入不同取代基(硝基、甲氧基)作为调控模块，系统调控探针的光物理性质及其与GSH反应的动力学特性，开发了一系列香豆素-查尔酮类可逆型比率荧光探针(探针1~3). 结果表明，所有探针均在生理浓度范围(0~10 mM)内对GSH有良好的比率荧光响应，其解离常数(Kd = 4.61~8.25 mM)适用于细胞内GSH检测. 其中，探针1硝基与酮羰基的协同吸电子效应，使其不仅具有最高的灵敏度与最显著的比率信号变化，对GSH的响应也最为迅速，仅需约5分钟可达平衡，反应速率常数2.54 M-1s-1. 可逆性实验证实探针1对GSH响应还具有最突出的可逆循环特性. 荧光成像研究进一步验证了其对活细胞内GSH比率成像的可行性. 本工作通过理性的调控模块设计，为活细胞GSH动态变化的荧光成像研究提供了性能优异的工具.

关键词: 荧光探针, 香豆素, 查尔酮, 谷胱甘肽

Abstract: Based on a modular design strategy, this study developed a series of coumarin-chalcone-based reversible ratiometric fluorescent probes (Probes 1~3), using 7-aminocoumarin as the fluorophore and 2'-hydroxychalcone as the GSH reaction center. Different substituents (nitro, methoxy) were introduced at the 5-position of the chalcone phenyl ring as modulating modules to systematically tune the photophysical properties and reaction kinetics of the probes towards GSH. The results demonstrated that all probes exhibited a good ratiometric fluorescence response within the physiological concentration range of GSH (0~10 mM), with dissociation constants (Kd = 4.61~8.25 mM) suitable for intracellular GSH detection. Among them, Probe 1, by virtue of the synergistic electron-withdrawing effect of its nitro group and ketone carbonyl, not only displayed the highest sensitivity and the most significant ratiometric signal change, but also responded to GSH most rapidly, reaching equilibrium in approximately 5 minutes with a reaction rate constant of. 2.54 M-1s-1. Reversibility experiments confirmed that Probe 1 also possessed the most prominent reversible cycling characteristics. Fluorescence imaging studies further demonstrated the feasibility of ratiometric fluorescent imaging of GSH within live cells. The rational modular design in this work provides a high-performance tool for fluorescent imaging studies of dynamic GSH changes in living cells.

Key words: Fluorescent probe, Coumarin, Chalcone, Glutathione

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