Lou Xiaoding, Hong Yuning, Chen Sijie, Leung Chris Wai Tung, Zhao Na, Situ Bo, Lam Jacky Wing Yip, Tang Ben Zhong
1] HKUST Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, China [2] Department of Chemistry, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience, and Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong, China [3].
1] Department of Chemistry, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience, and Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong, China [2].
Sci Rep. 2014 Mar 7;4:4272. doi: 10.1038/srep04272.
In this work, we design and synthesize a malonitrile-functionalized TPE derivative (TPE-DCV), which can react with thiol group through thiol-ene click reaction, leading to the fluorescence change of the system. Combined with the unique AIE property, TPE-DCV can selectively detect glutathione (GSH) but not cysteine or homocysteine. As the cleavage of GSSG with the aid of glutathione reductase produces GSH, which turns on the fluorescence of TPE-DCV, the ensemble of TPE-DCV and GSSG can thus serve as a label-free sensor for enzymatic activity assay of glutathione reductase. We also apply TPE-DCV for the detection of intracellular GSH in living cells.
在本工作中,我们设计并合成了一种丙二腈功能化的TPE衍生物(TPE-DCV),其可通过硫醇-烯点击反应与硫醇基团发生反应,从而导致体系的荧光变化。结合独特的聚集诱导发光(AIE)性质,TPE-DCV能够选择性地检测谷胱甘肽(GSH),而不能检测半胱氨酸或高半胱氨酸。由于借助谷胱甘肽还原酶对谷胱甘肽二硫化物(GSSG)的裂解会产生GSH,从而开启TPE-DCV的荧光,因此TPE-DCV与GSSG的组合可作为一种用于谷胱甘肽还原酶酶活性测定的无标记传感器。我们还将TPE-DCV应用于活细胞内GSH的检测。