A selective glutathione probe based on AIE fluorogen and its application in enzymatic activity assay

Xiaoding Lou; Yuning Hong; Sijie Chen; Chris Wai Tung Leung; Na Zhao; Bo Situ; Jacky Wing Yip Lam; Ben Zhong Tang

doi:10.1038/srep04272

A selective glutathione probe based on AIE fluorogen and its application in enzymatic activity assay

Sci Rep. 2014 Mar 7:4:4272. doi: 10.1038/srep04272.

Authors

Xiaoding Lou¹, Yuning Hong², Sijie Chen³, Chris Wai Tung Leung³, Na Zhao³, Bo Situ³, Jacky Wing Yip Lam³, Ben Zhong Tang⁴

Affiliations

¹ 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].
² 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].
³ 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.
⁴ 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] Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Enzyme Activation
Enzyme Assays / methods*
Fluorescent Dyes* / chemistry
Glutathione / chemistry
Glutathione / metabolism*
Glutathione Reductase / metabolism
HeLa Cells
Humans
Kinetics

Substances

Fluorescent Dyes
Glutathione Reductase
Glutathione