Journal
CHINESE CHEMICAL LETTERS
Volume 31, Issue 11, Pages 2970-2974Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2020.07.001
Keywords
Cysteine; Rearrangement; In vivo imaging; Oxidative stress; Copper(II)
Categories
Funding
- National Natural Science Foundation of China [21775096, 21907062]
- Shanxi Province 1331 Project Key Innovation Team Construction Plan Cultivation Team [2018-CT-1]
- 2018 Xiangyuan County Solid Waste Comprehensive Utilization Science and Technology Project [2018XYSDJS-05]
- Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi [2019L0031]
- Key R&D Program of Shanxi Province [201903D421069]
- Natural Science Foundation of Shanxi Province of China [201901D111015]
- Shanxi Province Foundation for Returness [2017-026]
- Shanxi Collaborative Innovation Center of High Value-added Utilization of Coalrelated Wastes [2015-10-B3]
- Scientific Instrument Center of Shanxi University [201512]
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Cysteine (Cys) plays an important role in regulating cellular redox balance. But due to the constant changes in the concentration of Cys in organisms, fast response sensors are urgent required for practical application. In this work, a fluorescent probe with a fast response was developed by linking coumarin derivatives containing alpha,beta-unsaturated ketones to NBD. The PET effect made the system non-fluorescent. When the probe reacted with Cys, the bond between the coumarin derivative and the NBD was cut off, meanwhile a rapid rearrangement and reactive site passivation occurred. Then two fluorophores with the same emission peak are released, among them, strong fluorescence signal of NBD dominated. Thus, although the similar reaction occurred for Hcy, the rate of NBD derivative rearrangement was slow, in a short time, fluorescence signal was still weak. As for GSH, cleavage could occur, but no rearrange within the NBD molecule due to GSH with large volume. Because of strong fluorescent emission, this probe was successfully used in biological imaging about cell and zebrafish. More importantly, the probe was successfully used to evaluate the oxidative stress caused by copper(II) in living cells. This fluorescence strategy and application will provide a new way of studying intracellular oxidative stress processes and damage. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
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