Citation: Na Zhou, Fangjun Huo, Yongkang Yue, Kaiqing Ma, Caixia Yin. Rearrangement regulated cysteine fluorescent probe for cellular oxidative stress evaluation induced by copper(II)[J]. Chinese Chemical Letters, ;2020, 31(11): 2970-2974. doi: 10.1016/j.cclet.2020.07.001 shu

Rearrangement regulated cysteine fluorescent probe for cellular oxidative stress evaluation induced by copper(II)

Na Zhou ^a ,
Fangjun Huo ^b ,
Yongkang Yue ^a ,
Kaiqing Ma ^a ,
Caixia Yin ^{a, *,}

a.
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China
b.
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China

yincx@sxu.edu.cn

Received Date: 12 May 2020
Revised Date: 29 June 2020
Accepted Date: 29 June 2020
Available Online: 15 November 2020

Figures(5)

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 α, β-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.
- Cysteine,
- Rearrangement,
- In vivo imaging,
- Oxidative stress,
- Copper(II)
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