Citation: Zesi Wang, Jiao Li, Jiao Chen, Zifeng Cao, Hui Li, Yaopeng Cao, Quanquan Li, Mengyao She, Ping Liu, Shengyong Zhang, Jianli Li. A NIR fluorescent probe for imaging thiophenol in the living system and revealing thiophenol-induced oxidative stress[J]. Chinese Chemical Letters, ;2023, 34(8): 108507. doi: 10.1016/j.cclet.2023.108507 shu

A NIR fluorescent probe for imaging thiophenol in the living system and revealing thiophenol-induced oxidative stress

Zesi Wang ^{a, 1} ,
Jiao Li ^{a, 1} ,
Jiao Chen ^{a, b} ,
Zifeng Cao ^a ,
Hui Li ^a ,
Yaopeng Cao ^a ,
Quanquan Li ^{a, c} ,
Mengyao She ^{a, b} ,
Ping Liu ^a ,
Shengyong Zhang ^a ,
Jianli Li ^{a, *,}

a.
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China
b.
Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, Biomedicine Key Laboratory of Shaanxi Province, Lab of Tissue Engineering, College of Life Sciences, Northwest University, Xi'an 710127, China
c.
Shaanxi Key Laboratory of Earth Surface System and Environmental Carrying Capacity, College of Urban and Environmental Sciences, Northwest University, Xi'an 710127, China

lijianli@nwu.edu.cn

Received Date: 7 March 2023
Revised Date: 20 April 2023
Accepted Date: 23 April 2023
Available Online: 28 April 2023

Figures(7)

Thiophenol (PhSH) is an important raw material for organic synthesis, while its high toxicity to organisms makes it an environmental pollutant. Therefore, it is crucial to accurately detect PhSH and explore its metabolic process in the living system. Herein, a near-infrared (NIR) fluorescent probe TEM-FB was developed for sensing PhSH with a turn-on fluorescent signal at 719 nm and a large Stokes shift (198 nm) based on generating the intramolecular charge transfer (ICT) process. TEM-FB shows high specificity and significant sensitivity towards PhSH (detection limit: 10 nmol/L) via the aromatic nucleophilic substitution mechanism. Furthermore, it was successfully applied to image PhSH in multiple cell lines and in zebrafish. Notably, we revealed the oxidative stress process caused by PhSH and demonstrated that the hydrogen peroxide (H₂O₂) in cells would alleviate the poisonousness from exogenous PhSH for the first time. This work provides a promising bioimaging tool for monitoring PhSH in living systems and visualizing the process of oxidative stress induced by PhSH.
- Fluorescent probe,
- Near-infrared,
- Oxidative stress,
- Thiophenol,
- Large Stokes shift,
- Dicyanoisophorone
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