基于亲电氯代反应的次氯酸荧光探针构建及细胞成像研究
收稿日期: 2021-01-22
修回日期: 2021-03-15
网络出版日期: 2021-04-06
基金资助
国家自然科学基金(21807077); 山西省自然科学青年基金(201801D221081); 山西省高等学校科技创新(201802100)
A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells
Received date: 2021-01-22
Revised date: 2021-03-15
Online published: 2021-04-06
Supported by
National Natural Science Foundation of China(21807077); Shanxi Provincial Natural Science Foundation for Youths(201801D221081); Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province(201802100)
设计并合成了一种简单的由吩噻嗪-茚酮共轭的新型次氯酸荧光探针PIOCl. 该探针实现了在生理条件下, 基于氯正离子(Cl+)引发独特亲电氯代反应机制的HOCl检测. 实验结果表明, 探针PIOCl对HOCl具有荧光“关-开”型响应, 检测前后荧光强度增加了600多倍, HOCl浓度在0~6.0 μmol/L呈良好的线性关系(R2=0.997), 检测限达1.40 nmol/L. 可实现低至0.25 μmol/L的裸眼检测以及快速响应(<3 s). 通过质谱实验、光谱实验和理论计算验证了 PIOCl对HOCl的识别机理. 利用荧光成像技术, 成功对细胞内源性和外源性HOCl进行了检测, 表明探针PIOCl在生物学上具有潜在的应用前景.
赵云 , 李艳芳 , 李蓉晓 , 王雅卿 , 樊晓霞 . 基于亲电氯代反应的次氯酸荧光探针构建及细胞成像研究[J]. 有机化学, 2021 , 41(5) : 1974 -1981 . DOI: 10.6023/cjoc202101038
A simple phenothiazine-indanone conjugated fluorescent probe PIOCl for HOCl was designed and synthesized. For the first time, a new fluorescent probe for HOCl based on Cl+ induced the unique electrophilic substitution reaction under the physiological conditions. The probe PIOCl was a turn-on response to HOCl, and the fluorescence intensity increased more than 600 times after addition of HOCl. In the range of HOCl concentration from 0 to 6.0 μmol/L, the fluorescence intensity had a good linear relationship with HOCl concentration ( R2=0.997), the detection limit was 1.40 nmol/L, and the naked eye detection as low as 0.25 μmol/L and rapid response (<3 s) can be achieved under 1.0 μmol/L HOCl. The sensing mechanism of probe PIOCl for HOCl was verified by NMR, HRMS and density function theory calculations. Using fluorescence imaging technology, the endogenous and exogenous HOCl has been successfully detected, which indicates that probe PIOCl has potential application prospects in analytical detection and pathological analysis.
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