A novel coumarin-thiazole conjugated ICT fluorescent probe for cysteine specific detection in food samples, living cells and zebrafish

IF 1.2 4区 化学 Q4 CHEMISTRY, ANALYTICAL
Xiaoyan CAO, Yifan WEI, Yingyue DING, Yichi ZHANG, Chuanqing REN, Qin WANG
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引用次数: 0

Abstract

Inspired by the advantageous properties of coumarin and thiazole fluorophores, we rationally designed and developed a novel coumarin-thiazole conjugated fluorescent probe (PC), featuring an acryloyl ester group as the triggering and responding entity for the specific identification of cysteine (Cys). Probe PC exhibited a distinct color change (colorless to bright green), a large Stokes shift, excellent sensitivity, high selectivity, and strong anti-interference capabilities. the density function theory (DFT), high-resolution mass spectrometry (HRMS), and proton nuclear magnetic resonance (1H NMR) assays further affirmed that the response mechanism encompasses an addition-cyclization reaction between the acryloyl domain of probe PC and the sulfhydryl and amino entities of Cys, engendering the liberation of a lustrous green fluorescent chromophore (PCOH) that can be visually discerned. Compared with previous reports, this is a new scaffold based on coumarin that achieves the quantitative determination of Cys in different food matrices in real-time. Furthermore, probe PC is effectively employed for visual imaging of Cys in A549 cells and five-day-old zebrafish, exhibiting low cytotoxicity and favorable cellular permeability, which demonstrated its practical application.
一种新型香豆素-噻唑偶联ICT荧光探针,用于食品样品、活细胞和斑马鱼中半胱氨酸的特异性检测
受香豆素和噻唑荧光团的优势特性启发,我们合理设计并开发了一种新型的香豆素-噻唑共轭荧光探针(PC),该探针以丙烯酰酯基为触发和响应实体,对半胱氨酸(Cys)进行特异性鉴定。探针PC表现出明显的颜色变化(无色到亮绿色),Stokes位移大,灵敏度好,选择性高,抗干扰能力强。密度泛函理论(DFT)、高分辨率质谱分析(HRMS)和质子核磁共振(1H NMR)进一步证实了响应机制包括探针PC的丙烯基结构域与Cys的巯基和氨基实体之间的加成-环化反应,从而释放出具有光泽的绿色荧光发色团(PCOH)。与以往报道相比,这是一种基于香豆素的新型支架,实现了不同食物基质中Cys的实时定量测定。此外,探针PC有效地用于A549细胞和5日龄斑马鱼的Cys视觉成像,具有低细胞毒性和良好的细胞通透性,证明了其实际应用价值。
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来源期刊
CiteScore
3.60
自引率
25.00%
发文量
17223
审稿时长
35 days
期刊介绍: Chinese Journal of Analytical Chemistry(CJAC) is an academic journal of analytical chemistry established in 1972 and sponsored by the Chinese Chemical Society and Changchun Institute of Applied Chemistry, Chinese Academy of Sciences. Its objectives are to report the original scientific research achievements and review the recent development of analytical chemistry in all areas. The journal sets up 5 columns including Research Papers, Research Notes, Experimental Technique and Instrument, Review and Progress and Summary Accounts. The journal published monthly in Chinese language. A detailed abstract, keywords and the titles of figures and tables are provided in English, except column of Summary Accounts. Prof. Wang Erkang, an outstanding analytical chemist, academician of Chinese Academy of Sciences & Third World Academy of Sciences, holds the post of the Editor-in-chief.
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