文献类型：期刊文献

英文题名：A novel nitroethylene-based porphyrin as a NIR fluorescence turn-on probe for biothiols based on the Michael addition reaction

作者：Wang, Qing[1,2];Ma, Fangtao[1,2];Tang, Weiqiang[3];Zhao, Shuangliang[3];Li, Chengjie[1,2];Xie, Yongshu[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat & Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Sch Chem Engn, State Key Lab Chem Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2018

卷号：148

起止页码：437

外文期刊名：DYES AND PIGMENTS

收录：;EI(收录号：20173904211541);WOS:【SCI-EXPANDED(收录号:WOS:000414106400050)】；

基金：This work was financially supported by NSFC (21472047, 21772041, 21702062), the Program for Professor of Special Appointment (Eastern Scholar, GZ2016006) at Shanghai Institutions of Higher Learning, Shanghai Pujiang Program (17PJ1401700), and the Fundamental Research Funds for the Central Universities (WK1616004, 222201717003, 222201714013).

语种：英文

外文关键词：Porphyrin; Nitroethylene; Fluorescent biothiol probe; Cell imaging

摘要：Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play essential roles in many physiological and pathological processes. In this work, three porphyrin derivatives, XQ1, XQ2 and XQ3, were synthesized by combining the porphyrin framework with nitroethylene, bis(methoxycarbonyl) ethylene and dicyanoethylene moieties, respectively. XQ1 was almost nonfluorescent, which could be utilized as a good starting point for developing fluorescence turn-on probes. Thus, XQ1 exhibits fast fluorescence enhancement and high selectivity towards the biothiols based on the Michael addition mechanism. It also exhibits high sensitivity towards the biothiols with the detection limits of 0.65 -1.1 mu M. In addition, XQ1 was successfully applied to cell imaging in living A549 cells for visualizing the biothiols. The results compose a good example of designing porphyrin derivatives for detecting biothiols, with the advantages of dramatic fluorescence enhancement in the NIR wavelength range, which exhibits good cell membrane permeability and practicability in detecting both exogenous and endogenous biothiols. (C) 2017 Elsevier Ltd. All rights reserved.