文献类型：期刊文献

英文题名：A novel p-aminophenylthio- and cyano-substituted BODIPY as a fluorescence turn-on probe for distinguishing cysteine and homocysteine from glutathione

作者：Wang, Qing[1];Wei, Xiaodong[1];Li, Chengjie[1];Xie, Yongshu[1]

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

年份：2018

卷号：148

起止页码：212

外文期刊名：DYES AND PIGMENTS

收录：;EI(收录号：20173804170962);WOS:【SCI-EXPANDED(收录号:WOS:000414106400024)】；

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, and the Fundamental Research Funds for the Central Universities (WK1616004, 222201717003).

语种：英文

外文关键词：Fluorescent probes; Biothiols; BODIPY; Cell imaging

摘要：Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play vital roles in various physiological and pathological processes. In this work, a BODIPY-based fluorescent probe XCN was synthesized from multi-step reactions. We first synthesized a BODIPY derivative with a cyano and a bromine moiety attached to the 8-diphenylaminophenyl substituent of BODIPY, followed by the reaction with p-aminothiophenol under basic condition. Interestingly, compound XCN was successfully obtained with the p-aminophenylthio moiety introduced into one of the a-positions of the pyrrolic units. This reaction may compose an efficient approach for synthesizing novel BODIPY derivatives with substituents attached to the pyrrolic unit without previously brominating it. XCN can be used as a fluorescence turn on probe to selectively detect Cys and Hcy using the cyano group as the recognition site, with the paminophenylthio moiety left unreacted. XCN was found to be nearly nonfluorescent, and it exhibits only slight fluorescence enhancement when treated with GSH. However, upon interaction with Cys or Hcy, the fluorescence was enhanced by 1081 and 1126 folds, respectively. In addition, XCN exhibits good selectivity and sensitivity towards Cys and Hcy over GSH and other amino acids in a wide pH range from 2 to 10 in aqueous buffers. Furthermore, XCN was successfully used for imaging biothiols in living A549 lung cancer cells. (C) 2017 Elsevier Ltd. All rights reserved.