A novel p-aminophenylthio- and cyano- substituted BODIPY as a fluorescence turn-on probe for distinguishing cysteine and homocysteine from glutathione. (January 2018)

• Record Type: Journal Article
• Authors: Wang, Qing; Wei, Xiaodong; Li, Chengjie; Xie, Yongshu
• Is Part Of: Dyes and pigments. Volume 148(2018)
• Page Start: 212
• Page End: 218
• Publication Date: 2018-01
• Subjects: Fluorescent probes -- Biothiols -- BODIPY -- Cell imaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.09.020
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 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 probeXCN 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, compoundXCN was successfully obtained with the p -aminophenylthio moiety introduced into one of the α-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 p -aminophenylthio 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. Graphical abstract: Highlights: A novel fluorescence turn-on probe based on a BODIPY moiety and a cyano group for discriminating Cys and Hcy from GSH. p -aminophenylthio moiety successfully introduced into one of the α-positions of BODIPY without previously brominating it. A novel biothiol probe based on the cyclization reaction between the cyano group and biothiols.