文献类型：期刊文献

英文题名：Combination of pyrrole and pyridine for constructing selective and sensitive Zn2+ probes

作者：Wei, Xiaodong[1,2];Wang, Qing[1,2];Tang, Weiqiang[3];Zhao, Shuangliang[3];Xie, Yongshu[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 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：2017

卷号：140

起止页码：320

外文期刊名：DYES AND PIGMENTS

收录：;EI(收录号：20170503309920);WOS:【SCI-EXPANDED(收录号:WOS:000395212100039)】；

基金：This work was financially supported by NSFC (21472047, 91227201 and 91434110), the Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning (GZ2016006), and the Fundamental Research Funds for the Central Universities (WK1616004).

语种：英文

外文关键词：Dipyrromethanes; Dipyrrins; Fluorescent zinc probes; Cell imaging

摘要：The selective and sensitive detection of zinc ions has been an important research topic because of the vital role played by zinc ions in numerous physiological activities, and fluorescent probes have emerged as effective and powerful tools for zinc detection because of their simplicity andcereal-time monitoring nature. In this work, with the purpose to improve the binding affinities and sensitivities of dipyrrin based fluorescent Zn2+ probes, strongly coordinating pyridyl moieties were introduced into dipyrrins. Aroylation of 5-pentafluorophenyl and 5-unsubstituted dipyrromethanes with picolinoyl chloride afforded two corresponding dipicolinoyl dipyrromethanes, which were further oxidized with 2,3-dichloro-5,6dicyano-1,4-benzoquinone (DDQ) to afford the expected 5-pentafluorophenyl-substituted dipicolinoyl dipyrrin and a unique unexpected dipicolinoyl dipyrrolyl ketone, respectively. Both of these compounds exhibited noticeable fluorescence "turn-on" responses specifically to Zn2+ over other metal cations, with fluorescence enhancements of 87 fold and 119 fold, respectively. However, because of the different substituents at the 5 positions and the different conjugation frameworks, distinct Zn2+ sensing behavior was observed. For the 5-pentafluorophenyl-substituted dipicolinoyl dipyrrin, the sensing of Zn2+ induced a color change from light orange to pink accompanied with enhanced red fluorescence. Whereas, the sensing of Zn2+ by the dipicolinoyl dipyrrolyl ketone induced the color change from nearly colorless to bright yellow and enhanced green fluorescence. Based on high binding affinities and the dramatic spectral responses, both of the probes exhibit high sensitivities towards Zn2+ with detection limits of 9.8 nM and 6.3 nM, respectively. In addition, fast responses within 10 s and wide applicable pH ranges are indicative of their potential applications as promising zinc probes. Finally, the 5pentafluorophenyl dipicolinoyl dipyrrin was successfully applied to cell imaging in Hela cells, demonstrating its practical applicability. It is noteworthy that the single crystal structure of a Zn2+ complex of the dipicolinoyl dipyrrolyl ketone was successfully analyzed by X-ray diffraction, which revealed an interesting tetranuclear Zn2+ coordination structure. These results provide further insights into the design of highly sensitive Zn2+ probes by introducing pyridyl moieties into dipyrrin platforms. (C) 2017 Elsevier Ltd. All rights reserved.