文献类型：期刊文献

英文题名：An AIE and ICT based NIR florescent probe for cysteine and homocysteine

作者：Bu, Lulu[1,2];Chen, Junqin[1,2];Wei, Xiaodong[1,2];Li, Xin[3];Agren, Hans[3];Xie, Yongshu[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong 130, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong 130, Shanghai 200237, Peoples R China;[3]KTH Royal Inst Technol, Dept Theoret Chem & Biol, SE-10691 Stockholm, Sweden

年份：2017

卷号：136

起止页码：724

外文期刊名：DYES AND PIGMENTS

收录：;EI(收录号：20163902851376);WOS:【SCI-EXPANDED(收录号:WOS:000387837200087)】；

基金：This work was financially supported by NSFC (21472047, 91227201), 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：Fluorescent probes; Biothiols; AIE; ICT; Cell imaging

摘要：A combination of aggregation-induced emission and intramolecular charge transfer was achieved by using a triphenylamine analogue and a dicyanovinyl moiety as the electron donating and accepting units, respectively. Hence, we designed and synthesized a probe with a D-pi-A framework as a near-infrared fluorescence turn-on probe for biothiols (cysteine and homocysteine). Owing to the remarkable intramolecular charge transfer effect as well as intramolecular rotations associated with the donor moiety, the probe exhibits extremely weak fluorescence; which becomes a good starting point for developing fluorescence "turn-on" probes. Upon reaction with cysteine or homocysteine utilizing the dicyanovinyl moiety, the intramolecular charge transfer character was weakened, and the reacting products were observed to aggregate in aqueous solutions, resulting in the aggregation-induced emission effect with red fluorescence at 651 and 656 nm, respectively. Hence, the probe could be used as a fluorescence "turn-on" sensor for cysteine and homocysteine, with the sensing time of less than 4 min and the detection limits of 8.4 mu M and 5.7 mu M towards cysteine and homocysteine, respectively. The probe could distinguish cysteine and homocysteine from glutathione. The sensing mechanism was systematically investigated by employing high resolution mass spectrometry, H-1 NMR and density functional theory calculations as well as checking the solvent viscosity dependent fluorescence, and thus the nucleophilic addition products, the intramolecular charge transfer character, and the aggregation-induced emission behaviour were clearly elucidated. It is noteworthy that the low cytotoxicity, the intrinsic aggregation induced emission nature and near-infrared emissions enable the application of the probe in living cell imaging. (C) 2016 Elsevier Ltd. All rights reserved.