文献类型：期刊文献

英文题名：Near-Infrared mitochondria-targeted fluorescent probe for cysteine based on difluoroboron curcuminoid derivatives

作者：Zhang, Peng[1,2];Guo, Zhi-Qian[1,2,3];Yan, Chen-Xu[1,2];Zhu, Wei-Hong[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

年份：2017

卷号：28

期号：10

起止页码：1952

外文期刊名：CHINESE CHEMICAL LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000426222000007)】；

基金：This work was supported by the National Natural Science Foundation of China for Excellent Young Scholars (No. 21622602), Distinguished Young Scholars (No. 21325625), Oriental Scholarship, Fok Ying Tong Education Foundation (No. 142014), the Fundamental Research Funds for the Central Universities 14 (Nos. WJ1616008, WK1013002), the State Key Laboratory of Fine 15 Chemicals (No. KF1509).

语种：英文

外文关键词：Near-infrared; Fluorescent probe; Dual-channel; Cysteine; Curcuminoid

摘要：Curcuminoid difluoroboron has attractive performance as a promising near-infrared (NIR) fluorescent dye. In this contribution, we designed and synthesized a mitochondria-targeted NIR fluorescent probe DFB1 based on difluoroboron curcuminoid scaffold for the detection of Cys (cysteine). DFB1 employs a curcumin analog as the NIR fluorophore, an acrylate group containing alpha, beta-unsaturated ketone as a functional trigger moiety for Cys, and a triphenylphosphonium (TPP) cation moiety for specifically targeting mitochondria. The remarkable shift of DFB1 with Cys was observed from 470 nm to 590 nm in absorption spectra and from 560 nm to 680 nm in emission spectra. Notably, DFB1 manifests significantly dual-channel and turn-on NIR fluorescent signals simultaneously in response to Cys concentration, which make it favorable for monitoring endogenous Cys activity in vivo. This probe has high sensitivity and selectivity for the detection of Cys over homocysteine (Hcy) and glutathione (GSH). This specific response for Cys was based on differences kinetics of intramolecular adduct/cyclizations. More importantly, biological experiments indicated that this probe could be utilized for the detection of endogenous mitochondrial Cys in living cells. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.