A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish
A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish
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一种新颖且简单的咪唑并[1,2-a]吡啶荧光探针，用于活细胞和斑马鱼中半胱氨酸的灵敏和选择性成像
DOI：
10.1016/j.aca.2019.01.023
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发表时间：
2019
影响因子：
6.2
通讯作者：
Hammock Bruce D
中科院分区：
文献类型：
--
作者：
Zhu Meiqing;Wang Lijun;Wu Xiaoqin;Na Risong;Wang Yi;Li Qing X;Hammock Bruce D
半胱氨酸（Cys）、同型半胱氨酸（Hcy）和谷胱甘肽（GSH）在生物体中起着重要的生理作用。它们的异常水平可以引起和指示各种疾病。设计合成了一种荧光探针2-（咪唑并[1，2-a]吡啶-2-基）苯基丙烯酸酯（IPPA），并通过NMR、FT-IR和HRMS对其进行了表征。对Cys的检测限为0.33 μM。准一级反应速率常数KCys3.18 × 10−3S− 1比KHcy 4.92 × 10−4S −1约高10倍，表明Cys与Hcy是可以区分的。此外，IPPA还具有抗干扰能力强、分子量小、高效低毒、细胞通透性好等特点。它已成功地用于HepG 2细胞和斑马鱼的成像。对小牛血清的荧光响应为该试剂的实际应用提供了有力的证据。因此，IPPA具有很高的生物测定应用潜力。
Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS.IPPAcan selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection ofIPPAfor Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction betweenIPPAand Cys was approximately 10 times that of the reaction betweenIPPAand Hcy (KCys3.18 × 10−3S−1vs KHcy4.92 × 10−4S−1), indicating that Cys can be distinguished from Hcy. In addition,IPPAexhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response ofIPPAfor calf serum are powerful proofs for practical application. Therefore,IPPAhas high potential for bioassay applications.