一种新型简单的咪唑并[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。
A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish.
机构信息
Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou, 450002, China; Key Laboratory of Agri-food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei, 230036, China.
Key Laboratory of Agri-food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei, 230036, China.
出版信息
Anal Chim Acta. 2019 Jun 13;1058:155-165. doi: 10.1016/j.aca.2019.01.023. Epub 2019 Jan 25.
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. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (K 3.18 × 10 Svs K 4.92 × 10 S), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits 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 of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications.
半胱氨酸（Cys）、同型半胱氨酸（Hcy）和谷胱甘肽（GSH）在生物体中发挥着许多至关重要的生理作用。它们的异常水平会导致并指示各种疾病。在本研究中，设计、合成并通过 NMR、FT-IR 和 HRMS 对小分子荧光探针 2-（咪唑并[1,2-a]吡啶-2-基）苯基丙烯酰胺（IPPA）进行了表征。由于荧光强度增强约 76 倍，IPPA 可以选择性地检测 Cys 而不是其他分析物。IPPA 对 Cys 的检测限为 0.33 μM。IPPA 与 Cys 的反应的假一级速率常数约为 IPPA 与 Hcy 的反应的 10 倍（K 3.18×10 S 对 K 4.92×10 S），表明 Cys 可以与 Hcy 区分开来。此外，IPPA 表现出强抗干扰能力、小分子、高效率、低毒性和良好的细胞通透性。它已成功用于 HepG2 细胞和斑马鱼的成像。IPPA 对小牛血清的荧光响应是实际应用的有力证明。因此，IPPA 在生物测定应用中具有很高的潜力。
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