摘要
基于迈克尔(Michael)加成反应机理,设计合成了一种简单的亚硫酸盐荧光探针(E)-3-乙基-1,1-二甲基-2-(2-(5-(4-硝基苯基)呋喃-2-基)乙烯基)-^(1)H-苯并[e]吲哚碘化物(NFBI),核磁共振氢谱(^(1)H NMR)、核磁共振碳谱(^(13)C NMR)和高分辨质谱图(HRMS)验证其结构。NFBI在磷酸盐:N,N-二甲基甲酰胺(PBS:DMF,1∶1,V∶V,pH 7.4)溶液中通过荧光信号“on-off”的变化快速识别SO_(2),且颜色由橙红色变为无色,借助^(1)H NMR和HRMS,研究了探针NFBI识别SO_(2)的机理。结果表明,探针NFBI对SO_(2)具有较快的响应速度(30 s)、较高的灵敏度和良好的选择性。更重要的是,探针NFBI具有低毒性和良好的膜通透性,能够可视化检测活细胞和斑马鱼中的SO_(2)。
Based on the Michael addition mechanism,(E)-3-ethyl-1,1-dimethyl-2-(2-(5-(4-nitrophenyl)furan-2-yl)vinyl)-1H-benzo[e]indole derivative(NFBI)was synthesized,and its structure was verified by^(1)H hydrogen magnetic resonance(^(1)H NMR),^(13)C NMR and high resolution mass spectrometry(HRMS).In the solution of PBS∶DMF(1∶1,V∶V,pH 7.4),NFBI can quickly recognize SO_(2) by the“on-off”change of fluorescence signal,and the color of the solution changed from orange red to colorless.The mechanism of SO_(2) recognition by NFBI probe was studied by NMR and HRMS.Notably,the probe NFBI has fast response time(30 s),high sensitivity and significant selectivity.The probe NFBI can detect SO_(3)^(2-) in living A549 cells and living zebrafish larvae.More importantly,the NFBI probe has low toxicity and good membrane permeability,and can visually detect SO_(2) in living cells and zebrafish.
作者
曹小燕
路宏朝
田光辉
任传清
CAO Xiaoyan;LU Hongzhao;TIAN Guanghui;REN Chuanqing(Key Laboratory of Catalysis in Shaanxi Province,College of Chemical and Environment Sciences,Shaanxi University of Technology,Hanzhong 723001,China;School of Biological Science and Engineering,Shaanxi University of Technology,Hanzhong 723001,China)
出处
《分析试验室》
EI
CAS
CSCD
北大核心
2022年第7期794-800,共7页
Chinese Journal of Analysis Laboratory
基金
陕西省教育厅重点实验室项目(20JS016)资助。
关键词
荧光探针
二氧化硫
裸眼识别
生物成像
fluorescent probe
sulfur dioxide
naked-eye recognition
bioimaging
