School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, Liaoning Province 114051, PR China.
School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, Liaoning Province 114051, PR China; Key Laboratory for Functional Material, Educational Department of Liaoning Province, University of Science and Technology Liaoning, Anshan, Liaoning Province 114051, PR China.
Methods. 2022 Aug;204:47-54. doi: 10.1016/j.ymeth.2022.04.007. Epub 2022 Apr 18.
Bisulfite (HSO) has been widely used as an important food additive in daily life. Furthermore, a normal amount of HSO plays a significant role in biological systems. However, excessive intake of HSO will lead to a variety of diseases. Therefore, it is of great significance to develop an efficient fluorescent probe that can be used for detection of HSO in biological systems and food samples. In this work, a near-infrared (NIR) emitted fluorescent probe (SZY) based on hemicyanine dye was successfully synthesized and applied to detect HSO in several food samples and live animals. The proposed nucleophilic addition sensing mechanism of SZY towards HSO has been confirmed by H NMR titration, high resolution mass spectrometry (HR-MS) and density functional theory (DFT) theoretical computation. The HSO-induced nucleophilic reaction with α,β-unsaturated CC binding of SZY results in the dramatic decline of the UV-vis absorption and remarkable quenching of the fluorescence emission. SZY features the advantages of near infrared emission (centered at 720 nm), high water solubility (in 98% aqueous solution), fast response time (50 s), large Stokes shift (244 nm) and low cytotoxicity. The probe SZY was successfully applied to image of HSO in live nude mouse and adult zebrafish. Semi-quantitatively analyzing the HSO level by "naked eye" in several food samples including canned fruit, white wine, white sugar and jasmine tea drinks has been realized by the colorimetric method.
亚硫酸氢盐（HSO）在日常生活中被广泛用作一种重要的食品添加剂。此外，适量的 HSO 在生物系统中起着重要作用。然而，过量摄入 HSO 会导致多种疾病。因此，开发一种能够用于检测生物系统和食品样品中 HSO 的高效荧光探针具有重要意义。在这项工作中，成功合成了基于半花菁染料的近红外（NIR）发射荧光探针（SZY），并将其用于检测几种食品样品和活体动物中的 HSO。通过 H NMR 滴定、高分辨率质谱（HR-MS）和密度泛函理论（DFT）理论计算，证实了 SZY 对 HSO 的亲核加成传感机制。HSO 与 SZY 的α,β-不饱和 CC 键的亲核反应导致其紫外-可见吸收显著下降，荧光发射显著猝灭。SZY 具有近红外发射（中心波长为 720nm）、高水溶性（在 98%水溶液中）、快速响应时间（50s）、大斯托克斯位移（244nm）和低细胞毒性的优点。探针 SZY 成功应用于活体裸鼠和成年斑马鱼中 HSO 的成像。通过比色法，实现了对包括罐装水果、白葡萄酒、白糖和茉莉花茶饮料在内的几种食品样品中 HSO 水平的“肉眼”半定量分析。
