Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, PR China.
Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, PR China.
Analyst. 2022 Jun 13;147(12):2712-2717. doi: 10.1039/d2an00623e.
As a common gaseous signaling molecule, hydrogen sulfide (HS) plays a vital role in physiology and pathology. The development of fluorescent probes for detecting HS has attracted widespread attention. However, most of the reported fluorescent probes with nitrobenzoxadiazole (NBD) as the recognition group have been widely used to simultaneously detect biothiols and HS, instead of specifically detecting HS. Herein, a novel NBD-based near-infrared (NIR) fluorescent probe named CX-N for the detection of HS is synthesized. The selectivity of CX-N for HS is significantly higher than that for biothiols and other potential interferences. After reacting with HS, CX-N shows a significant increase in NIR fluorescence (75-fold), large Stokes shift (155 nm) and fast response (4 min). And the possible response mechanism of CX-N to HS is given and confirmed by HPLC and HRMS. Based on the low cytotoxicity of CX-N, it has been used for HS imaging in live cells and zebrafish. More importantly, CX-N has also been successfully applied for the real-time imaging of HS in inflammatory and tumor mice based on its NIR emission, which provides a reliable platform for the specific recognition of HS in complex biological systems.
作为一种常见的气态信号分子，硫化氢 (HS) 在生理和病理中起着至关重要的作用。用于检测 HS 的荧光探针的发展引起了广泛关注。然而，大多数报道的以硝基苯并恶二唑 (NBD) 为识别基团的荧光探针已被广泛用于同时检测生物硫醇和 HS，而不是专门检测 HS。本文合成了一种新型的基于 NBD 的近红外 (NIR) 荧光探针 CX-N，用于检测 HS。CX-N 对 HS 的选择性明显高于生物硫醇和其他潜在干扰物。与 HS 反应后，CX-N 的 NIR 荧光显著增强（75 倍），Stokes 位移大（155nm），响应速度快（4 分钟）。并通过 HPLC 和 HRMS 给出并证实了 CX-N 与 HS 的可能反应机制。基于 CX-N 的低细胞毒性，已将其用于活细胞和斑马鱼中的 HS 成像。更重要的是，CX-N 还基于其近红外发射成功应用于炎症和肿瘤小鼠中 HS 的实时成像，为复杂生物体系中 HS 的特异性识别提供了可靠的平台。
