State Key Laboratory of Coordination Chemistry, State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China.
Analyst. 2019 Feb 25;144(5):1696-1703. doi: 10.1039/c8an01950a.
In this paper, we introduced a new strategy for converting aggregation-induced emission (AIE) to fluorescence emission in solution into the rational design of new fluorescent probes. Two fluorescent probes based on this strategy, namely, PDAM-Lyso and PDAM-Me, have been synthesized and tested both in vitro and in vivo. The fluorophores of the two probes are both phenothiazine molecules, which link to the diaminomaleonitrile (DAMN) moiety through imine bonds. In the presence of imine bonds, the probes emit red fluorescence in an aqueous solution caused by the AIE effect. As the imine bonds are selectively cut-off by HClO, the DAMN moiety gets removed, inducing blue fluorescence of the reaction product. In this way, the selectivity of the DAMN-based probes toward HClO against metal ions and other reactive oxygen species (ROS) was successfully improved. The imaging of endogenous and exogenous HClO with these two probes reveals that lysosome-targeting probes are of great advantage in the detection of natively generated HClO. Furthermore, the imaging of endogenous HClO in zebrafish suggests that PDAM-Lyso is capable of monitoring the generation of HClO in vivo, illustrating that this strategy is of great significance in designing new probes.
在本文中，我们介绍了一种新策略，即将聚集诱导发光（AIE）在溶液中的荧光发射转化为新荧光探针的合理设计。基于该策略合成了两种荧光探针，即 PDAM-Lyso 和 PDAM-Me，并在体外和体内进行了测试。这两种探针的荧光团都是吩噻嗪分子，通过亚胺键与二氨基马来腈（DAMN）部分连接。在亚胺键存在的情况下，探针在水溶液中发射红色荧光，这是由于 AIE 效应引起的。随着亚胺键被 HClO 选择性切断，DAMN 部分被去除，诱导反应产物的蓝色荧光。通过这种方式，成功提高了 DAMN 基探针对 HClO 相对于金属离子和其他活性氧（ROS）的选择性。使用这两种探针对内源性和外源性 HClO 的成像表明，溶酶体靶向探针在检测天然产生的 HClO 方面具有很大的优势。此外，在斑马鱼中内源性 HClO 的成像表明 PDAM-Lyso 能够监测体内 HClO 的产生，这表明该策略在设计新探针方面具有重要意义。
