College of Chemistry, Chemical Engineering and Material Science, Soochow University, 199 Ren'Ai Road, Suzhou 215123, China.
Technology School of Radiation Medicine and Protection, Medical College of Soochow University, School for Radiological and Interdisciplinary Sciences (RAD-X), Soochow University, Suzhou 215123, China.
J Mater Chem B. 2021 Mar 17;9(10):2524-2531. doi: 10.1039/d0tb02885a.
To develop a new class of neutral fluorescent dyes with mitochondrial staining capacity, a series of functional dyes were obtained from Nile Red (2a-e) and coumarin (3a-e) with different amide compounds via Suzuki coupling reactions. The Nile Red derivatives (2a-e) emitted red fluorescence (590-660 nm) and coumarin derivatives (3a-e) showed blue emission (455-490 nm) in organic solvents. In addition, they exhibited high fluorescence quantum yields (0.27-0.98) in organic solvents and excellent photostability (>92%). Moreover, all of them possessed low cytotoxicity. More importantly, Nile Red borate (2) and coumarin borate (3) only accumulated in lipid droplets, while after being modified by different amide compounds, dyes 2a-e and 3a-e could successfully target mitochondria in HeLa cancer cells via confocal fluorescence experiments. This work provides a new strategy for the design of neutral cellular probes for mitochondrial staining.
为了开发具有线粒体染色能力的新型中性荧光染料，我们通过 Suzuki 偶联反应，以尼罗红（2a-e）和香豆素（3a-e）为原料，得到了一系列不同酰胺化合物的功能染料。尼罗红衍生物（2a-e）在有机溶剂中发射红色荧光（590-660nm），香豆素衍生物（3a-e）显示蓝色发射（455-490nm）。此外，它们在有机溶剂中的荧光量子产率（0.27-0.98）较高，光稳定性（>92%）良好。而且，它们都具有低细胞毒性。更重要的是，硼酸尼罗红（2）和硼酸香豆素（3）仅在脂滴中积累，而经过不同酰胺化合物修饰后，染料 2a-e 和 3a-e 能够通过共聚焦荧光实验成功靶向 HeLa 癌细胞中的线粒体。这项工作为设计用于线粒体染色的中性细胞探针提供了新的策略。
