College of Chemistry and Materials Science, Hubei Engineering University, Hubei, Xiaogan 432100, P. R. China.
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, Tianjin University of Technology, Tianjin, 300384, P. R. China.
J Mater Chem B. 2020 Mar 4;8(9):1914-1921. doi: 10.1039/c9tb02593f.
Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. We were able to use DCQN to instantaneously and quantitatively determine the concentration of HSO3- with high specificity, a low detection limit (24 nM), a large Stokes shift (∼110 nm), and a high contrast ratio. Moreover, DCQN displayed good mitochondrion-targeting abilities and was in situ-activated by HSO3- to produce NIR fluorescence for imaging HSO3- in the mitochondria of live breast cancer cells. Furthermore, DCQN was used to monitor HSO3- in zebrafish with a high contrast ratio.
二氧化硫衍生物密切参与生物体中的一些生理过程，而这些物质的高水平会导致许多疾病。在此，我们通过将 2-(3,5,5-三甲基环己-2-亚基)丙二腈与 3-喹啉甲醛偶联，合理制备了一种线粒体靶向的、原位激活的近红外（NIR）荧光探针（DCQN）。DCQN 显示出 NIR 荧光开启信号，以指示 HSO3-的存在，同时通过 1,4-亲核加成反应从浅黄色到紫色发生相当大的增色效应。我们能够使用 DCQN 以高特异性、低检测限（24 nM）、大斯托克斯位移（∼110nm）和高对比度比来即时且定量地确定 HSO3-的浓度。此外，DCQN 表现出良好的线粒体靶向能力，并通过 HSO3-原位激活以产生 NIR 荧光，用于在活乳腺癌细胞的线粒体中成像 HSO3-。此外，DCQN 用于监测斑马鱼中的 HSO3-，具有高对比度比。
