CAS Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China.
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China.
Molecules. 2019 Jan 21;24(2):375. doi: 10.3390/molecules24020375.
A turn-on florescent probe (probe-KCP) was developed for highly selective detection of thiophenols based on a donor-excited photo-induced electron transfer mechanism. Herein, the synthesis of the probe, a chalcone derivative, through a simple straightforward combination of a carbazole-chalcone fluorophore with a 2,4-dinitrophenyl functional group. In a kinetic study of the probe-KCP for thiophenols, the probe displayed a short response time (30 min) and significant fluorescence enhancement. In selection and competition experiments, the probe-KCP exhibited excellent selectivity for thiophenols over glutathione (GSH), cysteine (Cys), sodium hydrosulfide (NaSH), and ethanethiol (C₂H₅SH) in addition to common anions and metal ions. Using the designed probe, we successfully monitored and quantified thiophenols, which are highly toxic. This turn-on fluorescence probe features a remarkably large Stokes shift (130 nm) and a short response time (30 min), and it is highly selective and sensitive (160-fold) in the detection of thiophenols, with marked fluorescence in the presence of thiophenols. probe-KCP responds to thiophenols with a good range of linearity (0⁻15 μM) and a detection limit of 28 nM (R² = 0.9946) over other tested species mentioned including aliphatic thiols, thiophenol analogues, common anions, and metal ions. The potential applications of this carbazole-chalcone fluorescent probe was successfully used to determine of thiophenols in real water samples and living cells with good performance and low cytotoxicity. Therefore, this probe has great potential application in environment and biological samples.
一种开环荧光探针（probe-KCP）被开发出来，用于基于供体激发光诱导电子转移机制的高选择性检测硫酚。在本文中，通过将咔唑-查尔酮荧光团与 2,4-二硝基苯官能团简单直接地组合，合成了探针，即查尔酮衍生物。在对硫酚的探针-KCP 的动力学研究中，探针显示出短的响应时间（30 分钟）和显著的荧光增强。在选择性和竞争实验中，探针-KCP 对硫酚表现出优异的选择性，对谷胱甘肽（GSH）、半胱氨酸（Cys）、硫氢化钠（NaSH）和乙硫醇（C₂H₅SH）以及常见阴离子和金属离子具有优异的选择性。使用设计的探针，我们成功地监测和定量了高度有毒的硫酚。这种开环荧光探针具有非常大的斯托克斯位移（130nm）和短的响应时间（30 分钟），并且在检测硫酚时具有高度的选择性和灵敏度（160 倍），在存在硫酚时具有明显的荧光。probe-KCP 对硫酚的响应具有良好的线性范围（0⁻15μM）和检测限为 28 nM（R²=0.9946），超过了包括脂肪族硫醇、硫酚类似物、常见阴离子和金属离子在内的其他测试物种。这种咔唑-查尔酮荧光探针的潜在应用成功地用于测定实际水样和活细胞中的硫酚，具有良好的性能和低细胞毒性。因此，该探针在环境和生物样品中具有很大的应用潜力。
