An excited-state intramolecular proton transfer (ESIPT)-based aggregation-induced emission active probe and its Cu(II) complex for fluorescence detection of cysteine
An excited-state intramolecular proton transfer (ESIPT)-based aggregation-induced emission active probe and its Cu(II) complex for fluorescence detection of cysteine
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一种基于激发态分子内质子转移（ESIPT）的聚集诱导发射活性探针及其用于半胱氨酸荧光检测的 Cu(II) 配合物
DOI：
10.1016/j.snb.2019.05.022
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发表时间：
2019-09-01
影响因子：
8.4
通讯作者：
Wu, Fang-Ying
中科院分区：
文献类型：
--
作者：
Fang, Hao;Wang, Ning;Wu, Fang-Ying
本工作基于ESIPT发光原理，通过简单的化学反应合成了一种有效且简单的聚集诱导发射（AIE）活性荧光探针- 2-羟基-1-萘-4-氨基安替比林(1)。在水中表现出较强的荧光增强。通过电镜和计算分析探讨了1的AIE机理。我们证明了分子内氢键和pi-pi堆叠的组合效应赋予了1这样的性质。重要的是，1与铜离子（Cu-1）的系综作为荧光探针，可以在其他干扰物质上对半胱氨酸（Cys）进行高选择性和敏感的开启荧光检测。在最优检测条件下，该探针在Cys浓度范围0 ~ 8 μ M之间具有良好的线性关系，估计Cys的检出限为84 nM。此外，该实验还显示了1对Cu2+和Cys的良好可逆性。由于该探针具有良好的生物相容性，通过CCK-assay评价，最终成功应用于Min6细胞内Cys的成像。
In this work, an effective and simple aggregation-induced emission (AIE) active fluorescent probe based on ESIPT luminescence principle, 2-hydroxy-1-naphthal-4-aminoantipyrine (1), was synthesized via a simple chemical reaction. It displayed strong fluorescence enhancement in water. The AIE mechanism of 1 was explored by electron microscopy and computational analysis. We demonstrate the combination effect of intramolecular hydrogen bonds and pi-pi stacking to endow 1 with such a property. Importantly, the ensemble of 1 with copper ions (Cu-1) as a fluorescent probe enables highly selective and sensitive turn-on fluorescence detection of cysteine (Cys) over other interfering substances. Under optimal detection conditions, this probe has a good linear relationship in the concentration range of Cys between 0 and 8 mu M, and the detection limit of Cys was estimated as 84 nM. Furthermore, this assay exhibits good reversibility of 1 to Cu2+ and Cys. Due to its good biocompatibility evaluated by CCK-assay, the probe Cu-1 was finally applied in imaging of Cys within Min6 cells successfully.