Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play essential roles in many physiological and pathological processes. In this work, three porphyrin derivatives, XQ1, XQ2 and XQ3, were synthesized by combining the porphyrin framework with nitroethylene, bis(methoxycarbonyl)ethylene and dicyanoethylene moieties, respectively. XQ1 was almost nonfluorescent, which could be utilized as a good starting point for developing fluorescence turn-on probes. Thus, XQ1 exhibits fast fluorescence enhancement and high selectivity towards the biothiols based on the Michael addition mechanism. It also exhibits high sensitivity towards the biothiols with the detection limits of 0.65–1.1 μM. In addition, XQ1 was successfully applied to cell imaging in living A549 cells for visualizing the biothiols. The results compose a good example of designing porphyrin derivatives for detecting biothiols, with the advantages of dramatic fluorescence enhancement in the NIR wavelength range, which exhibits good cell membrane permeability and practicability in detecting both exogenous and endogenous biothiols.

半胱氨酸（Cys），高半胱氨酸（Hcy）和谷胱甘肽（GSH）等生物硫醇在许多生理和病理过程中都起着至关重要的作用。在这项工作中，通过将卟啉骨架分别与硝基乙烯，双（甲氧基羰基）乙烯和二氰基乙烯部分结合，合成了三种卟啉衍生物XQ1，XQ2和XQ3。XQ1几乎是无荧光的，可以用作开发荧光开启探针的良好起点。因此，XQ1基于迈克尔加成机理，显示出快速的荧光增强和对生物硫醇的高选择性。它还对生物硫醇具有很高的灵敏度，检出限为0.65–1.1μM。此外，XQ1已成功应用于活A549细胞的细胞成像，以可视化生物硫醇。该结果构成了设计用于检测生物硫醇的卟啉衍生物的一个很好的例子，其优点是在NIR波长范围内荧光显着增强，在检测外源和内源性生物硫醇方面均表现出良好的细胞膜通透性和实用性。