Key Laboratory of Photochemical Conversion and Optoelectronic Materials and CityU-CAS Joint Laboratory of Functional Materials and Devices, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P.R. China.
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049, P.R. China.
Chem Asian J. 2017 Aug 17;12(16):2098-2103. doi: 10.1002/asia.201700583. Epub 2017 Jul 24.
The development of a fluorescent probe to distinguish between cysteine (Cys) and homocysteine (Hcy) is always a challenge owing to their structural similarity, and the simultaneous detection of Cys and Hcy by utilizing different emission channels is especially difficult. In this work, we designed and synthesized a new fluorescent probe to differentiate between Cys and Hcy on the basis of a coumarin derivative with a chlorine atom and an α,β-unsaturated aldehyde. Cys and Hcy induced different cascade reactions with the probe, which led to different products with distinct photophysical properties. The nonfluorescent probe responded to Cys and emitted strong blue fluorescence, whereas it reacted with Hcy and generated yellow fluorescence without interference from glutathione. In addition, the probe was successfully applied to distinguish between Cys and Hcy in living cells.
开发一种能够区分半胱氨酸 (Cys) 和高半胱氨酸 (Hcy) 的荧光探针一直是一个挑战，因为它们的结构相似，并且利用不同的发射通道同时检测 Cys 和 Hcy 尤其困难。在这项工作中，我们设计并合成了一种基于带有氯原子和α,β-不饱和醛的香豆素衍生物的新型荧光探针，以区分 Cys 和 Hcy。Cys 和 Hcy 与探针诱导不同的级联反应，生成具有不同光物理性质的不同产物。非荧光探针对 Cys 有响应并发出强蓝色荧光，而与 Hcy 反应则生成黄色荧光，不受谷胱甘肽的干扰。此外，该探针成功地应用于活细胞中 Cys 和 Hcy 的区分。
