摘要/Abstract
利用生物硫醇独特的亲核性, 报道了基于香豆素的荧光传感器C1和C2, 可实现对半胱氨酸和同型半胱氨酸的检测. 化合物C1对Hcy/Cys表现出明显的荧光增强响应. 通过结构的微调, 设计并合成了比率荧光传感器C2. 在化合物C2的溶液中加入Hcy/Cys之后, 溶液的最大发射峰蓝移了近100 nm, 最大吸收光谱蓝移了近95 nm. 传感器C2具有较高的选择性, 对Hcy的响应远远大于对Cys、GSH及其他氨基酸的响应. 传感器C2对Hcy有较高的灵敏度, 检出限低达2.8×10 –7 mol/L. 并且, 化合物C2可以穿透细胞膜, 用于HeLa细胞中Hcy的比率荧光成像.
关键词: 化学传感器, 生物硫醇, 比率荧光, 分子内电荷转移, 细胞成像
Novel reactive probes (C1 and C2) towards homocysteine/cysteine (Hcy/Cys) were designed and synthesized, based on the unique nucleophilic nature of bio-thiols. In the presence of Hcy/Cys, probe C1 displayed remarkable fluorescence enhancement. Meanwhile, ratiometric fluorescent probe C2 was designed through subtle structure adjustment. Differently, compound C2 displayed dramatic blue-shift in both fluorescence (100 nm) and absorption (95 nm) spectra upon the addition of Hcy/Cys. By virtue of the specific nucleophilic reaction, probe C2 had outstanding selectivity towards Hcy over Cys, GSH and other amino acids. The detection limit of probe C2 was calculated to be as low as 2.8×10 –7 mol/L. Moreover, C2 was successfully applied to microscopic imaging for the detection of Hcy in HeLa cells with ratiometric fluorescent methods.
Key words: chemosensor, bio-thiols, ratiometric fluorescence, intramolecular charge transfer, cell imaging
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