Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, No. 2, Beiyijie, Zhongguancun, Haidian District, Beijing 100190, China.
Talanta. 2011 Jan 15;83(3):1050-6. doi: 10.1016/j.talanta.2010.11.023. Epub 2010 Nov 18.
A novel fluorescent probe is designed and synthesized for the determination of cysteine in biological samples by incorporating 2,4-dinitrobenzenesulfonyl (DBS) group as a quencher into the BODIPY skeleton. The BODIPY-based probe itself shows weak fluorescence due to the strong intramolecular charge transfer process. Upon reaction with cysteine, however, the probe produces a rapid and large fluorescence enhancement through the removal of the DBS unit by nucleophilic aromatic substitution. This valuable property leads to the development of a new and simple method for cysteine assay. Under the optimized conditions, the fluorescence enhancement value is directly proportional to the concentration of cysteine in the range 2-12 μM, with a detection limit of 30 nM (S/N=3). The applicability of the developed method has been successfully demonstrated on the determination of non-protein cysteine in human serum. Compared to most of the existing fluorescent probes proposed for cysteine, the BODIPY-based one exhibits an excellent overall performance in terms of selectivity, sensitivity and simplicity.
设计并合成了一种新型荧光探针,通过将 2,4-二硝基苯磺酰基 (DBS) 基团引入 BODIPY 骨架中作为猝灭剂,用于生物样品中半胱氨酸的测定。BODIPY 基探针本身由于强分子内电荷转移过程而表现出微弱的荧光。然而,与半胱氨酸反应后,通过亲核芳香取代去除 DBS 单元,探针产生快速且大幅度的荧光增强。这一有价值的特性为半胱氨酸分析开发了一种新的简单方法。在优化条件下,荧光增强值与胱氨酸浓度在 2-12 μM 范围内呈直接比例关系,检测限为 30 nM(S/N=3)。该方法的适用性已成功应用于人血清中非蛋白半胱氨酸的测定。与大多数已提出的用于半胱氨酸的荧光探针相比,基于 BODIPY 的探针在选择性、灵敏度和简单性方面表现出优异的整体性能。