摘要/Abstract

生命体内小分子硫醇，如半胱氨酸（Cys）、同型半胱氨酸（Hcy）和谷胱甘肽（GSH），在多种生理和病理过程中发挥重要作用.以氟硼二吡咯（BODIPY）为荧光团，硝基烯烃为识别基团，经三步简单有机合成，构建了一个打开型硫醇荧光探针.密度泛函理论计算结果表明，硝基通过光诱导电子转移（PET）机制淬灭BODIPY荧光.光谱测试结果表明，探针与硫醇发生迈克尔加成反应，响应迅速，选择性好，灵敏度高，对GSH的检测极限低至11×10^-9 mol/L.荧光共聚焦成像结果表明，探针可用于HeLa细胞和斑马鱼内源生物硫醇荧光成像研究.
关键词: 硫醇, 硝基烯烃, 荧光探针, 生物成像
Intracellular small-molecule thiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play pivotal roles in several physiological and pathological processes. A bodipy-nitroolefin-conjugated fluorescent probe based on photoinduced electron transfer (PET) mechanism was designed and successfully constructed. The probe selectively responds to biothiols by Michael addition reaction of the sulfhydryl group to the double bond activated by Nitroolefin moiety and gives an off-on fluorescent response. The fluorescence detection limit for GSH was calculated to be 11×10^-9 mol/L. The results of fluorescence confocal imaging indicated that the probe has appreciable cell permeability and can serve as a fluorescent probe for detecting biothiols in living cells and zebrafish.
Key words: thiol, nitroolefin, fluorescent probe, bioimaging


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