基于香豆素的比率荧光传感器对同型半胱氨酸/半胱氨酸的检测及生物成像
收稿日期: 2019-04-09
修回日期: 2019-05-14
网络出版日期: 2019-06-06
基金资助
国家自然科学基金(21704032);湖北省自然科学基金(2018CFB454);“机电汽车”湖北省优势特色学科群开放基金资助项目(XKQ2019038)
Ratiometric Fluorescent Probe for Homocysteine and CysteineBased on the Aldehyde Functionalized Coumarin and SuccessfulBioimaging Application
Received date: 2019-04-09
Revised date: 2019-05-14
Online published: 2019-06-06
Supported by
Project supported by the National Natural Science Foundation of China(21704032);The Natural Science Foundation of Hubei Province(2018CFB454);The Hubei Superior and Distinctive Discipline Group of “Mechatronics and Automobiles”(XKQ2019038)
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.
程晓红 , 徐可 , 屈少华 , 阮志军 . 基于香豆素的比率荧光传感器对同型半胱氨酸/半胱氨酸的检测及生物成像[J]. 有机化学, 2019 , 39(10) : 2835 -2842 . DOI: 10.6023/cjoc201904020
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.
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