基于黄酮的长波长荧光探针用于检测体外和体内生物硫醇
收稿日期: 2022-06-11
修回日期: 2022-08-10
网络出版日期: 2022-09-15
基金资助
河南省科技攻关(212102311030); 河南省科技攻关(222102310671); 河南省教育厅基金(22A350012)
A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo
Received date: 2022-06-11
Revised date: 2022-08-10
Online published: 2022-09-15
Supported by
Key Science and Technology Program of Henan Province(212102311030); Key Science and Technology Program of Henan Province(222102310671); Foundation of Henan Educational Committee(22A350012)
半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)等生物硫醇在生理和病理过程中起着至关重要的作用, 尤其是GSH在肿瘤细胞中过度表达, 可以作为肿瘤的生物标志物. 然而, 同时区分活的正常细胞和肿瘤细胞存在着困难和挑战, 因此设计并合成了一种基于N,N-二甲氨基萘黄酮(3)的肉眼可见“关-开”型长波长荧光探针(4). 该探针对生物硫醇具有较高的选择性和较低的检测限, 机理研究表明, 生物硫醇催化探针的酯键断裂, 生成了强荧光的黄酮3. 该探针可用于活细胞和小鼠体内生物硫醇成像, 并且对正常肝细胞HL-7702和肝癌细胞HepG2进行选择性成像.
周思仪 , 丁旭 , 赵永梅 , 李景华 , 罗稳 . 基于黄酮的长波长荧光探针用于检测体外和体内生物硫醇[J]. 有机化学, 2023 , 43(1) : 178 -185 . DOI: 10.6023/cjoc202206016
Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in physiological and pathological processes. GSH, especially, is overexpressed in numerous types of tumor cells and could be considered as a biomarker. However, owing to the difficulty and challenge in sensing normal and cancer cells simultaneously, it is important to solve this problem in biological processes. Herein, a naked-eye visible, “off-on” long-wavelength fluorescent probe (4) based on N,N-(dimethylamino)naphthalenyl flavone (3) was designed and synthesized. This probe showed high selectivity for biothiols and low detection limits. The mechanism study revealed that biothiols catalyzed the cleavage of the ester bond, and strongly fluorescent flavone 3 was released. Probe 4 could be used for the imaging of biothiols in living cells and mice. In addition, the probe was optimized to achieve the selective imaging of normal hepatocyte HL-7702 and heptocarcinoma cell HepG2.
Key words： long-wavelength; fluorescence probe; flavone; biothiol
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