A Novel Fluorescence Probe Based on Azamonardine for Detecting and Imaging Cysteine in Cells and Zebrafish with High Selectivity and Sensitivity

被引:1
作者
Zhao, Yixu [1 ,2 ]
Wang, Ting [3 ,4 ]
Abdulkhaleq, Ahmed Mohammed Ali [4 ]
Zuo, Zhongfu [1 ,2 ]
Peng, Yongjin [5 ]
Zhou, Xibin [4 ]
机构
[1] Jinzhou Med Univ, Dept Anat Histol & Embryol, Jinzhou 121001, Peoples R China
[2] Jinzhou Med Univ, Liaoning Key Lab Diabetic Cognit & Percept Dysfunc, Jinzhou 121001, Peoples R China
[3] Kunming Univ Sci & Technol, Fac Life Sci & Technol, Kunming 650500, Peoples R China
[4] Jinzhou Med Univ, Coll Pharm, Jinzhou 121001, Peoples R China
[5] Jinzhou Med Univ, Coll Basic Sci, Jinzhou 121001, Peoples R China
来源
MOLECULES | 2023年 / 28卷 / 17期
关键词
cysteine; fluorescent probe; azamonardine; cellular imaging; TOTAL HOMOCYSTEINE; IN-VITRO; ACID; GLUTATHIONE; DESIGN; SENSOR; URINE; ASSAY;
D O I
10.3390/molecules28176246
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A novel fluorescent probe based on azamonardine (Aza) fluorophore was designed and synthesized for the highly selective detection of cysteine (Cys) in vivo and in vitro. After reacting with acryloyl chloride, the fluorescence of Aza is effectively quenched, resulting in the formation of the Aza-acryl probe. Upon the addition of Cys, the ester bond of Aza-acryl is cleaved, releasing a new compound (Compound 1) with strong fluorescence, thereby achieving fluorescence turn-on detection of Cys. The structure of Aza-acryl was characterized using X-ray crystallography and NMR spectroscopy. Additionally, density functional theory was employed to elucidate the quenching mechanism of the acyl group on the Aza. Aza-acryl exhibits high selectivity towards Cys and distinguishes it from other biothiols such as homocysteine (Hcy) and glutathione (GSH). The mechanism of Aza-acryl for detecting Cys was investigated through HPLC, NMR spectroscopy, high-resolution mass spectrometry, and reaction kinetics experiments. Aza-acryl demonstrates excellent imaging capabilities for Cys in cells and zebrafish, providing a reliable and selectable tool for the detection and imaging of Cys in biological systems.
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页数:17
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