首页|基于四苯乙烯的新型黄酮合成、AIE性质和细胞成像

基于四苯乙烯的新型黄酮合成、AIE性质和细胞成像

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四苯乙烯(TPE)是一个典型的聚集诱导发光(AIE)分子.本文基于TPE结构,以1,3-苯二酚为起始原料,合成了一个新的含TPE片段的黄酮化合物(TPF)并进行了结构鉴定,研究了 TPF在不同溶剂和混合溶剂中的光谱学性质.结果显示:TPF在四氢呋喃和水的混合溶剂中,发光强度随含水体积的增加明显增强,含水体积为70%时荧光最强.结合理论计算发现:TPF分子为螺旋桨构型,使其在不良溶剂中发生聚集,使得分子运动受限从而导致荧光增强现象.体外细胞毒性测试结果表明:TPF对HepG2的毒性较低,在40 μM浓度下细胞生存率仍高于85%.另外,TPF能够进入HepG2细胞并用于活细胞内荧光成像.因此TPF可以作为报告基团用于荧光探针的设计.
Synthesis,AIE Properties and Cell Imaging of Novel Tetraphenylethylene-based Flavonoid
Tetraphenylene(TPE)is a typical aggregation-induced emission(AIE)molecule.In this paper,a novel flavonoid(TPF)was synthesized and characterized based on TPE scaffold using 1,3-benzenediol as starting material.The spectroscopic properties of TPF in different solvents and mixed solvents were investigated,and the results showed that the fluorescence intensity(FI)of TPF in mixed solvents of THF and water increased with the increase of volumetric water content,and FI was the strongest in 70%volumetric water content.Based on theoretical calculations,it was found that TPF had propeller configuration,and the aggregation of molecules in poor solvents led to the restriction of the movement and thus led to the AIE phenomenon.In vitro cytotoxicity tests showed that TPF had low toxicity against HepG2,and the cell survival rate was higher than 85%at a concentration of 40 μM.In addition,TPF was able to enter HepG2 cells and be used for fluorescence imaging in living cells.Therefore,TPF can be used as a reporter for the design of fluorescent probes.

flavonoidtetraphenylethylenesynthesisaggregation-induced emissioncellular imaging

赵永梅、谢京娇、杜志涵、罗稳

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河南应用技术职业学院制药工程学院,河南开封 475004

河南大学天然药物创新与转化重点实验室,河南开封 475004

黄酮 四苯乙烯 合成 聚集诱导发光 细胞成像

河南省科技攻关计划项目开封市科技攻关计划项目

2421023104272303062

2024

合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
年,卷(期):2024.32(9)