Inclusion complex of emodin and glycyrrhetinic acid-conjugated-β-cyclodextrin to target liver cells: synthesis, characterization, and bioactivity in vitro and in vivo

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2022-01-03 DOI:10.1007/s10847-021-01123-0

Song-Cu Yu, Yi-Ting Hou, Chin-Mu Hsu, Fuu-Jen Tsai, Yuhsin Tsai

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引用次数: 1

Abstract

The objective of this study is to prepare a novel delivery vector, glycyrrhetinic acid -conjugated-β-cyclodextrin (GA-CD) for liver targeting, and investigate the effects of the emodin-GA-CD inclusion complex (E-GA-CD complex) on liver cancer therapy. GA-CD was synthesized from GA and CD, and was used to encapsulate emodin to form an E-GA-CD complex. Proton nuclear magnetic resonance spectroscopy, two-dimensional rotating-frame Overhauser effect spectroscopy, and differential scanning calorimetry were used to characterize GA-CD and the E-GA-CD complex. Liver cell targeting bioactivity of the E-GA-CD complex was investigated by cellular uptake, cell viability, and biodistribution. In vitro results revealed that the E-GA-CD complex exhibited increased cellular uptake and cytotoxicity against Hep3B cells compared to free emodin. In vivo biodistribution results indicated that mice treated with the E-GA-CD complex exhibited greater emodin uptake in liver tissue than emodin-treated mice, suggesting that the E-GA-CD complex was effective in targeting liver cells.

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大黄素与甘草次酸共轭-β-环糊精靶肝细胞包合物:合成、表征及体内外生物活性

本研究的目的是制备一种新的肝脏靶向递送载体甘草酸共轭-β-环糊精(GA-CD)，并研究大黄素-GA-CD包合物(E-GA-CD复合物)在肝癌治疗中的作用。以GA和CD为原料合成GA-CD，并包封大黄素形成E-GA-CD配合物。采用质子核磁共振谱、二维旋转框架奥弗豪瑟效应谱和差示扫描量热法对GA-CD和E-GA-CD配合物进行了表征。通过细胞摄取、细胞活力和生物分布研究了肝细胞靶向E-GA-CD复合物的生物活性。体外结果显示，与游离大黄素相比，E-GA-CD复合物对Hep3B细胞的细胞摄取和细胞毒性增加。体内生物分布结果表明，与大黄素处理的小鼠相比，E-GA-CD复合物在肝组织中表现出更大的大黄素摄取，这表明E-GA-CD复合物对肝细胞有效。

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science

CiteScore

4.10

自引率

8.70%

发文量

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.