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

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 us...

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Bibliographic Details
Published in:Journal of inclusion phenomena and macrocyclic chemistry 2022-04, Vol.102 (3-4), p.339-346
Main Authors: Yu, Song-Cu, Hou, Yi-Ting, Hsu, Chin-Mu, Tsai, Fuu-Jen, Tsai, Yuhsin
Format: Article
Language:English
Subjects:
Biocompatibility
Biodistribution
Biological activity
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Cyclodextrins
Food Science
In vivo methods and tests
Inclusion complexes
Liver
NMR spectroscopy
Organic Chemistry
Original Article
Overhauser effect
Spectrum analysis
Toxicity
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Summary: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.
ISSN:1388-3127
1573-1111
DOI:10.1007/s10847-021-01123-0