Cellular delivery and enhanced anticancer activity of berberine complexed with a cationic derivative of γ-cyclodextrin

Bioorganic & Medicinal Chemistry
Iwona PopiołekKrzysztof Szczubiałka

Abstract

A cationic derivative of γ-cyclodextrin (GCD) modified with propylenediamine (PDA) was synthesized. It was shown that the derivative (GCD-PDA) is mucoadhesive and resistant to the digestion with ∝-amylase indicating that it may constitute an efficient oral delivery vehicle. GCD-PDA formed an inclusion complex with berberine (BBR), an alkaloid displaying a multitude of beneficial physiological effects. The complexed BBR penetrates a lipid membrane easier than the free one. Both uncomplexed BBR and that complexed with GCD-PDA was delivered to normal (NMuMG) and cancerous (4T1) murine mammary gland cells. In the normal cells both free and complexed BBR was homogeneously dispersed in the cytoplasm and was nontoxic up to 131 μM. In the cancerous cells uncomplexed BBR was also homogeneously dispersed but it was toxic to about 25% of cells at 131 μM, while the GCD-PDA/BBR complex was preferably localized in lysosomes and its toxicity doubled at this concentration compared to that of free BBR. Moreover, free BBR and GCD-PDA/BBR showed even more efficient inhibitory effect against murine melanoma (B16-F10) cells than against 4T1 cells.

Citations

Apr 5, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Solomon Habtemariam
Jun 26, 2020·Drug Design, Development and Therapy·Guanyu LiMing Zhao
Jun 17, 2020·Colloids and Surfaces. B, Biointerfaces·Hossein MajidzadehMichael R Hamblin
Jul 17, 2021·The Journal of Physical Chemistry. B·Goutam ChakrabortyHaridas Pal
Sep 16, 2021·Journal of Food Biochemistry·Moazzama AkbarMuhammad Ajmal Shah
Oct 9, 2021·Current Drug Delivery·Teng Meng Sheng, Palanirajan Vijayaraj Kumar

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