β and γ-Cyclodextrin dimers: design, characterization and <i>in silico</i> studies to explore the cooperative effect of the cavities

Piana, Luana La; Basile, Livia; Ragusa, Chiara; Milardi, Danilo; Zito, Valeria; Vecchio, Graziella

doi:10.1039/d2nj04649k

New J. Chem.

2023

DOI: 10.1039/d2nj04649k

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β and γ-Cyclodextrin dimers: design, characterization and in silico studies to explore the cooperative effect of the cavities

Luana La Piana

Livia Basile

Chiara Ragusa

et al.

Abstract: Cyclodextrins can encapsulate various molecules and have exciting applications in supramolecular, pharmaceutical, material, food and environmental chemistry. Typically, the encapsulation into the cyclodextrin cavity confers to the guest improved solubility,...

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Cited by 4 publications

References 37 publications

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Cyclodextrin Dimers Functionalized with Biotin as Nanocapsules for Active Doxorubicin Delivery Against MCF‐7 Breast Cell Line

Bognanni,

Scuderi,

Giglio

et al. 2024

ChemMedChem

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Cyclodextrin dimers have been investigated as potential nanocapsules of biomolecules. The presence of two cavities can improve the stability of inclusion complexes, working as a hydrophilic sandwich of poorly water‐soluble species. Here, we designed new β‐ and γ‐cyclodextrin dimers functionalized with biotin as a targeting unit and tested the new bioconjugates as doxorubicin delivery systems in cancer cells. Biotin can recognize the Sodium‐dependent Multivitamin Transporter (SMVT) receptor, encoded by the Solute Carrier Family 5 Member 6 (SLC5A6) gene and improve the uptake of drugs. We evaluated the expression of the SLC5A6 transcript in human cell lines to select the best cell model (MCF‐7) for the in vitro studies.Furthermore, in the cell lines, we investigated the transcript levels of genes correlated to biotin cell availability, Holocarboxylase Synthetase (or HCS encoded by HLCS gene) and Biotinidase (encoded by BTD gene) enzymes. Moreover, the expression of ATP Binding Cassette Subfamily G Member 2 transporter (encoded by ABCG2 gene), which may play a role in doxorubicin resistance, has been investigated. The antiproliferative activity of the doxorubicin complexes with the dimers has been determined to study the effect of the biotin moiety on the cytotoxicity in MCF‐7 cancer cells.

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Cyclodextrin Dimers Functionalized with Biotin as Nanocapsules for Active Doxorubicin Delivery Against MCF‐7 Breast Cell Line

Bognanni,

Scuderi,

Giglio

et al. 2024

ChemMedChem

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Inclusion Complexation of Flavonoids with Cyclodextrin: Molecular Docking and Experimental Study

Ming Liu,

Yun Zhou,

Qiang Jiang

et al. 2024

ChemistrySelect

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In our work, the inclusion ability and binding pattern of flavonoids (catechin, iso‐liquiritigenin, luteolin, puerarin, rutin, and curcumin) with β‐cyclodextrin (β‐CD) and curcumin (CUR) with CDs (α‐CD, β‐CD, γ‐CD, dimethyl‐β‐CD, Hydroxypropyl‐β‐CD, and glucosyl‐β‐CD) were studied by molecular docking. The results showed that CUR among the six flavonoids was more likely to form stable inclusion complexes with β‐CD, and the HP‐β‐CD is the most suitable for CUR inclusion among the 6 types of CD. Phase solubility studies showed that CUR with β‐CD or HP‐β‐CD, respectively, could form stable inclusion complexes in a stoichiometric ratio of 1 : 1. The CUR/β‐CD and CUR/HP‐β‐CD inclusion complexes (ICs) were prepared by freeze‐drying method. The successful preparation of IC was confirmed by SEM images, FT‐IR spectra, and TG‐DSC. The results of in vitro release showed that the release of CUR from IC prepared with β‐CD or HP‐β‐CD could be improved significantly, and the release effect of HP‐β‐CD was better than that of β‐CD. The inclusion with CD could be used to improve the solubility and bioavailability of CUR.

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Carboxymethyl potato starch hydrogels encapsulated cyclodextrin metal-organic frameworks for enantioselective loading of S-naproxen and its programmed release

Zhang,

Yin,

Zuo

et al. 2024

International Journal of Biological Macromolecules

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β and γ-Cyclodextrin dimers: design, characterization and in silico studies to explore the cooperative effect of the cavities

Abstract: Cyclodextrins can encapsulate various molecules and have exciting applications in supramolecular, pharmaceutical, material, food and environmental chemistry. Typically, the encapsulation into the cyclodextrin cavity confers to the guest improved solubility,...

Cited by 4 publications

References 37 publications

Cyclodextrin Dimers Functionalized with Biotin as Nanocapsules for Active Doxorubicin Delivery Against MCF‐7 Breast Cell Line

Cyclodextrin Dimers Functionalized with Biotin as Nanocapsules for Active Doxorubicin Delivery Against MCF‐7 Breast Cell Line

Inclusion Complexation of Flavonoids with Cyclodextrin: Molecular Docking and Experimental Study

Carboxymethyl potato starch hydrogels encapsulated cyclodextrin metal-organic frameworks for enantioselective loading of S-naproxen and its programmed release

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