Cyclodextrin dimers: A versatile approach to optimizing encapsulation and their application to therapeutic extraction of toxic oxysterols

Anderson, Amelia M.; Kirtadze, Tamari; Dinh, D.; Barnes, Carolyn; Campo, Angielyn; Clemens, Daniel M.; García‐Fandiño, Rebeca; Piñeiro, Ángel; O’Connor, Matthew S.

doi:10.1016/j.ijpharm.2021.120522

Cited by 13 publications

(17 citation statements)

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“…Given the amphiphilic nature of CyD, the binding affinity of cholesterol and/or similar molecules results from different factors like hydrophobic interactions, van der Waals forces, and complementarity of the shape and size between host and guest molecules. 33 Thanks to the ability to fully embed cholesterol and/or similar molecules, CyD dimers can be more efficient in term of molecular docking in comparison to their native CyD 34 (Table 1).…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2023

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Section: Resultsmentioning

confidence: 99%

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

et al. 2023

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“…Data were derived from 2D ROESY NMR experiments in CD 3 OD. [ 80 ] Structure of c) cholesterol, d) 7‐keto cholesterol, and e) 27‐hydroxycholesterol.…”

Section: Intrinsic Therapeutic Activity Of Pcydsmentioning

confidence: 99%

“…Recently, O'Connors group has published on CyD dimers designed for the extraction of atherogenic 7‐KC from cells and tissues (Figure 7). [ 80 ] As a next step the design and preparation of oligomers and polymers with specific affinity toward oxysterols are expected.…”

Section: Intrinsic Therapeutic Activity Of Pcydsmentioning

confidence: 99%

“…Figure 7 shows an example of cholesterol complexes with two 𝛽CyD dimers reported by Anderson et al whose structure was determined by 2D ROESY NMR. [80]…”

Section: Intrinsic Therapeutic Activity Of Pcydsmentioning

confidence: 99%

“…Schemes for a) butyl-linked (DS ≈ 8) and b) triazole-linked (DS ≈ 3) dimers of HP𝛽CD (DS ≈ 4.6, Table2) complexing with cholesterol (crystal structure reference CCDC reference: 184885). Data were derived from 2D ROESY NMR experiments in CD 3 OD [80]. Structure of c) cholesterol, d) 7-keto cholesterol, and e) 27-hydroxycholesterol.…”

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confidence: 99%

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Implementation of Water‐Soluble Cyclodextrin‐Based Polymers in Biomedical Applications: How Far Are We?

Agnes

Pancani

Fenyvesi

et al. 2022

Macromolecular Bioscience

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Cyclodextrin-based polymers can be prepared starting from the naturally occurring monomers following green and low-cost procedures. They can be selectively derivatized pre-or post-polymerization allowing to fine-tune functionalities of ad hoc customized polymers. Preparation nowadays has reached the 100 g scale thanks also to the interest of industries in these extremely versatile compounds. During the last 15 years, these macromolecules have been the object of intense investigations in view of possible biomedical applications as the ultimate goal and large amounts of scientific data are now available. Compared to their monomeric models, already used in the formulation of various therapeutic agents, they display superior behavior in terms of their solubility in water and solubilizing power toward drugs incompatible with biological fluids. Moreover, they allow the combination of more than one type of therapeutic agent in the polymeric system. In this review, a complete state of the art on the knowledge and potentialities of water-soluble cyclodextrin-based polymers as therapeutic agents as well as carrier systems for different types of therapeutics to implement combination therapy is provided. Finally, a perspective on their assets for innovation in disease treatment as well as their limits that still need to be addressed is given. Introduction Cyclodextrins at First SightCyclodextrins (CyDs) are water soluble, biocompatible macrocyclic oligosaccharides, made of 𝛼-d-glucopyranose units joined by 𝛼(1-4) linkages (Figure 1a). [1,2] These natural macrocycles

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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: A versatile approach to optimizing encapsulation and their application to therapeutic extraction of toxic oxysterols

Cited by 13 publications

References 68 publications

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

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

Implementation of Water‐Soluble Cyclodextrin‐Based Polymers in Biomedical Applications: How Far Are We?

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

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