Cyclodextrin-membrane interaction in drug delivery and membrane structure maintenance

Hammoud, Zahraa; Khreich, Nathalie; Auezova, Lizette; Fourmentin, Sophie; Elaı̈ssari, Abdelhamid; Greige‐Gerges, Hélène

doi:10.1016/j.ijpharm.2019.03.063

Cited by 84 publications

(51 citation statements)

References 130 publications

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“…These mechanisms enrich the opportunities that cyclodextrin molecules not only enhance solubility of hydrophobic drugs but also enhance the permeation of drug molecules across the membrane. [138] Fenyves et al, 2014 investigated the penetration activity of fluorescently labeled randomly methylated-beta-cyclodextrin (FITC-RAMEB) on Caco-2 cell layer and studied the cellular permeability of CyD on intestinal cells. The possible reported mechanism of the cellular uptake of the water-soluble FITC-RAMEB was by fluid phase endocytosis in Caco-2 cells.…”

Section: Cyclodextrins In Bio Imaging and Therapeutic Applicationsmentioning

confidence: 99%

Recent Advances in Host–Guest Self‐Assembled Cyclodextrin Carriers: Implications for Responsive Drug Delivery and Biomedical Engineering

Wankar

Kotla

Gera

et al. 2020

Adv Funct Materials

370

220

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This Review is an overview of the unique characteristics of cyclodextrin in forming an inclusion complex via host-guest noncovalent interactions. The modification of cyclodextrin advances its application as a pharmaceutical solubilizer, fabrication of functional molecular machines such as polyrotaxane, polypseudorotaxane, and polycatenanes and grafting of cyclodextrin with different linear, branched chain polymers. The different stimuli-based supramolecular assemblies involving cyclodextrin as a key mediator with linked triggering responses on payload release is highlighted. In addition, the applications of cyclodextrin in diagnostic imaging and medical devices is briefly demonstrated. Cyclodextrin is a relatively low cost, biocompatible, biodegradable, and highly explored material with low toxicity for drug formulation, drug delivery, and wide varieties of other biomedical applications such as those in medical devices fabrication, biosensor, tissue engineering, and bio-imaging. The toxicological profile of cyclodextrin is well established and safe for human consumption in food and medicine.

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Section: Cyclodextrins In Bio Imaging and Therapeutic Applicationsmentioning

confidence: 99%

Recent Advances in Host–Guest Self‐Assembled Cyclodextrin Carriers: Implications for Responsive Drug Delivery and Biomedical Engineering

Wankar

Kotla

Gera

et al. 2020

Adv Funct Materials

370

220

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“…At high concentrations (above 1 mmol l À1 ), CDs can be toxic and are able to extract cell membrane components (Liang et al 2012;Hill et al 2013). For hydroxypropyl CD derivatives, toxic concentrations are even higher (Bar and Ulitzur 1994;Hammoud et al 2019). Conventional liposomes were found to be inactive towards most bacteria as they present a low degree of interaction with cell envelopes (Peng et al 2015), but can be destabilized by particular bacteria like Staphyococcus aureus that produces some pore-forming toxins (Cui et al 2015).…”

Section: Discussionmentioning

confidence: 99%

Antibacterial activity of free or encapsulated selected phenylpropanoids against Escherichia coli and Staphylococcus epidermidis

et al. 2020

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Aims Antibacterial activities of phenylpropenes (PPs) (eugenol, isoeugenol, estragole and trans‐anethole) and hydroxycinnamic acids (HCAs) (p‐coumaric, caffeic and ferulic acids) were assessed against Escherichia coli and Staphylococcus epidermidis. Effect of cyclodextrin and liposome encapsulation on the PPs activity was also evaluated. Methods and Results All PPs inhibited the bacterial growth in the hundred micromolar range, while HCAs did not, as determined by broth macrodilution. Anethole and estragole showed a higher efficiency than eugenol and isoeugenol, and E. coli was more susceptible than S. epidermidis. Hydroxypropyl‐β‐cyclodextrin/PP complexes and anethole‐loaded Lipoid S100‐liposomes were prepared by freeze‐drying and ethanol injection respectively. Both formulations were substantially less active than free PPs. For instance, E. coli growth inhibition was about 14% for all HP‐β‐CD/PP complexes evaluated at MIC50 values of free PPs (P < 0·05), and about 12% for liposomal anethole evaluated at minimal bactericidal concentration value of free anethole (P < 0·05). Conclusions Hydrophobicity appears to be crucial for PPs antibacterial activity. Encapsulation in cyclodextrin and liposome seems to retain the PPs preventing their interaction with bacteria. Significance and Impact of the Study This study highlights the structural features of simple phenylpropanoids related to their antibacterial activity. The limitations of conventional encapsulation systems on the activity of PPs should be considered in future applications.

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“…CDs are glucose oligomers consisting of at least 6 (α-1,4)-linked α-D-glucopyranose units, that have a truncated funnel-shaped cage structure, with a hydrophobic inner cavity and hydrophilic outer surface (Fenyvesi and Szente, 2016;Hammoud et al, 2019;Liu et al, 2019;Loftsson et al, 2005).…”

Section: Chemical Structure and Propertiesmentioning

confidence: 99%

“…• increased solubility of both CDs and their inclusion complexes (Hammoud et al, 2019;Hedges, 2009;Varan et al, 2017);…”

Section: Chemical Structure and Propertiesmentioning

confidence: 99%

Cyclodextrins – development and applications of these versatile oligosaccharides

2020

Biomater Tissue Eng Bull

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. Cyclodextrins (CDs) are cyclic oligossacharides which have been known and studied for almost 130 years. This review aims to highlight the most important findings registered over this time, the physicochemical properties, preparation methods and uses of cyclodextrins, with special focus on their recently discovered applications. Due to their unique conformation, cyclodextrins are able to encapsulate a wide range of chemical entities, impacting on their solubility, bioavailability, stability, and shelf-life. Their complex formation properties together with the production from natural sources opens the door for cyclodextrins to be used in numerous and varied industries. However, the most important consumer of these versatile sugars is represented by the biomedical domain, where cyclodextrins find uses in drug formulations, delivery systems, medical textiles, implantable devices, tissue engineering, and many other connex applications. Moreover, intense research is still performed for this compounds, to develop and extend their therapeutic potential and serve as promising alternatives for treatment of severe diseases.

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Cyclodextrin-membrane interaction in drug delivery and membrane structure maintenance

Cited by 84 publications

References 130 publications

Recent Advances in Host–Guest Self‐Assembled Cyclodextrin Carriers: Implications for Responsive Drug Delivery and Biomedical Engineering

Recent Advances in Host–Guest Self‐Assembled Cyclodextrin Carriers: Implications for Responsive Drug Delivery and Biomedical Engineering

Antibacterial activity of free or encapsulated selected phenylpropanoids against Escherichia coli and Staphylococcus epidermidis

Cyclodextrins – development and applications of these versatile oligosaccharides

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