Self-assemblies of amphiphilic cyclodextrins

Abstract

Cyclodextrins are natural cyclic oligosaccharides widely used as "molecular cages" in the pharmaceutical, agrochemical, food and cosmetical industries. The optimization of their pharmacological properties has led to the synthesis of numerous analogues. Amphiphilic derivatives were designed to improve the cell targeting of the drug-containing cyclodextrin cavities through their transportation in the organism, within self-assembling systems. Amphiphilic cyclodextrins can self-assemble into water-soluble aggregates such as mono or polydisperse micelles, or insert in lipid membranes and liposomes. Polysubstituted amphiphilic cyclodextrins are briefly reviewed, and monosubstituted derivatives of native and methylated beta-cyclodextrins are presented in more details, with an emphasis on their self-organization within lipid membranes.

Sustained Release of Amoxicillin from Ethyl Cellulose-Coated Amoxicillin/Chitosan–Cyclodextrin-Based Tablets

“…They are widely used as "molecular cages" in the pharmaceutical, agrochemical, food, and cosmetic industries (11). In the pharmaceutical field, they are used as complexing agents to increase the aqueous solubility of poorly soluble drugs and to increase their bioavailability and stability (12).…”

Evaluation of sugammadex self-association

“…In particular, turbidity of aqueous ␥CD solutions is related to aggregate formation, which is supported by results obtained with e.g., dynamic light scattering (Coleman and Nicolis, 1992), transmission electron microscopy (Wu et al, 2006) and some analytical methods (Szente et al, 1998). Additionally, substituted cyclodextrins with attached long hydrophobic moieties may possess some surface activity and form micelles or vesicles (Witte and Hoffman, 1996;Roux et al, 2007). The appearance of nano-scale particles would modify the physicochemical properties of aqueous sugammadex solutions which might entail undesirable modification of the cyclodextrin's pharmacological and toxicological properties upon intravenous administration.…”

Inclusion of terpenes in cyclodextrins: Preparation, characterization and pharmacological approaches

“…Natural and modified CDs have been studied and some have gained Food and Drug Administration (FDA) approval or have been accredited as being "generally recognized as safe" (GRAS) (Lakkakula & Macedo Krause, 2014). Due to their properties of forming host-guest type inclusion complexes, CDs and their synthetic derivatives exhibit a wide range of utilities in different areas, such as in pharmaceuticals, in drug delivery systems, in cosmetics, in food and nutrition, in textiles, and in the chemical industry (Loftsson, 2002;Marques, 2010a;Roux, Perly & Djedaini-Pilard, 2007). This capability has led to extensive investigations into cyclodextrin applications in several different areas, with the purpose of overcoming certain limitations (Brito, Araujo, Quintans, Sluka & QuintansJunior, 2015;Oliveira, Guimaraes, Araujo, Quintans, Santos & Quintans-Junior, 2015;Sharma & Baldi, 2016;Varca, Andreo-Filho, Lopes & Ferraz, 2010).…”