J Pharm Sci. Sep;(9) doi: / Epub Mar Self-Assembly of Cyclodextrins and Their Complexes in. Cyclodextrins. Book chapters and reviews: 1. H. Dodziuk, "Molecules with holes. Cyclodextrins", in "Cyclodextrins and Their. Complexes. Chemistry, Analytical. What the activity-based download Cyclodextrins and wants. God, and to the client of the concrete and online certificate. about of the work of the word and of all.


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Biomedical applications are foreseen for nanoencapsulation of drug molecules in the hydrophobic interchain volumes and nanocavities of the amphiphilic cyclodextrins serving as drug carriers or pharmaceutical excipientsanticancer phototherapy, gene delivery, as well as for protection of instable active ingredients cyclodextrins and their complexes inclusion complexation in nanostructured media.

Introduction Self-assembled nanomaterials of amphiphilic molecules have attracted considerable recent interest for diverse biomedical applications including the development of drug delivery systems and stimuli-responsive nanodevices [ 12345678910 ]. The investigations of the structure-property and structure-activity relationships are thus cyclodextrins and their complexes fundamental importance.


Grafting of hydrophobic moieties on the primary or the secondary faces of natural cyclodextrins and their complexes cyclic oligosaccharides forming nanocavity structures confers them an amphiphilic character [ 1112131415161718192021 ].

Synthesis of various modified cyclodextrins has been undertaken because such amphiphilic compounds may self-organize in aqueous phase to form supramolecular assemblies cyclodextrins and their complexes drug carriers of high stability upon dilution [ 22232425262728 ].

The combination between the ability of the cyclodextrin derivatives to form colloidal suspensions of nano-sized dispersed particles and their capacity to form inclusion complexes with hydrophobic drugs has distinguished these systems as pretty valuable for drug encapsulation [ 2930313233343536373839 ].

An important feature for the drug delivery field comes from the fact that the majority cyclodextrins and their complexes amphiphilic cyclodextrins are considered to be non-hemolytic and non-cytotoxic [ 404142434445464748 ]. Mixed amphiphilic nanostructures of phospholipids and modified cyclodextrin have been of special interest because these systems may display high affinity for interaction with biological membranes [ 495051525354555657 ].

The first part of this review briefly presents the cyclodextrins and their complexes classes of amphiphilic cyclodextrins.

Self-Assembly of Cyclodextrins and Their Complexes in Aqueous Solutions.

The second part describes the supramolecular assemblies of amphiphilic cyclodextrins alone or in self-assembled mixtures with other molecules of therapeutic significance.

Different potential applications of the nanoassemblies formed by amphiphilic cyclodextrins upon interaction with biomolecules and other amphiphiles are outlined in the last part of the review. Cyclodextrin modifications can be performed by enzymatic pathways [ 172022 ] or by chemical conjugation reactions using amino, amido, thio, ester, ether or fluoro bonds [ 11124261626364656667 ].

The versatility of this approach has led to the synthesis of a huge number of amphiphilic cyclodextrin systems [ 686970 cyclodextrins and their complexes, 71727374cyclodextrins and their complexes76777879808182 ].

Cyclodextrins and Their Complexes

Three major classes of amphiphilic cyclodextrins can be distinguished as a function of the modifications of the cyclodextrin cyclodextrins and their complexes The first two categories of compounds may be subdivided also into monosubstituted and persubstituted amphiphilic cyclodextrins and their complexes.

Figure 1 shows a few examples of modified cyclodextrins as representative derivatives in this review on self-assembled amphiphilic nanoarchitectures. Amphiphilic cyclodextrins obtained by modifications of the macrocycle: The chemical structures in bdeand f depict the compounds studied in refs.

Copyright American Chemical Society. Methylation of the secondary cyclodextin faces in aefg yields permethylated derivatives.

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Monosubstituted Amphiphilic Cyclodextrins Amphiphilic cyclodextrins, monosubstituted on the primary face, have been obtained by anchoring cyclodextrins and their complexes single hydrophobic moieties such as cholesterol, alkyl chains of variable lengths, fluorinated chains, or more complex synthetic cyclodextrins and their complexes and phospholipidyl substituents see for instance Figure 1 b,c.

One of the purposes of the design and preparation of these amphiphilic derivatives has been the development of nanocarriers with an affinity for insertion into model lipid bilayers and natural biological membranes. Another purpose has been the formation of colloidal supramolecular aggregates, in which the cyclodextrin cavities may serve as drug transporter units.


However, at relatively high concentrations, CDs can spontaneously self-assemble to form visible microparticles in aqueous mediums and formation of such visible particles may cause product rejections.

Formation of subvisible CD aggregates are also known cyclodextrins and their complexes affect analytical results during product development.

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