Cyclodextrin-based nanostructures

doi:10.1016/j.pmatsci.2021.100869

Progress in Materials Science

Volume 124, February 2022, 100869

https://doi.org/10.1016/j.pmatsci.2021.100869 Get rights and content

Abstract

Cyclodextrins (CDs) are a unique class of molecules that are naturally available via degradation of starchy molecules. Their toroidal structure and abundant presence of hydroxyl groups have given scientists exceptional leverage resulting in synthesizing novel molecules for applications ranging from food packaging, controlled release of small molecules, antibacterial coating, agriculture, and air and water filtration. With the advent of nanotechnology, CDs have positioned itself in a variety of forms such as their ability to act as capping/reducing agents for metallic nanoparticles, or form stable nanofibers or nanoparticles or nano micelles, which can be subsequently utilized for sophisticated applications. In this review, we summarize researches on the presence of CDs in various aspects of nanotechnology ranging from nanoparticles, nanorods, nanomicelles, to nanofibers. In addition, through this review, we provide state-of-the-art applications that are being carried out using these nanostructures.

Section snippets

Introduction to cyclodextrins

Cyclodextrins (CDs) belong to a family of molecular cages consisting of cyclic α-1,4-linked oligosaccharides with hydrophilic outer surfaces and a lipophilic central cavity. The inherent ability of CDs to form “host–guest” assemblies makes it possible to tune the properties of the guest molecules. Historically, CDs were first discovered in 1891 by a French scientist, A. Villiers, through the bacterial digestion of starch leading to isolation of a crystalline substance. The composition of the

Synthesis of native cyclodextrins

The synthesis of CDs via chemical routes has not taken on any commercial significance due to the large numbers of required complex reactions and processes [1], [2], [3], [4]. Instead, commonly used native CDs on the market, i.e., α-, β-, and γ-CDs, are almost always synthesized by the enzymatic conversion of starch using cyclodextrin glucanotransferases (CGTases; EC 2.4.1.19) [5], [6], [7], [8]. Typically, CGTases produce a CD mixture with different cavity sizes, and therefore the cost of

Host-Guest Interactions: Driving force

The most remarkable characteristic of CDs is their capability to form inclusion compounds with a variety of molecules through non-covalent interactions. Some of the driving forces for their complexation processes are hydrophobic, electrostatic, and dipole–dipole interactions, van der Waals forces, hydrogen bonding, and charge transfer interactions [45]. In addition, relief of conformational strain and the release of high enthalpic water molecules from the CD cavities have also been attributed

Cyclodextrin-based micelles

Like most soluble particles, CD molecules aggregate and self-assemble in aqueous solutions. This self-assembly and the extent of such self-assembly depends on several factors including the CD type, CD (or IC) concentration, temperature, surfactant type, and ionic strength of the surfactant or CD [76]. In general, the solute concentrations have to exceed a critical concentration, also called the critical aggregation (CAC) or critical micelle concentration (CMC) for the aggregation to occur. For

Cyclodextrin-based nanoparticles

Nanoparticles (NPs) are classically defined as particles that have sizes less than one micron in all dimensions. More recently, this definition has been updated to reflect particles that have less than 100 nm as only at these sizes are NPs highly effective in drug delivery applications [139]. This is due to the capability of the NPs at sub-100 nm to efficiently cross the blood–brain barrier (BBB) resulting in increased uptake by the cells, and therefore higher biologic activity [139]. Based on

Cyclodextrin-based nanorods

CDs are attractive for facile fabrication of nanorod assemblies owing to their unique structural architecture and functional groups. As an example, Wu et al. demonstrated directed end-to-end assembly of gold nanorods (GNRs) utilizing host–guest interaction based on recognition of symmetric trans-bis azo compounds by thiol-β-cyclodextrin (SH-β-CD) [252]. The guest can then subsequently be included in the HS-β-CD hydrophobic cavity forming 1:2 ICs (BiAzo@CD). Towards the goal of GNRs, BiAzo@CD,

Cyclodextrin-based nanofibers

One-dimensional (1D) nanostructures such as nanofibers (NFs) offer many possibilities for the development of advanced materials [275]. When compared to other nanofiber fabrication methods, for example: melt fibrillation, thermal drawing, nanolithography, and self-assembly, etc.,electrospinning is getting more and more attention in academia and in industry due to its versatility and cost-effectiveness in producing NFs from a variety of polymeric and non-polymeric materials [276], [277]. The

Cyclodextrin-metal organic frameworks

Metal-organic frameworks (MOFs), also known as porous coordination polymers, first reported in the 1990s, have emerged as an intriguing class of porous crystalline materials [363], [364]. MOFs are highly tunable hybrid materials crafted from metal ions/clusters connected by organic bridging ligands through coordination bonds [365]. Because of their highly tunable characteristics, MOFs with intriguing properties such as, high surface areas, high porosities, modifiable size, and shapes have been

Concluding remarks

Cyclodextrins offer unique possibilities for fabricating versatile supramolecular structures in various forms with potential ramifications ranging from pharmacologics, water and air filtration, catalysis, analytical instruments, anti-bacterial/fungal membranes, and food packaging applications. With such versatility observed with CDs, it is no easy task to indentify optimal CD-types and structures required for specific applications. As this review suggests, the current scientific literature

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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¹: Equal contributing authors.

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Cyclodextrin-based nanostructures

Abstract

Section snippets

Introduction to cyclodextrins

Synthesis of native cyclodextrins

Host-Guest Interactions: Driving force

Cyclodextrin-based micelles

Cyclodextrin-based nanoparticles

Cyclodextrin-based nanorods

Cyclodextrin-based nanofibers

Cyclodextrin-metal organic frameworks

Concluding remarks

Declaration of Competing Interest

Tetrahedron Lett

Carbohydr Res

Biochim Biophys Acta (BBA) - Prot Struct Mol Enzymol

J Biotechnol

Tetrahedron

Eur J Org Chem

Tetrahedron Lett

Carbohydr Res

Tetrahedron Lett

Tetrahedron Lett

Carbohydr Res

Adv Drug Deliv Rev

Coord Chem Rev

Process Biochem

Drug Discovery Today

Food Hydrocolloids

J Pharm Biomed Anal

J Pharm Biomed Anal

Int J Pharm

Int J Pharm

Int J Pharm

Polymer

J Pharm Sci

Tetrahedron Lett

Carbohydr Res

J Drug Delivery Sci Technol

Carbohydr Res

Drug Discovery Today

Eur J Pharm Biopharm

Int J Pharm

Int J Pharm

Int J Pharm

Eur Polym J

Carbohydr Polym

J Colloid Interface Sci

Polymer

Intramolecular glycosylation

Beilstein J Org Chem

Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation

J Org Chem

Enzymatic production of cyclodextrins

Appl Microbiol Biotechnol

Engineering of cyclodextrin glucanotransferases and the impact for biotechnological applications

Appl Microbiol Biotechnol

Preparation and analyses of cyclodextrin

Cyclodextrin Chemistry

Application of cyclodextrin glucanotransferase to the synthesis of useful oligosaccharides and glycosides

Enzymes in preparing cyclodextrins

Sur la fermentation de la fécule par l’action du ferment butyrique

Compt Rend Acad Sci

Review: A History of Cyclodextrins

Chem Rev

Über thermophile Bakterien aus verschiedenen Speisen und Milch

Zeitschrift für Untersuchung der Nahrungs-und Genussmittel, sowie der Gebrauchsgegenstände

Bildung kristallisierter polysaccharide (dextrine) aus stärkekleister durch microben

Zentralbl Bakteriol Parasitenk Abt

The Conversion of Starch to Crystalline Dextrins by the Action of a New Type of Amylase Separated from Cultures of Aerobacillus macerans

J Am Chem Soc

Amylolytic enzymes: Types, structures and specificities