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Cyclodextrin Chemistry

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (10 November 2016) | Viewed by 93914

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Prof. Dr. Bernard Martel

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University of Lille, UMET CNRS8207, 59655 Villeneuve d'Ascq, France
Interests: polymerization; polymers; polymeric materials; polymer synthesis; polymer science; material characterization; biomaterials; hybrid materials; polymeric biomaterials; biopolymers
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Dear Colleagues,

Cyclodextrins (CDs) are a family of torus shaped cyclic oligomers obtained from starch and composed of six, seven, or eight α-(1,4) linked glucopyranose subunits (respectively a, b, and gCD). Due to their cyclic structure they present an apolar cavity, which is at the origin of their remarkable encapsulation properties towards the lipophilic part of a wide range of active molecules. Thanks to their inclusion properties, CDs have drawn the attention of academic and industrial researchers since the early 1980s with several hundreds of papers and patents, up to now with almost 20,000 published references. The field of applications of CDs is always increasing and nowadays concerns biotechnologies, soil remediation, wastewaters treatment, analytical chemistry, drug vectorization and drug delivery, pharmaceutical excipients, flavor and fragrance stabilization and controlled release, biomaterials, catalysis, self-healing materials, etc. This is the primary reason why cyclodextrins have attracted great interest in a variety of industries, including those related to food, pharmaceuticals, cosmetics, chemicals, and agriculture. This Special Issue aims to provide a forum for the dissemination of the latest information on new chemical methods for access to advanced CD-based systems useable in the aforementioned applications domains and industries.

Prof. Dr. Bernard Martel
Guest Editor

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Keywords

cyclodextrins in advanced materials
cyclodextrins based stimuli-responsive systems
green chemistry processes based on cyclodextrins
cyclodextrins based catalysts
syntheses of cyclodextrins derivates and polymers
applications of cyclodextrins
cyclodextrins polymers and hydrogels in pharmacy, cosmetic formulations, in food and in biomaterials for vectorization and/or controled release of active substances
cyclodextrins involved in environmental depollution (air, soils, waste waters, sediments)
nano materials and nano-structured coatings containing cyclodextrins

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Related Special Issue

Cyclodextrin Chemistry 2018 in Molecules (12 articles)

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4354 KiB

Open AccessArticle

Encapsulation of the Antioxidant R-(+)-α-Lipoic Acid in Permethylated α- and β-Cyclodextrins: Thermal and X-ray Structural Characterization of the 1:1 Inclusion Complexes

by Mino R. Caira, Susan A. Bourne and Buntubonke Mzondo

Molecules 2017, 22(6), 866; https://doi.org/10.3390/molecules22060866 - 23 May 2017

Cited by 8 | Viewed by 6014

Abstract

The naturally occurring compound α-lipoic acid (ALA) is implicated in manifold critical biological roles and its potent antioxidant properties and potential for treatment of various diseases have led to its widespread use as a dietary supplement. However, shortcomings of poor aqueous solubility and low thermal stability have hampered its development as a medicinal agent, prompting the use of cyclodextrins (CDs) to address these problems. The paucity of published structural data on the nature of the interactions between ALA and CDs motivated the present study, which describes the synthesis and X-ray structural elucidation of crystalline inclusion complexes between the biologically relevant R-(+)-α-lipoic acid (RALA) and the host molecules permethylated α-CD (TMA) and permethylated β-CD (TMB). Single crystal X-ray diffraction of TMA·RALA·6H₂O and TMB·RALA revealed significantly different orientations of the RALA molecule within the TMA and TMB cavities, but in both cases the guest molecule is fully encapsulated by the respective parent host molecules and residues of CD molecules of neighboring complex units. While pure RALA melted at 46–48 °C, combined thermal analysis techniques indicated that on heating the respective complexes, the release of RALA occurred at significantly higher onset temperatures, in the range 150–170 °C. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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632 KiB

Open AccessArticle

Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling

by László Jicsinszky, Marina Caporaso, Emanuela Calcio Gaudino, Cristina Giovannoli and Giancarlo Cravotto

Molecules 2017, 22(3), 485; https://doi.org/10.3390/molecules22030485 - 19 Mar 2017

Cited by 13 | Viewed by 5227

Abstract

A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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5089 KiB

Open AccessArticle

Preparation of Photoirradiation Molecular Imprinting Polymer for Selective Separation of Branched Cyclodextrins

by Haoran Fan, Jinpeng Wang, Qingran Meng, Xueming Xu, Tianming Fan and Zhengyu Jin

Molecules 2017, 22(2), 288; https://doi.org/10.3390/molecules22020288 - 21 Feb 2017

Cited by 10 | Viewed by 6555

Abstract

In the present study, photoirradiation molecularly imprinted polymer (MIP) with azobenzene was used as a functional monomer for the selective separation of the branched cyclodextrins. The functional monomer 4-methacryloyloxy azobenzene (MAA) and the molecular template 6-O-α-d-maltosyl-β-cyclodextrin (G2-β-CD) were implemented for the molecular imprinting. The core-shell structure of photoirradiation MIP was visualized by the transmission electron microscopy (TEM). With Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA), we identified that G2-β-CD was imprinted into the polymer and removed from the MIP. The binding association constant (K_a) and the maximum number of the binding site (N_max) were 1.72 × 10⁴ M⁻¹ and 7.93 μmol·g⁻¹ MIP, respectively. With alternate irradiation at 365 and 440 nm light, the prepared MIP reversibly released and rebound to the G2-β-CD, which resulted in the nearly zero amount of G2-β-CD in the solution. The HPLC results indicated that the purity of G2-β-CD could reach 90.8% after going through MIP. The main finding of our study was that the photoirradiation of MIP was an easy and effective method for the selective separation of the branched cyclodextrins. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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11503 KiB

Open AccessArticle

Transition Metal Complexes Coordinated by Water Soluble Phosphane Ligands: How Cyclodextrins Can Alter the Coordination Sphere?

by Michel Ferreira, Hervé Bricout, Sébastien Tilloy and Eric Monflier

Molecules 2017, 22(1), 140; https://doi.org/10.3390/molecules22010140 - 17 Jan 2017

Cited by 6 | Viewed by 6631

Abstract

The behaviour of platinum(II) and palladium(0) complexes coordinated by various hydrosoluble monodentate phosphane ligands has been investigated by ³¹P{¹H} NMR spectroscopy in the presence of randomly methylated β-cyclodextrin (RAME-β-CD). This molecular receptor can have no impact on the organometallic complexes, induce the formation of phosphane low-coordinated complexes or form coordination second sphere species. These three behaviours are under thermodynamic control and are governed not only by the affinity of RAME-β-CD for the phosphane but also by the phosphane stereoelectronic properties. When observed, the low-coordinated complexes may be formed either via a preliminary decoordination of the phosphane followed by a complexation of the free ligand by the CD or via the generation of organometallic species complexed by CD which then lead to expulsion of ligands to decrease their internal steric hindrance. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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4074 KiB

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Alpha- and Beta-Cyclodextrin Inclusion Complexes with 5-Fluorouracil: Characterization and Cytotoxic Activity Evaluation

by Cristina Di Donato, Margherita Lavorgna, Roberto Fattorusso, Carla Isernia, Marina Isidori, Gaetano Malgieri, Concetta Piscitelli, Chiara Russo, Luigi Russo and Rosa Iacovino

Molecules 2016, 21(12), 1644; https://doi.org/10.3390/molecules21121644 - 1 Dec 2016

Cited by 41 | Viewed by 7809

Abstract

Cyclodextrins are natural macrocyclic oligosaccharides able to form inclusion complexes with a wide variety of guests, affecting their physicochemical and pharmaceutical properties. In order to obtain an improvement of the bioavailability and solubility of 5-fluorouracil, a pyrimidine analogue used as chemotherapeutic agent in the treatment of the colon, liver, and stomac cancers, the drug was complexed with alpha- and beta-cyclodextrin. The inclusion complexes were prepared in the solid state by kneading method and characterized by Fourier transform-infrared (FT-IR) spectroscopy and X-ray powder diffractometry. In solution, the 1:1 stoichiometry for all the inclusion complexes was established by the Job plot method and the binding constants were determined at different pHs by UV-VIS titration. Furthermore, the cytotoxic activity of 5-fluorouracil and its complexation products were evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on MCF-7 (breast cancer cell line), Hep G2 (hepatocyte carcinoma cell line), Caco-2 (colon adenocarcinoma cell line), and A-549 (alveolar basal epithelial carcinoma cell line). The results showed that both inclusion complexes increased the 5-fluorouracil capability of inhibiting cell growth. In particular, 5-fluorouracil complexed with beta-cyclodextrin had the highest cytotoxic activity on MCF-7; with alpha-cyclodextrin the highest cytotoxic activity was observed on A-549. The IC₅₀ values were equal to 31 and 73 µM at 72 h, respectively. Our results underline the possibility of using these inclusion complexes in pharmaceutical formulations for improving 5-fluorouracil therapeutic efficacy. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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1712 KiB

Open AccessArticle

Factors Affecting the Formation of 2:1 Host:Guest Inclusion Complexes of 2-[(R-Phenyl)amine]-1,4-naphthalenediones (PAN) in β- and γ-Cyclodextrins

by Christopher K. Jankowski, Christine Lamouroux, Manuel Jiménez-Estrada, Sebastien Arseneau and Brian D. Wagner

Molecules 2016, 21(11), 1568; https://doi.org/10.3390/molecules21111568 - 18 Nov 2016

Cited by 8 | Viewed by 8449

Abstract

The molecular hosts cyclodextrins form inclusion complexes with a wide variety of guests, resulting in complexes with various host:guest stoichiometries. In the case of a series of 19 1,4-naphthoquinolines as guests with either β- or γ-cyclodextrin studied using electrospray mass spectroscopy, in most cases only 1:1 complexes were observed, with 2:1 host:guest complexes observed in just 6 out of 38 host:guest combinations. It is shown that these higher-order complexes were observed only in the case of small (or no) electronically withdrawing substituents, and were much less likely in the case of the larger γ-cyclodextrin host. The size and electronic properties of the substituents involved shows that both steric and electronic factors must be taken into account in predicting which cyclodextrin host:guest stoichiometries will be stable enough to form (or once formed, be robust enough to be observed in the ESI-MS experiments). It is clear that the prediction of host-guest stoichiometry for a specific host-guest pair is complicated, and involves a subtle interplay of both electronic and steric factors. However, there are definite trends, which can be used to help predict host:guest stoichiometry for a given host-guest pair. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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3644 KiB

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Evidence of the Disassembly of α-Cyclodextrin-octylamine Inclusion Compounds Conjugated to Gold Nanoparticles via Thermal and Photothermal Effects

by Nataly Silva, Silvana Moris, Maximiliano Díaz, Nicolás Yutronic, Erika Lang, Boris Chornik, Marcelo J. Kogan and Paul Jara

Molecules 2016, 21(11), 1444; https://doi.org/10.3390/molecules21111444 - 29 Oct 2016

Cited by 9 | Viewed by 6291

Abstract

Cyclodextrin (CD) molecules form inclusion compounds (ICs), generating dimers that are capable of encapsulating molecules derived from long-chain hydrocarbons. The aim of this study is to evaluate the structural changes experienced by ICs in solution with increasing temperatures. For this, a nuclear magnetic resonance (¹H-NMR) titration was performed to determinate the stoichiometric α-cyclodextrin (α-CD):octylamine (OA) 2:1 and binding constant (k = 2.16 M⁻²) of ICs. Solution samples of α-CD-OA ICs conjugated with gold nanoparticles (AuNPs) were prepared, and ¹H-NMR spectra at different temperatures were recorded. Comparatively, ¹H-NMR spectra of the sample irradiated with a laser with tunable wavelengths, with plasmons of conjugated AuNPs, were recorded. In this work, we present evidence of the disassembly of ICs conjugated with AuNPs. Thermal studies demonstrated that, at 114 °C, there are reversible rearrangements of the host and guests in the ICs in a solid state. Migration movements of the guest molecules from the CD cavity were monitored via temperature-dependent ¹H-NMR, and were verified comparing the chemical shifts of octylamine dissolved in deuterated dimethylsulfoxide (DMSO-d₆) with the OA molecule included in α-CD dissolved in the same solvent. It was observed that, at 117 °C, OA exited the α-CD cavity. CD IC dimer disassembly was also observed when the sample was irradiated with green laser light. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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2080 KiB

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Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates

by Hwanhee Kim, Yiluo Hu, Daham Jeong, Bong-Hyun Jun, Eunae Cho and Seunho Jung

Molecules 2016, 21(7), 963; https://doi.org/10.3390/molecules21070963 - 22 Jul 2016

Cited by 10 | Viewed by 8146

Abstract

Amphiphilic cyclodextrin (CD) has been the object of growing scientific attention because of its two recognition sites, the cavity and the apolar heart, formed by self-assembly. In the present study, mono[6-deoxy-6-(octadecanamido)]-β-CD and mono[6-deoxy-6-(octadecenamido)]-β-CD were successfully synthesized by reacting mono-6-amino-6-deoxy-β-CD with N-hydroxysuccinimide esters of corresponding fatty acids in DMF. The structures were analyzed using nuclear magnetic resonance spectroscopy and mass spectrometry. The amphiphilic β-CDs were able to form self-assembled nano-vesicles in water, and the supramolecular architectures were characterized using fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. Using the cavity-type nano-vesicles, all-trans-retinol was efficiently encapsulated; it was then stabilized against the photo-degradation. Therefore, the present fatty amide-β-CD conjugate will be a potential molecule for carrier systems in cosmetic and pharmaceutical applications. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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2482 KiB

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Characterization and Enhanced Antioxidant Activity of the Cysteinyl β-Cyclodextrin-Baicalein Inclusion Complex

by Hwanhee Kim, Hu Yiluo, Seyeon Park, Jae Yung Lee, Eunae Cho and Seunho Jung

Molecules 2016, 21(6), 703; https://doi.org/10.3390/molecules21060703 - 27 May 2016

Cited by 21 | Viewed by 7170

Abstract

Baicalein is a type of flavonoid isolated from the roots of a medicinal plant, Scutellaria baicalensis. Although it has attracted considerable attention due to its antiviral, anti-tumor, and anti-inflammatory activities, its limited aqueous solubility inhibits the clinical application of this flavonoid. The present study aimed to prepare and characterize a host-guest complex in an effort to improve the solubility and antioxidant activity of baicalein. The host molecule is a macrocyclic β-cyclodextrin (β-CD) functionalized with cysteine for a synergetic effect. The structure of the synthesized cysteinyl β-CD was analyzed using nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The inclusion complex with baicalein was studied by UV-vis, NMR spectroscopy, scanning electron microscopy, and X-ray powder diffractometry. The formed cysteinyl β-CD/baicalein inclusion complex efficiently improved the solubility and antioxidant ability of baicalein. Therefore, we suggest that the present cysteinyl β-CD is a potential host molecule for inclusion complexation and for bioavailability augmentation. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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Review

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2768 KiB

Open AccessReview

Electrospun Fibers of Cyclodextrins and Poly(cyclodextrins)

by Alejandro Costoya, Angel Concheiro and Carmen Alvarez-Lorenzo

Molecules 2017, 22(2), 230; https://doi.org/10.3390/molecules22020230 - 3 Feb 2017

Cited by 46 | Viewed by 8641

Abstract

Cyclodextrins (CDs) can endow electrospun fibers with outstanding performance characteristics that rely on their ability to form inclusion complexes. The inclusion complexes can be blended with electrospinnable polymers or used themselves as main components of electrospun nanofibers. In general, the presence of CDs promotes drug release in aqueous media, but they may also play other roles such as protection of the drug against adverse agents during and after electrospinning, and retention of volatile fragrances or therapeutic agents to be slowly released to the environment. Moreover, fibers prepared with empty CDs appear particularly suitable for affinity separation. The interest for CD-containing nanofibers is exponentially increasing as the scope of applications is widening. The aim of this review is to provide an overview of the state-of-the-art on CD-containing electrospun mats. The information has been classified into three main sections: (i) fibers of mixtures of CDs and polymers, including polypseudorotaxanes and post-functionalization; (ii) fibers of polymer-free CDs; and (iii) fibers of CD-based polymers (namely, polycyclodextrins). Processing conditions and applications are analyzed, including possibilities of development of stimuli-responsive fibers. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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1916 KiB

Open AccessReview

The Potential of Cyclodextrins as Novel Active Pharmaceutical Ingredients: A Short Overview

by Massimiliano Pio Di Cagno

Molecules 2017, 22(1), 1; https://doi.org/10.3390/molecules22010001 - 25 Dec 2016

Cited by 94 | Viewed by 9096

Abstract

Cyclodextrins (CDs) are cyclic oligosaccharides of natural origin that were discovered more than 100 years ago. The peculiar cone-like conformation of the sugar ring, expressing a lipophilic cavity and a hydrophilic external surface, allows these substances to spontaneously complex poorly soluble compounds in an aqueous environment. For more than 50 years, these substances have found applicability in the pharmaceutical and food industries as solubilizing agents for poorly soluble chemical entities. Nowadays, several research groups all over the world are investigating their potential as active pharmaceutical ingredients (APIs) for the treatment of several illnesses (e.g., hypercholesterolemia, cancer, Niemann-Pick Type C disease). The aim of this review is to briefly retrace cyclodextrins’ legacy as complexing agents and describe the current and future prospects of this class of chemical entities in pharmaceutics as new APIs. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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1510 KiB

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Cyclodextrins as Emerging Therapeutic Tools in the Treatment of Cholesterol-Associated Vascular and Neurodegenerative Diseases

by Caroline Coisne, Sébastien Tilloy, Eric Monflier, Daniel Wils, Laurence Fenart and Fabien Gosselet

Molecules 2016, 21(12), 1748; https://doi.org/10.3390/molecules21121748 - 20 Dec 2016

Cited by 94 | Viewed by 12780

Abstract

Cardiovascular diseases, like atherosclerosis, and neurodegenerative diseases affecting the central nervous system (CNS) are closely linked to alterations of cholesterol metabolism. Therefore, innovative pharmacological approaches aiming at counteracting cholesterol imbalance display promising therapeutic potential. However, these approaches need to take into account the existence of biological barriers such as intestinal and blood-brain barriers which participate in the organ homeostasis and are major defense systems against xenobiotics. Interest in cyclodextrins (CDs) as medicinal agents has increased continuously based on their ability to actively extract lipids from cell membranes and to provide suitable carrier system for drug delivery. Many novel CD derivatives are constantly generated with the objective to improve CD bioavailability, biocompatibility and therapeutic outcomes. Newly designed drug formulation complexes incorporating CDs as drug carriers have demonstrated better efficiency in treating cardiovascular and neurodegenerative diseases. CD-based therapies as cholesterol-sequestrating agent have recently demonstrated promising advances with KLEPTOSE^® CRYSMEB in atherosclerosis as well as with the 2-hydroxypropyl-β-cyclodextrin (HPβCD) in clinical trials for Niemann-Pick type C disease. Based on this success, many investigations evaluating the therapeutical beneficial of CDs in Alzheimer’s, Parkinson’s and Huntington’s diseases are currently on-going. Full article

(This article belongs to the Special Issue Cyclodextrin Chemistry)

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