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Special Issue "Cyclodextrin Chemistry 2018"

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

Deadline for manuscript submissions: 15 March 2019

Special Issue Editor

Guest Editor
Prof. Dr. Bernard Martel

Unité Matériaux et Transformations (UMET) UMR CNRS 8207, Universite des Sciences et Technologies de Lille, Villeneuve d'Ascq Cedex, France
Website | E-Mail
Interests: cyclodextrin polymers; functional textiles; water decontamination; biomaterials; drug delivery systems; antibacterial materials

Special Issue Information

Dear Colleagues,

Cyclodextrins (CDs) are a family starch derivates discovered by Villiers in 1891, of which a cyclic structure was evidenced in the 1930s by Freudenberg, followed by the exploration of their remarkable encapsulation properties from the 1950–1970. Cyclodextrins applications have, thereafter, increased, involving many academic and industrial researchers who have published up to 40,000 papers (including more than 2000 in 2016) and almost 800 patents (Scopus source) up to now. Studies and applications firstly focused on "native" alpha/beta/gamma-cyclodextrins, but chemists have rapidly tuned their properties through chemical modifications with substituent groups, polymerization reactions, and materials surfaces modifications. Furthermore, the versatility of cyclodextrins was still extended thanks to the emergence of nanotechnologies. This "modern period" has paved the way for increasing application fields of cyclodextrins, such as biotechnologies, soil remediation, wastewaters treatment, analytical chemistry, drug vectorization and drug delivery, pharmaceutical excipients, flavor and fragrance stabilization, controlled release, biomaterials, homogeneous, biphasis and heterogeneous catalysis, self-healing materials, etc. Such versatile properties of cyclodextrins explain why cyclodextrins have attracted a great deal of interest in a variety of industries, including those related to food, pharmaceuticals, cosmetics, chemicals, and agriculture. This Special Issue on cyclodextrin chemistry aims to provide a forum for the dissemination of the latest information on new chemical methods for access to advanced cyclodextrins-based systems, useable in the aforementioned application domains and industries.

Prof. Dr. Bernard Martel
Guest Editor

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

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 in food
  • cyclodextrins-based hydrogels
  • cosmetic formulations
  • cyclodextrin 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

Related Special Issue

Published Papers (8 papers)

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Research

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Open AccessFeature PaperArticle A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation
Molecules 2018, 23(7), 1714; https://doi.org/10.3390/molecules23071714
Received: 6 June 2018 / Revised: 30 June 2018 / Accepted: 10 July 2018 / Published: 13 July 2018
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Abstract
Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin
[...] Read more.
Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin is weakly soluble in water and unstable in aqueous medium, cyclodextrins (CDs) were considered for the development of a new moringin formulation, with a view to improving its solubility and stability in aqueous solution for use as an anti-inflammatory. A combined structural study using proton nuclear magnetic resonance (1H-NMR), diffusion-ordered spectroscopy (DOSY) and ion mobility mass spectrometry (IM-MS) is reported, highlighting the formation of a 1:1 α-CD/moringin inclusion complex. The association constant K was determined (1300 M−1 at 300 K). Completion of the structural characterization was performed by T-ROESY and MS/MS experiments, which evidenced the mode of penetration of moringin into α-CD. Finally, the “chaperone-like” properties of α-CD with respect to the stability of moringin have been highlighted. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Open AccessFeature PaperArticle Controlled Release of DEET Loaded on Fibrous Mats from Electrospun PMDA/Cyclodextrin Polymer
Molecules 2018, 23(7), 1694; https://doi.org/10.3390/molecules23071694
Received: 11 June 2018 / Revised: 29 June 2018 / Accepted: 9 July 2018 / Published: 11 July 2018
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Abstract
Electrospun beta-cyclodextrin (βCD)-based polymers can combine a high surface-to-volume ratio and a high loading/controlled-release-system potential. In this work, pyromellitic dianhydride (PMDA)/βCD-based nanosponge microfibers were used to study the capability to host a common insect repellent (N,N-diethyl-3-toluamide (DEET)) and to
[...] Read more.
Electrospun beta-cyclodextrin (βCD)-based polymers can combine a high surface-to-volume ratio and a high loading/controlled-release-system potential. In this work, pyromellitic dianhydride (PMDA)/βCD-based nanosponge microfibers were used to study the capability to host a common insect repellent (N,N-diethyl-3-toluamide (DEET)) and to monitor its release over time. Fibrous samples characterized by an average fibrous diameter of 2.8 ± 0.8 µm were obtained and subsequently loaded with DEET, starting from a 10 g/L diethyl ether (DEET) solution. The loading capacity of the system was assessed via HPLC/UV–Vis analysis and resulted in 130 mg/g. The releasing behavior was followed by leaving fibrous DEET-loaded nanosponge samples in air at room temperature for a period of between 24 h and 2 weeks. The releasing rate and the amount were calculated by thermogravimetric analysis (TGA), and the release of the repellent was found to last for over 2 weeks. Eventually, both the chemical composition and sample morphology were proven to play a key role for the high sample loading capacity, determining the microfibers’ capability to be applied as an effective controlled-release system. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Open AccessArticle A Novel Cyclodextrin-Functionalized Hybrid Silicon Wastewater Nano-Adsorbent Material and Its Adsorption Properties
Molecules 2018, 23(6), 1485; https://doi.org/10.3390/molecules23061485
Received: 20 May 2018 / Revised: 9 June 2018 / Accepted: 13 June 2018 / Published: 19 June 2018
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Abstract
A novel cyclodextrin-functionalized hybrid silicon nano-adsorbent material (6-EA-β-CD-Si) was synthesized via the nucleophilic substitution method. The structure was detected by Fourier transform infrared (FT-IR), X-ray, thermogravimetric analysis, and Brunauer-Emmett-Teller (BET) analysis. Results reveal that the BET surface area of 6-EA-β-CD-Si is 240 m
[...] Read more.
A novel cyclodextrin-functionalized hybrid silicon nano-adsorbent material (6-EA-β-CD-Si) was synthesized via the nucleophilic substitution method. The structure was detected by Fourier transform infrared (FT-IR), X-ray, thermogravimetric analysis, and Brunauer-Emmett-Teller (BET) analysis. Results reveal that the BET surface area of 6-EA-β-CD-Si is 240 m2/g and the average pore size is 4.16 nm. The adsorption properties of 6-EA-β-CD-Si onto methylene blue (MB) were studied and fitted with adsorption kinetic models. Both the Freundlich adsorption isotherm model and pseudo-second-order model were fitted with well shows that the multi-layer adsorption with chemisorption and physisorption co-existing in the system. The maximum adsorption capacities are 39.37, 39.21, 36.90, and 36.36 mg/g at temperatures 303, 313, 323, and 333 K, respectively. The maximum removal rate of MB could reach 99.5%, indicating the potential application value of 6-EA-β-CD-Si in wastewater treatment. The adsorption mechanisms of 6-EA-β-CD-Si showed that the hydrophobic cave of β-CD plays an important role on the adsorption of MB. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Open AccessArticle Hydroxypropyl-β-cyclodextrin for Delivery of Baicalin via Inclusion Complexation by Supercritical Fluid Encapsulation
Molecules 2018, 23(5), 1169; https://doi.org/10.3390/molecules23051169
Received: 27 April 2018 / Revised: 11 May 2018 / Accepted: 11 May 2018 / Published: 14 May 2018
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Abstract
Over the years, various methods have been developed to enhance the solubility of insoluble drugs; however, most of these methods are time-consuming and labor intensive or involve the use of toxic materials. A method that can safely and effectively enhance the solubility of
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Over the years, various methods have been developed to enhance the solubility of insoluble drugs; however, most of these methods are time-consuming and labor intensive or involve the use of toxic materials. A method that can safely and effectively enhance the solubility of insoluble drugs is lacking. This study adopted baicalin as an insoluble drug model, and used hydroxypropyl-β-cyclodextrin for the delivery of baicalin via the inclusion complexation by supercritical fluid encapsulation. Different parameters for the complex preparation as well as the physicochemical properties of the complex have been investigated. Our results showed that when compared to the conventional solution mixing approach, supercritical fluid encapsulation enables a more precise control of the properties of the complex, and gives higher loading and encapsulation efficiency. It is anticipated that our reported method can be useful in enhancing the preparation efficiency of inclusion complexes, and can expand the application potential of insoluble herbal ingredients in treatment development and pharmaceutical formulation. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Review

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Open AccessFeature PaperReview Cyclodextrin-Enabled Polymer Composites for Packaging
Molecules 2018, 23(7), 1556; https://doi.org/10.3390/molecules23071556
Received: 28 May 2018 / Revised: 19 June 2018 / Accepted: 21 June 2018 / Published: 27 June 2018
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Abstract
Cyclodextrin complexes of fragrances, antimicrobial agents, dyes, insecticides, UV-filters can be incorporated into polymers (packaging films, trays, containers) either to ensure the slow release or a homogeneous distribution of the complexed substances. This way the propagation of microorganisms on surface of enwrapped products
[...] Read more.
Cyclodextrin complexes of fragrances, antimicrobial agents, dyes, insecticides, UV-filters can be incorporated into polymers (packaging films, trays, containers) either to ensure the slow release or a homogeneous distribution of the complexed substances. This way the propagation of microorganisms on surface of enwrapped products is decelerated, or the product is made more attractive by slowly released fragrances, protected against UV-light-induced deterioration, oxidation, etc. Incorporating empty cyclodextrins into the packaging material an aroma barrier packaging is produced, which decelerates the loss of the aroma from the packaged food, prevents the penetration of undesired volatile pollutants from the environment, like components of exhaust gases, cigarette smoke, and reduces the migration of plasticizers, residual solvents and monomers, etc. Applying cyclodextrins in active packaging allows to preserve the quality of food and ensures a longer shelf-life for the packaged items. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Open AccessReview Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review
Molecules 2018, 23(5), 1204; https://doi.org/10.3390/molecules23051204
Received: 30 April 2018 / Revised: 13 May 2018 / Accepted: 15 May 2018 / Published: 17 May 2018
Cited by 3 | PDF Full-text (2114 KB) | HTML Full-text | XML Full-text
Abstract
Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion
[...] Read more.
Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion complexes. Such a property is interestingly employed to retain volatile guests and reduce their volatility. Within this scope, the starting crucial point for a suitable and careful characterization of an inclusion complex is to assess the value of the formation constant (Kf), also called stability or binding constant. This task requires the application of the appropriate analytical method and technique. Thus, the aim of the present paper is to give a general overview of the main analytical tools used for the determination of Kf values for CD/volatile inclusion complexes. This review emphasizes on the advantages, inconvenients and limits of each applied method. A special attention is also dedicated to the improvement of the current methods and to the development of new techniques. Further, the applicability of each technique is illustrated by a summary of data obtained from the literature. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Open AccessFeature PaperReview Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes
Molecules 2018, 23(5), 1161; https://doi.org/10.3390/molecules23051161
Received: 13 April 2018 / Revised: 7 May 2018 / Accepted: 8 May 2018 / Published: 11 May 2018
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Abstract
Cyclodextrins (CDs), a group of oligosaccharides formed by glucose units bound together in a ring, show a promising ability to form complexes with drug molecules and improve their physicochemical properties without molecular modifications. The stoichiometry of drug/CD complexes is most frequently 1:1. However,
[...] Read more.
Cyclodextrins (CDs), a group of oligosaccharides formed by glucose units bound together in a ring, show a promising ability to form complexes with drug molecules and improve their physicochemical properties without molecular modifications. The stoichiometry of drug/CD complexes is most frequently 1:1. However, natural CDs have a tendency to self-assemble and form aggregates in aqueous media. CD aggregation can limit their solubility. Through derivative formation, it is possible to enhance their solubility and complexation capacity, but this depends on the type of substituent and degree of substitution. Formation of water-soluble drug/CD complexes can increase drug permeation through biological membranes. To maximize drug permeation the amount of added CD into pharmaceutical preparation has to be optimized. However, solubility of CDs, especially that of natural CDs, is affected by the complex formation. The presence of pharmaceutical excipients, such as water-soluble polymers, preservatives, and surfactants, can influence the solubilizing abilities of CDs, but this depends on the excipients’ physicochemical properties. The competitive CD complexation of drugs and excipients has to be considered during formulation studies. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Other

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Open AccessFeature PaperConcept Paper Development of Dipicolylamine-Modified Cyclodextrins for the Design of Selective Guest-Responsive Receptors for ATP
Molecules 2018, 23(3), 635; https://doi.org/10.3390/molecules23030635
Received: 27 February 2018 / Revised: 9 March 2018 / Accepted: 11 March 2018 / Published: 12 March 2018
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Abstract
The construction of supramolecular recognition systems based on specific host–guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent
[...] Read more.
The construction of supramolecular recognition systems based on specific host–guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD–Cu2+ complexes (Cu·1α, Cu·1β, and Cu·1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu·1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host–guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+–DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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