Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
7.8
5.6
Journals
IJMS
Special Issues
Current Uses and Applications of Cyclodextrins
ijms-logo
Submit to IJMS Review for IJMS Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

Current Uses and Applications of Cyclodextrins

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: closed (31 March 2024) | Viewed by 3747

Special Issue Editors

Prof. Dr. Zoltan Juvancz

E-Mail Website
Guest Editor
Rejtő Sándor Faculty of Light Industry and Environmental Engineering, Environmental Engineering and Natural Sciences Institute, Óbuda University, Doberdó út 6, H-034 Budapest, Hungary
Interests: chromatography; chiral separations; cyclodextrins; GC; SFC; CE
Dr. Cecilia Cagliero

E-Mail Website
Guest Editor
Department of Drug Science and Technology, University of Turin, 10125 Torino, Italy
Interests: natural compounds; phytochemical analysis; sample preparation; gas chromatography; HPLC; ionic liquids; deep eutectic solvents; chiral analysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent years, chiral separations have become increasingly important, where cyclodextrins play crucial roles. Cyclodextrins are cyclic oligosaccharide molecules, which contain six, seven, or eight D(+)-glucopyranose units, assigned by Greek letters α, β, and γ, respectively. The cyclodextrins can encapsulate suitable substances in their apolar cavities, forming noncovalent host–guest inclusion complexes. The internal cavities of cyclodextrins provide protection against the evaporation, oxidation, light-induced decomposition of sensitive guest substances. Cyclodextrin inclusion complexes have been used as controlled release formulation devices for a long time.

One of the most widely used applications of cyclodextrins relates to their utilization as chiral selectors. They have several chiral centres, with five in every glucose unit. The chemical modifications of hydroxyl groups of cyclodextrins (i.e., acyl, alkyl, hydroxyalkyl, carboxyalkyl, suphoalkyl, and phosphate, etc.) provide further chiral recognition properties with their interactions. The chiral recognition properties of a cyclodextrin depend on the size, geometry, and chemical characters of its cavity. Chemically modified cyclodextrins have flexible structures, enabling enantioseparations via an induced fit. Several chiral centres, various interaction abilities, and the induced fit of derivatized cyclodextrins demonstrate the chiral recognitions across a broad spectrum of enantiomers.

The majority of chiral separations have been used with cyclodextrin selectors in gas chromatography and capillary electrophoresis. The cyclodextrins have also been frequently used for chiral separation in HPLC, SFC, and membrane separations.

This Special Issue provides a comprehensive updated overview on the usefulness of cyclodextrins as chiral selectors.

Prof. Dr. Zoltan Juvancz
Dr. Cecilia Cagliero
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. 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
  • chiral separations
  • GC, HPLC, SFC, and CE
  • chiral recognition mechanisms
  • structure–chiral selectivity relationships
  • a combination of chromatographic and structure determination methods (e.g., MS, NMR, CD, etc.)

Published Papers (4 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

10 pages, 548 KiB  
Article
Transport Properties in Multicomponent Systems Containing Cyclodextrins and Nickel Ions
by Sónia I. G. Fangaia, Daniela S. A. Silva, Ana Messias, Pedro M. G. Nicolau, Artur J. M. Valente, M. Melia Rodrigo and Ana C. F. Ribeiro
Int. J. Mol. Sci. 2024, 25(8), 4328; https://doi.org/10.3390/ijms25084328 - 13 Apr 2024
Viewed by 401
Abstract
In this work, we propose a comprehensive experimental study of the diffusion of nickel ions in combination with different cyclodextrins as carrier molecules for enhanced solubility and facilitated transport. For this, ternary mutual diffusion coefficients measured by Taylor dispersion method are reported for [...] Read more.
In this work, we propose a comprehensive experimental study of the diffusion of nickel ions in combination with different cyclodextrins as carrier molecules for enhanced solubility and facilitated transport. For this, ternary mutual diffusion coefficients measured by Taylor dispersion method are reported for aqueous solutions containing nickel salts and different cyclodextrins (that is, α-CD, β-CD, and γ-CD) at 298.15 K. A combination of Taylor dispersion and other methods, such as UV-vis spectroscopy, will be used to obtain complementary information on these systems. The determination of the physicochemical properties of these salts with CDs in aqueous solution provides information that allows us to understand solute–solvent interactions, and gives a significant contribution to understanding the mechanisms underlying diffusional transport in aqueous solutions, and, consequently, to mitigating the potential toxicity associated with these metal ions. For example, using mutual diffusion data, it is possible to estimate the number of moles of each ion transported per mole of the cyclodextrin driven by its own concentration gradient. Full article
(This article belongs to the Special Issue Current Uses and Applications of Cyclodextrins)
►▼ Show Figures

Figure 1

17 pages, 2683 KiB  
Article
The Applicability of Chromatographic Retention Modeling on Chiral Stationary Phases in Reverse-Phase Mode: A Case Study for Ezetimibe and Its Impurities
by Elek Ferencz, Éva-Katalin Kelemen, Mona Obreja, Gergő Tóth, Melinda Urkon, Arnold Zöldhegyi, Emese Sipos and Zoltán-István Szabó
Int. J. Mol. Sci. 2023, 24(22), 16097; https://doi.org/10.3390/ijms242216097 - 8 Nov 2023
Cited by 1 | Viewed by 776
Abstract
Mechanistic modeling is useful for predicting and modulating selectivity even in early chromatographic method development. This approach is also in accordance with current analytical quality using design principles and is highly welcomed by the authorities. The aim of this study was to investigate [...] Read more.
Mechanistic modeling is useful for predicting and modulating selectivity even in early chromatographic method development. This approach is also in accordance with current analytical quality using design principles and is highly welcomed by the authorities. The aim of this study was to investigate the separation behavior of two different types of chiral stationary phases (CSPs) for the separation of ezetimibe and its related substances using the mechanistic retention modeling approach offered by the Drylab software (version 4.5) package. Based on the obtained results, both CSPs presented with chemoselectivity towards the impurities of ezetimibe. The cyclodextrin-based CSP displayed a higher separation capacity and was able to separate seven related substances from the active pharmaceutical ingredient, while the cellulose-based column enabled the baseline resolution of six impurities from ezetimibe. Generally, the accuracy of predicted retention times was lower for the polysaccharide CSP, which could indicate the presence of additional secondary interactions between the analytes and the CSP. It was also demonstrated that the combination of mechanistic modeling and an experimental design approach can be applied to method development on CSPs in reverse-phase mode. The applicability of the methods was tested on spiked artificial placebo samples, while intraday and long-term (2 years) method repeatability was also challenged through comparing the obtained retention times and resolution values. The results indicated the excellent robustness of the selected setpoints. Overall, our findings indicate that the chiral columns could offer orthogonal selectivity to traditional reverse-phase columns for the separation of structurally similar compounds. Full article
(This article belongs to the Special Issue Current Uses and Applications of Cyclodextrins)
►▼ Show Figures

Figure 1

16 pages, 2750 KiB  
Article
Structure–Chiral Selectivity Relationships of Various Mandelic Acid Derivatives on Octakis 2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-gamma-cyclodextrin Containing Gas Chromatographic Stationary
by Levente Repassy, Zoltan Juvancz, Rita Bodane-Kendrovics, Zoltan Kaleta, Csaba Hunyadi and Gergo Riszter
Int. J. Mol. Sci. 2023, 24(20), 15051; https://doi.org/10.3390/ijms242015051 - 10 Oct 2023
Cited by 1 | Viewed by 1130
Abstract
Frequently, a good chiral separation is the result of long trial and error processes. The three-point interaction mechanisms require the fair geometrical fitting and functional group compatibility of the interacting groups. Structure–chiral selectivity correlations are guidelines that can be established via trough systematic [...] Read more.
Frequently, a good chiral separation is the result of long trial and error processes. The three-point interaction mechanisms require the fair geometrical fitting and functional group compatibility of the interacting groups. Structure–chiral selectivity correlations are guidelines that can be established via trough systematic studies using model compounds. The enantiorecognition of the test compounds was studied on an octakis 2,3-Di-O-acetyl-6-O-tert-butyldimethylsilyl-gamma-cyclodextrin (TBDMSDAGCD) chiral selector. In our work, mandelic acid and its variously substituted compounds were used as model compounds to establish adaptable rules for other enantiomeric pairs. The mandelic acid and its modified compounds were altered at both their carboxyl and hydroxyl positions to test the key interaction forces of the chiral recognition processes. Ring- and alkyl-substituted mandelic acid derivatives were also used in our experiments. The chiral selectivity values of 20 test compounds were measured and extrapolated to 100 °C. The hydrogen donor abilities of test compounds improved their chiral selectivities. The inclusion phenomenon also played a role in chiral recognition processes in several cases. Enantiomer elution reversals were observed for different derivatives of hydroxyl groups, providing evidence for the multimodal character of the selector. The results of our research can serve as guidelines to achieve appropriate chiral separation for other enantiomeric pairs. Full article
(This article belongs to the Special Issue Current Uses and Applications of Cyclodextrins)
►▼ Show Figures

Figure 1

24 pages, 3937 KiB  
Article
Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior
by Israel González-Méndez, Kendra Sorroza-Martínez, Ignacio González-Sánchez, Jesús Gracia-Mora, María Josefa Bernad-Bernad, Marco Cerbón, Ernesto Rivera and Anatoly K. Yatsimirsky
Int. J. Mol. Sci. 2023, 24(19), 14422; https://doi.org/10.3390/ijms241914422 - 22 Sep 2023
Cited by 2 | Viewed by 939
Abstract
The synthesis of a new family of ethylenediaminetetraacetic acid (EDTA) core dimers and G0 dendrimers end-capped with two and four β-cyclodextrin (βCD) moieties was performed by click-chemistry conjugation, varying the spacers attached to the core. The structure analyses were achieved in DMSO-d [...] Read more.
The synthesis of a new family of ethylenediaminetetraacetic acid (EDTA) core dimers and G0 dendrimers end-capped with two and four β-cyclodextrin (βCD) moieties was performed by click-chemistry conjugation, varying the spacers attached to the core. The structure analyses were achieved in DMSO-d6 and the self-inclusion process was studied in D2O by 1H-NMR spectroscopy for all platforms. It was demonstrated that the interaction with adamantane carboxylic acid (AdCOOH) results in a guest-induced shift of the self-inclusion effect, demonstrating the full host ability of the βCD units in these new platforms without any influence of the spacer. The results of the quantitative size and water solubility measurements demonstrated the equivalence between the novel EDTA-βCD platforms and the classical PAMAM-βCD dendrimer. Finally, we determined the toxicity for all EDTA-βCD platforms in four different cell lines: two human breast cancer cells (MCF-7 and MDA-MB-231), human cervical adenocarcinoma cancer cells (HeLa), and human lung adenocarcinoma cells (SK-LU-1). The new EDTA-βCD carriers did not present any cytotoxicity in the tested cell lines, which showed that these new classes of platforms are promising candidates for drug delivery. Full article
(This article belongs to the Special Issue Current Uses and Applications of Cyclodextrins)
►▼ Show Figures

Figure 1

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-4
Back to TopTop