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Cyclodextrins: Properties and Applications, 3rd Edition
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Cyclodextrins: Properties and Applications, 3rd Edition

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Macromolecules".

Deadline for manuscript submissions: closed (30 September 2025) | Viewed by 1856

Special Issue Editors

Prof. Dr. Miguel A. Esteso

E-Mail Website
Guest Editor
Faculty of Health Sciences, Catholic University of Ávila, Calle Los Canteros s/n, 05005 Ávila, Spain
Interests: electrochemical thermodynamics; electrolyte solutions; thermodynamic and transport properties; pharmacological chemistry; cyclodextrins
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Carmen M. Romero

E-Mail Website
Guest Editor
Departamento de Química, Universidad Nacional de Colombia, Calle 44 # 45-67 Bloque B9, Bogotá, Colombia
Interests: water and aqueous solutions; chemical thermodynamics; physicochemical behavior of systems that are of biological interest; physicochemical; surface and transport properties of aqueous solutions
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrins (CDs) continue to attract extensive research attention, primarily in relation to their properties as complexing agents and as carriers of different substances, attributes that render them excellent candidates for use in both fundamental and technological applications. For example, the use of these substances as participants in controlled release systems or as promoters of the improved solubility of certain poorly soluble substances is of great interest.

Despite their theoretical and applied importance, little is known about the potentialities of these molecules, necessitating a greater knowledge and understanding of the structure and properties of these macrocycles. In this sense, modifying the structure of the standard CDs in order to obtain new iterations with greater complexing capacity towards different substances, either as a consequence of their inclusion within the cavity of the CD or their bonding to the external portion of the CD, is a promising line of study.

In this Special Issue, research papers or comprehensive reviews related to advances in the knowledge of structure, properties and applications of cyclodextrins (CDs) are welcome.

Prof. Dr. Miguel A. Esteso
Prof. Dr. Carmen M. Romero
Guest Editors

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Keywords

  • cyclodextrins
  • controlled release systems
  • structure modification
  • thermodynamic properties
  • transport properties

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Published Papers (4 papers)

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Research

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13 pages, 1143 KB  
Article
Enantioselective Complexation of Xylopinine: A Cyclodextrin-Assisted CE and NMR Study
by Erzsébet Várnagy, Gergő Tóth, Sándor Hosztafi, Milo Malanga, Ida Fejős and Szabolcs Béni
Int. J. Mol. Sci. 2025, 26(19), 9405; https://doi.org/10.3390/ijms26199405 - 26 Sep 2025
Viewed by 272
Abstract
Tetrahydroprotoberberine alkaloids (THPBs) are bioactive natural products bearing stereogenic centers that frequently exhibit enantiomer-specific pharmacological effects. Xylopinine (XPN), a representative THPB, shows cytotoxic, antimicrobial, and antimalarial activity in vitro, and displays pronounced stereoselectivity in vivo, with the naturally occurring (S)-enantiomer emphasizing [...] Read more.
Tetrahydroprotoberberine alkaloids (THPBs) are bioactive natural products bearing stereogenic centers that frequently exhibit enantiomer-specific pharmacological effects. Xylopinine (XPN), a representative THPB, shows cytotoxic, antimicrobial, and antimalarial activity in vitro, and displays pronounced stereoselectivity in vivo, with the naturally occurring (S)-enantiomer emphasizing the need for reliable enantioselective analysis. In this study, we present the synthesis of racemic XPN from norlaudanosine, and its first comprehensive cyclodextrin-assisted capillary electrophoresis screening dedicated to the enantioseparation of XPN. Sulfated- and sulfobutyl-ether-β-cyclodextrin (S-β-CyD, SBE-β-CyD) provided efficient resolution (Rs > 3), while heptakis-(6-deoxy-6-(2-carboxyethyl)thio)-β-CyD (subetadex, SBX) yielded outstanding separation (Rs > 9). The enantiomer migration order was consistently R,S, except when using SBE-β-CyD, which showed the inverse sequence. Chiral HPLC using a Chiralpak AD column in polar organic mode with methanol modified with 0.1% diethylamine as mobile phase enabled the semi-preparative isolation of XPN enantiomers, with the (S)-enantiomer exceeding 95% purity. The absolute configuration was confirmed by circular dichroism spectroscopy. 1H NMR titration and 2D rotating-frame nuclear Overhauser effect correlation spectroscopy (ROESY) consistently revealed multi-site recognition of XPN by SBX, supporting the inclusion of both aromatic rings (A and D). Full article
(This article belongs to the Special Issue Cyclodextrins: Properties and Applications, 3rd Edition)
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31 pages, 4438 KB  
Article
Investigation of Host-Guest Inclusion Complexes Between Carmustine and α-Cyclodextrin: Synthesis, Characterization, and Evaluation
by Katarzyna Strzelecka, Dominika Janiec, Jan Sobieraj, Adam Kasiński, Marzena Kuras, Aldona Zalewska, Łukasz Szeleszczuk, Marcin Sobczak, Marta K. Dudek and Ewa Oledzka
Int. J. Mol. Sci. 2025, 26(19), 9386; https://doi.org/10.3390/ijms26199386 - 25 Sep 2025
Viewed by 397
Abstract
Carmustine (BCNU) is a powerful alkylating agent primarily used in the chemotherapeutic treatment of malignant brain tumors. However, its clinical application faces significant constraints due to its lipophilicity, low thermal stability, and rapid degradation in physiological environments. To tackle these challenges, our research [...] Read more.
Carmustine (BCNU) is a powerful alkylating agent primarily used in the chemotherapeutic treatment of malignant brain tumors. However, its clinical application faces significant constraints due to its lipophilicity, low thermal stability, and rapid degradation in physiological environments. To tackle these challenges, our research aimed at the development and detailed characterization of α-cyclodextrin (α-CD) inclusion complexes (ICs) with BCNU employing three different synthesis techniques: co-grinding, cryomilling, and co-precipitation. The selected synthetic methods displayed variations dependent on the technique used, affecting the efficiency, inclusion ratios, and drug-loading capacities, with co-precipitation achieving the most favorable complexation parameters. Structural elucidation through 1H NMR chemical shifts analysis indicated that only partial inclusion of BCNU occurred within α-CD in ICs produced via co-grinding, while cryomilling and co-precipitation allowed for complete inclusion. Multimodal spectroscopic analyses (FT-IR, UV-Vis, 13C CP MAS NMR, and ESI-MS) further substantiated the effective encapsulation of BCNU within α-CD, and systematic solubility assessments via Job’s continuous variation and the Benesi-Hildebrand method revealed a 1:1 host-guest stoichiometry. The ICs obtained were evaluated for BCNU release in vitro at pH levels of 4, 5, 6.5, and 7.4. The mechanism of BCNU drug release was determined to be Fickian diffusion, with the highest cumulative release noted in the acidic microenvironment. These findings collectively validate the effectiveness of α-CD as a functional excipient for the modulation of BCNU’s physicochemical properties through non-covalent complexation. This strategy shows potential for increasing the stability and solubility of BCNU, which may enhance its therapeutic effectiveness in the treatment of brain tumors. Full article
(This article belongs to the Special Issue Cyclodextrins: Properties and Applications, 3rd Edition)
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12 pages, 381 KB  
Article
γ-Cyclodextrin Co-Ingestion Enhances the Bioavailability of Perilla Oil, Regardless of Inclusion Complex Formation
by Keisuke Yoshikiyo, Hidehisa Shimizu, Hitomi Okada, Atsunori Hasegawa and Tatsuyuki Yamamoto
Int. J. Mol. Sci. 2025, 26(16), 7776; https://doi.org/10.3390/ijms26167776 - 12 Aug 2025
Viewed by 641
Abstract
Perilla oil, a plant-derived lipid rich in α-linolenic acid (ALA), has demonstrated enhanced bioavailability when administered as an inclusion complex with γ-cyclodextrin (γ-CD). Crucially, it remains unclear whether this enhancement requires complex formation or can be achieved simply by co-ingestion. To address this, [...] Read more.
Perilla oil, a plant-derived lipid rich in α-linolenic acid (ALA), has demonstrated enhanced bioavailability when administered as an inclusion complex with γ-cyclodextrin (γ-CD). Crucially, it remains unclear whether this enhancement requires complex formation or can be achieved simply by co-ingestion. To address this, we compared the effects of a γ-CD–perilla oil inclusion complex to the effects of a physical mixture of the two on the plasma fatty acid profiles of rats fed these preparations for four weeks. Both treatment groups showed significant alterations in plasma fatty acid composition compared to the control group. Notably, our results indicated no significant differences between the inclusion complex and physical mixture groups. These findings suggest that γ-CD facilitates the intestinal absorption of perilla oil through co-ingestion, irrespective of its complexation status. This highlights the potential of γ-CD as a practical and effective delivery aid for improving the bioavailability of ALA-rich oils. Further studies are warranted to elucidate the underlying mechanisms and their applicability to human nutrition. Full article
(This article belongs to the Special Issue Cyclodextrins: Properties and Applications, 3rd Edition)
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Review

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42 pages, 2695 KB  
Review
Exploring Cyclodextrin-Based Nanosponges as Drug Delivery Systems: Evaluation of Spectroscopic Methods for Examining Structure and Dynamics of Nanosponges
by Bartłomiej Pyrak, Karolina Rogacka-Pyrak and Tomasz Gubica
Int. J. Mol. Sci. 2025, 26(19), 9342; https://doi.org/10.3390/ijms26199342 - 24 Sep 2025
Viewed by 288
Abstract
Cyclodextrin-based nanosponges (CDNSs) are novel polymers composed of cross-linked cyclodextrin (CD) macrocyclic units, whose characteristics make them great candidates for drug delivery systems with adjustable properties for the drug release process. Examination of the molecular structure and dynamics of CDNSs is a necessary [...] Read more.
Cyclodextrin-based nanosponges (CDNSs) are novel polymers composed of cross-linked cyclodextrin (CD) macrocyclic units, whose characteristics make them great candidates for drug delivery systems with adjustable properties for the drug release process. Examination of the molecular structure and dynamics of CDNSs is a necessary starting point in the first step toward their broad application. Spectroscopic methods are effective analytical tools for probing the structure–property relationships of polymer structures. Infrared (IR) and Raman spectroscopies provide insight into the behavior of hydrogen bond (H-bond) networks influencing the properties of CDNS polymeric networks. Scattering techniques such as inelastic neutron scattering (INS) and Brillouin light scattering (BLS) probe elastic properties, while small-angle neutron scattering (SANS) examines the structural inhomogeneities and water sorption abilities of CDNS materials. Complete evaluation is possible using nuclear magnetic resonance (NMR), which can provide data on CDNS network dynamics. This article summarizes the results of a wide examination of CDNSs with the use of spectroscopic methods and reveals the links between the microscopic behavior and macroscopic properties of CDNSs, enabling the customization of their properties for various biomedical purposes. Full article
(This article belongs to the Special Issue Cyclodextrins: Properties and Applications, 3rd Edition)
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