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A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications

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

Deadline for manuscript submissions: 31 December 2024 | Viewed by 7610

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Special Issue Editors

Dr. Éva Fenyvesi

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Guest Editor

CycloLab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary
Interests: cyclodextrin polymers; environmental applications; analysis of cyclodextrins and complexes

Dr. Lajos Szente

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Guest Editor

CycloLab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary
Interests: cyclodextrins in drug delivery; cyclodextrins as active ingredients; applications in food; cosmetics
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Prof. Dr. Gustavo González-Gaitano

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1. Department of Chemistry, School of Science, Universidad de Navarra, 31080 Pamplona, Spain
2. SUMBET (Supramolecular Materials for Biomedical and Environmental Technologies), Universidad de Navarra, C/ Irunlarrea 1, 31080 Pamplona, Spain
3. BIOMA (Instituto de Biodiversidad y Medioambiente), Universidad de Navarra, C/ Irunlarrea 1, 31080 Pamplona, Spain
Interests: supramolecular chemistry; cyclodextrins; colloids; polymers; hydrogels; nanocomposites; scattering methods
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Special Issue Information

Dear Colleagues,

The papers in this Special Issue are derived from works presented at the 7th European Cyclodextrin Conference on 5–8 September 2023 in Budapest. Manuscripts in various fields of cyclodextrin chemistry and applications are its scope, including the latest results in cyclodextrin production and enzymology, synthesis and the characterization of novel cyclodextrin derivatives, modern tools for studying complexation, nanotechnology, self-assembling systems, drug delivery, gene/RNA delivery, therapeutic and diagnostic applications of pure cyclodextrins and their complexes, uses in food, cosmetic and other industries, as well as environmental technologies.

This Special Issue is dedicated to Professor József Szejtli on the 90^th anniversary of his birth in 1933. Professor Szejtli played a fundamental role in developing cyclodextrins by devoting his life to these cyclic carbohydrates. Professor Szejtli is internationally recognized for his outstanding contributions to various fields in cyclodextrin science. He is often mentioned as the “Godfather of Cyclodextrins.” The EuroCD_2023 conference follows the traditions started by Professor Szejtli in 1981: the first International Cyclodextrin Symposium in Budapest.

The International Journal of Molecular Sciences is an international, peer-reviewed, open-access journal providing an advanced forum for biochemistry, molecular and cell biology, molecular biophysics, molecular medicine, and all aspects of molecular research in chemistry. It has an impact factor of 6.208 and is ranked JCR - Q1 in Biochemistry & Molecular Biology. IJMS has offered a special publication fee: a 450 CHF discount for all the participants of the EuroCD2023 conference.

Manuscripts will be accepted from 1st August to 30th November 2023.

Dr. Éva Fenyvesi
Dr. Lajos Szente
Prof. Dr. Gustavo Gonzalez-Gaitano
Guest Editors

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Published Papers (7 papers)

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Research

15 pages, 2683 KiB

Open AccessArticle

Cross-Linked Thiolated Hydroxypropil-β-Cyclodextrin for Pulmonary Drug Delivery

by Luca Cerri, Chiara Migone, Lucia Vizzoni, Brunella Grassiri, Angela Fabiano, Anna Maria Piras and Ylenia Zambito

Int. J. Mol. Sci. 2024, 25(17), 9394; https://doi.org/10.3390/ijms25179394 - 29 Aug 2024

Viewed by 653

Abstract

Inhalable formulations with cyclodextrins (CDs) as solubility and absorption enhancers show promise for pulmonary delivery. Thiolated hydroxypropyl-β-cyclodextrin (HP-β-CD-SH) has mucoadhesive properties, enhancing drug absorption. Moreover, it has self-aggregation capability, which could further improve absorption and drug stability, as well as reduce irritation. This study aims to stabilize CD nanoaggregates using bifunctional cross-linkers and evaluate their benefits for lung drug delivery compared to pristine HP-β-CD-SH. Methods: The effectiveness of cross-linked HP-β-CD-SH nanoparticles (HP-β-CD-SH-NP) was compared to transient nanoaggregates in enhancing the activity of dexamethasone (DMS) and olive leaf extracts (OLE). DMS, a poorly soluble drug commonly used in lung treatments, and OLE, known for its antioxidant properties, were chosen. Drug-loaded HP-β-CD-SH-NP were prepared and nebulized onto a lung epithelial Air–Liquid Interface (ALI) model, assessing drug permeation and activity. Results: HP-β-CD-SH with 25% thiolation was synthesized via microwave reaction, forming 150 nm nanoaggregates and stabilized 400 nm HP-β-CD-SH-NP. All carriers showed good complexing ability with DMS and OLE and were biocompatible in the lung ALI model. HP-β-CD-SH promoted DMS absorption, while stabilized HP-β-CD-SH-NP protected against oxidative stress. Conclusion: HP-β-CD-SH is promising for lung delivery, especially as stabilized nanoaggregates, offering versatile administration for labile molecules like natural extracts. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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21 pages, 6272 KiB

Open AccessArticle

Variation of Cyclodextrin (CD) Complexation with Biogenic Amine Tyramine: Pseudopolymorphs of β-CD Inclusion vs. α-CD Exclusion, Deep Atomistic Insights

by Thammarat Aree

Int. J. Mol. Sci. 2024, 25(14), 7983; https://doi.org/10.3390/ijms25147983 - 22 Jul 2024

Viewed by 777

Abstract

Tyramine (TRM) is a biogenic catecholamine neurotransmitter, which can trigger migraines and hypertension. TRM accumulated in foods is reduced and detected using additive cyclodextrins (CDs) while their association characteristics remain unclear. Here, single-crystal X-ray diffraction and density functional theory (DFT) calculation have been performed, demonstrating the elusive pseudopolymorphs in β-CD inclusion complexes with TRM base/HCl, β-CD·0.5TRM·7.6H₂O (1) and β-CD·TRM HCl·4H₂O (2) and the rare α-CD·0.5(TRM HCl)·10H₂O (3) exclusion complex. Both 1 and 2 share the common inclusion mode with similar TRM structures in the round and elliptical β-CD cavities, belong to the monoclinic space group P2₁, and have similar herringbone packing structures. Furthermore, 3 differs from 2, as the smaller twofold symmetry-related, round α-CD prefers an exclusion complex with the twofold disordered TRM–H⁺ sites. In the orthorhombic P2₁2₁2 lattice, α-CDs are packed in a channel-type structure, where the column-like cavity is occupied by disordered water sites. DFT results indicate that β-CD remains elliptical to suitably accommodate TRM, yielding an energetically favorable inclusion complex, which is significantly contributed by the β-CD deformation, and the inclusion complex of α-CD with the TRM aminoethyl side chain is also energetically favorable compared to the exclusion mode. This study suggests the CD implications for food safety and drug/bioactive formulation and delivery. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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12 pages, 2259 KiB

Open AccessArticle

A Comparative Investigation of the Pulmonary Vasodilating Effects of Inhaled NO Gas Therapy and Inhalation of a New Drug Formulation Containing a NO Donor Metabolite (SIN-1A)

by Attila Oláh, Bálint András Barta, Mihály Ruppert, Alex Ali Sayour, Dávid Nagy, Tímea Bálint, Georgina Viktória Nagy, István Puskás, Lajos Szente, Levente Szőcs, Tamás Sohajda, Endre Zima, Béla Merkely and Tamás Radovits

Int. J. Mol. Sci. 2024, 25(14), 7981; https://doi.org/10.3390/ijms25147981 - 22 Jul 2024

Viewed by 916

Abstract

Numerous research projects focused on the management of acute pulmonary hypertension as Coronavirus Disease 2019 (COVID-19) might lead to hypoxia-induced pulmonary vasoconstriction related to acute respiratory distress syndrome. For that reason, inhalative therapeutic options have been the subject of several clinical trials. In this experimental study, we aimed to examine the hemodynamic impact of the inhalation of the SIN-1A formulation (N-nitroso-N-morpholino-amino-acetonitrile, the unstable active metabolite of molsidomine, stabilized by a cyclodextrin derivative) in a porcine model of acute pulmonary hypertension. Landrace pigs were divided into the following experimental groups: iNO (inhaled nitric oxide, n = 3), SIN-1A-5 (5 mg, n = 3), and SIN-1A-10 (10 mg, n = 3). Parallel insertion of a PiCCO system and a pulmonary artery catheter (Swan-Ganz) was performed for continuous hemodynamic monitoring. The impact of iNO (15 min) and SIN-1A inhalation (30 min) was investigated under physiologic conditions and U46619-induced acute pulmonary hypertension. Mean pulmonary arterial pressure (PAP) was reduced transiently by both substances. SIN-1A-10 had a comparable impact compared to iNO after U46619-induced pulmonary hypertension. PAP and PVR decreased significantly (changes in PAP: −30.1% iNO, −22.1% SIN-1A-5, −31.2% SIN-1A-10). While iNO therapy did not alter the mean arterial pressure (MAP) and systemic vascular resistance (SVR), SIN-1A administration resulted in decreased MAP and SVR values. Consequently, the PVR/SVR ratio was markedly reduced in the iNO group, while SIN-1A did not alter this parameter. The pulmonary vasodilatory impact of inhaled SIN-1A was shown to be dose-dependent. A larger dose of SIN-1A (10 mg) resulted in decreased PAP and PVR in a similar manner to the gold standard iNO therapy. Inhalation of the nebulized solution of the new SIN-1A formulation (stabilized by a cyclodextrin derivative) might be a valuable, effective option where iNO therapy is not available due to dosing difficulties or availability. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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11 pages, 1528 KiB

Open AccessArticle

Chiral Selectivities of Permethylated α-, β-, and γ-Cyclodextrins Containing Gas Chromatographic Stationary Phases towards Ibuprofen and Its Derivatives

by Zoltan Juvancz, Rita Bodane-Kendrovics, Csaba Agoston, Balazs Czegledi, Zoltan Kaleta, Laszlo Jicsinszky and Gergo Riszter

Int. J. Mol. Sci. 2024, 25(14), 7802; https://doi.org/10.3390/ijms25147802 - 16 Jul 2024

Viewed by 741

Abstract

Ibuprofen is a well-known and broadly used, nonsteroidal anti-inflammatory and painkiller medicine. Ibuprofen is a chiral compound, and its two isomers have different biological effects, therefore, their chiral separation is necessary. Ibuprofen and its derivatives were used as model compounds to establish transportable structure chiral selectivity relationships. Chiral selectors were permethylated α-, β-, and γ-cyclodextrins containing gas chromatographic stationary phases. The chiral selectivity of ibuprofen as a free acid and its various alkyl esters (methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and isoamyl esters) derivatives were tested at different temperatures. Every tested stationary phase was capable of the chiral separations of ibuprofen in its free acid form. The less strong included S optical isomers eluted before R optical isomers in every separate case. The results offer to draw transportable guidelines for the chiral selectivity vs. analyte structures. It was recognized that the S isomers of free ibuprofen acid showed an overloading phenomenon, but the R isomer did not. The results were supported by molecular modeling studies. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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23 pages, 6799 KiB

Open AccessArticle

Long-Chain Alkylthio Cyclodextrin Derivatives for Modulation of Quorum-Sensing-Based Bioluminescence in Aliivibrio fischeri Model System

by Éva Fenyvesi, Zsófia Berkl, Laura Ligethy, Ildikó Fekete-Kertész, Márton Csizmazia, Milo Malanga, István Puskás, Levente Szőcs, Róbert Iványi, István Kese, Erzsébet Varga, Lajos Szente and Mónika Molnár

Int. J. Mol. Sci. 2024, 25(13), 7139; https://doi.org/10.3390/ijms25137139 - 28 Jun 2024

Viewed by 809

Abstract

Quorum sensing (QS) allows bacteria to coordinate their activities by producing and detecting low-molecular-weight signal molecules based on population density, thereby controlling the infectivity of bacteria through various virulence factors. Quorum-sensing inhibition is a promising approach to tackle bacterial communication. Cyclodextrins (CDs) are a class of cyclic oligosaccharides that reversibly encapsulate the acyl chain of the signal molecules, thereby preventing their binding to receptors and interrupting bacterial communication. This results in the inhibition of the expression of various properties, including different virulence factors. To examine the potential quorum-quenching (QQ) ability of newly prepared cyclodextrin derivatives, we conducted short-term tests using Aliivibrio fischeri, a heterotrophic marine bacterium capable of bioluminescence controlled by quorum sensing. α- and β-cyclodextrins monosubstituted with alkylthio moieties and further derivatized with quaternary ammonium groups were used as the test agents. The effect of these cyclodextrins on the quorum-sensing system of A. fischeri was investigated by adding them to an exponential growth phase of the culture and then measuring bioluminescence intensity, population growth, and cell viability. Our results demonstrate that the tested cyclodextrins have an inhibitory effect on the quorum-sensing system of A. fischeri. The inhibitory effect varies based on the length of the alkyl chain, with alkylthio substitution enhancing it and the presence of quaternary ammonium groups decreasing it. Our findings suggest that cyclodextrins can be a promising therapeutic agent for the treatment of bacterial infections. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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16 pages, 2971 KiB

Open AccessArticle

Carboxymethyl β-Cyclodextrin Assistance for the 4-Nitrophenol Reduction Using Cobalt-Based Layered Double Hydroxides

by Alexia Demeester, Fatima Douma, Renaud Cousin, Stéphane Siffert, Gwladys Pourceau, Anne Wadouachi, Anne Ponchel, Eric Monflier and Sébastien Noël

Int. J. Mol. Sci. 2024, 25(12), 6390; https://doi.org/10.3390/ijms25126390 - 9 Jun 2024

Viewed by 1132

Abstract

Cobalt-aluminum-layered double hydroxides containing carboxymethyl β-cyclodextrin (CMβCD) were synthesized by coprecipitation and evaluated as a cobalt source for the 4-nitrophenol reduction in an aqueous medium. Several physicochemical techniques (XRD, FTIR, TGA) indicated the intercalation of the anionic cyclodextrin without damages to the hydrotalcite-type structure. These lamellar cobalt-aluminum hybrid materials (CoAl_CMβCD) were evaluated in the 4-nitrophenol reduction and showed higher activities in comparison with the CMβCD-free standard material (CoAl_CO₃). To rationalize these results, a set of experimental controls going from physical mixtures of CoAl_CO₃ with different cyclodextrins to other cobalt-based materials were investigated, highlighting the beneficial effects of both the layered double hydroxide and CMβCD-based hybrid structures. CMβCD also showed a beneficial effect as an additive during the 4-nitrophenol reduction. CoAl_CO₃, dispersed in a fresh CMβCD solution could be re-used for five successive cycles without the loss of activity. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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16 pages, 4152 KiB

Open AccessArticle

Advantages of Induced Circular Dichroism Spectroscopy for Qualitative and Quantitative Analysis of Solution-Phase Cyclodextrin Host–Guest Complexes

by Márta Kraszni, Balázs Balogh, István Mándity and Péter Horváth

Int. J. Mol. Sci. 2024, 25(1), 412; https://doi.org/10.3390/ijms25010412 - 28 Dec 2023

Viewed by 1430

Abstract

The presence of a chiral or chirally perturbed chromophore in the molecule under investigation is a fundamental requirement for the appearance of a circular dichroism (CD) spectrum. For native and for most of the substituted cyclodextrins, this condition is not applicable, because although chiral, cyclodextrins lack a chromophore group and therefore have no characteristic CD spectra over 220 nm. The reason this method can be used is that if the guest molecule has a chromophore group and this is in the right proximity to the cyclodextrin, it becomes chirally perturbed. As a result, the complex will now provide a CD signal, and this phenomenon is called induced circular dichroism (ICD). The appearance of the ICD spectrum is clear evidence of the formation of the complex, and the spectral sign and intensity is a good predictor of the structure of the complex. By varying the concentration of cyclodextrin, the ICD signal changes, resulting in a saturation curve, and from these data, the stability constant can be calculated for a 1:1 complex. This article compares ICD and NMR spectroscopic and molecular modeling results of cyclodextrin complexes of four model compounds: nimesulide, fenbufen, fenoprofen, and bifonazole. The results obtained by the different methods show good agreement, and the structures estimated from the ICD spectra are supported by NMR data and molecular modeling. Full article

(This article belongs to the Special Issue A Commemorative Issue in Honor of József Szejtli: Advances in Cyclodextrin Chemistry and Its Applications)

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