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Biomolecules
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Perspectives of Cyclodextrins II
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Perspectives of Cyclodextrins II

A special issue of Biomolecules (ISSN 2218-273X). This special issue belongs to the section "Chemical Biology".

Deadline for manuscript submissions: closed (15 July 2023) | Viewed by 9087

Special Issue Editor

Dr. Susana Braga

E-Mail Website
Guest Editor
Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: cyclodextrin inclusion compounds; solid-solid reactions by mechanochemistry; API solubilisation; stabilisation of antioxidant and anti-inflammatory natural products; 2D and 3D metal coordination complexes for local treatment of osteosarcoma and osteoporosis therapy; innovative medicines for leishmaniasis based on inorganic complexes
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Following a very successful first run, we are pleased to announce the launch of a new edition of a Special Issue on cyclodextrins.

Cyclodextrins (CDs), since first being reported by Villiers in 1891, have already witnessed the turning of two centuries. In the 20th century, these molecules found many applications in varied areas such as pharmaceuticals, food, nutrition, cosmetics, crop science, catalysis and analytical chemistry. Now, in the 21st century, CDs are expanding their range of applications even further, gaining acceptance in new fields. In healthcare, some CDs are employed as novel medicines or as components in vaccines. The most striking example is the use of hydroxypropyl-beta-cyclodextrin, under the label of cryopreservative, in Janssen’s vaccine against SARS-CoV-2 infection, ad26.cov2.s. In bioremediation, the natural sustainability of CDs and their unique host–guest chemistry make them ideal components for the retrieval of noble metals from waste slurry or to remediate water effluent from all sorts of contaminants. Progress in the field of materials science places cyclodextrins in a wide range of novel materials with a plethora of applications. This Special Issue will create a forum for the presentation of the most relevant progress made by the millennial generation of cyclodextrins, looking at the innovations of the last two decades, highlighting their importance in helping address the challenges brought about by the recent pandemic events, and projecting research into the future.

The international cyclodextrin scientific community is invited to present review articles addressing the innovative aspects of CDs in the 21st century or, alternatively, to present strongly original research papers reporting breakthrough applications of CDs.

I look forward to reading your contributions.

Dr. Susana Braga
Guest Editor

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. Biomolecules 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 2700 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

  • host-guest chemistry
  • data processing and curing
  • healthcare applications
  • nutraceutical applications
  • sustainability

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Published Papers (15 papers)

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Editorial

Jump to: Research, Review

2 pages, 184 KiB  
Editorial
Peering into the Kaleidoscope of Cyclodextrins
by Susana Santos Braga
Biomolecules 2021, 11(1), 121; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11010121 - 19 Jan 2021
Viewed by 1740
Abstract
Cyclodextrins (CDs) are known to us for 130 years, yet they remain ever as new and as fascinating as in their early years, when Villiers marveled at the unexpected growth of “beautiful radiated crystals” in the alcoholic media of his experiments on bacterial [...] Read more.
Cyclodextrins (CDs) are known to us for 130 years, yet they remain ever as new and as fascinating as in their early years, when Villiers marveled at the unexpected growth of “beautiful radiated crystals” in the alcoholic media of his experiments on bacterial fermentation of starches, or when Freudenberg struggled to solve the puzzle of their unusual shape and structure [...] Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)

Research

Jump to: Editorial, Review

15 pages, 3767 KiB  
Article
Electrospinning of Cyclodextrin–Oligolactide Derivatives
by Alena Opalkova Siskova, Liviu Sacarescu, Andrej Opalek, Jaroslav Mosnacek and Cristian Peptu
Biomolecules 2023, 13(2), 203; https://0-doi-org.brum.beds.ac.uk/10.3390/biom13020203 - 19 Jan 2023
Cited by 6 | Viewed by 1727
Abstract
The materials used for the preparation of electrospun mats exhibit a large variety. Among them, cyclodextrins (CDs) and their derivatives have received thorough attention. Herein, we focus on the preparation of electrospun fibers based on biodegradable cyclodextrin–oligolactide (CDLA) derivatives, which may be qualified [...] Read more.
The materials used for the preparation of electrospun mats exhibit a large variety. Among them, cyclodextrins (CDs) and their derivatives have received thorough attention. Herein, we focus on the preparation of electrospun fibers based on biodegradable cyclodextrin–oligolactide (CDLA) derivatives, which may be qualified as polymer-free cyclodextrin. CDLA was prepared by ring opening of L-lactide initiated by the β-cyclodextrin. A clear structural image of the high-purity CDLA product was proved by MALDI MS. Preparation of the electrospun mats was optimized by taking into consideration the electrospinning parameters such as applied voltage, needle-to-collector distance, flow rate, the concentration of cyclodextrin solutions, and solvent type. The obtained electrospun fibers were morphologically characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), and small-angle X-ray scattering (SAXS). SEM allowed the optimization of the electrospinning process to obtain beadless fibers with submicronic diameters. Further analysis by TEM and SAXS revealed the inner structural features of the CDLA-based filaments. Our results showed that the high purity CDLA materials, structurally well-defined at the molecular level, are suitable for the preparation of electrospun mats by using dimethylformamide or a water/acetonitrile mixture as electrospinning solvents, similar to lower molecular weight commercial cyclodextrin derivatives. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins II)
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23 pages, 3149 KiB  
Article
Structural Studies of Piperine Inclusion Complexes in Native and Derivative β-Cyclodextrins
by Elias Christoforides, Athena Andreou, Andreas Papaioannou and Kostas Bethanis
Biomolecules 2022, 12(12), 1762; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12121762 - 26 Nov 2022
Cited by 5 | Viewed by 2514
Abstract
Piperine (PN), the primary pungent alkaloid in black pepper shows several biological activities such as antioxidant, antimicrobial and anti-cancerogenic effects. Similar to other alkaloids, PN is characterized by poor water solubility. One way to improve its solubility and thus its biological activities is [...] Read more.
Piperine (PN), the primary pungent alkaloid in black pepper shows several biological activities such as antioxidant, antimicrobial and anti-cancerogenic effects. Similar to other alkaloids, PN is characterized by poor water solubility. One way to improve its solubility and thus its biological activities is by forming inclusion complexes with suitable cyclodextrins. In this work PN inclusion complexes in native β-cyclodextrin (β-CD), its methylated (randomly methylated (RM-β-CD), heptakis-(2,6-di-O-methyl)-β-CD (DM-β-CD) and heptakis-(2,3,6-tri-O-methyl)-β-CD (TM-β-CD)) and 2-hydroxypropylated (HP-β-CD) derivatives are investigated using physicochemical methods, such as phase solubility study and X-ray crystallography complemented by theoretical (molecular dynamics simulations) studies. The determination of the crystal structure of the PN inclusion complexes in β-CD, DM-β-CD and TM-β-CD, reveals the formation of 1:2 guest:host inclusion complexes in the crystalline state. The guest PN molecule threads the hydrophobic cavities of the hosts which are arranged as couples in a tail-to-tail mode in the case of PN/β-CD and in a head-to-tail mode in the cases of PN/DM-β-CD and PN/TM-β-CD. MD studies based on the crystallographically determined structures and docked models show the stability of the examined complexes in an aqueous environment whereas the binding affinity of PN for the host molecules is calculated by the MM/GBSA method. Finally, phase-solubility studies of PN with β-CD, RM-β-CD and HP-β-CD are presented, indicating a Bs-type for the PN/β-CD complex and an AL-type for the PN/RM-β-CD and PN/HP-β-CD complexes with 1:1 guest:host stoichiometry. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins II)
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21 pages, 5157 KiB  
Article
Investigation of the Drug Carrier Properties of Insoluble Cyclodextrin Polymer Microspheres
by Ádám Haimhoffer, Alexandra Vas, Gabriella Árvai, Éva Fenyvesi, László Jicsinszky, István Budai, Attila Bényei, Géza Regdon, Jr., Ágnes Rusznyák, Gábor Vasvári, Judit Váradi, Ildikó Bácskay, Miklós Vecsernyés and Ferenc Fenyvesi
Biomolecules 2022, 12(7), 931; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12070931 - 02 Jul 2022
Cited by 6 | Viewed by 1865
Abstract
The investigation of the usability of solid insoluble β-cyclodextrin polymers (βCDP) in micro-sized, controlled drug delivery systems has only recently attracted interest. Our aim was to form complexes with poorly soluble active pharmaceutical ingredients (APIs) with two types of βCDP for drug delivery [...] Read more.
The investigation of the usability of solid insoluble β-cyclodextrin polymers (βCDP) in micro-sized, controlled drug delivery systems has only recently attracted interest. Our aim was to form complexes with poorly soluble active pharmaceutical ingredients (APIs) with two types of βCDP for drug delivery applications. Solid insoluble cyclodextrin polymer of irregular shape (βCDPIS) and cyclodextrin microbeads (βCDPB) were used in the experiments. Morphology, surface area, size distribution and swelling capacity of carriers were investigated. We created complexes with two APIs, curcumin and estradiol, and applied powder X-ray diffraction, FTIR and thermal analysis (TGA/DSC) to prove the complexation. Finally, the dissolution, biocompatibility and permeation of APIs on Caco-2 cells were investigated. The size of the beads was larger than 100 µm, their shape was spherical and surfaces were smooth; while the βCDPIS particles were around 4 µm with irregular shape and surface. None of the polymers showed any cytotoxic effect on Caco-2 cells. Both carriers were able to extract curcumin and estradiol from aqueous solutions, and the dissolution test showed prolonged estradiol release. Caco-2 permeability tests were in accordance with the complexation abilities and dissolution of the complexes. This study offers useful data for further pharmaceutical applications of insoluble cyclodextrin polymers. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins II)
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20 pages, 6121 KiB  
Article
Inclusion of Hydroxycinnamic Acids in Methylated Cyclodextrins: Host-Guest Interactions and Effects on Guest Thermal Stability
by Lee E. Hunt, Susan A. Bourne and Mino R. Caira
Biomolecules 2021, 11(1), 45; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11010045 - 31 Dec 2020
Cited by 7 | Viewed by 2250
Abstract
There is ongoing interest in exploiting the antioxidant activity and other medicinal properties of natural monophenolic/polyphenolic compounds, but their generally low aqueous solubility limits their applications. Numerous studies have been undertaken to solubilize such compounds via supramolecular derivatization with co-crystal formation with biocompatible [...] Read more.
There is ongoing interest in exploiting the antioxidant activity and other medicinal properties of natural monophenolic/polyphenolic compounds, but their generally low aqueous solubility limits their applications. Numerous studies have been undertaken to solubilize such compounds via supramolecular derivatization with co-crystal formation with biocompatible coformer molecules and cyclodextrin (CD) complexation being two successful approaches. In this study, eight new crystalline products obtained by complexation between methylated cyclodextrins and the bioactive phenolic acids (ferulic, hydroferulic, caffeic, and p-coumaric acids) were investigated using thermal analysis (hot stage microscopy, thermogravimetry, differential scanning calorimetry) and X-ray diffraction. All of the complexes crystallized as ternary systems containing the host CD, a phenolic acid guest, and water. On heating each complex, the primary thermal events were dehydration and liberation of the respective phenolic acid component, the mass loss for the latter step enabling determination of the host-guest stoichiometry. Systematic examination of the X-ray crystal structures of the eight complexes enabled their classification according to the extent of inclusion of each guest molecule within the cavity of its respective CD molecule. This revealed three CD inclusion compounds with full guest encapsulation, three with partial guest inclusion, and two that belong to the rare class of ‘non-inclusion’ compounds. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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26 pages, 9462 KiB  
Article
Rings, Hexagons, Petals, and Dipolar Moment Sink-Sources: The Fanciful Behavior of Water around Cyclodextrin Complexes
by Pablo F. Garrido, Martín Calvelo, Rebeca Garcia-Fandiño and Ángel Piñeiro
Biomolecules 2020, 10(3), 431; https://0-doi-org.brum.beds.ac.uk/10.3390/biom10030431 - 10 Mar 2020
Cited by 15 | Viewed by 4345
Abstract
The basket-like geometry of cyclodextrins (CDs), with a cavity able to host hydrophobic groups, makes these molecules well suited for a large number of fundamental and industrial applications. Most of the established CD-based applications rely on trial and error studies, often ignoring key [...] Read more.
The basket-like geometry of cyclodextrins (CDs), with a cavity able to host hydrophobic groups, makes these molecules well suited for a large number of fundamental and industrial applications. Most of the established CD-based applications rely on trial and error studies, often ignoring key information at the atomic level that could be employed to design new products and to optimize their use. Computational simulations are well suited to fill this gap, especially in the case of CD systems due to their low number of degrees of freedom compared with typical macromolecular systems. Thus, the design and validation of solid and efficient methods to simulate and analyze CD-based systems is key to contribute to this field. The behavior of supramolecular complexes critically depends on the media where they are embedded, so the detailed characterization of the solvent is required to fully understand these systems. In the present work, we use the inclusion complex formed by two α-CDs and one sodium dodecyl sulfate molecule to test eight different parameterizations of the GROMOS and AMBER force fields, including several methods aimed to increase the conformational sampling in computational molecular dynamics simulation trajectories. The system proved to be extremely sensitive to the employed force field, as well as to the presence of a water/air interface. In agreement with previous experiments and in contrast to the results obtained with AMBER, the analysis of the simulations using GROMOS showed a quick adsorption of the complex to the interface as well as an extremely exotic behavior of the water molecules surrounding the structure both in the bulk aqueous solution and at the water surface. The chirality of the CD molecule seems to play an important role in this behavior. All together, these results are expected to be useful to better understand the behavior of CD-based supramolecular complexes such as adsorption or aggregation driving forces, as well as to introduce new methods able to speed up general MD simulations. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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18 pages, 1923 KiB  
Article
Solid γ-Cyclodextrin Inclusion Compound with Gingerols, a Multi-Component Guest: Preparation, Properties and Application in Yogurt
by Joana M. Pais, Bruna Pereira, Filipe A. Almeida Paz, Susana M. Cardoso and Susana S. Braga
Biomolecules 2020, 10(2), 344; https://0-doi-org.brum.beds.ac.uk/10.3390/biom10020344 - 22 Feb 2020
Cited by 13 | Viewed by 4119
Abstract
Gingerols from the rhizome of fresh ginger (Zingiber officinale) were obtained by a simple extraction, followed by purification. The gingerols extract was composed of 6-gingerol (54%), 8-gingerol (20%), and 10-gingerol (26%). It was included into γ-cyclodextrin by classic co-dissolution procedures. Solid-state [...] Read more.
Gingerols from the rhizome of fresh ginger (Zingiber officinale) were obtained by a simple extraction, followed by purification. The gingerols extract was composed of 6-gingerol (54%), 8-gingerol (20%), and 10-gingerol (26%). It was included into γ-cyclodextrin by classic co-dissolution procedures. Solid-state characterisation of γ-cyclodextrin·gingerols shows that this inclusion compound features 1:1 host-to-guest stoichiometry and that it is a microcrystalline powder with a crystalline cell that belongs to the tetragonal space group 4212, having the host molecules stacked in infinite channels where the gingerols are accommodated. In chimico studies with ABTS•+ scavenging, NO• scavenging, β-carotene peroxidation, and 5-LOX inhibition show that γ-cyclodextrin is a suitable carrier for gingerols, because it does not alter their reactivity towards these substances. Yogurt was tested as a matrix for the incorporation of gingerols and γ-cyclodextrin·gingerols into foodstuff. The colour of the fortified yogurt suffered little alterations. In the case of yogurt with the inclusion compound, γ-cyclodextrin·gingerols, as fortificant, these alterations were not perceptible to the naked eye. Moreover, yogurt with γ-cyclodextrin·gingerols showed a good antioxidant activity, thus being suitable for use in nutraceutical applications. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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18 pages, 4145 KiB  
Article
New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling
by Estefania Oliva, David Mathiron, Sébastien Rigaud, Eric Monflier, Emmanuel Sevin, Hervé Bricout, Sébastien Tilloy, Fabien Gosselet, Laurence Fenart, Véronique Bonnet, Serge Pilard and Florence Djedaini-Pilard
Biomolecules 2020, 10(2), 339; https://0-doi-org.brum.beds.ac.uk/10.3390/biom10020339 - 20 Feb 2020
Cited by 14 | Viewed by 3856
Abstract
Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). [...] Read more.
Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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29 pages, 5943 KiB  
Article
Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex †
by Valentina Venuti, Vincenza Crupi, Barbara Fazio, Domenico Majolino, Giuseppe Acri, Barbara Testagrossa, Rosanna Stancanelli, Federica De Gaetano, Agnese Gagliardi, Donatella Paolino, Giuseppe Floresta, Venerando Pistarà, Antonio Rescifina and Cinzia A. Ventura
Biomolecules 2019, 9(10), 531; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9100531 - 25 Sep 2019
Cited by 52 | Viewed by 4249
Abstract
Idebenone (IDE) is an antioxidant drug active at the level of the central nervous system (CNS), whose poor water solubility limits its clinical application. An IDE/2-hydroxypropyl-β-cyclodextrin (IDE/HP-β-CD) inclusion complex was investigated by combining experimental methods and theoretical approaches. Furthermore, [...] Read more.
Idebenone (IDE) is an antioxidant drug active at the level of the central nervous system (CNS), whose poor water solubility limits its clinical application. An IDE/2-hydroxypropyl-β-cyclodextrin (IDE/HP-β-CD) inclusion complex was investigated by combining experimental methods and theoretical approaches. Furthermore, biological in vitro/ex vivo assays were performed. Phase solubility studies showed an AL type diagram, suggesting the presence of a 1:1 complex with high solubility. Scanning electron microscopy (SEM) allowed us to detect the morphological changes upon complexation. The intermolecular interactions stabilizing the inclusion complex were experimentally characterized by exploring the complementarity of Fourier-transform infrared spectroscopy in attenuated total reflectance geometry (FTIR-ATR) with mid-infrared light, Fourier-transform near-infrared (FT-NIR) spectroscopy, and Raman spectroscopy. From the temperature evolution of the O–H stretching band of the complex, the average enthalpy ΔHHB of the hydrogen bond scheme upon inclusion was obtained. Two-dimensional (2D) rotating frame Overhauser effect spectroscopy (ROESY) analysis and computational studies involving molecular modeling and molecular dynamics (MD) simulation demonstrated the inclusion of the quinone ring of IDE inside the CD ring. In vitro/ex vivo studies evidenced that complexation produces a protective effect of IDE against the H2O2-induced damage on human glioblastoma astrocytoma (U373) cells and increases IDE permeation through the excised bovine nasal mucosa. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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13 pages, 3168 KiB  
Article
Pharmacokinetic Properties of Fluorescently Labelled Hydroxypropyl-Beta-Cyclodextrin
by Judit Váradi, Anca Hermenean, Rudolf Gesztelyi, Viktória Jeney, Enikő Balogh, László Majoros, Milo Malanga, Éva Fenyvesi, Lajos Szente, Ildikó Bácskay, Miklós Vecsernyés, Pálma Fehér, Zoltán Ujhelyi, Gábor Vasvári, István Árvai, Ágnes Rusznyák, Cornel Balta, Hildegard Herman and Ferenc Fenyvesi
Biomolecules 2019, 9(10), 509; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9100509 - 20 Sep 2019
Cited by 16 | Viewed by 4314
Abstract
2-Hydroxypropyl-beta-cyclodextrin (HPBCD) is utilized in the formulation of pharmaceutical products and recently orphan designation was granted for the treatment of Niemann–Pick disease, type C. The exact mechanism of HPBCD action and side effects are not completely explained. We used fluorescently labelled hydroxypropyl-beta-cyclodextrin (FITC-HPBCD) [...] Read more.
2-Hydroxypropyl-beta-cyclodextrin (HPBCD) is utilized in the formulation of pharmaceutical products and recently orphan designation was granted for the treatment of Niemann–Pick disease, type C. The exact mechanism of HPBCD action and side effects are not completely explained. We used fluorescently labelled hydroxypropyl-beta-cyclodextrin (FITC-HPBCD) to study its pharmacokinetic parameters in mice and compare with native HPBCD data. We found that FITC-HPBCD has fast distribution and elimination, similar to HPBCD. Interestingly animals could be divided into two groups, where the pharmacokinetic parameters followed or did not follow the two-compartment, first-order kinetic model. Tissue distribution studies revealed, that a significant amount of FITC-HPBCD could be detected in kidneys after 60 min treatment, due to its renal excretion. Ex vivo fluorescent imaging showed that fluorescence could be measured in lung, liver, brain and spleen after 30 min of treatment. To model the interaction and cellular distribution of FITC-HPBCD in the wall of blood vessels, we treated human umbilical vein endothelial cells (HUVECs) with FITC-HPBCD and demonstrated for the first time that this compound could be detected in the cytoplasm in small vesicles after 30 min of treatment. FITC-HPBCD has similar pharmacokinetic to HPBCD and can provide new information to the detailed mechanism of action of HPBCD. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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18 pages, 3064 KiB  
Article
Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer
by Eszter Fliszár-Nyúl, Beáta Lemli, Sándor Kunsági-Máté, Lajos Szente and Miklós Poór
Biomolecules 2019, 9(9), 428; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9090428 - 30 Aug 2019
Cited by 21 | Viewed by 3270
Abstract
Alternariol is an Alternaria mycotoxin that appears in fruits, tomatoes, oilseeds, and corresponding products. Chronic exposure to it can induce carcinogenic and xenoestrogenic effects. Cyclodextrins (CDs) are ring-shaped molecules built up by glucose units, which form host–guest type complexes with some mycotoxins. Furthermore, [...] Read more.
Alternariol is an Alternaria mycotoxin that appears in fruits, tomatoes, oilseeds, and corresponding products. Chronic exposure to it can induce carcinogenic and xenoestrogenic effects. Cyclodextrins (CDs) are ring-shaped molecules built up by glucose units, which form host–guest type complexes with some mycotoxins. Furthermore, insoluble CD polymers seem suitable for the extraction/removal of mycotoxins from aqueous solutions. In this study, the interactions of alternariol with β- and γ-CDs were tested by employing fluorescence spectroscopic and modeling studies. Moreover, the removal of alternariol from aqueous solutions by insoluble β-CD bead polymer (BBP) was examined. Our major observations/conclusions are the following: (1) CDs strongly increased the fluorescence of alternariol, the strongest enhancement was induced by the native γ-CD at pH 7.4. (2) Alternariol formed the most stable complexes with the native γ-CD (logK = 3.2) and the quaternary ammonium derivatives (logK = 3.4–3.6) at acidic/physiological pH and at pH 10.0, respectively. (3) BBP effectively removed alternariol from aqueous solution. (4) The alternariol-binding ability of β-CD polymers was significantly higher than was expected based on their β-CD content. (5) CD technology seems a promising tool to improve the fluorescence detection of alternariol and/or to develop new mycotoxin binders to decrease alternariol exposure. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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15 pages, 2773 KiB  
Article
Cyclodextrins Can Entrap Zearalenone-14-Glucoside: Interaction of the Masked Mycotoxin with Cyclodextrins and Cyclodextrin Bead Polymer
by Zelma Faisal, Eszter Fliszár-Nyúl, Luca Dellafiora, Gianni Galaverna, Chiara Dall’Asta, Beáta Lemli, Sándor Kunsági-Máté, Lajos Szente and Miklós Poór
Biomolecules 2019, 9(8), 354; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9080354 - 09 Aug 2019
Cited by 14 | Viewed by 4111
Abstract
Zearalenone (ZEN) is a Fusarium-derived xenoestrogenic mycotoxin. In plants, zearalenone-14-O-β-d-glucoside (Z14G) is the major conjugated metabolite of ZEN, and is a masked mycotoxin. Masked mycotoxins are plant-modified derivatives, which are not routinely screened in food and feed samples. [...] Read more.
Zearalenone (ZEN) is a Fusarium-derived xenoestrogenic mycotoxin. In plants, zearalenone-14-O-β-d-glucoside (Z14G) is the major conjugated metabolite of ZEN, and is a masked mycotoxin. Masked mycotoxins are plant-modified derivatives, which are not routinely screened in food and feed samples. Cyclodextrins (CDs) are cyclic oligosaccharides built up from D-glucopyranose units. CDs can form stable host–guest type complexes with lipophilic molecules (e.g., with some mycotoxins). In this study, the interaction of Z14G with native and chemically modified β- and γ-CDs was examined employing fluorescence spectroscopy and molecular modeling. Furthermore, the removal of Z14G from aqueous solution by insoluble β-CD bead polymer (BBP) was also tested. Our results demonstrate that Z14G forms the most stable complexes with γ-CDs under acidic and neutral conditions (K ≈ 103 L/mol). Among the CDs tested, randomly methylated γ-CD induced the highest increase in the fluorescence of Z14G (7.1-fold) and formed the most stable complexes with the mycotoxin (K = 2 × 103 L/mol). Furthermore, BBP considerably reduced the Z14G content of aqueous solution. Based on these observations, CD technology seems a promising tool to improve the fluorescence analytical detection of Z14G and to discover new mycotoxin binders which can also remove masked mycotoxins (e.g., Z14G). Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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Review

Jump to: Editorial, Research

13 pages, 2051 KiB  
Review
Molecular Mind Games: The Medicinal Action of Cyclodextrins in Neurodegenerative Diseases
by Susana Santos Braga
Biomolecules 2023, 13(4), 666; https://0-doi-org.brum.beds.ac.uk/10.3390/biom13040666 - 12 Apr 2023
Cited by 1 | Viewed by 2183
Abstract
Cyclodextrins are often used as molecular carriers for small active ingredients in medicine. Recently, the intrinsic medicinal activity of some of these compounds has been under investigation, mainly related to their ability to interfere with cholesterol and, therefore, prevent and treat cholesterol-related diseases [...] Read more.
Cyclodextrins are often used as molecular carriers for small active ingredients in medicine. Recently, the intrinsic medicinal activity of some of these compounds has been under investigation, mainly related to their ability to interfere with cholesterol and, therefore, prevent and treat cholesterol-related diseases such as cardiovascular disease and neuronal diseases arising from altered cholesterol and lipid metabolism. One of the most promising compounds within the cyclodextrin family is 2-hydroxypropyl-β-cyclodextrin (HPβCD), owing to its superior biocompatibility profile. This work presents the most recent advances in the research and clinical use of HPβCD against Niemann–Pick disease, a congenital condition involving cholesterol accumulation inside lysosomes in brain cells, Alzheimer’s and Parkinson’s. HPβCD plays a complex role in each of these ailments, going beyond the mere sequestering of cholesterol molecules and involving an overall regulation of protein expression that helps restore the normal functioning of the organism. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins II)
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19 pages, 2358 KiB  
Review
Cyclodextrins: Emerging Medicines of the New Millennium
by Susana Santos Braga
Biomolecules 2019, 9(12), 801; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9120801 - 28 Nov 2019
Cited by 114 | Viewed by 7803
Abstract
Cyclodextrins, since their discovery in the late 19th century, were mainly regarded as excipients. Nevertheless, developments in cyclodextrin research have shown that some of these hosts can capture and include biomolecules, highlighting fatty acids and cholesterol, which implies that they are not inert [...] Read more.
Cyclodextrins, since their discovery in the late 19th century, were mainly regarded as excipients. Nevertheless, developments in cyclodextrin research have shown that some of these hosts can capture and include biomolecules, highlighting fatty acids and cholesterol, which implies that they are not inert and that their action may be used in specific medicinal purposes. The present review, centered on literature reports from the year 2000 until the present day, presents a comprehensive description of the known biological activities of cyclodextrins and their implications for medicinal applications. The paper is divided into two main sections, one devoted to the properties and applications of cyclodextrins as active pharmaceutical ingredients in a variety of pathologies, from infectious ailments to cardiovascular dysfunctions and metabolic diseases. The second section is dedicated to the use of cyclodextrins in a range of biomedical technologies. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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17 pages, 25645 KiB  
Review
Nanoscale Restructuring of Polymer Materials to Produce Single Polymer Composites and Miscible Blends
by Alan E. Tonelli
Biomolecules 2019, 9(6), 240; https://0-doi-org.brum.beds.ac.uk/10.3390/biom9060240 - 19 Jun 2019
Cited by 3 | Viewed by 3091
Abstract
I summarize work conducted in our laboratories over the past 30 years using small host molecules to restructure polymer materials at the nanometer level. Certain small molecules, such as the cyclic starches cyclodextrins (CDs) and urea (U) can form non-covalent crystalline inclusion compounds [...] Read more.
I summarize work conducted in our laboratories over the past 30 years using small host molecules to restructure polymer materials at the nanometer level. Certain small molecules, such as the cyclic starches cyclodextrins (CDs) and urea (U) can form non-covalent crystalline inclusion compounds (ICs) with a range of guest molecules, including many polymers. In polymer-CD- and -U-ICs, guest polymer chains reside in narrow channels created by the host molecule crystals, where they are separated and highly extended. When the host crystalline lattice is carefully removed, the guest polymer chains coalesce into a bulk sample with an organization that is distinct from that normally produced from its melt or from solution. Amorphous regions of such coalesced polymer samples have a greater density, likely with less chain entanglement and more chain alignment. As a consequence, after cooling from their melts, coalesced amorphous polymers show glass-transition temperatures (Tgs) that are elevated above those of samples prepared from their solutions or melts. Upon cooling from their melts, coalesced samples of crystallizable polymers show dramatically-increased abilities to crystallize more rapidly and much closer to their melting temperatures (Tms). These unique behaviors of polymers coalesced from their CD- and U-ICs are unexpectedly resistant to extended annealing above their Tgs and Tms. Taking advantage of this behavior permits us to create polymer materials with unique and improved properties. Among these are amorphous polymers with elevated Tgs and semi-crystalline polymers with finer more uniform morphologies. Improved mechanical properties can be achieved through self-nucleation with small amounts of the same polymer made rapidly crystallizable through coalescence from its CD- or U-IC. This can lead to single polymer composites with as-received polymer matrices and self-nucleated reinforcements. Through simultaneous formation and subsequent coalescence from their common CD–ICs, stable well-mixed blends can be achieved between any two or more polymers, despite their inherent immiscibilities. Such coalesced and well-mixed blends are also resistant to phase segregation when heated for extensive periods well above their Tgs and Tms. Full article
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
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