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Cyclodextrin Chemistry and Toxicology

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

Deadline for manuscript submissions: closed (15 February 2021) | Viewed by 56081

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Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, University of Campania “Luigi Vanvitelli”, Via Antonio Vivaldi 43, 81100 Caserta, Italy
Interests: environmental toxicology; cytotoxic activity; antigenotoxic activity and antimicrobial activity of pure compounds
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E-Mail Website
Guest Editor
Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, University of Campania “Luigi Vanvitelli”, Via Antonio Vivaldi 43, 81100 Caserta, Italy
Interests: environmental toxicology; biological activities of xenobiotics
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, University of Campania “Luigi Vanvitelli”, Caserta, Italy
Interests: cyclodextrin; inclusion complex; preparation methods; drug delivery systems; X-ray diffraction; crystal structure
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrins (CDs) are cyclic, water-soluble oligosaccharides composed of six (α-CD), seven (β-CD), or eight (γ-CD) D(+)-glucose units linked by α-1,4 bonds. Obtained from starch, CDs are considered natural molecules. Their typical toroidal-like structure consists of an apolar internal cavity and a polar external surface, allowing for the physical inclusion of a wide range of active molecules, especially with aromatic rings. Thanks to their characteristics, CDs have numerous applications in several fields, namely: biotechnologies, green chemistry, cosmetic formulations/fragrance stabilization, analytical chemistry, drug delivery, and pharmaceutical excipients. In fact, nowadays, there are already numerous food products and pharmaceutical formulations on the market containing natural CDs. To further increase the benefits of these molecules, they can undergo chemical modifications producing synthetic CD derivatives. This Special Issue aims to implement the information regarding the use of cyclodextrins and their molecular complexes, to evaluate their potential role in multiple applications.

Prof. Dr. Marina Isidori
Prof. Dr. Margherita Lavorgna
Prof. Dr. Margherita Lavorgna
Guest Editors

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Keywords

  • inclusion complexes
  • cyclodextrins derivates
  • biological activities
  • cyclodextrins and the improvement of theraphy efficacy
  • cyclodextrins involved in environmental remediation
  • cyclodextrins: food and innovative packaging
  • applications of cyclodextrins in cosmetic
  • cyclodextrins in textile formulations
  • cyclodextrins and controlled release of molecules included
  • nano-materials and nano-structured coatings containing cyclodextrins

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Related Special Issue

Published Papers (14 papers)

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Research

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14 pages, 2811 KiB  
Article
The Effect of α-, β- and γ-Cyclodextrin on Wheat Dough and Bread Properties
by Anne-Sophie Schou Jødal, Tomasz Pawel Czaja, Frans W. J. van den Berg, Birthe Møller Jespersen and Kim Lambertsen Larsen
Molecules 2021, 26(8), 2242; https://doi.org/10.3390/molecules26082242 - 13 Apr 2021
Cited by 4 | Viewed by 2256
Abstract
Cyclodextrins (CDs) are cyclic oligosaccharides that have found widespread application in numerous fields. CDs have revealed a number of various health benefits, making them potentially useful food supplements and nutraceuticals. In this study, the impact of α-, β-, and γ-CD at different concentrations [...] Read more.
Cyclodextrins (CDs) are cyclic oligosaccharides that have found widespread application in numerous fields. CDs have revealed a number of various health benefits, making them potentially useful food supplements and nutraceuticals. In this study, the impact of α-, β-, and γ-CD at different concentrations (up to 8% of the flour weight) on the wheat dough and bread properties were investigated. The impact on dough properties was assessed by alveograph analysis, and it was found that especially β-CD affected the viscoelastic properties. This behavior correlates well with a direct interaction of the CDs with the proteins of the gluten network. The impact on bread volume and bread staling was also assessed. The bread volume was in general not significantly affected by the addition of up to 4% CD, except for 4% α-CD, which slightly increased the bread volume. Larger concentrations of CDs lead to decreasing bread volumes. Bread staling was investigated by texture analysis and low field nuclear magnetic resonance spectroscopy (LF-NMR) measurements, and no effect of the addition of CDs on the staling was observed. Up to 4% CD can, therefore, be added to wheat bread with only minor effects on the dough and bread properties. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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11 pages, 972 KiB  
Article
Exploring Charged Polymeric Cyclodextrins for Biomedical Applications
by Noemi Bognanni, Francesco Bellia, Maurizio Viale, Nadia Bertola and Graziella Vecchio
Molecules 2021, 26(6), 1724; https://doi.org/10.3390/molecules26061724 - 19 Mar 2021
Cited by 6 | Viewed by 2391
Abstract
Over the years, cyclodextrin uses have been widely reviewed and their proprieties provide a very attractive approach in different biomedical applications. Cyclodextrins, due to their characteristics, are used to transport drugs and have also been studied as molecular chaperones with potential application in [...] Read more.
Over the years, cyclodextrin uses have been widely reviewed and their proprieties provide a very attractive approach in different biomedical applications. Cyclodextrins, due to their characteristics, are used to transport drugs and have also been studied as molecular chaperones with potential application in protein misfolding diseases. In this study, we designed cyclodextrin polymers containing different contents of β- or γ-cyclodextrin, and a different number of guanidinium positive charges. This allowed exploration of the influence of the charge in delivering a drug and the effect in the protein anti-aggregant ability. The polymers inhibit Amiloid β peptide aggregation; such an ability is modulated by both the type of CyD cavity and the number of charges. We also explored the effect of the new polymers as drug carriers. We tested the Doxorubicin toxicity in different cell lines, A2780, A549, MDA-MB-231 in the presence of the polymers. Data show that the polymers based on γ-cyclodextrin modified the cytotoxicity of doxorubicin in the A2780 cell line. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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17 pages, 20701 KiB  
Article
Risperidone/Randomly Methylated β-Cyclodextrin Inclusion Complex—Compatibility Study with Pharmaceutical Excipients
by Laura Sbârcea, Ionuț-Mihai Tănase, Adriana Ledeți, Denisa Cîrcioban, Gabriela Vlase, Paul Barvinschi, Marinela Miclău, Renata-Maria Văruţ, Oana Suciu and Ionuț Ledeți
Molecules 2021, 26(6), 1690; https://doi.org/10.3390/molecules26061690 - 17 Mar 2021
Cited by 11 | Viewed by 2994
Abstract
Risperidone (RSP) is an atypical antipsychotic drug used in treating schizophrenia, behavioral, and psychological symptoms of dementia and irritability associated with autism. The drug substance is practically insoluble in water and exhibits high lipophilicity. It also presents incompatibilities with pharmaceutical excipients such as [...] Read more.
Risperidone (RSP) is an atypical antipsychotic drug used in treating schizophrenia, behavioral, and psychological symptoms of dementia and irritability associated with autism. The drug substance is practically insoluble in water and exhibits high lipophilicity. It also presents incompatibilities with pharmaceutical excipients such as magnesium stearate, lactose, and cellulose microcrystalline. RSP encapsulation by randomly methylated β-cyclodextrin (RM-β-CD) was performed in order to enhance drug solubility and stability and improve its biopharmaceutical profile. The inclusion complex formation was evaluated using thermal methods, powder X-ray diffractometry (PXRD), universal-attenuated total reflectance Fourier transform infrared (UATR-FTIR), UV spectroscopy, and saturation solubility studies. The 1:1 stoichiometry ratio and the apparent stability constant of the inclusion complex were determined by means of the phase solubility method. The compatibility between the supramolecular adduct and pharmaceutical excipients starch, anhydrous lactose, magnesium stearate, and cellulose microcrystalline was studied employing thermoanalytical tools (TG-thermogravimetry/DTG-derivative thermogravimetry/HF-heat flow) and spectroscopic techniques (UATR-FTIR, PXRD). The compatibility study reveals that there are no interactions between the supramolecular adduct with starch, magnesium stearate, and cellulose microcrystalline, while incompatibility with anhydrous lactose is observed even under ambient conditions. The supramolecular adduct of RSP with RM-β-CD represents a valuable candidate for further research in developing new formulations with enhanced bioavailability and stability, and the results of this study allow a pertinent selection of three excipients that can be incorporated in solid dosage forms. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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13 pages, 1910 KiB  
Article
Cytotoxicity of β-Cyclodextrins in Retinal Explants for Intravitreal Drug Formulations
by Manisha Prajapati, Gustav Christensen, François Paquet-Durand and Thorsteinn Loftsson
Molecules 2021, 26(5), 1492; https://doi.org/10.3390/molecules26051492 - 9 Mar 2021
Cited by 7 | Viewed by 3993
Abstract
Cyclodextrins (CDs) have been widely used as pharmaceutical excipients for formulation purposes for different delivery systems. Recent studies have shown that CDs are able to form complexes with a variety of biomolecules, such as cholesterol. This has subsequently paved the way for the [...] Read more.
Cyclodextrins (CDs) have been widely used as pharmaceutical excipients for formulation purposes for different delivery systems. Recent studies have shown that CDs are able to form complexes with a variety of biomolecules, such as cholesterol. This has subsequently paved the way for the possibility of using CDs as drugs in certain retinal diseases, such as Stargardt disease and retinal artery occlusion, where CDs could absorb cholesterol lumps. However, studies on the retinal toxicity of CDs are limited. The purpose of this study was to examine the retinal toxicity of different beta-(β)CD derivatives and their localization within retinal tissues. To this end, we performed cytotoxicity studies with two different CDs—2-hydroxypropyl-βCD (HPβCD) and randomly methylated β-cyclodextrin (RMβCD)—using wild-type mouse retinal explants, the terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay, and fluorescence microscopy. RMβCD was found to be more toxic to retinal explants when compared to HPβCD, which the retina can safely tolerate at levels as high as 10 mM. Additionally, studies conducted with fluorescent forms of the same CDs showed that both CDs can penetrate deep into the inner nuclear layer of the retina, with some uptake by Müller cells. These results suggest that HPβCD is a safer option than RMβCD for retinal drug delivery and may advance the use of CDs in the development of drugs designed for intravitreal administration. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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14 pages, 2044 KiB  
Article
Effect of Water Microsolvation on the Excited-State Proton Transfer of 3-Hydroxyflavone Enclosed in γ-Cyclodextrin
by Khanittha Kerdpol, Rathawat Daengngern, Chanchai Sattayanon, Supawadee Namuangruk, Thanyada Rungrotmongkol, Peter Wolschann, Nawee Kungwan and Supot Hannongbua
Molecules 2021, 26(4), 843; https://doi.org/10.3390/molecules26040843 - 5 Feb 2021
Cited by 8 | Viewed by 2832
Abstract
The effect of microsolvation on excited-state proton transfer (ESPT) reaction of 3-hydroxyflavone (3HF) and its inclusion complex with γ-cyclodextrin (γ-CD) was studied using computational approaches. From molecular dynamics simulations, two possible inclusion complexes formed by the chromone ring (C-ring, Form I) and the [...] Read more.
The effect of microsolvation on excited-state proton transfer (ESPT) reaction of 3-hydroxyflavone (3HF) and its inclusion complex with γ-cyclodextrin (γ-CD) was studied using computational approaches. From molecular dynamics simulations, two possible inclusion complexes formed by the chromone ring (C-ring, Form I) and the phenyl ring (P-ring, Form II) of 3HF insertion to γ-CD were observed. Form II is likely more stable because of lower fluctuation of 3HF inside the hydrophobic cavity and lower water accessibility to the encapsulated 3HF. Next, the conformation analysis of these models in the ground (S0) and the first excited (S1) states was carried out by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations, respectively, to reveal the photophysical properties of 3HF influenced by the γ-CD. The results show that the intermolecular hydrogen bonding (interHB) between 3HF and γ-CD, and intramolecular hydrogen bonding (intraHB) within 3HF are strengthened in the S1 state confirmed by the shorter interHB and intraHB distances and the red-shift of O–H vibrational modes involving in the ESPT process. The simulated absorption and emission spectra are in good agreement with the experimental data. Significantly, in the S1 state, the keto form of 3HF is stabilized by γ-CD, explaining the increased quantum yield of keto emission of 3HF when complexing with γ-CD in the experiment. In the other word, ESPT of 3HF is more favorable in the γ-CD hydrophobic cavity than in aqueous solution. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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12 pages, 5182 KiB  
Article
Inclusion Compound of Efavirenz and γ-Cyclodextrin: Solid State Studies and Effect on Solubility
by Susana Santos Braga, Firas El-Saleh, Karyna Lysenko and Filipe A. Almeida Paz
Molecules 2021, 26(3), 519; https://doi.org/10.3390/molecules26030519 - 20 Jan 2021
Cited by 9 | Viewed by 2856
Abstract
Efavirenz is an antiretroviral drug of widespread use in the management of infections with human immunodeficiency virus type 1 (HIV-1). Efavirenz is also used in paediatrics, but due to its very poor aqueous solubility the liquid formulations available resort to oil-based excipients. In [...] Read more.
Efavirenz is an antiretroviral drug of widespread use in the management of infections with human immunodeficiency virus type 1 (HIV-1). Efavirenz is also used in paediatrics, but due to its very poor aqueous solubility the liquid formulations available resort to oil-based excipients. In this report we describe the interaction of γ-cyclodextrin with efavirenz in solution and in the solid state. In aqueous solution, the preferential host–guest stoichiometry was determined by the continuous variation method using 1H NMR, which indicated a 3:2 host-to-guest proportion. Following, the solid inclusion compound was prepared at different stoichiometries by co-dissolution and freeze-drying. Solid-state characterisation of the products using FT-IR, 13C{1H} CP-MAS NMR, thermogravimetry, and X-ray powder diffraction has confirmed that the 3:2 stoichiometry is the adequate starting condition to isolate a solid inclusion compound in the pure form. The effect of γ-cyclodextrin on the solubility of efavirenz is studied by the isotherm method. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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8 pages, 961 KiB  
Article
Thermal Degradation of Linalool-Chemotype Cinnamomum osmophloeum Leaf Essential Oil and Its Stabilization by Microencapsulation with β-Cyclodextrin
by Hui-Ting Chang, Chun-Ya Lin, Li-Sheng Hsu and Shang-Tzen Chang
Molecules 2021, 26(2), 409; https://doi.org/10.3390/molecules26020409 - 14 Jan 2021
Cited by 29 | Viewed by 3788
Abstract
The thermal degradation of linalool-chemotype Cinnamomum osmophloeum leaf essential oil and the stability effect of microencapsulation of leaf essential oil with β-cyclodextrin were studied. After thermal degradation of linalool-chemotype leaf essential oil, degraded compounds including β-myrcene, cis-ocimene and trans-ocimene, were formed [...] Read more.
The thermal degradation of linalool-chemotype Cinnamomum osmophloeum leaf essential oil and the stability effect of microencapsulation of leaf essential oil with β-cyclodextrin were studied. After thermal degradation of linalool-chemotype leaf essential oil, degraded compounds including β-myrcene, cis-ocimene and trans-ocimene, were formed through the dehydroxylation of linalool; and ene cyclization also occurs to linalool and its dehydroxylated products to form the compounds such as limonene, terpinolene and α-terpinene. The optimal microencapsulation conditions of leaf essential oil microcapsules were at a leaf essential oil to the β-cyclodextrin ratio of 15:85 and with a solvent ratio (ethanol to water) of 1:5. The maximum yield of leaf essential oil microencapsulated with β-cyclodextrin was 96.5%. According to results from the accelerated dry-heat aging test, β-cyclodextrin was fairly stable at 105 °C, and microencapsulation with β-cyclodextrin can efficiently slow down the emission of linalool-chemotype C. osmophloeum leaf essential oil. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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21 pages, 4329 KiB  
Article
The Budesonide-Hydroxypropyl-β-Cyclodextrin Complex Attenuates ROS Generation, IL-8 Release and Cell Death Induced by Oxidant and Inflammatory Stress. Study on A549 and A-THP-1 Cells
by Jules César Bayiha, Brigitte Evrard, Didier Cataldo, Pascal De Tullio and Marie-Paule Mingeot-Leclercq
Molecules 2020, 25(21), 4882; https://doi.org/10.3390/molecules25214882 - 22 Oct 2020
Cited by 5 | Viewed by 3322
Abstract
Synthetic glucocorticoids such as budesonide (BUD) are potent anti-inflammatory drugs commonly used to treat patients suffering from chronic inflammatory diseases. A previous animal study reported a higher anti-inflammatory activity with a 2-hydroxypropyl-β-cyclodextrin (HPβCD)-based formulation of BUD (BUD:HPβCD). This study investigated, on cellular models [...] Read more.
Synthetic glucocorticoids such as budesonide (BUD) are potent anti-inflammatory drugs commonly used to treat patients suffering from chronic inflammatory diseases. A previous animal study reported a higher anti-inflammatory activity with a 2-hydroxypropyl-β-cyclodextrin (HPβCD)-based formulation of BUD (BUD:HPβCD). This study investigated, on cellular models (A549 and A-THP-1), the effect of BUD:HPβD in comparison with BUD and HPβCD on the effects induced by oxidative and inflammatory stress as well as the role of cholesterol. We demonstrated the protective effect afforded by BUD:HPβCD against cytotoxicity and ROS generation induced by oxidative and inflammatory stress. The effect observed for BUD:HPβCD was comparable to that observed with HPβCD with no major effect of cholesterol content. We also demonstrated (i) the involvement of the canonical molecular pathway including ROS generation, a decrease in PI3K/Akt activation, and decrease in phosphorylated/unphosphorylated HDAC2 in the effect induced by BUD:HPβCD, (ii) the maintenance of IL-8 decrease with BUD:HPβCD, and (iii) the absence of improvement in glucocorticoid insensitivity with BUD:HPβCD in comparison with BUD, in conditions where HDAC2 was inhibited. Resulting from HPβCD antioxidant and anticytotoxic potential and protective capacity against ROS-induced PI3K/Akt signaling and HDAC2 inhibition, BUD:HPβCD might be more beneficial than BUD alone in a context of concomitant oxidative and inflammatory stress. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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18 pages, 5460 KiB  
Article
Understanding Surface Interaction and Inclusion Complexes between Piroxicam and Native or Crosslinked β-Cyclodextrins: The Role of Drug Concentration
by Giuseppina Raffaini and Fabio Ganazzoli
Molecules 2020, 25(12), 2848; https://doi.org/10.3390/molecules25122848 - 19 Jun 2020
Cited by 23 | Viewed by 3986
Abstract
Drug concentration plays an important role in the interaction with drug carriers affecting the kinetics of release process and toxicology effects. Cyclodextrins (CDs) can solubilize hydrophobic drugs in water enhancing their bioavailability. In this theoretical study based on molecular mechanics and molecular dynamics [...] Read more.
Drug concentration plays an important role in the interaction with drug carriers affecting the kinetics of release process and toxicology effects. Cyclodextrins (CDs) can solubilize hydrophobic drugs in water enhancing their bioavailability. In this theoretical study based on molecular mechanics and molecular dynamics methods, the interactions between β-cyclodextrin and piroxicam, an important nonsteroidal anti-inflammatory drug, were investigated. At first, both host–guest complexes with native β-CD in the 1:1 and in 2:1 stoichiometry were considered without assuming any initial a priori inclusion: the resulting inclusion complexes were in good agreement with literature NMR data. The interaction between piroxicam and a β-CD nanosponge (NS) was then modeled at different concentrations. Two inclusion mechanisms were found. Moreover, piroxicam can interact with the external NS surface or with its crosslinkers, also forming one nanopore. At larger concentration, a nucleation process of drug aggregation induced by the first layer of adsorbed piroxicam molecules is observed. The flexibility of crosslinked β-CDs, which may be swollen or quite compact, changing the surface area accessible to drug molecules, and the dimension of the aggregate nucleated on the NS surface are important factors possibly affecting the kinetics of release, which shall be theoretically studied in more detail at specific concentrations. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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18 pages, 2042 KiB  
Article
Biological Effect Evaluation of Glutathione-Responsive Cyclodextrin-Based Nanosponges: 2D and 3D Studies
by Monica Argenziano, Federica Foglietta, Roberto Canaparo, Rita Spagnolo, Carlo Della Pepa, Fabrizio Caldera, Francesco Trotta, Loredana Serpe and Roberta Cavalli
Molecules 2020, 25(12), 2775; https://doi.org/10.3390/molecules25122775 - 16 Jun 2020
Cited by 13 | Viewed by 3103
Abstract
This study aims to evaluate the bioeffects of glutathione-responsive β-cyclodextrin-based nanosponges (GSH-NSs) on two- (2D) and three-dimensional (3D) cell cultures. The bioeffects of two types of GSH-NS formulations, with low (GSH-NS B) and high (GSH-NS D) disulfide-bond content, were evaluated on 2D colorectal [...] Read more.
This study aims to evaluate the bioeffects of glutathione-responsive β-cyclodextrin-based nanosponges (GSH-NSs) on two- (2D) and three-dimensional (3D) cell cultures. The bioeffects of two types of GSH-NS formulations, with low (GSH-NS B) and high (GSH-NS D) disulfide-bond content, were evaluated on 2D colorectal (HCT116 and HT-29) and prostatic (DU-145 and PC3) cancer cell cultures. In particular, the cellular uptake of GSH-NS was evaluated, as their effects on cell growth, mitochondrial activity, membrane integrity, cell cycle distribution, mRNA expression, and reactive oxygen species production. The effect of GSH-NSs on cell growth was also evaluated on multicellular spheroids (MCS) and a comparison of the GSH-NS cell growth inhibitory activity, in terms of inhibition concentration (IC)50 values, was performed between 2D and 3D cell cultures. A significant decrease in 2D cell growth was observed at high GSH-NS concentrations, with the formulation with a low disulfide-bond content, GSH-NS B, being more cytotoxic than the formulation with a high disulfide-bond content, GSH-NS D. The cell growth decrease induced by GSH-NS was owing to G1 cell cycle arrest. Moreover, a significant down-regulation of mRNA expression of the cyclin genes CDK1, CDK2, and CDK4 and up-regulation of mRNA expression of the cyclin inhibitor genes CDKN1A and CDKN2A were observed. On the other hand, a significant decrease in MCS growth was also observed at high GSH-NS concentrations, but not influenced by the nanosponge disulfide-bond content, with the MCS IC50 values being significantly higher than those obtained on 2D cell cultures. GSH-NSs are suitable nanocarries as they provoke limited cellular effects, as cell cycle arrest only occurred at concentrations significantly higher than those used for drug delivery. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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12 pages, 1737 KiB  
Article
Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins
by Hiba Mohamed Ameen, Sándor Kunsági-Máté, Balázs Bognár, Lajos Szente, Miklós Poór and Beáta Lemli
Molecules 2019, 24(24), 4565; https://doi.org/10.3390/molecules24244565 - 13 Dec 2019
Cited by 15 | Viewed by 2898
Abstract
Sulfamethazine is a representative member of the sulfonamide antibiotic drugs; it is still used in human and veterinary therapy. The protonation state of this drug affects its aqueous solubility, which can be controlled by its inclusion complexes with native or chemically-modified cyclodextrins. In [...] Read more.
Sulfamethazine is a representative member of the sulfonamide antibiotic drugs; it is still used in human and veterinary therapy. The protonation state of this drug affects its aqueous solubility, which can be controlled by its inclusion complexes with native or chemically-modified cyclodextrins. In this work, the temperature-dependent (298–313 K) interaction of sulfamethazine with native and randomly methylated β-cyclodextrins have been investigated at acidic and neutral pH. Surprisingly, the interaction between the neutral and anionic forms of the guest molecule and cyclodextrins with electron rich cavity are thermodynamically more favorable compared to the cationic guest. This property probably due to the enhanced formation of zwitterionic form of sulfamethazine in the hydrophobic cavities of cyclodextrins. Spectroscopic measurements and molecular modeling studies indicated the possible driving forces (hydrophobic interaction, hydrogen bonding, and electrostatic interaction) of the complex formation, and highlighted the importance of the reorganization of the solvent molecules during the entering of the guest molecule into the host’s cavity. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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Review

Jump to: Research

18 pages, 2518 KiB  
Review
Research Progress on Synthesis and Application of Cyclodextrin Polymers
by Yuan Liu, Ting Lin, Cui Cheng, Qiaowen Wang, Shujin Lin, Chun Liu and Xiao Han
Molecules 2021, 26(4), 1090; https://doi.org/10.3390/molecules26041090 - 19 Feb 2021
Cited by 23 | Viewed by 5042
Abstract
Cyclodextrins (CDs) are a series of cyclic oligosaccharides formed by amylose under the action of CD glucosyltransferase that is produced by Bacillus. After being modified by polymerization, substitution and grafting, high molecular weight cyclodextrin polymers (pCDs) containing multiple CD units can be obtained. [...] Read more.
Cyclodextrins (CDs) are a series of cyclic oligosaccharides formed by amylose under the action of CD glucosyltransferase that is produced by Bacillus. After being modified by polymerization, substitution and grafting, high molecular weight cyclodextrin polymers (pCDs) containing multiple CD units can be obtained. pCDs retain the internal hydrophobic-external hydrophilic cavity structure characteristic of CDs, while also possessing the stability of polymer. They are a class of functional polymer materials with strong development potential and have been applied in many fields. This review introduces the research progress of pCDs, including the synthesis of pCDs and their applications in analytical separation science, materials science, and biomedicine. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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27 pages, 6434 KiB  
Review
Cyclodextrin-Based Contrast Agents for Medical Imaging
by Yurii Shepelytskyi, Camryn J. Newman, Vira Grynko, Lauren E. Seveney, Brenton DeBoef, Francis T. Hane and Mitchell S. Albert
Molecules 2020, 25(23), 5576; https://doi.org/10.3390/molecules25235576 - 27 Nov 2020
Cited by 9 | Viewed by 3863
Abstract
Cyclodextrins (CDs) are naturally occurring cyclic oligosaccharides consisting of multiple glucose subunits. CDs are widely used in host–guest chemistry and biochemistry due to their structural advantages, biocompatibility, and ability to form inclusion complexes. Recently, CDs have become of high interest in the field [...] Read more.
Cyclodextrins (CDs) are naturally occurring cyclic oligosaccharides consisting of multiple glucose subunits. CDs are widely used in host–guest chemistry and biochemistry due to their structural advantages, biocompatibility, and ability to form inclusion complexes. Recently, CDs have become of high interest in the field of medical imaging as a potential scaffold for the development of a large variety of the contrast agents suitable for magnetic resonance imaging, ultrasound imaging, photoacoustic imaging, positron emission tomography, single photon emission computed tomography, and computed tomography. The aim of this review is to summarize and highlight the achievements in the field of cyclodextrin-based contrast agents for medical imaging. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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28 pages, 3941 KiB  
Review
The Role of β-Cyclodextrin in the Textile Industry—Review
by Fabricio Maestá Bezerra, Manuel José Lis, Helen Beraldo Firmino, Joyce Gabriella Dias da Silva, Rita de Cassia Siqueira Curto Valle, José Alexandre Borges Valle, Fabio Alexandre Pereira Scacchetti and André Luiz Tessaro
Molecules 2020, 25(16), 3624; https://doi.org/10.3390/molecules25163624 - 9 Aug 2020
Cited by 73 | Viewed by 11237
Abstract
β-Cyclodextrin (β-CD) is an oligosaccharide composed of seven units of D-(+)-glucopyranose joined by α-1,4 bonds, which is obtained from starch. Its singular trunk conical shape organization, with a well-defined cavity, provides an adequate environment for several types of molecules to be included. Complexation [...] Read more.
β-Cyclodextrin (β-CD) is an oligosaccharide composed of seven units of D-(+)-glucopyranose joined by α-1,4 bonds, which is obtained from starch. Its singular trunk conical shape organization, with a well-defined cavity, provides an adequate environment for several types of molecules to be included. Complexation changes the properties of the guest molecules and can increase their stability and bioavailability, protecting against degradation, and reducing their volatility. Thanks to its versatility, biocompatibility, and biodegradability, β-CD is widespread in many research and industrial applications. In this review, we summarize the role of β-CD and its derivatives in the textile industry. First, we present some general physicochemical characteristics, followed by its application in the areas of dyeing, finishing, and wastewater treatment. The review covers the role of β-CD as an auxiliary agent in dyeing, and as a matrix for dye adsorption until chemical modifications are applied as a finishing agent. Finally, new perspectives about its use in textiles, such as in smart materials for microbial control, are presented. Full article
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
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