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Cyclodextrins: Recent Advances in Chemistry and Applications
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Cyclodextrins: Recent Advances in Chemistry and Applications

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

Deadline for manuscript submissions: closed (15 July 2021) | Viewed by 33113

Special Issue Editors

Prof. Dr. Estrella Núñez Delicado

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Guest Editor
Department of Food Technology and Nutrition, Molecular Recognition and Encapsulation Group (REM), UCAM Universidad Católica de Murcia (UCAM), Murcia, Spain
Interests: cyclodextrins; complexation; polymers; emerging pollutants; water descontamination; phenolic compounds
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. José Antonio Gabaldón Hernández

E-Mail Website
Guest Editor
Department of Food Technology and Nutrition, Molecular Recognition and Encapsulation Group (REM), UCAM Universidad Católica de Murcia (UCAM), Murcia, Spain
Interests: cyclodextrins; nanomaterials; polymers; drug delivery; food; health; environment
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrins (CDs) are a family of cyclic oligosaccharides composed of 6, 7 or 8 α-(1,4) linked glucopyranose subunits. They possess a trunk-conical supramolecular structure, which permits them to form inclusion complexes with many molecules. Because of their inclusion complex formation ability, the properties of the complexed molecules could be modified significantly. For example, poorly water-soluble drugs could increase their apparent water solubility. Because of molecular complexation phenomena, CDs are widely used in different industrial products, technologies, and analytical methods. Their negligible cytotoxic effects are an important attribute in applications such as drugs carrier, food and flavors, cosmetics, packing, textiles, separation processes or environment remediation. In addition, the possibility of using CD polymers to modify their chemical properties has resulted in an increase in the number of publications about the use of these compounds in different areas.

This Special Issue on cyclodextrin chemistry and applications aims to provide a forum for the dissemination of the latest research and advances in the chemical modification, polymerization, and use of cyclodextrins in different areas.

Prof. Dr. Estrella Núñez Delicado
Prof. Dr. José Antonio Gabaldón Hernández
Guest Editors

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Keywords

  • cyclodextrins in nanotechnology
  • cyclodextrins in biotechnology
  • cyclodextrins in food
  • cyclodextrins in medicine and pharmacology
  • cyclodextrins in textile industry
  • cyclodextrins in cosmetics
  • cyclodextrins in environment
  • cyclodextrins in catalysis
  • modifieds cyclodextrins
  • cyclodextrin complexes characterization

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Published Papers (6 papers)

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Research

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18 pages, 3984 KiB  
Article
Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes
by María Isabel Rodríguez-López, María Teresa Mercader-Ros, Carmen Lucas-Abellán, José Antonio Pellicer, Alfonso Pérez-Garrido, Horacio Pérez-Sánchez, María Josefa Yáñez-Gascón, José Antonio Gabaldón and Estrella Núñez-Delicado
Molecules 2020, 25(21), 5069; https://doi.org/10.3390/molecules25215069 - 1 Nov 2020
Cited by 25 | Viewed by 4019
Abstract
The objective of the present study is to obtain linalool- cyclodextrin (CDs) solid complexes for possible applications in the food industry. For this purpose, a detailed study of linalool complexation was carried out at different pH values, to optimize the type of CDs [...] Read more.
The objective of the present study is to obtain linalool- cyclodextrin (CDs) solid complexes for possible applications in the food industry. For this purpose, a detailed study of linalool complexation was carried out at different pH values, to optimize the type of CDs and reaction medium that support the highest quantity of encapsulated linalool. Once demonstrated the ability of hydroxypropyl-β-cyclodextrin (HP-β-CDs), to form inclusion complexes with linalool (KC = 921 ± 21 L mol−1) and given their greater complexation efficacy (6.788) at neutral pH, HP-β-CDs were selected to produce solid inclusion complexes by using two different energy sources, ultrasounds and microwave irradiation, subsequently spraying the solutions obtained in the Spray Dryer. To provide scientific solidity to the experimental results, the complexes obtained were characterized by using different instrumental techniques in order to confirm the inclusion of linalool in the HP-β-CDs hydrophobic cavity. The linalool solid complexes obtained were characterized by using 1H nuclear magnetic resonance (1H-NMR) and 2D nuclear magnetic resonance (ROSEY), differential scanning calorimetry, thermogravimetry and Fourier transform infrared spectrometry. Moreover, the structure of the complex obtained were also characterized by molecular modeling. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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15 pages, 6560 KiB  
Article
Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments
by Monica-Cornelia Sardaru, Oana Carp, Elena-Laura Ursu, Anda-Mihaela Craciun, Corneliu Cojocaru, Mihaela Silion, Vladyslava Kovalska, Ionel Mangalagiu, Ramona Danac and Alexandru Rotaru
Molecules 2020, 25(19), 4397; https://doi.org/10.3390/molecules25194397 - 24 Sep 2020
Cited by 8 | Viewed by 3173
Abstract
We have designed and synthesized a series of novel, supramolecular, long-lived fluorescent probes based on the host-guest inclusion complexes formation between fluorescent indolizinyl-pyridinium salts and β-cyclodextrin. Fluorescence and electrospray ionisation mass spectrometry experiments, supported by theoretical molecular docking studies, were utilized in the [...] Read more.
We have designed and synthesized a series of novel, supramolecular, long-lived fluorescent probes based on the host-guest inclusion complexes formation between fluorescent indolizinyl-pyridinium salts and β-cyclodextrin. Fluorescence and electrospray ionisation mass spectrometry experiments, supported by theoretical molecular docking studies, were utilized in the monitoring of the inclusion complexes formation, evidencing the appearance of corresponding 1:1 and 1:2 species. Additionally, the influence of the guest molecule over the aggregation processes of the cyclodextrin inclusion complexes was investigated by transmission electron microscopy. The absence of cytotoxicity, cellular permeability, long-lived intracellular fluorescence, and in time specific accumulation within acidic organelles identified the investigated supramolecular entities as remarkable candidates for intracellular fluorescence probes. Co-staining experiments using specific organelle markers revealed the fact that, after a 24-h incubation period, the inclusion complexes accumulate predominantly in lysosomes rather than in mitochondria. This study opens new possibilities for a broad range of fluorescent dyes with solubility and high toxicity issues, able to form inclusion complexes with β-cyclodextrin, to be tested as intracellular fluorescence probes. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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13 pages, 3425 KiB  
Article
Thymol Encapsulated into HP-β-Cyclodextrin as an Alternative to Synthetic Fungicides to Induce Lemon Resistance against Sour Rot Decay
by Vicente Serna-Escolano, María Serrano, Daniel Valero, María Isabel Rodríguez-López, José Antonio Gabaldón, Salvador Castillo, Juan Miguel Valverde, Pedro Javier Zapata, Fabián Guillén and Domingo Martínez-Romero
Molecules 2020, 25(18), 4348; https://doi.org/10.3390/molecules25184348 - 22 Sep 2020
Cited by 18 | Viewed by 2988
Abstract
Consumers demand the use of eco-friendly fungicides to treat fruit and vegetables and governmental authorities have unauthorized the application of chemical antifungals for the efficient control of sour rot. In the present research, the microwave irradiation (MW) method was used to encapsulate thymol [...] Read more.
Consumers demand the use of eco-friendly fungicides to treat fruit and vegetables and governmental authorities have unauthorized the application of chemical antifungals for the efficient control of sour rot. In the present research, the microwave irradiation (MW) method was used to encapsulate thymol into 2-hydroxylpropyl-beta-cyclodextrin (HP-β-CD) and the effect of these HP-β-CD on controlling sour rot in citrus fruit, caused by Geotrichum citri-aurantii, was evaluated. Amounts of 25 and 50 mM of HP-β-CD-thymol were used, and compared with propiconazole, to control the decay of inoculated lemon fruit. The treatments were performed in curative and preventive experiments. The incidence and severity of Geotrichum citri-aurantii in 25 and 50 mM HP-β-CD-thymol-treated fruit were reduced in both experiments. The preventive 50 mM HP-β-CD-thymol treatment showed the best effect, reducing the sour rot, respiration rate and fruit weight loss during storage at 20 °C. HP-β-CD-thymol increased polyphenol concentration and the activity of antioxidant enzymes, such as catalase (CAT), ascorbate peroxidase (APX) and peroxidase (POD) in lemon peel, and the highest effects were found with the 50-mM dose. In conclusion, the results show that the use of thymol encapsulated by MW into HP-β-CD could be an effective and sustainable tool, a substitute to the synthetic fungicides, for G. citri-auriantii control in citrus fruit. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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12 pages, 1435 KiB  
Article
Enantioseparation and Determination of Mephedrone and Its Metabolites by Capillary Electrophoresis Using Cyclodextrins as Chiral Selectors
by Pavel Řezanka, Denisa Macková, Radek Jurok, Michal Himl and Martin Kuchař
Molecules 2020, 25(12), 2879; https://doi.org/10.3390/molecules25122879 - 23 Jun 2020
Cited by 8 | Viewed by 3839
Abstract
Mephedrone, a psychoactive compound derived from cathinone, is widely used as a designer drug. The determination of mephedrone and its metabolites is important for understanding its possible use in medicine. In this work, a method of capillary electrophoresis for the chiral separation of [...] Read more.
Mephedrone, a psychoactive compound derived from cathinone, is widely used as a designer drug. The determination of mephedrone and its metabolites is important for understanding its possible use in medicine. In this work, a method of capillary electrophoresis for the chiral separation of mephedrone and its metabolites was developed. Carboxymethylated β-cyclodextrin was selected as the most effective chiral selector from seven tested cyclodextrin derivates. Based on the simplex method, the optimal composition of the background electrolyte was determined: at pH 2.75 and 7.5 mmol·L−1 carboxymethylated β-cyclodextrin the highest total resolution of a mixture of analytes was achieved. For mephedrone and its metabolites, calibration curves were constructed in a calibration range from 0.2 to 5 mmol·L−1; limits of detection, limits of quantification, precision, and repeatability were calculated, and according to Mandel’s fitting test, the linear calibration ranges were determined. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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Review

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52 pages, 5008 KiB  
Review
Mono-6-Substituted Cyclodextrins—Synthesis and Applications
by Petr Kasal and Jindřich Jindřich
Molecules 2021, 26(16), 5065; https://doi.org/10.3390/molecules26165065 - 21 Aug 2021
Cited by 12 | Viewed by 5645
Abstract
Cyclodextrins are well known supramolecular hosts used in a wide range of applications. Monosubstitution of native cyclodextrins in the position C-6 of a glucose unit represents the simplest method how to achieve covalent binding of a well-defined host unit into the more complicated [...] Read more.
Cyclodextrins are well known supramolecular hosts used in a wide range of applications. Monosubstitution of native cyclodextrins in the position C-6 of a glucose unit represents the simplest method how to achieve covalent binding of a well-defined host unit into the more complicated systems. These derivatives are relatively easy to prepare; that is why the number of publications describing their preparations exceeds 1400, and the reported synthetic methods are often very similar. Nevertheless, it might be very demanding to decide which of the published methods is the best one for the intended purpose. In the review, we aim to present only the most useful and well-described methods for preparing different types of mono-6-substituted derivatives. We also discuss the common problems encountered during their syntheses and suggest their optimal solutions. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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29 pages, 13062 KiB  
Review
Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase
by Jae-ung Lee, Sung-Sik Lee, Sungyul Lee and Han Bin Oh
Molecules 2020, 25(18), 4048; https://doi.org/10.3390/molecules25184048 - 4 Sep 2020
Cited by 43 | Viewed by 12256
Abstract
Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the [...] Read more.
Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations. Full article
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
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