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Cyclodextrin-Containing Polymers

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A special issue of Polymers (ISSN 2073-4360). This special issue belongs to the section "Biomacromolecules, Biobased and Biodegradable Polymers".

Deadline for manuscript submissions: closed (31 March 2019) | Viewed by 50841

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Prof. Dr. Francesco Trotta

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Departement of Chemistry, University of Turin, Via Pietro Giuria 7, 10125 Turin, Italy
Interests: cyclodextrin modification and functionalization; cyclodextrin nanosponges preparation and applications; drug delivery systems; biopolymers; membrane technology
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Prof. Dr. Andrea Mele

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Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, Piazza L. da Vinci 32, 20133 Milano, Italy
Interests: cyclodextring chemistry; structure and dynamics of cyclodextrins' inclusion complexes via NMR spectroscopy; cyclodextrin nanosponges and their applications; transport properties of solutes encapsulated in cyclodextrin polymers and related hydrogels; cyclodextrins' properties in ionic liquids and deep eutectic solvents
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Dear Colleagues,

Despite the fact that cyclodextrins have been known about for a long time, being discovered by Villiers in 1891, they still present innovative applications and widespread uses. More recently, cyclodextrin-containing polymers have received a great deal of attention from researchers, as they are able to improve encapsulation properties, increase loading capacity, enhance the solubility and stability of hosted active molecules, etc. Soluble linear, branched and grafted cyclodextrin polymers are reported and insoluble cross linked one have also been reported. The aim of this Special Issue of Polymers focuses on the current state-of-the-art of cyclodextrin-containing polymers, covering several aspects, such as synthetic routes, structural and dynamic characterization using spectroscopic methods, transport properties of encapsulated substrates, molecular structure and morphology, rheology, and studies of cyclodextrin polymers in the dry and swollen states. Additionally, applications in different fields, such as drug delivery, cosmetics, food, advanced materials, agriculture, decontamination processes, catalysis, packaging, etc., will be considered.

Prof. Francesco Trotta
Prof. Andrea Mele
Guest Editors

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Keywords

Cyclodextrins
Cyclodextrin polymers
Drug delivery
Molecular recognition
Molecular encapsulation
Structural assessment
Dynamic properties
Supramolecular chemistry

Published Papers (13 papers)

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Research

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18 pages, 4009 KiB

Open AccessArticle

CD Oxyanions as a Tool for Synthesis of Highly Anionic Cyclodextrin Polymers

by Tomasz Girek, Kinga Koziel, Beata Girek and Wojciech Ciesielski

Polymers 2020, 12(12), 2845; https://doi.org/10.3390/polym12122845 - 29 Nov 2020

Cited by 5 | Viewed by 2305

Abstract

Water soluble highly anionic β-cyclodextrin-based polymers were synthesized by reaction between cyclodextrin oxyanion and pyromellitic anhydride. The synthesis method utilizes activation hydroxyl groups in anhydrous glucopyranosyl units (AGU) in the DMF solution with the use of NaH. In these conditions, like in the case of the cyclodextrin reactions in the highly alkaline media, there is a nucleophilic substitution of difunctional compounds, which develops a polymer network with various cyclodextrin substitution. Different molar ratios of the reagents were investigated in terms of molecular size, chemical structure and water solubility of the polymers. The separation of the polymer due to particle size by ultrafiltration process and HPSEC-MALLS-RI and MALDI-TOF MS measurements for molecular mass analysis were employed. The IR, H NMR, SEM, DSC and TG measurements were taken for the structural characterization of the polymers. Additionally, the solubility test and metal ion complexation processes were also investigated in a wide range of pH. These polymers could be used in several areas such as: improving the aqueous solubility of poor water-soluble molecules, removing heavy metals from waste water, protecting degradable substances or synthesizing new drug delivery systems. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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14 pages, 3630 KiB

Open AccessArticle

Eco-Friendly β-cyclodextrin and Linecaps Polymers for the Removal of Heavy Metals

by Alberto Rubin Pedrazzo, Alessandra Smarra, Fabrizio Caldera, Giorgia Musso, Nilesh Kumar Dhakar, Claudio Cecone, Asma Hamedi, Ilaria Corsi and Francesco Trotta

Polymers 2019, 11(10), 1658; https://doi.org/10.3390/polym11101658 - 11 Oct 2019

Cited by 35 | Viewed by 4592

Abstract

Environment-friendly nanosponges, having a high content of carboxyl groups, were synthesized by crosslinking β-cyclodextrin and linecaps, a highly soluble pea starch derivative, with citric acid in water. Additionally, pyromellitic nanosponges were prepared by reacting β-cyclodextrin and linecaps with pyromellitic dianhydride in dimethyl sulfoxide and used in comparison with the citric nanosponges. After ion-exchange of the carboxyl groups H⁺ with sodium ions, the ability of the nanosponges to sequester heavy metal cations was investigated. At a metal concentration of 500 ppm, the pyromellitate nanosponges exhibited a higher retention capacity than the citrate nanosponges. At lower metal concentrations (≤50 ppm) both the citrate and the pyromellitate nanosponges showed high retention capacities (up to 94% of the total amount of metal), while, in the presence of interfering sea water salts, the citrate nanosponges were able to selectively adsorb a significantly higher amount of heavy metals than the pyromellitate nanosponges, almost double in the case of Cu²⁺. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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18 pages, 2041 KiB

Open AccessEditor’s ChoiceArticle

Adsorption of Direct Blue 78 Using Chitosan and Cyclodextrins as Adsorbents

by Ainoa Murcia-Salvador, José A. Pellicer, María I. Fortea, Vicente M. Gómez-López, María I. Rodríguez-López, Estrella Núñez-Delicado and José A. Gabaldón

Polymers 2019, 11(6), 1003; https://doi.org/10.3390/polym11061003 - 05 Jun 2019

Cited by 65 | Viewed by 4014

Abstract

The dyeing industry is one of the most polluting in the world. The adsorption of dyes by polymeric matrixes can be used to minimize the discharge of dyes into the environment. In the present study, chitosan-NaOH and β-cyclodextrin-epichlorohydrin polymers were used to remove the dye Direct Blue 78 from a wastewater model. To understand the adsorption behavior of Direct Blue 78 onto the polymers, adsorption rate and maximum adsorption capacity were calculated using kinetic tests and isotherm curves respectively. The kinetic data and mechanism of the adsorption process were analyzed by three models and the equilibrium data by three adsorption isotherms; also the different thermodynamic parameters were calculated. Results showed that the adsorption process follows pseudo-second-order kinetics in both polymers and the Langmuir isotherm best-fitted data for chitosan-NaOH polymer and the Freundlich isotherm for the β-CDs-EPI polymer. The adsorption process is exothermic in both cases and spontaneous for the β-CDs-EPI polymer to a certain temperature and not spontaneous for the chitosan-NaOH polymer and β-CDs-EPI polymer at higher temperatures. The complementary action of an advanced oxidation process eliminated >99% of the dye from water. The coupled process seems to be suitable for reducing the environmental impact of the dyeing industry. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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13 pages, 1934 KiB

Open AccessArticle

A Way to Increase the Bioaccesibility and Photostability of Roflumilast, a COPD Treatment, by Cyclodextrin Monomers

by Adrián Matencio, Samanta Hernández-García, Francisco García-Carmona and José Manuel López-Nicolás

Polymers 2019, 11(5), 801; https://doi.org/10.3390/polym11050801 - 04 May 2019

Cited by 15 | Viewed by 3190

Abstract

Roflumilast is an orally available inhibitor of phosphodiesterase (PDE) type 4, which is widely used in chronic obstructive pulmonary diseases. However, it has low solubility and adverse effects include diarrhea and nausea. Since its solubilization may improve treatment and, dismissing any adverse effects, its interaction with cyclodextrins (CDs) was studied. The Higuchi-Connors method was used to determine the complexation constant with different CDs, pH values and temperatures. Molecular docking was used to predict interaction between the complexes. An in vitro digestion experiment was carried out to test roflumilast protection. Finally, the photostability of the complex was evaluated. The complex formed with β-CD had the highest K₁₁ value (646 ± 34 M⁻¹), although this value decreased with increasing temperature. Similarly, K₁₁ decreased as the pH increased. In vitro digestion showed that CDs protect the drug during digestion and even improve its bioaccessibility. Finally, CDs reduced the drug’s extreme photosensitivity, originating a fluorescence signal, which is described for first time. The kinetic parameters of the reaction were obtained. This study not only completes the complexation study of roflumilast-CD, but also points to the need to protect roflumilast from light, suggesting that tablets containing the drug might be reformulated. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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20 pages, 6387 KiB

Open AccessArticle

Molecular Assembly between Weak Crosslinking Cyclodextrin Polymer and trans-Cinnamaldehyde for Corrosion Inhibition towards Mild Steel in 3.5% NaCl Solution: Experimental and Theoretical Studies

by Yucong Ma, Baomin Fan, Tingting Zhou, Hua Hao, Biao Yang and Hui Sun

Polymers 2019, 11(4), 635; https://doi.org/10.3390/polym11040635 - 08 Apr 2019

Cited by 40 | Viewed by 3943

Abstract

Constructing molecular assembly between a soluble cyclodextrin polymer (SCDP) and an anticorrosive component is conducive to increasing the availability of a corrosion inhibitor with low molecular polarity in aqueous solution. The SCDP was prepared via the weak crosslinking effect of glutaraldehyde using β-cyclodextrin as the subunit, whose structure was confirmed by proton nuclear magnetic resonance spectra (¹H NMR), X-ray diffraction and morphology. An assembly between SCDP (host) and trans-cinnamaldehyde (guest, CA) was constructed, and the intermolecular interactions were disclosed by Fourier transform infrared spectra (FTIR). The corrosion inhibition of SCDP/CA assembly for mild steel in 3.5% NaCl solution was assessed through electrochemical and surface analyses. ¹H NMR results showed that exterior hydroxyls of β-cyclodextrin were the active sites for crosslinking. Hydrogen bonds might be the binding force between SCDP and CA according to FTIR analyses. Electrochemical measurements revealed that SCDP/CA assembly could suppress both cathodic and anodic reactions and enhance the polarization impedance for mild steel in the corrosive medium with a maximum efficiency of 92.2% at 30 °C. Surface analyses showed that CA molecules could be released from the assembly followed by the energy competition mechanism, and solely adsorb on the steel surface in parallel form, which was further evidenced by theoretical modeling. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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11 pages, 7103 KiB

Open AccessArticle

Cyclodextrin-Polypyrrole Coatings of Scaffolds for Tissue Engineering

by Jan Lukášek, Šárka Hauzerová, Kristýna Havlíčková, Kateřina Strnadová, Karel Mašek, Martin Stuchlík, Ivan Stibor, Věra Jenčová and Michal Řezanka

Polymers 2019, 11(3), 459; https://doi.org/10.3390/polym11030459 - 11 Mar 2019

Cited by 10 | Viewed by 2918

Abstract

Polypyrrole is one of the most investigated conductive polymers used for tissue engineering applications because of its advantageous properties and the ability to promote different cell types’ adhesion and proliferation. Together with β-cyclodextrin, which is capable of accommodating helpful biomolecules in its cavity, it would make a perfect couple for use as a scaffold for tissue engineering. Such scaffolds were prepared by the polymerisation of 6-(pyrrol-3-yl)hexanoic acid on polycaprolactone microfibres with subsequent attachment of β-cyclodextrin on the polypyrrole layer. The materials were deeply characterised by several physical and spectroscopic techniques. Testing of the cyclodextrin enriched composite scaffold revealed its better performance in in vitro experiments compared with pristine polycaprolactone or polypyrrole covered polycaprolactone scaffolds. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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15 pages, 3738 KiB

Open AccessEditor’s ChoiceArticle

Enhanced Formaldehyde Removal from Air Using Fully Biodegradable Chitosan Grafted β-Cyclodextrin Adsorbent with Weak Chemical Interaction

by Zujin Yang, Hongchen Miao, Zebao Rui and Hongbing Ji

Polymers 2019, 11(2), 276; https://doi.org/10.3390/polym11020276 - 06 Feb 2019

Cited by 35 | Viewed by 4923

Abstract

Formaldehyde (HCHO) is an important indoor air pollutant. Herein, a fully biodegradable adsorbent was synthesized by the crosslinking reaction of β-cyclodextrin (β-CD) and chitosan via glutaraldehyde (CGC). The as-prepared CGC showed large adsorption capacities for gaseous formaldehyde. To clarify the adsorption performance of the as-synthesized HCHO adsorbents, changing the adsorption parameters performed various continuous flow adsorption tests. It was found that the adsorption data agreed best with the Freundlich isotherm, and the HCHO adsorption kinetic data fitted well with the pseudo second order model. The breakthrough curves indicated that the HCHO adsorbing capacity of CGC was up to 15.5 mg/g, with the inlet HCHO concentration of 46.1 mg/m³, GHSV of 28 mL/min, and temperature of 20 °C. The regeneration and reusability of the adsorbent were evaluated and CGC was found to retain its adsorptive capacity after four cycles. The introduction of β-CD was a key factor for the satisfied HCHO adsorption performance of CGC. A plausible HCHO adsorption mechanism by CGC with the consideration of the synergistic effects of Schiff base reaction and the hydrogen bonding interaction was proposed based on in situ DRIFTS studies. The present study suggests that CGC is a promising adsorbent for the indoor formaldehyde treatment. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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17 pages, 7647 KiB

Open AccessArticle

Influence of the Soluble–Insoluble Ratios of Cyclodextrins Polymers on the Viscoelastic Properties of Injectable Chitosan–Based Hydrogels for Biomedical Application

by Carla Palomino-Durand, Marco Lopez, Frédéric Cazaux, Bernard Martel, Nicolas Blanchemain and Feng Chai

Polymers 2019, 11(2), 214; https://doi.org/10.3390/polym11020214 - 26 Jan 2019

Cited by 16 | Viewed by 4064

Abstract

Injectable pre-formed physical hydrogels provide many advantages for biomedical applications. Polyelectrolyte complexes (PEC) formed between cationic chitosan (CHT) and anionic polymers of cyclodextrin (PCD) render a hydrogel of great interest. Given the difference between water-soluble (PCDs) and water-insoluble PCD (PCDi) in the extension of polymerization, the present study aims to explore their impact on the formation and properties of CHT/PCD hydrogel obtained from the variable ratios of PCDi and PCDs in the formulation. Hydrogels CHT/PCDi/PCDs at weight ratios of 3:0:3, 3:1.5:1.5, and 3:3:0 were elaborated in a double–syringe system. The chemical composition, microstructure, viscoelastic properties, injectability, and structural integrity of the hydrogels were investigated. The cytotoxicity of the hydrogel was also evaluated by indirect contact with pre-osteoblast cells. Despite having similar shear–thinning and self-healing behaviors, the three hydrogels showed a marked difference in their rheological characteristics, injectability, structural stability, etc., depending on their PCDi and PCDs contents. Among the three, all the best above-mentioned properties, in addition to a high cytocompatibility, were found in the hydrogel 3:1.5:1.5. For the first time, we gained a deeper understanding of the role of the PCDi/PCDs in the injectable pre-formed hydrogels (CHT/PCDi/PCDs), which could be further fine-tuned to enhance their performance in biomedical applications. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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15 pages, 6574 KiB

Open AccessArticle

Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations

by Khanittha Kerdpol, Jintawee Kicuntod, Peter Wolschann, Seiji Mori, Chompoonut Rungnim, Manaschai Kunaseth, Hisashi Okumura, Nawee Kungwan and Thanyada Rungrotmongkol

Polymers 2019, 11(1), 145; https://doi.org/10.3390/polym11010145 - 16 Jan 2019

Cited by 18 | Viewed by 4326

Abstract

2-Hydroxypropyl-β-cyclodextrin (HPβCD) has unique properties to enhance the stability and the solubility of low water-soluble compounds by inclusion complexation. An understanding of the structural properties of HPβCD and its derivatives, based on the number of 2-hydroxypropyl (HP) substituents at the α-d-glucopyranose subunits is rather important. In this work, replica exchange molecular dynamics simulations were performed to investigate the conformational changes of single- and double-sided HP-substitution, called 6-HPβCDs and 2,6-HPβCDs, respectively. The results show that the glucose subunits in both 6-HPβCDs and 2,6-HPβCDs have a lower chance of flipping than in βCD. Also, HP groups occasionally block the hydrophobic cavity of HPβCDs, thus hindering drug inclusion. We found that HPβCDs with a high number of HP-substitutions are more likely to be blocked, while HPβCDs with double-sided HP-substitutions have an even higher probability of being blocked. Overall, 6-HPβCDs with three and four HP-substitutions are highlighted as the most suitable structures for guest encapsulation, based on our conformational analyses, such as structural distortion, the radius of gyration, circularity, and cavity self-closure of the HPβCDs. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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12 pages, 5468 KiB

Open AccessArticle

Preparation of β-Cyclodextrin Inclusion Complex and Its Application as an Intumescent Flame Retardant for Epoxy

by Xueying Shan, Kuanyu Jiang, Jinchun Li, Yan Song, Ji Han and Yuan Hu

Polymers 2019, 11(1), 71; https://doi.org/10.3390/polym11010071 - 05 Jan 2019

Cited by 26 | Viewed by 3689

Abstract

A new P-N containing the flame retardant, which was namely N,N′-dibutyl-phosphate diamide (DBPDA), was synthesized and it was assembled into the cavity of β-cyclodextrin (β-CD) to form an inclusion complex (IC). The structure and properties of IC were characterized by Fourier transform infraredspectroscopy (FTIR), wide-angle X-ray diffraction (WAXD), ¹H nuclear magnetic resonance (¹H NMR), scanning electron microscopy with X-ray microanalysis (SEM-EDS), differential scanning calorimeter (DSC) and thermal gravimetric analysis (TGA). ¹H NMR and SEM-EDS were also used to identify the molar ratio of β-CD/DBPDA in IC and the results from the analyses indicated that their molar ratio was 1:1. In order to test the flame retardant effect of IC, it was added to epoxy (EP). IC was proposed to be able to act as an intumescent flame retardant (IFR) system in EP through a combination of β-CD and DBPDA properties during the combustion process. β-CD is a biomass carbon source, which has the advantages of environmental protection and low cost. Furthermore, DBPDA is both a source of acid and gas. When IC was heated, IC had the advantage of acting as both a carbon source and foam forming agent, while the DBPDA component were able to directly generate phosphoric acid and NH₃ in situ. The impact of IC in low additive amounts on flame retardancy of EP was studied by the cone calorimeter test. When only 3 wt % IC was incorporated, the peak values of heat release rate (pHRR) and smoke production rate (pSPR) of EP were reduced by 22.9% and 33.3% respectively, which suggested that IC could suppress the heat and smoke release efficiently. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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Review

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29 pages, 5900 KiB

Open AccessReview

Cyclodextrins and Cyclodextrin Derivatives as Green Char Promoters in Flame Retardants Formulations for Polymeric Materials. A Review

by Maria Paola Luda and Marco Zanetti

Polymers 2019, 11(4), 664; https://doi.org/10.3390/polym11040664 - 11 Apr 2019

Cited by 29 | Viewed by 4810

Abstract

Polymers are intrinsically flammable materials; hence, fire retardance (FR) is required in their most common applications (i.e., electronic and construction, to mention some). Recently, it has been reported that cyclodextrin (CD) and cyclodextrin derivatives are beginning to be introduced into Intumescent Fire Retardant (IFR) formulations in place of pentaerythritol, which is used in IFRs that are currently on the market. Since IFRs are of less environmental concern than their hazardous halogen containing counterparts, the use of natural origin compounds in IFRs provides a way to comply with green chemistry issues. BCD and BCD derivatives presence in IFR mixtures promotes a higher yield of blowing gases and char when polymeric materials undergo combustion. Both processes play important roles in intumescence. The key rule to obtain in insulating compact char is the good dispersion of the nanoparticles in the matrix, which can be achieved by functionalizing nanoparticles with BCD derivatives. Moreover, CD derivatives are attractive because of their nanosized structure and their ability to form inclusion complexes with many compounds used as FR components, reducing their release to the environment during their shelf life of FR items. Often, fire retardance performed by BCD and BCD derivatives accompanies other relevant properties, such as improved mechanical resistance, washability resistance, self healing ability, thermal conductivity, etc. The application of CD fire retardant additives in many polymers, such as poly(lactic acid), poly(propylene), poly(vinyl acetate), poly(methyl methacrylate), linear low density poly(ethylene), polyamides, and polyesters are comprehensively reviewed here. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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9 pages, 1180 KiB

Open AccessEditor’s ChoiceReview

Supramolecular Cyclodextrin-Based Hydrogels for Controlled Gene Delivery

by Ana Rey-Rico and Magali Cucchiarini

Polymers 2019, 11(3), 514; https://doi.org/10.3390/polym11030514 - 19 Mar 2019

Cited by 35 | Viewed by 4037

Abstract

Controlled delivery of gene transfer vectors is a powerful strategy to enhance the temporal and spatial presentation of therapeutic agents in a defined target. Hydrogels are adapted biomaterials for gene delivery capable of acting as a localized depot of genes while maintaining the long term local availability of DNA vectors at a specific location. Supramolecular hydrogels based on cyclodextrins (CDs) have attracted considerable attention as potential biomaterials in a broad range of drug delivery applications. Their unique characteristics of thixotropicity and low cytotoxicity due to their production under mild conditions make them potential candidates to form injectable delivery systems. This work aims to provide an overview of the use of CD-based polypseudorotaxane hydrogels as controlled gene delivery systems for different applications in regenerative medicine. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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14 pages, 6857 KiB

Open AccessReview

Polymers Containing Non-Covalently Bound Cyclodextrins

by Alan E. Tonelli

Polymers 2019, 11(3), 425; https://doi.org/10.3390/polym11030425 - 05 Mar 2019

Cited by 2 | Viewed by 2353

Abstract

We summarize and review the formation, characterization, behaviors, and possible uses of polymers that are threaded through, but only partially covered by cyclodextrins (CDs), which we call non-stoichiometric polymer–CD inclusion compounds (ICs) or non-stoichiometric (n-s) polymer–CD ICs. Emphasis is placed on comparison of the behaviors of unthreaded neat polymers with those that are threaded through and partially covered by CDs. These comparisons lead to several suggested uses for (n-s) polymer–CD ICs. Full article

(This article belongs to the Special Issue Cyclodextrin-Containing Polymers)

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