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Special Issue "Chitin and Chitosan Derivatives: Biological Activities and Application"

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

Deadline for manuscript submissions: closed (15 October 2017)

Special Issue Editor

Guest Editor
Prof. Dr. Már Másson

Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík, Iceland
Website | E-Mail
Interests: chitosan and chitosan conjugates; synthesis; structure activity relationship (SAR); spectroscopy; antimicrobial chitosan conjugates and natural compound derivatives; photochemistry; NMR analysis; nanomedicine; nanoparticles; regenerative medicine; antimicrobial activity; absorption enhancers; photodynamic therapy; cancer therapy; mathematical modeling and design of experiment (DOE)

Special Issue Information

Dear Colleagues,

Chitin and chitosan (poly β-1,4 linked D-glucosamine and N-acetyl-D-glucosamine) are biocompatible biopolymers with some unique biological properties. They have found applications in a number of fields, including medicine, pharmaceuticals, food processing, cosmetics, and agriculture. The use of these biopolymers is growing and research activities continue to increase; however, there are certain limitations for the use unmodified chitin and chitosan, mainly because the structural variation of the unmodified polymer is restricted to changes in the degree of N-acetylation and the molecular weight. Thus, there is more focus on the chemical modification of chitin and chitosan to make chitosan derivatives (conjugates). This promises to significantly expand utility in various fields, where these biopolymers have been used, and will also lead to novel applications. Many types of functional groups, including lipophilic and charged groups, have been introduced in order to enhance the bioactivity or desired physicochemical properties. Bioactive moieties, such as drugs, natural compounds, and various biomacromolecules, can be conjugated to the polymer backbone to give new types of materials that can be designed to function as drug delivery systems, components for constructing nanoparticles that can target certain cell types, imaging agents, and materials that have been tailored for certain regenerative properties. Chemically-reactive groups can also be introduced to promote polymerization or non-covalent bonding between polymer chains. These materials can be used to prepare stable bioactive coatings, hydrogels, and other types of complex biomaterials. To fully reach the potential of this new field, there are number of challenges that researchers must overcome. There is still a great deal of room to develop new efficient synthesis and grafting procedures. In order to further the understanding of the structural activity and structure property relationships, improved tools and methods for accurate structural and physicochemical characterization will be essential. A better understanding of how bioactivity can be improved, without increasing the potential for of adverse effects, is needed. In response to these developments, and in order to encourage researchers from different backgrounds to share the results, Molecules is launching this Special Issue. Topics can include, but are not limited to:

  • Synthesis
  • Grafting
  • Polymerization
  • Photochemistry
  • Enzyme Catalyzed Reactions
  • Reaction Mechanism
  • Structure Characterization (including NMR)
  • Physicochemical characteristics
  • Structure property relationship
  • Bioactivity
  • Antimicrobial properties
  • Anticancer properties
  • Regenerative properties
  • Structure Activity Relationship
  • Drug Delivery
  • Gene Delivery
  • Metabolism
  • Toxicology
  • Nanoparticles
  • Biomaterials
  • Coatings
  • Gels
  • Composite materials

Prof. Dr. Már Másson
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 papers will be 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. Molecules 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 1800 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

  • Chitosan conjugates
  • Chitosan derivatives
  • Chitin derivatives
  • Medicina chemistry
  • Polymer chemistry
  • Bioactivity

References

  1. Pestov, A.; Bratskaya, S. Chitosan and Its Derivatives as Highly Efficient Polymer Ligands. Molecules 2016, 21, 330. 
  2. Ramirez-Estrada, K.; Vidal-Limon, H.; Hidalgo, D.; Moyano, E.; Golenioswki, M.; Cusidó, R.M.; Palazon, J. Elicitation, an Effective Strategy for the Biotechnological Production of Bioactive High-Added Value Compounds in Plant Cell Factories. Molecules 2016, 21, 182. 
  3. Ruocco, N.; Costantini, S.; Guariniello, S.; Costantini, M. Polysaccharides from the Marine Environment with Pharmacological, Cosmeceutical and Nutraceutical Potential. Molecules 2016, 21, 551. 
  4. Ohkawa, K. Nanofibers of Cellulose and Its Derivatives Fabricated Using Direct Electrospinning. Molecules 2015, 20, 9139-9154. 
  5. Ifuku, S. Chitin and Chitosan Nanofibers: Preparation and Chemical Modifications. Molecules 2014, 19, 18367-18380.

Published Papers (10 papers)

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Research

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Open AccessArticle Biodegradable Chitosan Decreases the Immune Response to Trichinella spiralis in Mice
Molecules 2017, 22(11), 2008; doi:10.3390/molecules22112008
Received: 15 September 2017 / Revised: 12 November 2017 / Accepted: 16 November 2017 / Published: 18 November 2017
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Abstract
The purpose of this study was to evaluate the potential of chitosan units released during natural degradation of the polymer to activate the immune system against T. spiralis infection. High molecular weight chitosan was injected intraperitoneally into C57BL/6 mice. Flow cytometry and cytokine
[...] Read more.
The purpose of this study was to evaluate the potential of chitosan units released during natural degradation of the polymer to activate the immune system against T. spiralis infection. High molecular weight chitosan was injected intraperitoneally into C57BL/6 mice. Flow cytometry and cytokine concentration, measured by ELISA, were used to characterize peritoneal cell populations during T. spiralis infection. The strong chemo-attractive properties of chitosan caused considerable infiltration into the peritoneal cavity of CD11b+ cells, with reduced expression of MHC class II, CD80, CD86, Dectin-1 or CD23 receptors in comparison to T. spiralis-infected mice. After prolonged chitosan biodegradation, cell populations expressing IL-4R, MR and Dectin-1 receptors were found to coexist with elevated IL-6, IL-10, TGF-β and IgA production. IgA cross-reacted with T. spiralis antigen and chitosan. It was found that chitosan treatment attracted immune cells with low activity, which resulted in the number of nematodes increasing. The glucosamine and N-acetyl-D-glucosamine residues were recognized by wheat germ agglutinin (WGA) lectin and therefore any biodegradable chitosan units may actively downregulate the immune response to the parasite. The findings are relevant for both people and animals treated with chitosan preparations. Full article
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Open AccessFeature PaperArticle Synthesis, Characterization and Biological Activities of Biopolymeric Schiff Bases Prepared with Chitosan and Salicylaldehydes and Their Pd(II) and Pt(II) Complexes
Molecules 2017, 22(11), 1987; doi:10.3390/molecules22111987
Received: 27 October 2017 / Revised: 10 November 2017 / Accepted: 13 November 2017 / Published: 16 November 2017
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Abstract
In an attempt to enhance chitosan biological activities, biopolymeric Schiff bases of chitosan and different salicylaldehydes and their palladium(II) and platinum(II) complexes were synthesized and tested. The chemical structures of these derivatives were characterized using 1H-NMR, FTIR spectroscopy and XPRD. Thermal analysis
[...] Read more.
In an attempt to enhance chitosan biological activities, biopolymeric Schiff bases of chitosan and different salicylaldehydes and their palladium(II) and platinum(II) complexes were synthesized and tested. The chemical structures of these derivatives were characterized using 1H-NMR, FTIR spectroscopy and XPRD. Thermal analysis was done through TGA/DTG-DTA. Electronic absorption spectra and surface morphologies were analyzed by SEM-EDAX. Chitosan and its derivatives were evaluated for their in vitro antimicrobial activity against two common bacterial and fungal plant pathogens Pseudomonas syringae pv. tomato and Fusarium graminearum, respectively, and for their antitumor activity against a human breast cancer cell line (MCF-7). It was found that, compared to the nonmodified chitosan, chitosan modified with Schiff bases and their complexes was highly toxic against the MCF-7 cell line and had antibacterial effects against P. syringea. However, the modified chitosan derivatives had less pronounced antifungal effects against F. graminearum compared to the nonmodified chitosan, suggesting different modes of action. Full article
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Open AccessArticle Development of Gallic Acid-Modified Hydrogels Using Interpenetrating Chitosan Network and Evaluation of Their Antioxidant Activity
Molecules 2017, 22(11), 1976; doi:10.3390/molecules22111976
Received: 14 October 2017 / Revised: 4 November 2017 / Accepted: 13 November 2017 / Published: 15 November 2017
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Abstract
In this work, antioxidant hydrogels were prepared by the construction of an interpenetrating chitosan network and functionalization with gallic acid. The poly(2-hydroxyethyl methacrylate) p(HEMA)-based hydrogels were first synthesized and subsequently surface-modified with an interpenetrating polymer network (IPN) structure prepared with methacrylamide chitosan via
[...] Read more.
In this work, antioxidant hydrogels were prepared by the construction of an interpenetrating chitosan network and functionalization with gallic acid. The poly(2-hydroxyethyl methacrylate) p(HEMA)-based hydrogels were first synthesized and subsequently surface-modified with an interpenetrating polymer network (IPN) structure prepared with methacrylamide chitosan via free radical polymerization. The resulting chitosan-IPN hydrogels were surface-functionalized with gallic acid through an amide coupling reaction, which afforded the antioxidant hydrogels. Notably, gallic-acid-modified hydrogels based on a longer chitosan backbone exhibited superior antioxidant activity than their counterpart with a shorter chitosan moiety; this correlated to the amount of gallic acid attached to the chitosan backbone. Moreover, the surface contact angles of the chitosan-modified hydrogels decreased, indicating that surface functionalization of the hydrogels with chitosan-IPN increased the wettability because of the presence of the hydrophilic chitosan network chain. Our study indicates that chitosan-IPN hydrogels may facilitate the development of applications in biomedical devices and ophthalmic materials. Full article
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Open AccessArticle Effects of Chitooligosaccharide Coating Combined with Selected Ionic Polymers on the Stimulation of Ornithogalum saundersiae Growth
Molecules 2017, 22(11), 1903; doi:10.3390/molecules22111903
Received: 15 October 2017 / Revised: 2 November 2017 / Accepted: 4 November 2017 / Published: 4 November 2017
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Abstract
Recently, agricultural and horticultural sectors have shown an increased interest in the use of biopolymers and their derivatives as growth biostimulators. So far, coating is a little known method of applying the biostimulators. Our three-year study investigated coating the bulbs of Ornithogalum saundersiae
[...] Read more.
Recently, agricultural and horticultural sectors have shown an increased interest in the use of biopolymers and their derivatives as growth biostimulators. So far, coating is a little known method of applying the biostimulators. Our three-year study investigated coating the bulbs of Ornithogalum saundersiae with chitooligosaccharide (COS), sodium alginate, carrageenan, gellan gum and xanthan gum. The coating method was based on the formation of polyelectrolyte complexes. The COS with 48,000 g mol−1 molecular weight was contained by means of controlled free-radical degradation. Biopolymer coatings stimulated plant growth and flowering, total chlorophyll content, total polyphenol content and the levels of nitrogen, phosphorus, potassium and boron. The plants grown from the bulbs coated with COS + gellan gum exhibited the most vigorous growth, were first to flower, showed the highest antioxidant activity (DPPH), and the greatest content of pigments, polyphenols, l-ascorbic acid, potassium, phosphorus, zinc and manganese. These results suggest COS formulated with gellan gum shows promise as a potential biostimulator of plant growth. Full article
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Open AccessArticle Visible Light-Cured Glycol Chitosan Hydrogel Containing a Beta-Cyclodextrin-Curcumin Inclusion Complex Improves Wound Healing In Vivo
Molecules 2017, 22(9), 1513; doi:10.3390/molecules22091513
Received: 30 July 2017 / Revised: 7 September 2017 / Accepted: 8 September 2017 / Published: 10 September 2017
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Abstract
Scarless wound healing is ideal for patients suffering from soft tissue defects. In this study, we prepared a novel wet dressing (β-CD-ic-CUR/GC) based on the visible light-cured glycol chitosan (GC) hydrogel and inclusion complex between beta-cyclodextrin (β-CD) and curcumin (CUR). We also evaluated
[...] Read more.
Scarless wound healing is ideal for patients suffering from soft tissue defects. In this study, we prepared a novel wet dressing (β-CD-ic-CUR/GC) based on the visible light-cured glycol chitosan (GC) hydrogel and inclusion complex between beta-cyclodextrin (β-CD) and curcumin (CUR). We also evaluated its efficacy in the acceleration of wound healing as compared to that of CUR-loaded GC (CUR/GC). The conjugation of glycidyl methacrylate (GM) to GC for photo-curing was confirmed by 1H-NMR measurement, and the photo-cured GC hydrogel was characterized by the analyses of rheology, swelling ratio, SEM and degradation rate. After visible light irradiation, the surface/cross-sectional morphologies and storage (G′)/loss (G′′) moduli revealed the formation of hydrogel with interconnected porosity. The dressing β-CD-ic-CUR/GC exhibited a controlled release of 90% CUR in a sustained manner for 30 days. On the other hand, CUR/GC showed CUR release of 16%. β-CD acted as an excipient in improving the water-solubility of CUR and affected the release behavior of CUR. The in vivo animal tests including measurement of the remaining unhealed wound area and histological analyses showed that β-CD-ic-CUR/GC may have potential as a wet dressing agent to enhance soft tissue recovery in open fractures. Full article
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Open AccessArticle Preparation and Characterization of Novel Cationic Chitosan Derivatives Bearing Quaternary Ammonium and Phosphonium Salts and Assessment of Their Antifungal Properties
Molecules 2017, 22(9), 1438; doi:10.3390/molecules22091438
Received: 14 August 2017 / Accepted: 29 August 2017 / Published: 31 August 2017
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Abstract
Chitosan is an abundant and renewable polysaccharide, its derivatives exhibit attractive bioactivities and the wide applications in various biomedical fields. In this paper, two novel cationic chitosan derivatives modified with quaternary phosphonium salts were successfully synthesized via trimethylation, chloride acetylation, and quaternization with
[...] Read more.
Chitosan is an abundant and renewable polysaccharide, its derivatives exhibit attractive bioactivities and the wide applications in various biomedical fields. In this paper, two novel cationic chitosan derivatives modified with quaternary phosphonium salts were successfully synthesized via trimethylation, chloride acetylation, and quaternization with tricyclohexylphosphine and triphenylphosphine. The structures and properties of synthesized products in the reactions were characterized by FTIR spectroscopy, 1H-NMR, 31P-NMR, elemental and thermogravimetric analysis. The antifungal activities of chitosan derivatives against four kinds of phytopathogens, including Phomopsis asparagi, Watermelon fusarium, Colletotrichum lagenarium, and Fusarium oxysporum were tested using the radial growth assay in vitro. The results revealed that the synthesized cationic chitosan derivatives showed significantly improved antifungal efficiency compared to chitosan. It was reasonably suggested that quaternary phosphonium groups enabled the obviously stronger antifungal activity of the synthesized chitosans. Especially, the triphenylphosphonium-functionalized chitosan derivative inhibited the growth of Phomopsis asparagi most effectively, with inhibitory indices of about 80% at 0.5 mg/mL. Moreover, the data demonstrated that the substituted groups with stronger electron-withdrawing ability relatively possessed greater antifungal activity. The results suggest the possibility that cationic chitosan derivatives bearing quaternary phosphonium salts could be effectively employed as novel antifungal biomaterials for application in the field of agriculture. Full article
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Open AccessArticle Synthesis, Characterization and In Vitro Evaluation of a Novel Glycol Chitosan-EDTA Conjugate to Inhibit Aminopeptidase-Mediated Degradation of Thymopoietin Oligopeptides
Molecules 2017, 22(8), 1253; doi:10.3390/molecules22081253
Received: 21 June 2017 / Revised: 14 July 2017 / Accepted: 24 July 2017 / Published: 26 July 2017
Cited by 1 | PDF Full-text (3583 KB) | HTML Full-text | XML Full-text
Abstract
In this study, a novel conjugate consisting of glycol chitosan (GCS) and ethylene diamine tetraacetic acid (EDTA) was synthesized and characterized in terms of conjugation and heavy metal ion chelating capacity. Moreover, its potential application as a metalloenzyme inhibitor was evaluated with three
[...] Read more.
In this study, a novel conjugate consisting of glycol chitosan (GCS) and ethylene diamine tetraacetic acid (EDTA) was synthesized and characterized in terms of conjugation and heavy metal ion chelating capacity. Moreover, its potential application as a metalloenzyme inhibitor was evaluated with three thymopoietin oligopeptides in the presence of leucine aminopeptidase. The results from FTIR and NMR spectra revealed that the covalent attachment of EDTA to GCS was achieved by the formation of amide bonds between the carboxylic acid group of EDTA and amino groups of GCS. The conjugated EDTA lost part of its chelating capacity to cobalt ions compared with free EDTA as evidenced by the results of cobalt ion chelation-mediated fluorescence recovery of calcein. However, further investigation confirmed that GCS-EDTA at low concentrations significantly inhibited leucine aminopeptidase-mediated degradation of all thymopoietin oligopeptides. Full article
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Open AccessArticle Use of Chitosan-PVA Hydrogels with Copper Nanoparticles to Improve the Growth of Grafted Watermelon
Molecules 2017, 22(7), 1031; doi:10.3390/molecules22071031
Received: 16 May 2017 / Revised: 18 June 2017 / Accepted: 19 June 2017 / Published: 22 June 2017
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Abstract
Modern agriculture requires alternative practices that improve crop growth without negatively affecting the environment, as resources such as water and arable land grow scarcer while the human population continues to increase. Grafting is a cultivation technique that allows the plant to be more
[...] Read more.
Modern agriculture requires alternative practices that improve crop growth without negatively affecting the environment, as resources such as water and arable land grow scarcer while the human population continues to increase. Grafting is a cultivation technique that allows the plant to be more efficient in its utilization of water and nutrients, while nanoscale material engineering provides the opportunity to use much smaller quantities of consumables compared to conventional systems but with similar or superior effects. On those grounds, we evaluated the effects of chitosan-polyvinyl alcohol hydrogel with absorbed copper nanoparticles (Cs-PVA-nCu) on leaf morphology and plant growth when applied to grafted watermelon cultivar ‘Jubilee’ plants. Stomatal density (SD), stomatal index (SI), stoma length (SL), and width (SW) were evaluated. The primary stem and root length, the stem diameter, specific leaf area, and fresh and dry weights were also recorded. Our results demonstrate that grafting induces modifications to leaf micromorphology that favorably affect plant growth, with grafted plants showing better vegetative growth in spite of their lower SD and SI values. Application of Cs-PVA-nCu was found to increase stoma width, primary stem length, and root length by 7%, 8% and 14%, respectively. These techniques modestly improve plant development and growth. Full article
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Open AccessArticle Cu Nanoparticles in Hydrogels of Chitosan-PVA Affects the Characteristics of Post-Harvest and Bioactive Compounds of Jalapeño Pepper
Molecules 2017, 22(6), 926; doi:10.3390/molecules22060926
Received: 31 March 2017 / Revised: 24 May 2017 / Accepted: 31 May 2017 / Published: 2 June 2017
Cited by 3 | PDF Full-text (1185 KB) | HTML Full-text | XML Full-text
Abstract
Peppers are consumed all over the world due to the flavor, aroma, and color that they add to food. Additionally, they play a role in human health, as they contain a high concentration of bioactive compounds and antioxidants. The treatments used were an
[...] Read more.
Peppers are consumed all over the world due to the flavor, aroma, and color that they add to food. Additionally, they play a role in human health, as they contain a high concentration of bioactive compounds and antioxidants. The treatments used were an absolute control, Cs-PVA, and four treatments with 0.02, 0.2, 2, and 10 mg (nCu) g−1 (Cs-PVA). The application of Cu nanoparticles in chitosan-PVA hydrogels increases the content of capsaicin by up to 51% compared to the control. This application also increases the content of antioxidants ABTS [2,2′-azino-bis (3-ethylbenzothiazolin-6-sulfonic acid)] and DPPH (2,2-diphenyl-1-picrylhydrazyl), total phenols and flavonoids (4%, 6.6%, 5.9%, and 12.7%, respectively) in jalapeño pepper fruits stored for 15 days at room temperature; under refrigeration, it increases DPPH antioxidants, total phenols, and flavonoids (23.9%, 1.54%, and 17.2%, respectively). The application of Cu nanoparticles in chitosan-PVA hydrogels, even when applied to the substrate, not only has an effect on the development of the jalapeño pepper crop, but also modifies the post-harvest characteristics of the jalapeño pepper fruits. Full article
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Review

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Open AccessReview Versatile Chemical Derivatizations to Design Glycol Chitosan-Based Drug Carriers
Molecules 2017, 22(10), 1662; doi:10.3390/molecules22101662
Received: 8 August 2017 / Revised: 26 September 2017 / Accepted: 2 October 2017 / Published: 5 October 2017
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Abstract
Glycol chitosan (GC) and its derivatives have been extensively investigated as safe and effective drug delivery carriers because of their unique physiochemical and biological properties. The reactive functional groups such as the amine and hydroxyl groups on the GC backbone allow for easy
[...] Read more.
Glycol chitosan (GC) and its derivatives have been extensively investigated as safe and effective drug delivery carriers because of their unique physiochemical and biological properties. The reactive functional groups such as the amine and hydroxyl groups on the GC backbone allow for easy chemical modification with various chemical compounds (e.g., hydrophobic molecules, crosslinkers, and acid-sensitive and labile molecules), and the versatility in chemical modifications enables production of a wide range of GC-based drug carriers. This review summarizes the versatile chemical modification methods that can be used to design GC-based drug carriers and describes their recent applications in disease therapy. Full article
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