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Glycans in Design and Synthesis of Biofunctional Materials

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

Deadline for manuscript submissions: closed (15 December 2019) | Viewed by 32764

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Dr. Iva Pashkuleva

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Guest Editor

3Bs Research Group, University of Minho, Guimarães, Portugal
Interests: carbohydrates; glycosaminoglycans; self-assembly; extracellular matrix

Special Issue Information

Dear Colleagues,

Carbohydrates are the most abundant biomolecules on our planet, and are the main structural components and a source of energy in various biological systems. Their role, however, goes far beyond these simple functions: carbohydrates are involved in a plethora of recognition events triggering specific pathways and defining an organism's diversity. The functional decoration of biomolecules (e.g., proteins and lipids) with carbohydrates is known as glycosylation and it is a common post-translational modification used by nature to create bioscripts and/or to diversify the repertoire of the functionalised biomolecules beyond the bioactivities coded by their amino acids or nucleotide sequences. These diverse glycan roles have been used in different biomimicking approaches for the development of biomaterials. The success of these approaches is often compromised by the glycan modification needed for the subsequent processing, e.g., immobilisation or gelation. Glycan functionalisation is challenging because of the many functional groups that have to be protected in order to get one specific group to react. Modification can also compromise the glycans’ bioactivity as it is based on multivalent cooperative interactions involving different functional groups. The material design must also consider a physiologically relevant milieu, usually aqueous, where the molecular recognition can be impeded by the multiple hydrogen bonds simultaneously formed with the habitat. This Special Issue aims to present different approaches that use glycans or their derivatives with preserved bioactivity for the development of functional materials with molecular recognition.

Dr. Iva Pashkuleva
Guest Editor

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Keywords

biomaterials
glycopolymers
glycan-protein interactions
biomimics
scaffolds
bioactive surfaces
multivalent interactions

Published Papers (6 papers)

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Research

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16 pages, 3072 KiB

Open AccessArticle

Anti-Tumor Effects of Biomimetic Sulfated Glycosaminoglycans on Lung Adenocarcinoma Cells in 2D and 3D In Vitro Models

by Nada Al Matari, George Deeb, Hiba Mshiek, Ansam Sinjab, Humam Kadara, Wassim Abou-Kheir and Rami Mhanna

Molecules 2020, 25(11), 2595; https://doi.org/10.3390/molecules25112595 - 3 Jun 2020

Cited by 8 | Viewed by 2741

Abstract

Lung cancer development relies on cell proliferation and migration, which in turn requires interaction with extracellular matrix (ECM) components such as glycosaminoglycans (GAGs). The mechanisms through which GAGs regulate cancer cell functions are not fully understood but they are, in part, mediated by controlled interactions with cytokines and growth factors (GFs). In order to mechanistically understand the effect of the degree of sulfation (DS) of GAGs on lung adenocarcinoma (LUAD) cells, we synthesized sulfated alginate (AlgSulf) as sulfated GAG mimics with DS = 0.0, 0.8, 2.0, and 2.7. Human (H1792) and mouse (MDA-F471) LUAD cell lines were treated with AlgSulf of various DSs at two concentrations 10 and 100 µg/mL and their anti-tumor properties were assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), trypan blue exclusion, and wound healing assays for 2D models and sphere formation assay for the 3D model. The proliferation and number of live MDA-F471 cells at the concentration of 100 µg/mL decreased significantly with the increase in the DS of biomimetic GAGs. In addition, the increase in the DS of biomimetic GAGs decreased cell migration (p < 0.001 for DS = 2.0 and 2.7 compared to control) and decreased the diameter and number of spheres formed (p < 0.001). The increased DS of biomimetic GAGs attenuated the expression of cancer stem cell (CSC)/progenitor markers in the 3D cultures. In conclusion, GAG-mimetic AlgSulf with increased DS exhibit enhanced anti-proliferative and migratory properties while also reducing growth of KRAS-mutant LUAD spheres in vitro. We suggest that these anti-tumor effects by GAG-mimetic AlgSulf are possibly due to differential binding to GFs and consequential decreased cell stemness. AlgSulf may be suitable for applications in cancer therapy after further in vivo validation. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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31 pages, 12358 KiB

Open AccessFeature PaperArticle

Spin-Coated Polysaccharide-Based Multilayered Freestanding Films with Adhesive and Bioactive Moieties

by Joana Moreira, Ana C. Vale, Ricardo A. Pires, Gabriela Botelho, Rui L. Reis and Natália M. Alves

Molecules 2020, 25(4), 840; https://doi.org/10.3390/molecules25040840 - 14 Feb 2020

Cited by 18 | Viewed by 4117

Abstract

Freestanding films based on catechol functionalized chitosan (CHI), hyaluronic acid (HA), and bioglass nanoparticles (BGNPs) were developed by spin-coating layer-by-layer assembly (SA-LbL). The catechol groups of 3,4-dihydroxy-l-phenylalanine (DOPA) present in the marine mussels adhesive proteins (MAPs) are the main factors responsible for their characteristic strong wet adhesion. Then, the produced films were cross-linked with genipin to improve their stability in wet state. Overall, the incorporation of BGNPs resulted in thicker and bioactive films, hydrophilic and rougher surfaces, reduced swelling, higher weight loss, and lower stiffness. The incorporation of catechol groups onto the films showed a significant increase in the films’ adhesion and stiffness, lower swelling, and weight loss. Interestingly, a synergetic effect on the stiffness increase was observed upon the combined incorporation of BGNPs with catechol-modified polymers, given that such films were the stiffest. Regarding the biological assays, the films exhibited no negative effects on cellular viability, adhesion, and proliferation, and the BGNPs seemed to promote higher cellular metabolic activity. These bioactive LbL freestanding films combine enhanced adhesion with improved mechanical properties and could find applications in the biomedical field, such as guided hard tissue regeneration membranes. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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12 pages, 3357 KiB

Open AccessArticle

Bioorthogonal Labeling Reveals Different Expression of Glycans in Mouse Hippocampal Neuron Cultures during Their Development

by Diana Soares da Costa, João C. Sousa, Sandro Dá Mesquita, Nevena I. Petkova-Yankova, Fernanda Marques, Rui L. Reis, Nuno Sousa and Iva Pashkuleva

Molecules 2020, 25(4), 795; https://doi.org/10.3390/molecules25040795 - 12 Feb 2020

Cited by 3 | Viewed by 2871

Abstract

The expression of different glycans at the cell surface dictates cell interactions with their environment and other cells, being crucial for the cell fate. The development of the central nervous system is associated with tremendous changes in the cell glycome that is tightly regulated. Herein, we have employed bioorthogonal Cu-free click chemistry to image temporal distribution of different glycans in live mouse hippocampal neurons during their maturation in vitro. We show development-dependent glycan patterns with increased fucose and decreased mannose expression at the end of the maturation process. We also demonstrate that this approach is biocompatible and does not affect glycan transport although it relies on an administration of modified glycans. The applicability of this strategy to tissue sections unlocks new opportunities to study the glycan dynamics under more complex physiological conditions. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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15 pages, 2899 KiB

Open AccessArticle

Characterizing the Physical Properties and Cell Compatibility of Phytoglycogen Extracted from Different Sweet Corn Varieties

by Renjie Liu, Susan K. Boehlein, William F. Tracy, Marcio F. R. Resende, Jr. and Gregory A. Hudalla

Molecules 2020, 25(3), 637; https://doi.org/10.3390/molecules25030637 - 1 Feb 2020

Cited by 11 | Viewed by 3602

Abstract

Owing to its unique structure and properties, the glucose dendrimer phytoglycogen is gaining interest for medical and biotechnology applications. Although many maize variants are available from commercial and academic breeding programs, most applications rely on phytoglycogen extracted from the common maize variant, sugary1. Here we characterized the solubility, hydrodynamic diameter, water-binding properties, protein contaminant concentration, and cytotoxicity of phytoglycogens from different maize sources, A632su1, A619su1, Wesu7, and Ia453su1, harboring various sugary1 mutants. A619su1-SW phytoglycogen was cytotoxic while A632su1-SW phytoglycogen was not. A632su1-Pu phytoglycogen promoted cell growth, whereas extracts from A632su1-NE, A632su1-NC, and A632su1-CM were cytotoxic. Phytoglycogen extracted from Wesu7su1-NE using ethanol precipitation was cytotoxic. Acid-treatment improved Wesu7 phytoglycogen cytocompatibility. Protease-treated Wesu7 extracts promoted cell growth. Phytoglycogen extracted from Ia453su1 21 days after pollination (“Ia435su1 21DAP”) was cytotoxic, whereas phytoglycogen extracted at 40 days (“Ia435su1 40DAP”) was not. In general, size and solubility had no correlation with cytocompatibility, whereas protein contaminant concentration and water-binding properties did. A632su1-CM had the highest protein contamination among A632 mutants, consistent with its higher cytotoxicity. Likewise, Ia435su1 21DAP phytoglycogen had higher protein contamination than Ia435su1 40DAP. Conversely, protease-treated Wesu7 extracts had lower protein contamination than the other Wesu7 extracts. A632su1-NE, A632su1-NC, and A632su1-CM had similar water-binding properties which differed from those of A632su1-Pu and A632su1-SW. Likewise, water binding differed between Ia435su1 21DAP and Ia435su1 40DAP. Collectively, these data demonstrate that maize phytoglycogen extracts are not uniformly cytocompatible. Rather, maize variant, plant genotype, protein contaminants, and water-binding properties are determinants of phytoglycogen cytotoxicity. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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Review

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39 pages, 5925 KiB

Open AccessReview

Glycosaminoglycan-Inspired Biomaterials for the Development of Bioactive Hydrogel Networks

by Mariana I. Neves, Marco Araújo, Lorenzo Moroni, Ricardo M.P. da Silva and Cristina C. Barrias

Molecules 2020, 25(4), 978; https://doi.org/10.3390/molecules25040978 - 21 Feb 2020

Cited by 41 | Viewed by 8315

Abstract

Glycosaminoglycans (GAG) are long, linear polysaccharides that display a wide range of relevant biological roles. Particularly, in the extracellular matrix (ECM) GAG specifically interact with other biological molecules, such as growth factors, protecting them from proteolysis or inhibiting factors. Additionally, ECM GAG are partially responsible for the mechanical stability of tissues due to their capacity to retain high amounts of water, enabling hydration of the ECM and rendering it resistant to compressive forces. In this review, the use of GAG for developing hydrogel networks with improved biological activity and/or mechanical properties is discussed. Greater focus is given to strategies involving the production of hydrogels that are composed of GAG alone or in combination with other materials. Additionally, approaches used to introduce GAG-inspired features in biomaterials of different sources will also be presented. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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22 pages, 4339 KiB

Open AccessReview

Biological Role of Gellan Gum in Improving Scaffold Drug Delivery, Cell Adhesion Properties for Tissue Engineering Applications

by Thangavelu Muthukumar, Jeong Eun Song and Gilson Khang

Molecules 2019, 24(24), 4514; https://doi.org/10.3390/molecules24244514 - 10 Dec 2019

Cited by 76 | Viewed by 10583

Abstract

Over the past few decades, gellan gum (GG) has attracted substantial research interest in several fields including biomedical and clinical applications. The GG has highly versatile properties like easy bio-fabrication, tunable mechanical, cell adhesion, biocompatibility, biodegradability, drug delivery, and is easy to functionalize. These properties have put forth GG as a promising material in tissue engineering and regenerative medicine fields. Nevertheless, GG alone has poor mechanical strength, stability, and a high gelling temperature in physiological conditions. However, GG physiochemical properties can be enhanced by blending them with other polymers like chitosan, agar, sodium alginate, starch, cellulose, pullulan, polyvinyl chloride, xanthan gum, and other nanomaterials, like gold, silver, or composites. In this review article, we discuss the comprehensive overview and different strategies for the preparation of GG based biomaterial, hydrogels, and scaffolds for drug delivery, wound healing, antimicrobial activity, and cell adhesion. In addition, we have given special attention to tissue engineering applications of GG, which can be combined with another natural, synthetic polymers and nanoparticles, and other composites materials. Overall, this review article clearly presents a summary of the recent advances in research studies on GG for different biomedical applications. Full article

(This article belongs to the Special Issue Glycans in Design and Synthesis of Biofunctional Materials)

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