Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response
In the fast-developing field of tissue engineering there is a constant demand for new materials as scaffolds for cell seeding, which can better mimic a natural extracellular matrix as well as control cell behavior. Among other materials, polysaccharides are widely used for this purpose. One of the m...
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MDPI AG
2021-05-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/11/5731 |
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| author | Anna Golunova Nadiia Velychkivska Zuzana Mikšovská Václav Chochola Josef Jaroš Aleš Hampl Ognen Pop-Georgievski Vladimír Proks |
| author_facet | Anna Golunova Nadiia Velychkivska Zuzana Mikšovská Václav Chochola Josef Jaroš Aleš Hampl Ognen Pop-Georgievski Vladimír Proks |
| author_sort | Anna Golunova |
| collection | DOAJ |
| description | In the fast-developing field of tissue engineering there is a constant demand for new materials as scaffolds for cell seeding, which can better mimic a natural extracellular matrix as well as control cell behavior. Among other materials, polysaccharides are widely used for this purpose. One of the main candidates for scaffold fabrication is alginate. However, it lacks sites for cell adhesion. That is why one of the steps toward the development of suitable scaffolds for cells is the introduction of the biofunctionality to the alginate structure. In this work we focused on bone-sialoprotein derived peptide (TYRAY) conjugation to the molecule of alginate. Here the comparison study on four different approaches of peptide conjugation was performed including traditional and novel modification methods, based on 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide/<i>N</i>-hydroxy succinimide (EDC/NHS), 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (DMTMM), thiol-Michael addition and Cu-catalyzed azide–alkyne cycloaddition reactions. It was shown that the combination of the alginate amidation with the use of and subsequent Cu-catalyzed azide–alkyne cycloaddition led to efficient peptide conjugation, which was proven with both NMR and XPS methods. Moreover, the cell culture experiment proved the positive effect of peptide presence on the adhesion of human embryonic stem cells. |
| first_indexed | 2024-03-10T10:58:35Z |
| format | Article |
| id | doaj.art-756c84455cbb4e34934dacd83cde57bc |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T10:58:35Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-756c84455cbb4e34934dacd83cde57bc2023-11-21T21:40:22ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-05-012211573110.3390/ijms22115731Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell ResponseAnna Golunova0Nadiia Velychkivska1Zuzana Mikšovská2Václav Chochola3Josef Jaroš4Aleš Hampl5Ognen Pop-Georgievski6Vladimír Proks7Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Sq. 2, 16206 Prague, Czech RepublicInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Sq. 2, 16206 Prague, Czech RepublicInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Sq. 2, 16206 Prague, Czech RepublicDepartment of Histology and Embryology, Faculty of Medicine, Masaryk University, Kamenice 3, 62500 Brno, Czech RepublicDepartment of Histology and Embryology, Faculty of Medicine, Masaryk University, Kamenice 3, 62500 Brno, Czech RepublicDepartment of Histology and Embryology, Faculty of Medicine, Masaryk University, Kamenice 3, 62500 Brno, Czech RepublicInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Sq. 2, 16206 Prague, Czech RepublicInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Sq. 2, 16206 Prague, Czech RepublicIn the fast-developing field of tissue engineering there is a constant demand for new materials as scaffolds for cell seeding, which can better mimic a natural extracellular matrix as well as control cell behavior. Among other materials, polysaccharides are widely used for this purpose. One of the main candidates for scaffold fabrication is alginate. However, it lacks sites for cell adhesion. That is why one of the steps toward the development of suitable scaffolds for cells is the introduction of the biofunctionality to the alginate structure. In this work we focused on bone-sialoprotein derived peptide (TYRAY) conjugation to the molecule of alginate. Here the comparison study on four different approaches of peptide conjugation was performed including traditional and novel modification methods, based on 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide/<i>N</i>-hydroxy succinimide (EDC/NHS), 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (DMTMM), thiol-Michael addition and Cu-catalyzed azide–alkyne cycloaddition reactions. It was shown that the combination of the alginate amidation with the use of and subsequent Cu-catalyzed azide–alkyne cycloaddition led to efficient peptide conjugation, which was proven with both NMR and XPS methods. Moreover, the cell culture experiment proved the positive effect of peptide presence on the adhesion of human embryonic stem cells.https://www.mdpi.com/1422-0067/22/11/5731alginateadhesion-promoting peptidepolysaccharide modificationcell adhesionhESCNMR |
| spellingShingle | Anna Golunova Nadiia Velychkivska Zuzana Mikšovská Václav Chochola Josef Jaroš Aleš Hampl Ognen Pop-Georgievski Vladimír Proks Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response International Journal of Molecular Sciences alginate adhesion-promoting peptide polysaccharide modification cell adhesion hESC NMR |
| title | Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response |
| title_full | Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response |
| title_fullStr | Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response |
| title_full_unstemmed | Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response |
| title_short | Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response |
| title_sort | direct and indirect biomimetic peptide modification of alginate efficiency side reactions and cell response |
| topic | alginate adhesion-promoting peptide polysaccharide modification cell adhesion hESC NMR |
| url | https://www.mdpi.com/1422-0067/22/11/5731 |
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