TY - GEN A1 - Bourgat, Yannick A1 - Tiersch, Brigitte A1 - Koetz, Joachim A1 - Menzel, Henning T1 - Enzyme degradable polymersomes from chitosan-g-[poly-l-lysine-block-epsilon-caprolactone] copolymer T2 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe N2 - The scope of this study includes the synthesis of chitosan-g-[peptide-poly-epsilon-caprolactone] and its self-assembly into polymeric vesicles employing the solvent shift method. In this way, well-defined core-shell structures suitable for encapsulation of drugs are generated. The hydrophobic polycaprolactone side-chain and the hydrophilic chitosan backbone are linked via an enzyme-cleavable peptide. The synthetic route involves the functionalization of chitosan with maleimide groups and the preparation of polycaprolactone with alkyne end-groups. A peptide functionalized with a thiol group on one side and an azide group on the other side is prepared. Thiol-ene click-chemistry and azide-alkyne Huisgen cycloaddition are then used to link the chitosan and poly-epsilon-caprolactone chains, respectively, with this peptide. For a preliminary study, poly-l-lysin is a readily available and cleavable peptide that is introduced to investigate the feasibility of the system. The size and shape of the polymersomes are studied by dynamic light scattering and cryo-scanning electron microscopy. Furthermore, degradability is studied by incubating the polymersomes with two enzymes, trypsin and chitosanase. A dispersion of polymersomes is used to coat titanium plates and to further test the stability against enzymatic degradation. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - 1382 KW - chitosan KW - click chemistry KW - drug delivery system KW - enzyme KW - polymersomes KW - poly‐ ε ‐ caprolactone Y1 - 2020 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus4-566584 SN - 1866-8372 IS - 1 ER - TY - JOUR A1 - Bourgat, Yannick A1 - Tiersch, Brigitte A1 - Koetz, Joachim A1 - Menzel, Henning T1 - Enzyme degradable polymersomes from chitosan-g-[poly-l-lysine-block-epsilon-caprolactone] copolymer JF - Macromolecular bioscience N2 - The scope of this study includes the synthesis of chitosan-g-[peptide-poly-epsilon-caprolactone] and its self-assembly into polymeric vesicles employing the solvent shift method. In this way, well-defined core-shell structures suitable for encapsulation of drugs are generated. The hydrophobic polycaprolactone side-chain and the hydrophilic chitosan backbone are linked via an enzyme-cleavable peptide. The synthetic route involves the functionalization of chitosan with maleimide groups and the preparation of polycaprolactone with alkyne end-groups. A peptide functionalized with a thiol group on one side and an azide group on the other side is prepared. Thiol-ene click-chemistry and azide-alkyne Huisgen cycloaddition are then used to link the chitosan and poly-epsilon-caprolactone chains, respectively, with this peptide. For a preliminary study, poly-l-lysin is a readily available and cleavable peptide that is introduced to investigate the feasibility of the system. The size and shape of the polymersomes are studied by dynamic light scattering and cryo-scanning electron microscopy. Furthermore, degradability is studied by incubating the polymersomes with two enzymes, trypsin and chitosanase. A dispersion of polymersomes is used to coat titanium plates and to further test the stability against enzymatic degradation. KW - chitosan KW - click chemistry KW - drug delivery system KW - enzyme KW - polymersomes KW - poly‐ ε ‐ caprolactone Y1 - 2020 U6 - https://doi.org/10.1002/mabi.202000259 SN - 1616-5187 SN - 1616-5195 VL - 21 IS - 1 SP - 1 EP - 9 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Schneider, Matthias A1 - Günter, Christina A1 - Taubert, Andreas T1 - Co-deposition of a hydrogel/calcium phosphate hybrid layer on 3D printed poly(lactic acid) scaffolds via dip coating BT - Towards Automated Biomaterials Fabrication JF - Polymers N2 - The article describes the surface modification of 3D printed poly(lactic acid) (PLA) scaffolds with calcium phosphate (CP)/gelatin and CP/chitosan hybrid coating layers. The presence of gelatin or chitosan significantly enhances CP co-deposition and adhesion of the mineral layer on the PLA scaffolds. The hydrogel/CP coating layers are fairly thick and the mineral is a mixture of brushite, octacalcium phosphate, and hydroxyapatite. Mineral formation is uniform throughout the printed architectures and all steps (printing, hydrogel deposition, and mineralization) are in principle amenable to automatization. Overall, the process reported here therefore has a high application potential for the controlled synthesis of biomimetic coatings on polymeric biomaterials. KW - 3D printing KW - dip-coating KW - poly(lactic acid) KW - PLA KW - calcium phosphate KW - gelatin KW - chitosan KW - hydrogel KW - calcium phosphate hybrid material KW - biomaterials Y1 - 2018 U6 - https://doi.org/10.3390/polym10030275 SN - 2073-4360 VL - 10 IS - 3 PB - MDPI CY - Basel ER - TY - GEN A1 - Schneider, Matthias A1 - Günter, Christina A1 - Taubert, Andreas T1 - Co-deposition of a hydrogel/calcium phosphate hybrid layer on 3D printed poly(lactic acid) scaffolds via dip coating BT - Towards automated biomaterials fabrication T2 - Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe N2 - The article describes the surface modification of 3D printed poly(lactic acid) (PLA) scaffolds with calcium phosphate (CP)/gelatin and CP/chitosan hybrid coating layers. The presence of gelatin or chitosan significantly enhances CP co-deposition and adhesion of the mineral layer on the PLA scaffolds. The hydrogel/CP coating layers are fairly thick and the mineral is a mixture of brushite, octacalcium phosphate, and hydroxyapatite. Mineral formation is uniform throughout the printed architectures and all steps (printing, hydrogel deposition, and mineralization) are in principle amenable to automatization. Overall, the process reported here therefore has a high application potential for the controlled synthesis of biomimetic coatings on polymeric biomaterials. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - 1057 KW - 3D printing KW - dip-coating KW - poly(lactic acid) KW - PLA KW - calcium phosphate KW - gelatin KW - chitosan KW - hydrogel KW - calcium phosphate hybrid material KW - biomaterials Y1 - 2020 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus4-474427 SN - 1866-8372 IS - 1057 ER - TY - JOUR A1 - Pereira, Fernanda S. A1 - Nascimento, Heliara D. L. A1 - Magalhaes, Alvicler A1 - Peter, Martin G. A1 - Bataglion, Giovana Anceski A1 - Eberlin, Marcos N. A1 - Gonzalez, Eduardo R. P. T1 - ESI(+)-MS and GC-MS study of the hydrolysis of N-azobenzyl derivatives of chitosan JF - Molecules N2 - New N-p-chloro-, N-p-bromo-, and N-p-nitrophenylazobenzylchitosan derivatives, as well as the corresponding azophenyl and azophenyl-p-sulfonic acids, were synthesized by coupling N-benzylvchitosan with aryl diazonium salts. The synthesized molecules were analyzed by UV-Vis, FT-IR, H-1-NMR and N-15-NMR spectroscopy. The capacity of copper chelation by these materials was studied by AAS. Chitosan and the derivatives were subjected to hydrolysis and the products were analyzed by ESI(+)-MS and GC-MS, confirming the formation of N-benzyl chitosan. Furthermore, the MS results indicate that a nucleophilic aromatic substitution (SnAr) reaction occurs under hydrolysis conditions, yielding chloroaniline from N-p-bromo-, and N-p-nitrophenylazo-benzylchitosan as well as bromoaniline from N-p-chloro-, and N-p-nitrophenylazobenzyl-chitosan. KW - chitosan KW - N-azobenzylchitosan KW - ESI-MS KW - GC-MS KW - SnAr reaction Y1 - 2014 U6 - https://doi.org/10.3390/molecules191117604 SN - 1420-3049 VL - 19 IS - 11 SP - 17604 EP - 17618 PB - MDPI CY - Basel ER -