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Enzyme degradable polymersomes from chitosan-g-[poly-l-lysine-block-epsilon-caprolactone] copolymer
- 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 lightThe 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.…
Verfasserangaben: | Yannick BourgatGND, Brigitte TierschORCiD, Joachim KoetzORCiDGND, Henning MenzelORCiDGND |
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URN: | urn:nbn:de:kobv:517-opus4-566584 |
DOI: | https://doi.org/10.25932/publishup-56658 |
ISSN: | 1866-8372 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/33289254 |
Titel des übergeordneten Werks (Deutsch): | Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe |
Schriftenreihe (Bandnummer): | Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (1382) |
Publikationstyp: | Postprint |
Sprache: | Englisch |
Datum der Erstveröffentlichung: | 02.12.2020 |
Erscheinungsjahr: | 2020 |
Veröffentlichende Institution: | Universität Potsdam |
Datum der Freischaltung: | 19.03.2024 |
Freies Schlagwort / Tag: | chitosan; click chemistry; drug delivery system; enzyme; polymersomes; poly‐ ε ‐ caprolactone |
Ausgabe: | 1 |
Aufsatznummer: | 2000259 |
Seitenanzahl: | 11 |
Quelle: | Macromol. Biosci. 2021, 21, 2000259. https://doi.org/10.1002/mabi.202000259 |
Fördernde Institution: | Deutsche Forschungsgemeinschaft DFGGerman Research Foundation (DFG); [Me1057/18-1] |
Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer Review: | Referiert |
Publikationsweg: | Open Access / Green Open-Access |
Lizenz (Deutsch): | CC-BY-NC - Namensnennung, nicht kommerziell 4.0 International |
Externe Anmerkung: | Bibliographieeintrag der Originalveröffentlichung/Quelle |