Chitosan-4-mercaptobenzoic acid: synthesis and characterization of a novel thiolated chitosan
| Autor: | Gioconda Millotti, Eleonore Fröhlich, Duangkamon Sakloetsakun, Claudia Samberger, Andreas Bernkop-Schnürch |
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| Jazyk: | angličtina |
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
chitosan thiolated chitosan pKa biodegradability toxicity mucoadhesion in situ gelling Materials science Biocompatibility Thiomer technology industry and agriculture Excipient General Chemistry Polymer macromolecular substances equipment and supplies Chitosan carbohydrates (lipids) chemistry.chemical_compound chemistry Covalent bond Materials Chemistry Mucoadhesion medicine Organic chemistry Reactivity (chemistry) Nuclear chemistry medicine.drug |
| DOI: | 10.1039/b916528b |
| Popis: | Thiomers are thiolated polymers with excellent mucoadhesive properties. The aim of this study was to synthesize a novel thiolated chitosan with higher reactivity in order to further improve mucoadhesion. For this purpose, 4-mercaptobenzoic acid was chosen to be covalently attached to chitosan. The aromatic structure of the ligand should exhibit a higher reactivity due to a comparatively low pKa value of the thiol group, which was determined to be 6.8. Mucoadhesion, in situ gelation, biocompatibility and toxicity were evaluated. Chitosan-4-mercaptobenzoic acid was proved to be 60-fold more mucoadhesive compared to unmodified chitosan. After 24 hours, the viscosity of the novel thiomer solution increased 2974-fold compared to unmodified chitosan and after 48 hours 4487-fold. Chitosan-4-mercaptobenzoic acid tablets disintegrated twice as slowly as unmodified chitosan. Furthermore, the novel thiomer proved to be biodegradable and to be non-toxic. Due to the above mentioned properties, chitosan-4-mercaptobenzoic acid is a promising excipient for oral formulations or in situ gelling formulations. |
| Databáze: | OpenAIRE |
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