Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
SHR Neuro Krebs Kardio Lipid Stoffw Microb
Millotti, G; Samberger, C; Frohlich, E; Sakloetsakun, D; Bernkop-Schnurch, A.
Chitosan-4-mercaptobenzoic acid: synthesis and characterization of a novel thiolated chitosan
J MATER CHEM. 2010; 20(12): 2432-2440.
Doi: 10.1039/b916528b
Web of Science
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- Co-Autor*innen der Med Uni Graz
- Fröhlich Eleonore
- Meindl Claudia
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- Abstract:
- 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 pK(a) 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