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Modification and analysis of low-molecular chitosans
Moravcová, Dagmar ; Bosáková, Zuzana (advisor) ; Strašák, Tomáš (referee)
4 Abstract Chitosan is a natural biopolymer derived from chitin, found in the exoskeletons of crustaceans and fungi. It has gained considerable attention due to its biodegradability, biocompatibility, antimicrobial properties, and potential antitumor activities. Chitosan has cationic amino groups that enable interactions with various anionic compounds. Therefore, it is an ideal candidate for conjugation with monovalent bioactive compounds to form efficient multivalent conjugates. It was found that galectins, especially Gal-1 and Gal-3, are overexpressed in tumor cells. Several monovalent inhibitors derived from the parent inhibitor thiodigalactoside, also those modified with coumaryl groups, have been synthesized, which show a high selectivity and affinity towards Gal-3. The main goal of this work was to synthesize a chitosan-based carrier and conjugate it with ligands exhibiting selectivity and inhibitory effect towards Gal-3. The first step involved the modification of chitosan using a unique effective method based on solid-phase hydrolysis, which significantly reduces the consumption of chemical materials and, in addition, excessive losses during purification. At the same time, the chitosan carrier was functionalized with pentynoic acid. Furthermore, monovalent galectin ligands,...
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