Cationic cellulose and other polysaccharide derivatives are attractive targets for biomedical applications due to their propensity for electrostatically binding with anionic biomolecules, such as nucleic acids and certain proteins. However, relatively few practical synthetic methods have been described for their preparation. Herein, we report a useful and efficient strategy for cationic polysaccharide salt preparation by reaction of 6-bromo-6-deoxycellulose esters or 6-bromo-6-deoxy-curdlan with pyridine or 1-methylimidazole exclusively at the C-6 position, resulting in high degree of substitution (DS). These cationic polysaccharide derivatives bearing substantial, permanent positive charge exhibit surprising thermal stability, dissolve readily in water, and bind strongly with a hydrophilic and anionic surface. Availability of these cationic polysaccharide derivatives will accelerate structure-property relationship studies, i.e. for biomedical application potential including complexation of poly(nucleic acids) for delivery to cell nuclei, delivery of anionic drugs, and epithelial tight junction opening for oral protein delivery.

Efficient, regioselective path to cationic polysaccharides for biomedical applications

251st National Meeting (2016)

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