Tailorable antibacterial and cytotoxic chitosan derivatives by introducing quaternary ammonium salt and sulfobetaine

Abstract

Chitosan (CS) derivatives with improved water solubility, antibacterial activity and adequate biocompatibility are attracting increasingly interest in medical application. Herein, we have successfully synthesized isocyanate terminated quaternary ammonium salt (IQAS) and sulfopropylbetaine (ISB) to be readily covalently bounded to CS skeleton by selective reaction with amino and hydroxyl groups. And their molecular structures and crystallinity were confirmed by Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, and X-ray diffraction. The effect of the substitution degree, carbon chain length, content ratio of IQAS/ISB on their water solubility, antibacterial activity and cytotoxicity were systematically investigated, which shows that those properties of the CS derivatives can be tailored by adjusting the grafted antibacterial agents and their additive amount. The structure-property relationship of these CS derivatives may provide a solid guidance on the development of CS derivatives for more efficient practical applications.

Keywords: Antibacterial; Betaine; Chitosan; Quaternary ammonium salt; Water solubility.