Chitosan derivatives and their based nanoparticles: ultrasonic approach to the synthesis, antimicrobial and transfection properties

Abstract

In the present work, we demonstrate that alkylation of chitosan by alkyl halides, aza-Michael reaction with chitosan, and Ad_N-E reaction of chitosan with aldehydes can be efficiently mediated by ultrasound. An optimization of ultrasonic irradiation parameters allowed us to (i) accelerate the rate of the reactions dramatically, (ii) achieve high selectivity, and (iii) preserve integrity of the polysaccharide backbone avoiding its depolymerization. We evaluated antibacterial/antifungal and transfection activity of 8 different derivatives of chitosan and their based nanoparticles in vitro. Moreover, we studied antibacterial activity of the most efficient polymer and their based nanoparticles in vivo. The tested polymer proved to be superior to reference commercial antibiotics ampicillin and gentamicin.

Keywords: antibacterial activity; antifungal activity; chitosan; chitosan derivatives; transfection activity; ultrasound.