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• Ultrasound dramatically accelerates reactions of chitosan and affects their selectivity • Ultrasonic polymeranalogous transformations of chitosan is simple and convenient tool for chitosan derivatization • Chitosan derivatives and their nanoparticles possess outstanding antibacterial effect in vitro and in vivo • Triazolebetaine chitosan derivatives have pronounced in vitro transfection activity 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. [ABSTRACT FROM AUTHOR]