Diaminated Starch: A Competitor of Chitosan with Highly Mucoadhesive Properties due to Increased Local Cationic Charge Density

Abstract

The purpose of this study was to synthesize diaminated starch as a novel mucoadhesive polymer. Starch was tosylated and then reacted with ethylenediamine. The degree of amination was determined by 2,4,6-trinitrobenzene sulfonic acid assay. Properties of diaminated starch including solubility, cytotoxicity, swelling behavior, and mucoadhesion were compared to chitosan. Diaminated starch displayed 2083 ± 121.6 μmol of diamine substructures/g of polymer. At pH 6, diaminated starch exhibited a ζ potential of 6 mV, whereas it was close to zero in the case of unmodified starch. In addition, diaminated starch displayed water solubility over the entire pH range and minor cytotoxicity. The novel polymer showed pronounced swelling behavior in water increasing its initial weight 18- and 6-fold at pH 5 and 6, respectively. Moreover, diaminated starch exhibited 92-fold higher-mucoadhesivity properties than those of chitosan. According to these results, diaminated starch might be a promising novel excipient for the design of mucoadhesive formulations.