Synthesis, characterization and antimicrobial activity of biguanidinylated chitosan-g-poly[(R)-3-hydroxybutyrate

Abstract

Chitosan biguanidine hydrochloride (ChG) and low molecular weight poly[(R)-3-hydroxybutyrate] (PHB) were successfully prepared to overcome the solubility problem of chitosan and PHB and also to enhance antimicrobial activity of chitosan. The graft copolymers based on ChG and PHB (ChG-grafted PHB) were then prepared via condensation reaction of the carboxylic groups of PHB with the amino groups of ChG. These graft copolymers swell in water. The prepared graft copolymers were characterized by FTIR, 1H NMR, X-ray diffraction (XRD) and thermal analyses (TGA and DSC). TGA and DSC results revealed that the thermal stability and crystallinity of the graft copolymers were found to increase as the content of PHB increased. The antimicrobial activity of both ChG and ChG-grafted PHB, against Streptococcus pneumoniae, Bacillus subtilis, Escherichia coli (as examples of bacteria) and Aspergillus fumigatus, Geotricum candidum and Syncephalastrum recemosum (as examples of fungi), were tested. Among them, ChG and ChG-grafted PHB with the highest grafting percent investigated showed to possess relatively higher antimicrobial activity with low MIC values in the range of 0.49–3.90μgmL−1.