Preparation of O-diallylammonium chitosan with antibacterial activity and cytocompatibility

• Published in: Polymer international Vol. 62; no. 3; pp. 507 - 514
• Main Authors: Jou, Chi-Hsiung, Yang, Ming-Chien, Suen, Maw-Cherng, Yen, Chien-Kuo, Hung, Chia-Chun, Hwang, Mou-Chuan
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.03.2013; Wiley; Wiley Subscription Services, Inc
• Subjects: antibacterial activity; Applied sciences; chitosan; cytocompatibility; Exact sciences and technology; Klebsiella pneumoniae; Natural polymers; Physicochemistry of polymers; quaternary ammonium salt; Staphylococcus aureus; Starch and polysaccharides; Cell proliferation; Biological properties; antibacterial activity; quaternary ammonium salt; Experimental study; Bactericidal effect; Polyelectrolyte; Chemical modification; Chitosan derivatives; Preparation; Addition reaction; cytocompatibility; Biocompatibility; Oside polymer; Biomaterial; Chitosan; Antibacterial agent; Fibroblast; Quaternary ammonium polymer
• ISSN: 0959-8103; 1097-0126
• DOI: 10.1002/pi.4368

In this study, a derivative of chitosan, O‐hydroxy‐2,3‐propyl‐N‐methyl‐N,N‐diallylammonium chitosan methyl sulfate (O‐MDAACS), was synthesized by reacting chitosan with methyl diallyl ammonium. The O‐MDAACS was confirmed by Fourier transform infrared spectroscopy and 1H NMR. Characterization was conducted including X‐ray diffraction, differential scanning calorimetry and thermogravimetry. The antibacterial activities of O‐MDAACS against Staphylococcus aureus and Klebsiella pneumoniae were evaluated. The minimum inhibitory concentrations on O‐MDAACS were 3.7% and 23% of those on chitosan against S. aureus and K. pneumonia, respectively. The minimum bactericidal concentrations on O‐MDAACS were 7% and 36% of those on chitosan against S. aureus and K. pneumonia, respectively. Thus the antibacterial activity of O‐MDAACS was higher than that of chitosan. The cytocompatibility was evaluated in vitro with L929 fibroblasts. The results showed that after 72 h incubation the cell viability on O‐MDAACS was about 12% and 59% higher than those on chitosan and on control, respectively. © 2012 Society of Chemical Industry Synthesis of chitosan derivative (O‐MDAACS) with quaternary ammonium groups by reacting with methyl diallylammonium salt. The derivative exhibited higher antibacterial activity and no cytotoxicity against L929 fibroblasts.