Mucoadhesive 4-carboxybenzenesulfonamide-chitosan with antibacterial properties

The mucoadhesive property of chitosan, especially in an acidic (<pH 6.0) environment, was increased by conjugating an aromatic sulfonamide group at the C2-N position of chitosan. Four different feeding ratios of 4-carboxybenzensulfonamide (4-CBS) to chitosan in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride as a coupling agent were investigated. The 0.2:1 (w/w) ratio 4-CBS:chitosan revealed a 20-fold stronger mucoadhesion to mucin type II than the native chitosan in the simulated gastric fluid (SGF; pH 1.2), and a swelling ratio after 1 h in water, SGF and simulated intestinal fluid (pH 7.4) of about 2.9-, 3.0- and 3.4-fold higher than that of chitosan, respectively. In tissue culture, the 4-CBS-chitosan, like chitosan, were found to be non-cytotoxic to the Vero, KB, MCF-7 and NCI-H187 cell lines but showed potential antibacterial activity against Escherichia coli and Staphlyococcus aureus as model Gram-negative and Gram-positive bacteria, respectively.