title: Mucoadhesive 4-carboxybenzenesulfonamide-chitosan with antibacterial properties.
abstract: 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.
authors.affiliation: Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Phruetchika
authors.initials: P
authors.lastname: Suvannasara
authors.forename: Kotchakorn
authors.initials: K
authors.lastname: Juntapram
authors.forename: Nalena
authors.initials: N
authors.lastname: Praphairaksit
authors.forename: Krisana
authors.initials: K
authors.lastname: Siralertmukul
authors.forename: Nongnuj
authors.initials: N
authors.lastname: Muangsin
mesh_terms: D000107:Acetylation; D058956:Administration, Mucosal; D000327:Adsorption; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D048271:Chitosan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002522:Chlorocebus aethiops; D003692:Delayed-Action Preparations / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D052978:Disk Diffusion Antimicrobial Tests; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D007413:Intestinal Mucosa / Q000378:metabolism; D061986:MCF-7 Cells; D013211:Staphylococcus aureus / Q000187:drug effects; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014709:Vero Cells; D014783:Viscosity; D000096926:Benzenesulfonamides
chemical_list: D000900:Anti-Bacterial Agents; D048271:Chitosan; D003692:Delayed-Action Preparations; D013449:Sulfonamides; C583470:4-carboxybenzenesulfonamide-chitosan; D000096926:Benzenesulfonamides