title: Enhanced water-solubility and mucoadhesion of N,N,N-trimethyl-N-gluconate-N-homocysteine thiolactone chitosan.
abstract: A water-soluble chitosan with improved mucoadhesion was prepared by modifying 19.4% of the amine groups of chitosan to trimethylammonium and conjugation of gluconolactone (GLU) and homocysteine thiolactone (HT) onto the remaining amine groups of the chitosan backbone. The derived trimethyl-gluconate-HT-chitosan (TM-GN-HT-chitosan) was confirmed by Fourier Transform Infrared spectroscopy, NMR and thermogravimetric analysis. The total thiol and disulfide group level on the TM-GN-HT-chitosan were 17.96 ± 0.03 and 7.36 ± 0.03 μmol/g, respectively. The water solubility of the TM-GN-HT-chitosan conjugate was 79.0 ± 0.15%, more than that of TM-chitosan and chitosan, with an enhanced solubility over a broad pH range ranging from 85.6 ± 10.4% to 58.5±1.1% maximal solubility at pH 2 to 11. Finally, TM-GN-HT-chitosan showed a nearly ∼9.5-, 5.0- and 5.6-fold higher mucoadhesiveness than chitosan at pH 1.2, 4.0 and 6.4, respectively, and was optimal at pH 4.0.
authors.affiliation: Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Tawroong
authors.initials: T
authors.lastname: Chivangkul
authors.affiliation: Biomaterials and Bioorganic Chemistry Research Group, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Somchai
authors.initials: S
authors.lastname: Pengprecha
authors.affiliation: Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Panuwat
authors.initials: P
authors.lastname: Padungros
authors.affiliation: Metallurgy and Materials Science Research Institute, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Krisana
authors.initials: K
authors.lastname: Siraleartmukul
authors.affiliation: Department of Botany, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Sehanat
authors.initials: S
authors.lastname: Prasongsuk
authors.affiliation: Biomaterials and Bioorganic Chemistry Research Group, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. Electronic address: nongnuj.j@chula.ac.th.
authors.forename: Nongnuj
authors.initials: N
authors.lastname: Muangsin
mesh_terms: D048271:Chitosan / Q000737:chemistry*; D005942:Gluconates / Q000737:chemistry; D006710:Homocysteine / Q000031:analogs & derivatives / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry*
chemical_list: D005942:Gluconates; D007783:Lactones; C118071:N-trimethyl chitosan chloride; D014867:Water; D006710:Homocysteine; D048271:Chitosan; C007957:homocysteine thiolactone; C010730:beta-glucono-1,5-lactone
keywords: Cationic polymer; Mucoadhesive chitosan; Water-soluble chitosan