title: Design, synthesis, fabrication and in vitro evalution of mucoadhesive 5-amino-2-mercaptobenzimidazole chitosan as low water soluble drug carriers.
abstract: Mucoadhesive thiolated chitosan suitable as a carrier for low water soluble drugs was designed and synthesized by conjugating 5-amino-2-mercaptobenzimidazole (MBI) using methylacrylate (MA) as the linking agent. A 14.4% degree of substitution of MA, as determined by (1)H NMR analysis, and 11.86±0.01μmol thiol groups/g of polymer, as determined by Ellman's method, was obtained. The MBI-MA-chitosan had an 11-fold stronger mucoadhesive property compared to unmodified chitosan at pH 1.2, as determined by the periodic acid: Schiff colorimetric method. Chitosan, MA-chitosan and MBI-MA-chitosan were fabricated as well-formed microspheres using electrospray ionization, including an entrapment efficiency of simvastatin (SV) of over 80% for the MBI-MA-chitosan. The mucoadhesiveness of the SV-loaded MBI-MA-CS microspheres was still higher than that for SV-loaded chitosan at pH 1.2 and 6.4. The SV-loaded MBI-MA-CS microspheres revealed a reduced burst effect and an increased release rate (more than fivefold higher than pure SV) of SV over 12h.
authors.affiliation: Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Mullika
authors.initials: M
authors.lastname: Kongsong
authors.affiliation: Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Kultida
authors.initials: K
authors.lastname: Songsurang
authors.affiliation: Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Polkit
authors.initials: P
authors.lastname: Sangvanich
authors.affiliation: The Institute of Biotechnology and Genetic Engineering, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Krisana
authors.initials: K
authors.lastname: Siralertmukul
authors.affiliation: Biomaterials and Bioorganic Chemistry Research Group, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand. Electronic address: nongnuj.ms@gmail.com.
authors.forename: Nongnuj
authors.initials: N
authors.lastname: Muangsin
mesh_terms: D000268:Adhesiveness; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000378:metabolism; D048271:Chitosan / Q000138:chemical synthesis* / Q000378:metabolism; D004337:Drug Carriers / Q000138:chemical synthesis* / Q000378:metabolism; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D009077:Mucins / Q000378:metabolism; D014867:Water / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001562:Benzimidazoles; D004337:Drug Carriers; D009077:Mucins; D014867:Water; C030698:2-mercaptobenzimidazole; D048271:Chitosan
keywords: Drug carrier; Electrospray; Low water soluble drug; Microspheres; Mucoadhesive chitosan; Thiolated chitosan