title: Design, synthesis and in vitro evaluation of mucoadhesive p-coumarate-thiolated-chitosan as a hydrophobic drug carriers.
abstract: A hydrophobic mucoadhesive thiolated chitosan for hydrophobic drug delivery was designed and prepared by conjugating p-coumaric acid (pCA) to increase hydrophobic compatibility with drug via pi-pi interaction and then covalently linking homocysteine thiolactone (HT) to the pCA-chitosan to increase the mucoadhesive properties. The degree of substituted phenolics in the modified chitosan was about 7.21±0.05 mg gallic acid equivalents (GAE)/g. The pCA-HT-chitosan formed from a 24 h HT conjugation reaction time showed the highest yield of grafted thiol groups (~17.6 μmol/g) and the strongest mucoadhesive property, being about 10-, 2- and 1.6-fold more than that for the unmodified chitosan at pH 1.2, 4.0 and 6.4, respectively. Piperine (PIP) as a model hydrophobic drug was encapsulated in pCA-HT-chitosan microparticles via electrospray ionization with an encapsulation efficiency of over 80%. In vitro release studies showed a sustained release of PIP to >75% over 12 h between pH 1.2 and 6.4.
authors: Program of Petrochemistry and Polymer Science, Chulalongkorn University, Bangkok, Thailand.
authors: Thatthai
authors: T
authors: Pengpong
authors: Department of Chemistry, Chulalongkorn University, Bangkok, Thailand.
authors: Polkit
authors: P
authors: Sangvanich
authors: Metallurgy and Materials Science Research Institute, Chulalongkorn University, Bangkok, Thailand.
authors: Krisana
authors: K
authors: Sirilertmukul
authors: Biomaterials and Bioorganic Chemistry Research Group, Department of Chemistry, Chulalongkorn University, Bangkok, Thailand. Electronic address: nongnuj.j@chula.ac.th.
authors: Nongnuj
authors: N
authors: Muangsin
mesh_terms: D000269:Adhesives / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D048271:Chitosan / Q000737:chemistry* / Q000378:metabolism; D003373:Coumaric Acids / Q000737:chemistry* / Q000378:metabolism; D004337:Drug Carriers / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006710:Homocysteine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D009077:Mucins / Q000737:chemistry / Q000378:metabolism; D011422:Propionates; D013552:Swine
chemical_list: D000269:Adhesives; D003373:Coumaric Acids; D004337:Drug Carriers; D009077:Mucins; D011422:Propionates; D006710:Homocysteine; D048271:Chitosan; C007957:homocysteine thiolactone; C495469:p-coumaric acid
keywords: Chitosan; Drug delivery; Electrospray; Hydrophobic drug; Microspheres; Mucoadhesive polymer