Synthesis and characterization of chitosan-homocysteine thiolactone as a mucoadhesive polymer |
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Authors: | Kotchakorn JuntapramNalena Praphairaksit Krisana SiraleartmukulNongnuj Muangsin |
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Institution: | a Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand b Department of Biology, Faculty of Science, Srinakarinwirot University, Bangkok 10110, Thailand c Metallurgy and Materials Science Research Institute, Chulalongkorn University, 254 Phayathai Road, Bangkok 10330, Thailand d Center for Petroleum, Petrochemicals and Advanced Materials, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand |
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Abstract: | Two mucoadhesive thiolated polymers were synthesized by the covalent attachment of homocysteine thiolactone (HT) to chitosan and N,N,N-trimethyl-chitosan (TM-chitosan) at various chitosan:HT ratios. The amount of thiol and disulphide groups immobilized on the chitosan influenced the polymer's mucoadhesion positively and negatively, respectively, with the optimal chitosan:HT (w/w) ratio being found to be 1:0.1. The interaction between mucin and chitosan and its three derivatives was highest for the thiolated chitosan derivatives but was pH dependent. HT-chitosan and TM-HT-chitosan, with the thiol groups of 64.15 and 32.48 μmol/g, respectively, displayed a 3.67- and 6.33-fold stronger mucoadhesive property compared to that of the unmodified chitosan at pH 1.2, but these differences were only ∼1.7-fold at pH 6.4. The swelling properties of TM-HT-chitosan and HT-chitosan were higher than that of chitosan and TM-chitosan, attaining a swelling ratio of up to 240% and 140%, respectively, at pH 1.2 within 2 h. |
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Keywords: | Chitosan Mucoadhesive polymer Thiolated chitosan N N N-Trimethyl chitosan |
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