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Chitin-Methacrylate: Preparation, Characterization and Hydrogel Formation
Department of Chemistry, the National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Pharmacy, School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Highway, Crawley WA 6009, Australia
Department of Orthopedic Surgery, Singapore General Hospital, Outram Road, Singapore 16960, Singapore
Present address: Biosensors Interventional Technologies Pte Ltd, Block 10, Kaki Bukit Avenue 1, #06-01/04, Kampong Ubi Industrial Estate, Singapore 417942, Singapore
* Author to whom correspondence should be addressed.
Received: 11 August 2011; in revised form: 20 September 2011 / Accepted: 27 September 2011 / Published: 6 October 2011
Abstract: Chitin-methacrylate (CM) was prepared by the reaction of methacrylic acid on chitin in 5% LiCl/DMAc in the presence of N,N’-dicyclocarbodiimide and dimethylaminopyridine. The resultant chitin-methacrylate product was isolated in 61% yield and was found to be readily water-soluble. The derivative was found to be a mixture of methacrylate and methacrylic-dimethylaminopyridine complex substituents at the C-6 position in approximately equal amounts. In order to evaluate the activity of the methacrylate double bond, a chitin-methacrylate water solution was photo-crosslinked in the presence of Irgacure 2959 photo-initiator to generate CM-hydrogel. The CM-hydrogel was evaluated for its biodegradability characteristics by enzymatic degradation with lysozyme solutions of varying concentrations. Completely water-soluble products were obtained within 48 h. In vitro cytotoxicity assays of the CM-hydrogel and its extract against three cell lines, NCTC clone 929, IMR-90 and MG-63, indicated the hydrogel was non-cytotoxic with cells able to adhere and proliferate well on the hydrogel.
Keywords: chitin-methacrylate; chitin derivatization; hydrogel; degradation; cytotoxicity
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MDPI and ACS Style
Khor, E.; Wu, H.; Lim, L.Y.; Guo, C.M. Chitin-Methacrylate: Preparation, Characterization and Hydrogel Formation. Materials 2011, 4, 1728-1746.
Khor E, Wu H, Lim LY, Guo CM. Chitin-Methacrylate: Preparation, Characterization and Hydrogel Formation. Materials. 2011; 4(10):1728-1746.
Khor, Eugene; Wu, Hong; Lim, Lee Yong; Guo, Chang Ming. 2011. "Chitin-Methacrylate: Preparation, Characterization and Hydrogel Formation." Materials 4, no. 10: 1728-1746.