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Materials 2011, 4(10), 1728-1746; doi:10.3390/ma4101728
Article

Chitin-Methacrylate: Preparation, Characterization and Hydrogel Formation

1,* , 1,†
, 2
 and 3
1 Department of Chemistry, the National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore 2 Pharmacy, School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Highway, Crawley WA 6009, Australia 3 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 / Revised: 20 September 2011 / Accepted: 27 September 2011 / Published: 6 October 2011
(This article belongs to the Special Issue Carbohydrate Polymers)
Download PDF [1124 KB, 25 October 2011; original version 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 chitin-methacrylate; chitin derivatization; hydrogel; degradation; cytotoxicity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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