Macromolecular Research, Vol.17, No.10, 734-738, October, 2009
Facile Preparation of Biodegradable Glycol Chitosan Hydrogels Using Divinyladipate as a Crosslinker
E-mail:
Biodegradable, pH-sensitive, glycol chitosan (GC) hydrogels were prepared using divinyl adipate (DVA) as a crosslinker and acetic acid as a catalyst. DVA has highly reactive double vinyl ester groups and GC contains a high density of hydroxyl groups, with two in every glucosamine unit. The transesterification reaction between vinyl esters and hydroxyl groups produced crosslinked GC hydrogels. The initial crosslinking reaction was monitored by measuring the viscosity of the reaction mixture. When DVA was added to the GC solution and heated to 50 ℃, the viscosity
of the GC solution gradually increased, implying a crosslinking reaction and hydrogel formation. A new peak from the ester group was observed in the FTIR spectra of the GC hydrogels, confirming the crosslinking reaction. The synthesized GC hydrogel showed pH-dependent water absorbency, mainly due to the presence of amine groups (-NH2) at the C-2 position of the glucosamine unit of GC. The water absorbency greatly increased at acidic pH and slightly
decreased at alkaline pH. The GC hydrogel gradually degraded in 37 ℃ water due to hydrolysis of the ester bonds, which were intermolecular crosslinking sites. A red dye,
5-carboxyltetramethyl-rhodamine (CTMR), was entrapped in the GC hydrogels as a model compound. CTMR was released from GC hydrogels in two steps: an initial burst release mainly due to desorption and diffusion, and a second sustained release possibly due to gradual degradation.
- Hoffman AS, Adv. Drug Deliv. Rev., 43, 3 (2002)
- Lee KY, Mooney DJ, Chem. Rev., 101(7), 1869 (2001)
- Qiu Y, Park K, Adv. Drug Deliv. Rev., 53, 321 (2001)
- Kikuchi A, Okano T, Adv. Drug Deliv. Rev., 54, 53 (2002)
- Moon JR, Kim JH, Macromol. Res., 16(6), 489 (2008)
- Rao SB, Sharma CP, J. Biomed. Mater. Res., 34, 21 (1997)
- Shi C, Zhu Y, Ran X, Wang M, Su Y, Cheng T, J. Surg. Res., 133, 185 (2006)
- Cho YW, Cho YN, Chung SH, Yoo G, Ko SW, Biomaterials, 20, 2139 (1999)
- Berger J, Reist M, Mayer JM, Felt O, Gurny R, Eur. J. Pharm. Biopharm., 57, 35 (2004)
- Park KM, Joung YK, Park KD, Lee SY, Lee MC, Macromol. Res., 16(6), 517 (2008)
- Jeong K, Lee W, Cha J, Park CR, Cho YW, Kwon IC, Macromol. Res., 16(1), 57 (2008)
- Berger J, Reist M, Felt O, Peppas NA, Gurny R, Eur. J. Pharm. Biopharm., 57, 19 (2004)
- Han HD, Nam DE, Seo DH, Kim TW, Shin BC, Choi HS, Macromol. Res., 12(5), 507 (2004)
- Kang HS, Park SH, Lee YG, Son TI, J. Appl. Polym. Sci., 103, 386 (2006)
- Abdelaal MY, Abdel-Razik EA, Abdel-Bary EM, El-Sherbiny IM, J. Appl. Polym. Sci., 103(5), 2864 (2007)
- Ferreira L, Gil MH, Cabrita AMS, Dordick JS, Biomaterials, 26, 4707 (2005)
- Khmelnitsky YL, Budde C, Arnold JM, Usyatinsky A, Clark DS, Dordick JS, J. Am. Chem. Soc., 119(47), 11554 (1997)
- Kitagawa M, Tokiwa T, Fan H, Raku T, Tokiwa Y, Biotechnol. Lett., 22(10), 879 (2000)
- Chaudhary AK, Beckman EJ, Russell AJ, Biotechnol. Bioeng., 55(1), 227 (1997)
- Ferreira L, Gil MH, Chem. Mater., 14, 4009 (2002)
- EI-Sherbinyl IM, Abdel-Bary EM, Harding DRK, J. Appl. Polym. Sci., 102(2), 977 (2006)
- Zia KM, Barikani M, Bhatti IA, Zuber M, Bhatti HN, J. Appl. Polym. Sci., 110, 769 (2008)
- Hu X, Gao C, J. Appl. Polym. Sci., 110, 1059 (2008)