Photocurable O-Carboxymethyl Chitosan Derivatives for Biomedical Applications: Synthesis, In vitro Biocompatibility, and Their Wound Healing Effects

Ha-Na Na; Shin-Hye Park; Kwang-Il Kim; Mi Kyung Kim; Tae-Il Son

Macromolecular Research, Vol.20, No.11, 1144-1149, November, 2012

DOI10.1007/s13233-012-0167-2 Export Citation

Photocurable O-Carboxymethyl Chitosan Derivatives for Biomedical Applications: Synthesis, In vitro Biocompatibility, and Their Wound Healing Effects

Ha-Na Na, Shin-Hye Park, Kwang-Il Kim, Mi Kyung Kim¹, and Tae-Il Son^†

Department of Biotechnology and Bio-Environmental Technology (BET) Research Institute, Chung-Ang University, Gyeonggi, 456-756, Korea
¹Department of Pathology, College of Medicine, Chung-Ang University, Seoul, 156-756, Korea

E-mail:

In this work, photocurable water-soluble chitosan derivatives were prepared for biomedical applications by modifying water-soluble O-carboxymethyl chitosan (O-CMC) derivatives with furfuryl glycidyl ether (O-CMC/FGE). Successful derivatization of chitosan to the final product (O-CMC/FGE) was verified by UV and 1H NMR spectral analysis. The degree of photo-crosslinking was measured by a flow distance experiment after exposure to visible light for a certain period of time. The degree of crosslinking increased linearly in proportion to exposure time. The in vitro cell viability test revealed a lack of cytotoxicity of O-CMC/FGE against mouse 3T3 fibroblasts. However, poor cell attachment was observed for the cells seeded onto the photocured O-CMC/FGE; this is likely due to the anionic nature of this material. O-CMC/FGE displayed wound healing effects in an in vivo animal experiment using a burn wound model. Due to its good biocompatibility, wound healing effect, and mild cross-linking condition, together with an inhibitory effect on cell attachment, O-CMC/FGE would be a promising candidate as an anti-adhesion material for biomedical applications.

Keywords:O-carboxymethyl chitosan;furfuryl glycidyl ether;photo-curing;biomedical materials.

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[Referenced By]

[1] Dongming H, Heru S, Mathias U, Prog. Polym. Sci., 34, 62 (2009)

[2] Hatefi A, Amsden B, J. Control. Release., 80, 9 (2002)

[3] Minoru N, Yu Y, React. Funct. Polym., 68, 915 (2008)

[4] Chao Z, Jun W, Reinhart-King CA, Chu CC, Acta Biomater., 6, 3908 (2010)

[5] Doulabi ASH, Mirzadeh H, Imani M, Sharifi S, Atai M, Mehdipour-Ataei S, Polym. Adv. Technol., 19, 1199 (2008)

[6] Sanxiu L, Kristi S, J. Control. Release., 57, 291 (1999)

[7] Ding FC, Hsu SH, Chiang WY, J. Appl. Polym. Sci., 109(1), 589 (2008)

[8] Chiang WY, Lin WT, J. Appl. Polym. Sci., 51(11), 1901 (1994)

[9] Satyakam P, Ashwani KS, Garg BS, Gandhi RP, Gupta KC, Int. J. Pharm., 342, 184 (2007)

[10] Liu J, Nie J, Zhao Y, He Y, J. Photochem. Photobiol.Chem., 211, 20 (2010)

[11] Kaetsu I, Nakayama H, Uchida K, Sutani K, Radiat.Phys. Chem., 60, 513 (2010)

[12] Nakayama Y, Kameo T, Ohtaka A, Hirano Y, J. Photochem.Photobiol. Chem., 177, 205 (2006)

[13] Li C, Sajiki T, Nakayama Y, Fukui M, Matsuda T, J.Biomed. Mater. Res., 66B, 439 (2003)

[14] Nakayama Y, Matsuda T, J. Biomed. Mater. Res., 48, 511 (1999)

[15] Nakayama Y, Matsuda T, ASAIO J., 41, M374 (1995)

[16] Arai H, Tajima Y, Takeuchi K, J. Photopolym. Sci. Technol., 13, 103 (2000)

[17] Gandini A, Belgacem MN, Prog. Polym. Sci., 22, 1203 (1997)

[18] Tajima Y, Arai H, Tezuka Y, Ishii T, Takeuchi K, Fullerene Sci. Technol., 5, 1531 (1997)

[19] Takeuchi E, Tajima Y, Takeuchi K, J. Photopolym. Sci. Technol., 14, 139 (2001)

[20] Tajima Y, Tezuka Y, Ishii T, Takeuchi K, Polym. J., 29, 1016 (1997)

[21] Son TI, Sakuragi M, Takahashi S, Obuse S, Kang J, Fujishiro M, Matsushita H, Gong J, Shimizu S, Tajima Y, Yoshida Y, Suzuki K, Yamamoto T, Nakamura M, Ito Y, Acta Biomater., 6, 4005 (2010)

[22] Smeds KA, Grinstaff MW, J. Biomed. Mater. Res., 54, 115 (2001)

[23] Yeh J, Ling Y, Karp JM, Gantz J, Chandawarkar A, Eng G, Blumling J, Langer R,Khademhosseini A, Biomaterials., 27, 5391 (2006)

[24] Chou AI, Akintoye SO, Nicoll SB, Osteoarthr.Cartil., 17, 1377 (2009)

[25] Zhu A, Jin W, Yuan L, Yang G, Yu H, Wu H, Carbohydr. Polym., 68, 693 (2007)

[26] Dureja D, Tiwary AK, Gupta S, Int. J. Pharm., 213, 193 (2001)

[27] Zhu A, Chan-Park MB, Dai S, Li L, Colloids Surf B: Biointerfaces., 43, 143 (2005)

[28] Yaylaoglu MB, Korkusuz P, Ors F, Korkusuz U, Hasirci V, Biomaterials., 20, 711 (1999)

[29] Cima LG, Vacanti JP, Ingber D, Mooney D, Canger R, J. Biomech. Eng., 113, 143 (1991)

[30] Laurencin CT, El-Amin SF, Ibim SE, Wilough DA, Attawia M, Ambrocio AA, J. Biomed. Mater. Res., 30, 133 (1996)

[31] de Abreu FR, Campana-Filho SF, Carbohydr. Polym., 75, 216 (2009)

[32] Sashiwa H, Kawasaki N, Nakayama A, Muraki E, Yajima H, Aiba SI, Carbohydr. Res., 338, 557 (2003)

[33] Nah JW, Jang MK, J. Polym. Sci. A: Polym. Chem., 40(21), 3796 (2002)

[34] Liu XF, Guan YL, Yang DZ, Li Z, De Yao K, J. Appl. Polym. Sci., 79(7), 1324 (2001)

[35] An NT, Thien DT, Dong NT, Dung PL, Carbohydr.Polym., 75, 489 (2009)

[36] Sugimoto M, Morimoto M, Sashiwa H, Saimoto H, Shigemasa Y, Carbohydr. Polym., 36, 49 (1998)

[37] Tokura S, Nishi N, Tsutsumi A, Somorin O, Polym. J., 15, 485 (1983)

[38] Pang HT, Chen XG, Park HJ, Cha DS, Kennedy JF, Carbohydr. Polym., 26, 419 (2007)

[39] Twentyman PR, Luscombe M, Br. J. Cancer., 56, 279 (1987)

[40] Park S, Seo S, Na H, Kim K, Lee J, Woo H, Lee J, Seok H, Lee J, Chung S, Chung KH, Han DK, Ito Y, Jang E, Son T, Macromol. Res., 19(9), 921 (2011)

[41] Zhu AP, Fang N, Biomacromolecules, 6(5), 2607 (2005)

[42] Chen RN, Wang GM, Chen CH, Ho HO, Sheu MT, Biomacromolecules, 7(4), 1058 (2006)