Visible light-induced photocurable (forming a film) low molecular weight chitosan derivatives for biomedical applications: Synthesis, characterization and in vitro biocompatibility

Si Yoong Seo; Shin Hye Park; Hyung Jae Lee; Ha Na Na; Kwang Il Kim; Dong Keun Han; Jae Kwan Lee; Yoshihiro Ito; Tae Il Son

Journal of Industrial and Engineering Chemistry, Vol.18, No.4, 1258-1262, July, 2012

DOI10.1016/j.jiec.2012.01.006 Export Citation

Visible light-induced photocurable (forming a film) low molecular weight chitosan derivatives for biomedical applications: Synthesis, characterization and in vitro biocompatibility

Si Yoong Seo, Shin Hye Park, Hyung Jae Lee, Ha Na Na, Kwang Il Kim, Dong Keun Han¹, Jae Kwan Lee, Yoshihiro Ito², and Tae Il Son^†

Department of Biotechnology and Bio-Environmental Technology (BET) Research Institute, Chung-Ang University, Anseong, Gyeonggi-do 456-756, Republic of Korea
¹Biomaterials center, Korea Institute of science and technology(KIST), Seoul 130-650, Korea
²Nano Medical Engineering Laboratory, Riken Advanced Science Institute, 2-1 Hirosawa, Wako-Shi, Saitama 351-0198, Japan

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In this work, visible light-induced photocurable low molecular weight chitosan derivatives (F-LMC:furfuryl-low molecular weight chitosan) were prepared by nitrous acid decomposition followed by modification with furfuryl glycidyl ether. The structure of the decomposition products (LMC: low molecular weight chitosan) was characterized by FT-IR analysis. The structure and molecular weight of FLMC, prepared from the decomposition products by modification with furfuryl glycidyl ether, were characterized by 1H NMR and GPC analysis, respectively. F-LMC was initially water-soluble, but after the exposure to visible light, it became water-insoluble, indicating that F-LMC undergoes visible lightinduced inter- and intra-molecular cross-linking. The cross-linking was determined by concentration of F-LMC and time of exposure to visible light. The cytotoxicity test using fibroblast 3T3 showed no toxicity of F-LMC. Cross-linked F-LMC surface inhibited cell adherence.

Keywords:Chitosan;Low molecular weight chitosan;Furfuryl glycidyl ether;Photocurable polymers

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Zuniga A, Debbaudt A, Albertengo L, Rodriguez MS, Carbohydr. Polym., 79, 475 (2010)
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Kim CH, Shin CG, Shin KS, Son TI, J. Korean Ind. Eng. Chem., 10(4), 599 (1999)

[Referenced By]

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[1] Furukawa H, in: Araki T, Tran-Cong Q, Shibayama M (Eds.), Structure and Properties of Multiphase Polymeric Materials, Marcel Dekker, New York, 35 (1998)

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

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

[4] Matsuda T, Sugawara T, Langmuir, 11(6), 2272 (1995)

[5] Ito Y, Hasuda H, Kwon OH, Kang IK, Biomaterials., 26, 2401 (2005)

[6] Kim KI, Lee JW, Ito Y, Kang JH, Song KS, Jang EC, Son TI, J. Appl. Polym. Sci., 117(5), 3029 (2010)

[7] Lindhal T, Nature., 362, 709 (1993)

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

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

[10] Kim IY, Seo SJ, Moon HS, Yoo MK, Park IY, Kim BC, Cho CS, Biotechnol. Adv., 26, 1 (2008)

[11] Tanigawa T, Tanaka Y, Sashiwa H, Saimoto H, Shigemasa Y, in: Brine CJ, Sandford PA, Zikakis JP (Eds.), Advances in Chitin and Chitosan, Elsevier Applied Science, London, 206 (1992)

[12] Okamoto Y, Mianami S, Matsuhashi A, Sashiwa H, Saimoto H, Shigemasa Y, J. Vet. Med. Sci., 55, 743 (1993)

[13] Shahidi F, Abuzaytoun R, Adv. Food Nutr., 49, 93 (2005)

[14] Freier T, Koh HS, Kazazian K, Shoichet MS, Biomaterials., 26, 5872 (2005)

[15] Tokura S, Ueno K, Miyazaki S, Nishi N, Macromol. Symp., 120, 1 (1997)

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

[17] Zuniga A, Debbaudt A, Albertengo L, Rodriguez MS, Carbohydr. Polym., 79, 475 (2010)

[18] Hirano S, Kondo Y, Fujii K, Carbohydr. Res., 144, 338 (1985)

[19] Sashiwa H, Saimoto H, Shigemasa Y, Tokura S, Carbohydr. Res., 242, 167 (1993)

[20] Kim CH, Shin CG, Shin KS, Son TI, J. Korean Ind. Eng. Chem., 10(4), 599 (1999)