Preparation and In vivo Evaluation of Photo-Cured O-Carboxymethyl Chitosan Micro-Particle for Controlled Drug Delivery

Yun Heo; Shin-Hye Park; Si-Yoong Seo; Ju-Young Yun; Yoshihiro Ito; Tae-Il Son

Macromolecular Research, Vol.22, No.5, 541-548, May, 2014

DOI10.1007/s13233-014-2079-9 Export Citation

Preparation and In vivo Evaluation of Photo-Cured O-Carboxymethyl Chitosan Micro-Particle for Controlled Drug Delivery

Yun Heo, Shin-Hye Park, Si-Yoong Seo, Ju-Young Yun¹, Yoshihiro Ito², and Tae-Il Son^†

Department of Systems Biotechnology and Bio-Environmental Technology (BET) Research Institute, Chung-Ang University, Gyeonggi, 456-756, Korea
¹Korea Research Institute of Standards and Science, Yuseong, Daejeon, 305-340, Korea
²Nano Medical Engineering Laboratory, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

E-mail:

Medical advances have prompted the research and development of biomaterials. Especially, chitosan has emerged as new generation of biomaterials because it beneficial properties as a natural polymer, such as less toxic, biodegradable, and biocompatible than synthetic ones. The prepared azidophenyl O-carboxymethyl chitosan (Az-O-CMC) was characterized by FTIR, 1H NMR and particle-size analyzer. The hardening rate and cross-linking maintenance of the Az-O-CMC were investigated with its irradiation time and concentration. A photo-mask was used for observation of photoimmobilization. 3T3-L1 cells were cultured to determine effect of cytotoxicity. Protein release test was conducted to evaluate the immobilizing effect. In addition, animal test was investigated for wound healing application. In this study, the results indicate that immobilization of protein with Az-O-CMC will be useful for medical application.

Keywords:protein-immobilization;chitosan;carboxymethyl;photo-reactive;azidophenyl.

[References]

Cristallini C, Barbani N, Bianchi F, Silvestri D, Guerra GD, Biomed. Eng. App. Bas. Commun., 20, 321 (2008)
Li L, Kommareddy K, Pilz C, Zhou C, Fratzl P, Manjubala I, Acta Biomater., 6, 2525 (2010)
Combes C, Rey C, Biomaterials, 23, 2817 (2002)
Kim KI, Na HN, Ito Y, Son TI, Macromol. Res., 19(3), 216 (2011)
Hayakawa T, Yoshinari M, Kiba H, Yamamoto H, Nemoto K, Jansen JA, Biomaterials, 23, 1025 (2002)
Jayakumar R, Menon D, Manzoor K, Nair SV, Tamura H, Carbohydr. Polym., 82, 227 (2010)
Qu RJ, Sun YZ, Wang CH, Lu SL, Yu HM, Cheng GX, J. Appl. Polym. Sci., 84(2), 310 (2002)
Muzzarelli RAA, Tanfani F, Emanuelli M, Mariotti S, Carbohydr. Res., 107, 199 (1982)
Rigby JH, Kotnis AS, Tetrahedron. Lett., 28, 4943 (1987)
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)
Na HN, Park SH, Kim KI, Kim MK, Son TI, Macromol. Res., 20(11), 1144 (2012)
Felt O, Buri P, Gurny R, Drug Dev. Ind. Pharm., 24, 979 (1998)
Agnihotri SA, Mallikarjuna NN, Aminabhavi TM, J. Control. Release, 100, 5 (2004)
Lorenzo-Lamosa ML, Remunan-Lopez C, Vila-Jato JL, Alonso MJ, J. Control. Release, 52, 109 (1998)
Akiyama K, Kawazu K, Kobayashi A, Carbohydr. Res., 279, 151 (1995)
O’Fagain C, Biochim. Biophys. Acta, 1252, 1 (1995)
Brandts JF, Hunt L, J. Am. Chem. Soc., 89, 4826 (1967)
Kim DM, Lee BS, Kang JH, Choi J, Park K, Son TI, Jeong MH, Han DK, Macromol. Res., 19(5), 501 (2011)
Gekko K, Timasheff SN, Biochemistry, 20, 4667 (1981)
Gekko K, Timasheff SN, Biochemistry, 20, 4677 (1981)
Liu Y, Bolen DW, Biochemistry, 34, 12884 (1995)
Basta NT, Gradwohl R, Snethen KL, Schroder JL, J. Environ. Qual., 30, 1222 (2001)
Festa-Bianchet SDCM, Fournier F, J Wildl. Manage., 62, 745 (1998)
Zhu H, Srivastava R, Brown JQ, McShane MJ, Bioconjug. Chem., 16, 1451 (2005)
Souza JM, Giasson BI, Chen Q, Lee VM, Ischiropoulos H, J. Biol. Chem., 275, 18344 (2000)
Herbert CB, McLernon TL, Hypolite CL, Adams DN, Pikus L, Huang C, Fields GB, Letourneau PC, Distefano MD, Hu W, Chem. Biol., 4, 731 (1997)
Park SH, Seo SY, Lee HJ, Na HN, Lee JW, Woo HD, Son TI, Macromol. Res., 20(8), 842 (2012)
Ito Y, Soft Matter, 4, 46 (2008)
Ito Y, Hasuda H, Sakuragi M, Tsuzuki S, Acta Biomater., 3, 1024 (2007)
Matsuda T, Sugawara T, Langmuir, 11(6), 2272 (1995)
Tsai HC, Doong RA, Lin CF, Anal. Sci., 17, i269 (2001)
Hasuda H, Kwon OH, Kang IK, Ito Y, Biomaterials, 26, 2401 (2005)
Ito Y, Chen GP, Imanishi Y, Biotechnol. Prog., 12(5), 700 (1996)
Guo L, Kawazoe N, Fan Y, Ito Y, Tanaka J, Tateishi T, Zhang X, Chen G, Biomaterials, 29, 23 (2008)
Hahn R, Wagner S, Schmitz A, Reichl H, J. Power Sources, 131(1-2), 73 (2004)
Bradford MM, Anal. Biochem., 72, 248 (1976)
Chen SC, Wu YC, Mi FL, Lin YH, Yu LC, Sung HW, J. Control. Release, 96, 285 (2004)
Na HN, Kim KI, Han JH, Lee JG, Son TI, Han DK, Ito Y, Song KS, Jang EC, Macromol. Res., 18(10), 1001 (2010)

[Referenced By]

[1] Cristallini C, Barbani N, Bianchi F, Silvestri D, Guerra GD, Biomed. Eng. App. Bas. Commun., 20, 321 (2008)

[2] Li L, Kommareddy K, Pilz C, Zhou C, Fratzl P, Manjubala I, Acta Biomater., 6, 2525 (2010)

[3] Combes C, Rey C, Biomaterials, 23, 2817 (2002)

[4] Kim KI, Na HN, Ito Y, Son TI, Macromol. Res., 19(3), 216 (2011)

[5] Hayakawa T, Yoshinari M, Kiba H, Yamamoto H, Nemoto K, Jansen JA, Biomaterials, 23, 1025 (2002)

[6] Jayakumar R, Menon D, Manzoor K, Nair SV, Tamura H, Carbohydr. Polym., 82, 227 (2010)

[7] Qu RJ, Sun YZ, Wang CH, Lu SL, Yu HM, Cheng GX, J. Appl. Polym. Sci., 84(2), 310 (2002)

[8] Muzzarelli RAA, Tanfani F, Emanuelli M, Mariotti S, Carbohydr. Res., 107, 199 (1982)

[9] Rigby JH, Kotnis AS, Tetrahedron. Lett., 28, 4943 (1987)

[10] 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)

[11] Na HN, Park SH, Kim KI, Kim MK, Son TI, Macromol. Res., 20(11), 1144 (2012)

[12] Felt O, Buri P, Gurny R, Drug Dev. Ind. Pharm., 24, 979 (1998)

[13] Agnihotri SA, Mallikarjuna NN, Aminabhavi TM, J. Control. Release, 100, 5 (2004)

[14] Lorenzo-Lamosa ML, Remunan-Lopez C, Vila-Jato JL, Alonso MJ, J. Control. Release, 52, 109 (1998)

[15] Akiyama K, Kawazu K, Kobayashi A, Carbohydr. Res., 279, 151 (1995)

[16] O’Fagain C, Biochim. Biophys. Acta, 1252, 1 (1995)

[17] Brandts JF, Hunt L, J. Am. Chem. Soc., 89, 4826 (1967)

[18] Kim DM, Lee BS, Kang JH, Choi J, Park K, Son TI, Jeong MH, Han DK, Macromol. Res., 19(5), 501 (2011)

[19] Gekko K, Timasheff SN, Biochemistry, 20, 4667 (1981)

[20] Gekko K, Timasheff SN, Biochemistry, 20, 4677 (1981)

[21] Liu Y, Bolen DW, Biochemistry, 34, 12884 (1995)

[22] Basta NT, Gradwohl R, Snethen KL, Schroder JL, J. Environ. Qual., 30, 1222 (2001)

[23] Festa-Bianchet SDCM, Fournier F, J Wildl. Manage., 62, 745 (1998)

[24] Zhu H, Srivastava R, Brown JQ, McShane MJ, Bioconjug. Chem., 16, 1451 (2005)

[25] Souza JM, Giasson BI, Chen Q, Lee VM, Ischiropoulos H, J. Biol. Chem., 275, 18344 (2000)

[26] Herbert CB, McLernon TL, Hypolite CL, Adams DN, Pikus L, Huang C, Fields GB, Letourneau PC, Distefano MD, Hu W, Chem. Biol., 4, 731 (1997)

[27] Park SH, Seo SY, Lee HJ, Na HN, Lee JW, Woo HD, Son TI, Macromol. Res., 20(8), 842 (2012)

[28] Ito Y, Soft Matter, 4, 46 (2008)

[29] Ito Y, Hasuda H, Sakuragi M, Tsuzuki S, Acta Biomater., 3, 1024 (2007)

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

[31] Tsai HC, Doong RA, Lin CF, Anal. Sci., 17, i269 (2001)

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

[33] Ito Y, Chen GP, Imanishi Y, Biotechnol. Prog., 12(5), 700 (1996)

[34] Guo L, Kawazoe N, Fan Y, Ito Y, Tanaka J, Tateishi T, Zhang X, Chen G, Biomaterials, 29, 23 (2008)

[35] Hahn R, Wagner S, Schmitz A, Reichl H, J. Power Sources, 131(1-2), 73 (2004)

[36] Bradford MM, Anal. Biochem., 72, 248 (1976)

[37] Chen SC, Wu YC, Mi FL, Lin YH, Yu LC, Sung HW, J. Control. Release, 96, 285 (2004)

[38] Na HN, Kim KI, Han JH, Lee JG, Son TI, Han DK, Ito Y, Song KS, Jang EC, Macromol. Res., 18(10), 1001 (2010)