Preparation of photoreactive azidophenyl hyaluronic acid derivative: Protein immobilization for medical applications

Hyung-Jae Lee; Shin-Hye Park; Si-Yoong Seo; Young-Min Cho; Hee Dong Woo; Yoshihiro Ito; Tae-Il Son

Macromolecular Research, Vol.21, No.2, 216-220, February, 2013

DOI10.1007/s13233-013-1016-7 Export Citation

Preparation of photoreactive azidophenyl hyaluronic acid derivative: Protein immobilization for medical applications

Hyung-Jae Lee, Shin-Hye Park, Si-Yoong Seo, Young-Min Cho, Hee Dong Woo, Yoshihiro Ito, and Tae-Il Son^†

Department of Biotechnology, Chung-Ang University, Gyeonggi, 456-756, Korea

E-mail:

Photoreactive azidophenyl hyaluronic acid (Az-HA) derivative was synthesized to immobilize proteins such as epidermal growth factor (EGF) and bone morphogenetic protein (BMP). The photosensitizing group, 4-azidoaniline, was introduced to the carboxyl group of hyaluronic acid by a water soluble carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC). To characterize the synthesized Az-HA, Fourier transform infrared (FTIR), proton nuclear magnetic resonance (1H NMR) and ultraviolet/visible (UV/vis) absorbance spectroscopy were performed. We demonstrated protein immobilization by using fluorescein isothiocyanate conjugated albumin (FITCBSA) on Az-HA derivative surfaces that were patterned with micro scale. Cytotoxicity and relative cell proliferation tests of the Az-HA derivative were performed on an MG-63 human osteoblast cell line for biocompatibility.

Keywords:hyaluronic acid;4-azidoaniline;1-ethyl-3-(3-dimethylaminopropyl)carbodiimide;hydrochloride;photoreactive;protein immobilization

[References]

Mendelsohn J, Baselga J, Oncogene., 19, 6550 (2000)
Kurtzman AL, Govindarajan S, Vahle K, Jones JT, Heinrichs V, Patten PA, Curr. Opin Biotechnol., 12, 361 (2001)
Ohba M, Mizuki E, Uemori A, Anticancer Res., 29, 427 (2009)
Liu WR, Langer R, Kilbanov AM, Biotechnol. Bioeng., 37, 177 (1991)
Costantino HR, Langer R, Kilbanov AM, J. Pharm.Sci., 83, 1662 (1994)
Ogiwara K, Nagaoka M, Cho CS, Akaike T, Biotechnol. Lett., 27(20), 1633 (2005)
Ito Y, Chen G, Imanishi Y, Morooka T, Nishida E, Okabayashim Y, Kasuga M, J. Biochem., 129, 733 (2001)
Hou KC, Zaniewski R, Roy S, Biotechnol. Appl. Biochem., 13, 257 (1991)
Sun WQ, Davidson P, Chan HSO, Biochim. Biophys.Acta., 1425, 245 (1998)
Ito Y, Zheng J, Imanishi Y, Yonezawa K, Kasuga M, Proc. Natl. Acad. Sci. U.S.A., 93, 3598 (1996)
Chen G, Ito Y, Imanishi Y, Bioconjug. Chem., 8, 106 (1997)
Baudys M, Letourneur D, Liu F, Jozefonvicz J, Kim SW, Bioconjug. Chem., 9, 176 (1998)
Bennion J, Daggett V, Proc. Natl. Acad. Sci. U.S.A., 100, 5142 (2003)
Matsuda T, Miwa H, Moghaddam MJ, Iida F, ASAIO., 39, M327 (1993)
Hino N, Okazaki Y, Kobayashi T, Hayashi A, Sakamoto K, Yokoyama S, Nat. Methods., 2, 201 (2005)
Heuer TS, Brown PO, Biochemistry., 36, 10655 (1997)
Heuer TS, Brown PO, Biochemistry., 37, 6667 (1998)
Luo Y, Kirker KR, Prestwich GD, J. Control. Release., 69, 169 (2000)
Hyung W, Ko H, Park J, Lim E, Park SB, Park YJ, Yoon HG, Suh JS, Haam S, Huh YM, Biotechnol. Bioeng., 99, 442 (2007)
Leach JB, Bivens KA, Patrick CW, Schmidt CE, Biotechnol. Bioeng., 82, 578 (2002)
Leach JB, Schmidt CE, Biomaterials., 26, 125 (2005)
Yoo HS, Lee EA, Yoon JJ, Park TG, Biomaterials., 26, 1925 (2005)
Leach JB, Bivens KA, Collins CN, Schmidt CE, J Biomed. Mater. Res. A., 70, 74 (2004)
Bae MS, Yang DH, Lee JB, Heo DN, Kwon YD, Youn IC, Choi K, Hong JH, Kim GT, Choi YS, Hwang EH, Kwon IK, Biomaterials., 32, 8161 (2011)
Yeo Y, Highly CB, Bellas E, Ito T, Marini R, Langer R, Kohane DS, Biomaterials., 27, 4698 (2006)
Price RD, Berry MG, Navsaria HA, J. Plast. Reconstr.Aesthet. Surg., 60, 1110 (2007)
Kogan G, Soltes L, Stern R, Gemeiner P, Biotechnol. Lett., 29(1), 17 (2007)
Belloli R, J. Chem. Educ., 48, 422 (1971)
Thu HY, Yu WY, Che CM, J. Am. Chem. Soc., 128(28), 9048 (2006)
Savarin CG, Grise C, Murry JA, Reamer RA, Hughes DL, Org. Lett., 9, 981 (2007)
Li Z, Ding X, He C, J. Org. Chem., 71, 5876 (2006)
Barbucci R, Magnani A, Lamponi S, Pasqui D, Bryan S, Biomaterials., 24, 915 (2003)
Joddar B, Kitajima T, Ito Y, Biomaterials., 32, 8404 (2011)
Matsuda T, Sugawara T, J. Biomed. Mater. Res., 29, 749 (1995)
Ishiyama M, Miyazono Y, Sasamoto K, Ohkuraand Y, Ueno K, Talanta., 40, 1299 (1997)
Alkrad JA, Mrestani Y, Stroehl D, Wartewig S, Neubert R, J. Pharm. Biomed. Anal., 31, 545 (2003)
Barth A, Prog. Biophys. Mol. Biol., 74, 141 (2000)
Smeds KA, Serres AP, Hatchell DL, Grinstaff MW, J. Macromol. Sci. Pure Appl. Chem. A., 36, 981 (1999)
Hasuda H, Kwon OH, Kang IK, Ito Y, Biomaterials., 26, 2401 (2005)
Chen G, Ito Y, Imanishi Y, Magnani A, Lamponi S, Barbucci R, Bioconjug. Chem., 5, 730 (1997)

[Referenced By]

[1] Mendelsohn J, Baselga J, Oncogene., 19, 6550 (2000)

[2] Kurtzman AL, Govindarajan S, Vahle K, Jones JT, Heinrichs V, Patten PA, Curr. Opin Biotechnol., 12, 361 (2001)

[3] Ohba M, Mizuki E, Uemori A, Anticancer Res., 29, 427 (2009)

[4] Liu WR, Langer R, Kilbanov AM, Biotechnol. Bioeng., 37, 177 (1991)

[5] Costantino HR, Langer R, Kilbanov AM, J. Pharm.Sci., 83, 1662 (1994)

[6] Ogiwara K, Nagaoka M, Cho CS, Akaike T, Biotechnol. Lett., 27(20), 1633 (2005)

[7] Ito Y, Chen G, Imanishi Y, Morooka T, Nishida E, Okabayashim Y, Kasuga M, J. Biochem., 129, 733 (2001)

[8] Hou KC, Zaniewski R, Roy S, Biotechnol. Appl. Biochem., 13, 257 (1991)

[9] Sun WQ, Davidson P, Chan HSO, Biochim. Biophys.Acta., 1425, 245 (1998)

[10] Ito Y, Zheng J, Imanishi Y, Yonezawa K, Kasuga M, Proc. Natl. Acad. Sci. U.S.A., 93, 3598 (1996)

[11] Chen G, Ito Y, Imanishi Y, Bioconjug. Chem., 8, 106 (1997)

[12] Baudys M, Letourneur D, Liu F, Jozefonvicz J, Kim SW, Bioconjug. Chem., 9, 176 (1998)

[13] Bennion J, Daggett V, Proc. Natl. Acad. Sci. U.S.A., 100, 5142 (2003)

[14] Matsuda T, Miwa H, Moghaddam MJ, Iida F, ASAIO., 39, M327 (1993)

[15] Hino N, Okazaki Y, Kobayashi T, Hayashi A, Sakamoto K, Yokoyama S, Nat. Methods., 2, 201 (2005)

[16] Heuer TS, Brown PO, Biochemistry., 36, 10655 (1997)

[17] Heuer TS, Brown PO, Biochemistry., 37, 6667 (1998)

[18] Luo Y, Kirker KR, Prestwich GD, J. Control. Release., 69, 169 (2000)

[19] Hyung W, Ko H, Park J, Lim E, Park SB, Park YJ, Yoon HG, Suh JS, Haam S, Huh YM, Biotechnol. Bioeng., 99, 442 (2007)

[20] Leach JB, Bivens KA, Patrick CW, Schmidt CE, Biotechnol. Bioeng., 82, 578 (2002)

[21] Leach JB, Schmidt CE, Biomaterials., 26, 125 (2005)

[22] Yoo HS, Lee EA, Yoon JJ, Park TG, Biomaterials., 26, 1925 (2005)

[23] Leach JB, Bivens KA, Collins CN, Schmidt CE, J Biomed. Mater. Res. A., 70, 74 (2004)

[24] Bae MS, Yang DH, Lee JB, Heo DN, Kwon YD, Youn IC, Choi K, Hong JH, Kim GT, Choi YS, Hwang EH, Kwon IK, Biomaterials., 32, 8161 (2011)

[25] Yeo Y, Highly CB, Bellas E, Ito T, Marini R, Langer R, Kohane DS, Biomaterials., 27, 4698 (2006)

[26] Price RD, Berry MG, Navsaria HA, J. Plast. Reconstr.Aesthet. Surg., 60, 1110 (2007)

[27] Kogan G, Soltes L, Stern R, Gemeiner P, Biotechnol. Lett., 29(1), 17 (2007)

[28] Belloli R, J. Chem. Educ., 48, 422 (1971)

[29] Thu HY, Yu WY, Che CM, J. Am. Chem. Soc., 128(28), 9048 (2006)

[30] Savarin CG, Grise C, Murry JA, Reamer RA, Hughes DL, Org. Lett., 9, 981 (2007)

[31] Li Z, Ding X, He C, J. Org. Chem., 71, 5876 (2006)

[32] Barbucci R, Magnani A, Lamponi S, Pasqui D, Bryan S, Biomaterials., 24, 915 (2003)

[33] Joddar B, Kitajima T, Ito Y, Biomaterials., 32, 8404 (2011)

[34] Matsuda T, Sugawara T, J. Biomed. Mater. Res., 29, 749 (1995)

[35] Ishiyama M, Miyazono Y, Sasamoto K, Ohkuraand Y, Ueno K, Talanta., 40, 1299 (1997)

[36] Alkrad JA, Mrestani Y, Stroehl D, Wartewig S, Neubert R, J. Pharm. Biomed. Anal., 31, 545 (2003)

[37] Barth A, Prog. Biophys. Mol. Biol., 74, 141 (2000)

[38] Smeds KA, Serres AP, Hatchell DL, Grinstaff MW, J. Macromol. Sci. Pure Appl. Chem. A., 36, 981 (1999)

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

[40] Chen G, Ito Y, Imanishi Y, Magnani A, Lamponi S, Barbucci R, Bioconjug. Chem., 5, 730 (1997)