Surface Modification of Polyurethane Using Sulfonated PEG Grafted Polyrotaxane for Improved Biocompatibility

Hyung Dal Park; Jin Woo Bae; Ki Dong Park; Tooru Ooya; Nobuhiko Yui; Jun-Hyeog Jang; Dong Keun Han; Jung-Woog Shin

Macromolecular Research, Vol.14, No.1, 73-80, February, 2006

Hyung Dal Park, Jin Woo Bae, Ki Dong Park^†, Tooru Ooya¹, Nobuhiko Yui¹, Jun-Hyeog Jang², Dong Keun Han³, and Jung-Woog Shin⁴

Dept. of Molecular Science and Technology, Ajou University, Suwon 443-749, Korea
¹School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Tatsunokuchi, Ishikawa 923-1292, Japan
²Dept. of Biochemistry, College of Medicine, Inha University, Incheon 402-751, Korea
³Biomaterials Research Center, Korea Institute of Science and Technology, Seoul 136-791, Korea
⁴Dept. of Biomedical Engineering, Inje University, Gimhae 621-749, Korea

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Sulfonated poly(ethylene glycol) (PEG-SO3) grafted polyrotaxanes (PRx-PEG-SO3) were prepared in order to utilize the unique properties of PEG-SO3 and the supramolecular structure of PRx, in which PEG-SO3 grafted α-cyclodextrins ( α-CDs) were threaded onto PEG segments in a PEG-b-poly(propylene glycol) (PPG)-b-PEG triblock copolymer (Pluronic) chain capped with bulky end groups. Some of the PRx-PEG-SO3 demonstrated a higher anticoagulant activity in case of PRx-PEG-SO3 (P105), and compared with the control they showed a lower fibrinogen adsorption in PRx-PEG-SO3 (F68) and a higher binding affinity with fibroblast growth factor. The obtained results suggested that polyrotaxane incorporated with PEG-SO3 may be applicable to the surface modification of clinically used polymers, especially for blood/cell compatible medical devices.

Keywords:polyrotaxane;sulfonated polyethylene glycol;anticoagulant activity;protein adsorption;biocompatible

[References]

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Baier RE, Dutton RC, J. Biomed. Mater. Res., 3, 191 (1969)
Brash JL, Horbett TA, Proteins at Interfaces, American Chemical Society, Washington DC (1987)
Lee JH, Kopecek J, Andrade JD, J. Biomed. Mater. Res., 23, 351 (1989)
Park KD, Piao AZ, Jacobs H, Okano T, Kim SW, J. Polym. Sci. A: Polym. Chem., 29, 1725 (1991)
Harris JM, Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York (1992)
McPherson T, Kidane A, Szleifer I, Park K, Langmuir, 14(1), 176 (1998)
Amiji M, Park K, Biomaterials, 13, 682 (1992)
Tan JS, Butterfield DE, Voycheck CL, Caldwell KD, Li JT, Biomaterials, 14, 823 (1993)
McPherson TB, Shim HS, Park K, J. Biomed. Mater. Res. Appl. Biomater., 38, 289 (1997)
Kim YH, Kim DK, Park KD, Kim SH, Macromol. Symp., 118, 565 (1997)
Park KD, Suzuki K, Lee WK, Lee JE, Kim YH, Sakurai Y, Okano T, ASAIO J., 42, 876 (1996)
Park KD, Lee WK, Yun JY, Han DK, Kim YH, Kim HM, Kim KT, Biomaterials, 18, 47 (1997)
Folkman J, Weisz PB, Joullie MM, Li WW, Ewing WR, Science, 243, 1490 (1989)
Fujita M, Ishihara M, Simizu M, Obara K, Ishizuka T, Saito Y, Yura H, Morimoto Y, Takase B, Matsui T, Kikuchi M, Maehara T, Biomaterials, 25, 699 (2004)
Harada A, Li J, Kamachi M, Nature, 356, 325 (1992)
Harada A, Okada M, Li J, Kamachi M, Macromolecules, 28(24), 8406 (1995)
Harada A, Li J, Kamachi M, Nature, 364, 516 (1993)
Lee JH, Martic PA, Tan JS, J. Colloid Interface Sci., 131, 252 (1989)
Park HD, Lee WK, Ooya T, Park KD, Kim YH, Yui N, J. Biomed. Mater. Res., 60, 186 (2002)
Park HD, Lee WK, Ooya T, Park KD, Kim YH, Yui N, J. Biomed. Mater. Res., 66, 596 (2003)
Thomas L, Partielle Thromboplastinzeit, Labor und Diagnose Med, Verlagsgesellschaft, Marburg (1992)
Smith PK, Krohn RI, Hermanson GT, Anal. Biochem., 150, 76 (1985)
Alexandridis P, Holzwarth JF, Hatton TA, Macromolecules, 27(9), 2414 (1994)
Alexandridis P, Hatton TA, Colloids Surf. A: Physicochem. Eng. Asp., 96, 1 (1995)
Alban S, Kraus J, Franz G, Arzneimittelforschung, 42, 1005 (1992)
Alban S, Franz G, Pure Appl. Chem., 66, 2403 (1994)
Nishino T, Aizu Y, Nagumo T, Thromb. Res., 64, 723 (1991)
Munro MS, Quattrone AJ, Ellsworth SR, Kulkarni P, Eberhart RC, Trans. Amer. Soc. Artif. Intern. Organs, 27, 449 (1981)
Okano T, Nishiyama S, Shinohara I, Akaike T, Sakurai Y, Kataoka K, Tsuruta T, J. Biomed. Mater. Res., 15, 393 (1981)
Li JT, Caldwell KD, Colloids Surf. B: Biointerfaces, 7, 9 (1996)
Grawel TG, Cooper SL, J. Biomed. Mater. Res., 23, 311 (1989)
Santerre JP, VanderKamp NH, Brash JL, J. Biomed. Mater. Res., 26, 39 (1992)
Han DK, Park KD, Ryu GH, Kim UY, Min BG, Kim YH, J. Biomed. Mater. Res., 30, 23 (1989)
Kim SW, Lee RG, Oster H, Coleman D, Andrade JD, Trans. Amer. Soc. Artif. Intern. Organs, 20, 449 (1974)
Salzman EW, Lindon J, Brier D, Merril EW, Ann. NY Acad. Sci., 283, 114 (1997)

[Referenced By]

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[1] Baier RE, Artif. Organs, 2, 422 (1978)

[2] Baier RE, Dutton RC, J. Biomed. Mater. Res., 3, 191 (1969)

[3] Brash JL, Horbett TA, Proteins at Interfaces, American Chemical Society, Washington DC (1987)

[4] Lee JH, Kopecek J, Andrade JD, J. Biomed. Mater. Res., 23, 351 (1989)

[5] Park KD, Piao AZ, Jacobs H, Okano T, Kim SW, J. Polym. Sci. A: Polym. Chem., 29, 1725 (1991)

[6] Harris JM, Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York (1992)

[7] McPherson T, Kidane A, Szleifer I, Park K, Langmuir, 14(1), 176 (1998)

[8] Amiji M, Park K, Biomaterials, 13, 682 (1992)

[9] Tan JS, Butterfield DE, Voycheck CL, Caldwell KD, Li JT, Biomaterials, 14, 823 (1993)

[10] McPherson TB, Shim HS, Park K, J. Biomed. Mater. Res. Appl. Biomater., 38, 289 (1997)

[11] Kim YH, Kim DK, Park KD, Kim SH, Macromol. Symp., 118, 565 (1997)

[12] Park KD, Suzuki K, Lee WK, Lee JE, Kim YH, Sakurai Y, Okano T, ASAIO J., 42, 876 (1996)

[13] Park KD, Lee WK, Yun JY, Han DK, Kim YH, Kim HM, Kim KT, Biomaterials, 18, 47 (1997)

[14] Folkman J, Weisz PB, Joullie MM, Li WW, Ewing WR, Science, 243, 1490 (1989)

[15] Fujita M, Ishihara M, Simizu M, Obara K, Ishizuka T, Saito Y, Yura H, Morimoto Y, Takase B, Matsui T, Kikuchi M, Maehara T, Biomaterials, 25, 699 (2004)

[16] Harada A, Li J, Kamachi M, Nature, 356, 325 (1992)

[17] Harada A, Okada M, Li J, Kamachi M, Macromolecules, 28(24), 8406 (1995)

[18] Harada A, Li J, Kamachi M, Nature, 364, 516 (1993)

[19] Lee JH, Martic PA, Tan JS, J. Colloid Interface Sci., 131, 252 (1989)

[20] Park HD, Lee WK, Ooya T, Park KD, Kim YH, Yui N, J. Biomed. Mater. Res., 60, 186 (2002)

[21] Park HD, Lee WK, Ooya T, Park KD, Kim YH, Yui N, J. Biomed. Mater. Res., 66, 596 (2003)

[22] Thomas L, Partielle Thromboplastinzeit, Labor und Diagnose Med, Verlagsgesellschaft, Marburg (1992)

[23] Smith PK, Krohn RI, Hermanson GT, Anal. Biochem., 150, 76 (1985)

[24] Alexandridis P, Holzwarth JF, Hatton TA, Macromolecules, 27(9), 2414 (1994)

[25] Alexandridis P, Hatton TA, Colloids Surf. A: Physicochem. Eng. Asp., 96, 1 (1995)

[26] Alban S, Kraus J, Franz G, Arzneimittelforschung, 42, 1005 (1992)

[27] Alban S, Franz G, Pure Appl. Chem., 66, 2403 (1994)

[28] Nishino T, Aizu Y, Nagumo T, Thromb. Res., 64, 723 (1991)

[29] Munro MS, Quattrone AJ, Ellsworth SR, Kulkarni P, Eberhart RC, Trans. Amer. Soc. Artif. Intern. Organs, 27, 449 (1981)

[30] Okano T, Nishiyama S, Shinohara I, Akaike T, Sakurai Y, Kataoka K, Tsuruta T, J. Biomed. Mater. Res., 15, 393 (1981)

[31] Li JT, Caldwell KD, Colloids Surf. B: Biointerfaces, 7, 9 (1996)

[32] Grawel TG, Cooper SL, J. Biomed. Mater. Res., 23, 311 (1989)

[33] Santerre JP, VanderKamp NH, Brash JL, J. Biomed. Mater. Res., 26, 39 (1992)

[34] Han DK, Park KD, Ryu GH, Kim UY, Min BG, Kim YH, J. Biomed. Mater. Res., 30, 23 (1989)

[35] Kim SW, Lee RG, Oster H, Coleman D, Andrade JD, Trans. Amer. Soc. Artif. Intern. Organs, 20, 449 (1974)

[36] Salzman EW, Lindon J, Brier D, Merril EW, Ann. NY Acad. Sci., 283, 114 (1997)