Temperature- and pH-Controlled Hydrogelation of Poly(ethylene glycol)-Grafted Hyaluronic Acid by Inclusion Complexation with α-Cyclodextrin

Polymer Journal volume 36, pages338–344(2004)Cite this article

Abstract

A series of poly(ethylene glycol) (PEG)-grafted hyaluronic acid (HA) was prepared by condensation reaction with hydrazide-terminated PEG using water soluble carbodiimide. PEG-grafted HA (PgH) solutions exhibited hydrogelation on adding α-cyclodextrin (α-CD). The solid-state 13C CP/MAS NMR spectroscopic and powder X-Ray diffraction measurements revealed the formation of inclusion complex between the PEG grafts and α-CD. The gel-melting temperature increased with increasing the degree of substitution of the PEG grafts and decreasing pH of aqueous medium. These results indicate that PgH hydrogels were constructed by inclusion complexation between the PEG grafts and α-CD, and the gel-melting temperature could be controlled by both the degree of substitution of the PEG grafts and pH.

Download PDF

References

  1. 1

    T. Nishikawa, K. Akiyoshi, and J. Sunamoto, J. Am. Chem. Soc., 118, 6110 (1996).

  2. 2

    S. J. de Jong, B. van Eerdenbrugh, C. F. Van Nostrum, J. J. Kettenes-van den Bosch, and W. E. Hennink, J. Control. Release, 72, 47 (2001).

  3. 3

    B. S. Lele and A. S. Hoffman, J. Control. Release, 69, 237 (2000).

  4. 4

    J. Li, A. Harada, and M. Kamachi, Polym. J., 26, 1019 (1994).

  5. 5

    T. Ooya and N. Yui, Crit. Rev. Ther. Drug Carrier Syst., 16, 289 (1999).

  6. 6

    T. Ooya and N. Yui, Macromol. Chem. Phys., 199, 2311 (1998).

  7. 7

    T. Ooya and N. Yui, J. Control. Release, 58, 251 (1999).

  8. 8

    T. Ooya, M. Eguchi, and N. Yui, J. Am. Chem. Soc., 125, 13016 (2003).

  9. 9

    J. Watanabe, T. Ooya, and N. Yui, Chem. Lett., 10, 1031 (1998).

  10. 10

    J. Watanabe, T. Ooya, and N. Yui, J. Biomater. Sci., Polym. Ed., 10, 1275 (1999).

  11. 11

    T. Ichi, J. Watanabe, T. Ooya, and N. Yui, Biomacromolecules, 2, 204 (2001).

  12. 12

    K. M. Huh, T. Ooya, W. K. Lee, S. Sasaki, I. C. Kwon, S. Y. Jeong, and N. Yui, Macromolecules, 34, 8657 (2001).

  13. 13

    H. S. Choi, K. Kontani, K. M. Huh, S. Sasaki, T. Ooya, and N. Yui, Macromol. Biosci., 2, 298 (2002).

  14. 14

    K. Moriyama, T. Ooya, and N. Yui, J. Control. Release, 59, 77 (1999).

  15. 15

    S. T. Lim, G. P. Martin, D. J. Berry, and M. B. Brown, J. Control. Release, 15, 281 (2000).

  16. 16

    Y. Luo, M. R. Ziebell, and G. D. Prestwich, Biomacromolecules, 1, 208 (2000).

  17. 17

    Y. Luo, R. Kirker, and G. D. Prestwich, J. Control. Release, 3, 169 (2000).

  18. 18

    M. R. Kim and T. G. Park, J. Control. Release, 23, 69 (2002).

  19. 19

    L. S. Liu, A. Y. Thompson, M. A. Heidaran, and J. W. Poster, Biomaterials, 20, 1097 (1999).

  20. 20

    S. Ohya, Y. Nakayama, and T. Matsuda, Biomacromolecules, 2, 856 (2001).

  21. 21

    S. N. Park, J. C. Park, H. O. Kim, M. J. Song, and H. Suh, Biomaterials, 23, 1205 (2002).

  22. 22

    N. Yui, T. Okano, and Y. Sakurai, J. Control. Release, 22, 105 (1992).

  23. 23

    N. Yui, J. Nihira, T. Okano, and Y. Sakurai, J. Control. Release, 25, 133 (1993).

  24. 24

    T. Pouyani, G. S. Harbison, and G. D. Prestwich, J. Am. Chem. Soc., 116, 7515 (1994).

  25. 25

    A. Harada, J. Li, and M. Kamachi, Macromolecules, 26, 5698 (1993).

  26. 26

    M. J. Gidley and S. M. Bociek, J. Am. Chem. Soc., 110, 3820 (1988).

  27. 27

    T. Nakama, T. Ooya, and N. Yui, Macromol. Rapid Commun., in press (2004).

Download references

Author information

Affiliations

  1. School of Materials Science, Japan Advanced Institute of Science and Technology

    Tsuyoshi Nakama, Tooru Ooya & Nobuhiko Yui

Authors
  1. Tsuyoshi Nakama
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tooru Ooya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nobuhiko Yui
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Nakama, T., Ooya, T. & Yui, N. Temperature- and pH-Controlled Hydrogelation of Poly(ethylene glycol)-Grafted Hyaluronic Acid by Inclusion Complexation with α-Cyclodextrin. Polym J 36, 338–344 (2004). https://doi.org/10.1295/polymj.36.338

Download citation

Keywords

  • Hyaluronic Acid
  • Inclusion Complex
  • α-Cyclodextrin
  • Poly(ethylene glycol)
  • Hydrogelation

Further reading

Search

Quick links