Skip to main content
Log in

Photocurable O-carboxymethyl chitosan derivatives for biomedical applications: Synthesis, in vitro biocompatibility, and their wound healing effects

  • Articles
  • Published:
Macromolecular Research Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

An Erratum to this article was published on 01 November 2012

Abstract

In this work, photocurable water-soluble chitosan derivatives were prepared for biomedical applications by modifying water-soluble O-carboxymethyl chitosan (O-CMC) derivatives with furfuryl glycidyl ether (O-CMC/FGE). Successful derivatization of chitosan to the final product (O-CMC/FGE) was verified by UV and 1H NMR spectral analysis. The degree of photo-crosslinking was measured by a flow distance experiment after exposure to visible light for a certain period of time. The degree of crosslinking increased linearly in proportion to exposure time. The in vitro cell viability test revealed a lack of cytotoxicity of O-CMC/FGE against mouse 3T3 fibroblasts. However, poor cell attachment was observed for the cells seeded onto the photocured O-CMC/FGE; this is likely due to the anionic nature of this material. O-CMC/FGE displayed wound healing effects in an in vivo animal experiment using a burn wound model. Due to its good biocompatibility, wound healing effect, and mild cross-linking condition, together with an inhibitory effect on cell attachment, O-CMC/FGE would be a promising candidate as an anti-adhesion material for biomedical applications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H. Dongming, S. Heru, and U. Mathias, Prog. Polym. Sci., 34, 62 (2009).

    Article  Google Scholar 

  2. A. Hatefi and B. Amsden, J. Control. Release, 80, 9 (2002).

    Article  CAS  Google Scholar 

  3. N. Minoru and Y. Yu, React. Funct. Polym., 68, 915 (2008).

    Article  Google Scholar 

  4. Z. Chao, W. Jun, C. A. Reinhart-King, and C. C. Chu, Acta Biomater., 6, 3908 (2010).

    Article  Google Scholar 

  5. A. S. H. Doulabi, H. Mirzadeh, M. Imani, S. Sharifi, M. Atai, and S. Mehdipour-Ataei, Polym. Adv. Technol., 19, 1199 (2008).

    Article  CAS  Google Scholar 

  6. L. Sanxiu and S. Kristi, J. Control. Release, 57, 291 (1999).

    Article  Google Scholar 

  7. F.-C. Ding, S.-H. Hsu, and W.-Y. Chiang, J. Appl. Polym. Sci., 109, 589 (2008).

    Article  CAS  Google Scholar 

  8. W.-Y. Chiang and W.-T. L. Chiang, J. Appl. Polym. Sci., 51, 1901 (1994).

    Article  CAS  Google Scholar 

  9. P. Satyakam, K. S. Ashwani, B. S. Garg, R. P. Gandhi, and K. C. Gupta, Int. J. Pharm., 342, 184 (2007).

    Article  Google Scholar 

  10. J. Liu, J. Nie, Y. Zhao, and Y. He, J. Photochem. Photobiol. Chem., 211, 20 (2010).

    Article  CAS  Google Scholar 

  11. I. Kaetsu, H. Nakayama, K. Uchida, and K. Sutani, Radiat. Phys. Chem., 60, 513 (2010).

    Article  Google Scholar 

  12. Y. Nakayama, T. Kameo, A. Ohtaka, and Y. Hirano, J. Photochem. Photobiol. Chem., 177, 205 (2006).

    Article  CAS  Google Scholar 

  13. C. Li, T. Sajiki, Y. Nakayama, M. Fukui, and T. Matsuda, J. Biomed. Mater. Res., 66B, 439 (2003).

    Article  CAS  Google Scholar 

  14. Y. Nakayama and T. Matsuda, J. Biomed. Mater. Res., 48, 511 (1999).

    Article  CAS  Google Scholar 

  15. Y. Nakayama and T. Matsuda, ASAIO J., 41, M374 (1995).

    Article  CAS  Google Scholar 

  16. H. Arai, Y. Tajima, and K. Takeuchi, J. Photopolym. Sci. Technol., 13, 103 (2000).

    Article  CAS  Google Scholar 

  17. A. Gandini and M. N. Belgacem, Prog. Polym. Sci., 22, 1203 (1997).

    Article  CAS  Google Scholar 

  18. Y. Tajima, H. Arai, Y. Tezuka, T. Ishii, and K. Takeuchi, Fullerene Sci. Technol., 5, 1531 (1997).

    Article  CAS  Google Scholar 

  19. E. Takeuchi, Y. Tajima, and K. Takeuchi, J. Photopolym. Sci. Technol., 14, 139 (2001).

    Article  CAS  Google Scholar 

  20. Y. Tajima, Y. Tezuka, T. Ishii, and K. Takeuchi, Polym. J., 29, 1016 (1997).

    Article  CAS  Google Scholar 

  21. T. I. Son, M. Sakuragi, S. Takahashi, S. Obuse, J. Kang, M. Fujishiro, H. Matsushita, J. Gong, S. Shimizu, Y. Tajima, Y. Yoshida, K. Suzuki, T. Yamamoto, M. Nakamura, and Y. Ito, Acta Biomater., 6, 4005 (2010).

    Article  CAS  Google Scholar 

  22. K. A. Smeds and M. W. Grinstaff, J. Biomed. Mater. Res., 54, 115 (2001).

    Article  CAS  Google Scholar 

  23. J. Yeh, Y. Ling, J. M. Karp, J. Gantz, A. Chandawarkar, G. Eng, J. Blumling, R. Langer, and A. Khademhosseini, Biomaterials, 27, 5391 (2006).

    Article  CAS  Google Scholar 

  24. A. I. Chou, S. O. Akintoye, and S. B. Nicoll, Osteoarthr. Cartil., 17, 1377 (2009).

    Article  CAS  Google Scholar 

  25. A. Zhu, W. Jin, L. Yuan, G. Yang, H. Yu, and H. Wu, Carbohydr. Polym., 68, 693 (2007).

    Article  CAS  Google Scholar 

  26. H. Dureja, A. K. Tiwary, and S. Gupta, Int. J. Pharm., 213, 193 (2001).

    Article  CAS  Google Scholar 

  27. A. Zhu, M. B. Chan-Park, S. Dai, and L. Li, Colloids Surf B: Biointerfaces, 43, 143 (2005).

    Article  CAS  Google Scholar 

  28. M. B. Yaylaoglu, P. Korkusuz, F. Ors, U. Korkusuz, and V. Hasirci, Biomaterials, 20, 711 (1999).

    Article  CAS  Google Scholar 

  29. L. G. Cima, J. P. Vacanti, D. Ingber, D. Mooney, and R. Canger, J. Biomech. Eng., 113, 143 (1991).

    Article  CAS  Google Scholar 

  30. C. T. Laurencin, S. F. El-Amin, S. E. Ibim, D. A. Wilough, M. Attawia, and A. A. Ambrocio, J. Biomed. Mater. Res., 30, 133 (1996).

    Article  CAS  Google Scholar 

  31. F. R. de Abreu and S. P. Campana-Filho, Carbohydr. Polym., 75, 216 (2009).

    Google Scholar 

  32. H. Sashiwa, N. Kawasaki, A. Nakayama, E. Muraki, H. Yajima, and S.-I. Aiba, Carbohydr. Res., 338, 557 (2003).

    Article  CAS  Google Scholar 

  33. J.-W. Nah and M.-K. Jang, J. Polym. Sci. Part A: Polym. Chem., 40, 3796 (2002).

    Article  CAS  Google Scholar 

  34. X. F. Liu, Y. L. Guan, D. Z. Yang, Z. Li, and K. D. Yao, J. Appl. Polym. Sci., 79, 1324 (2001).

    Article  CAS  Google Scholar 

  35. N. T. An, D. T. Thien, N. T. Dong, and P. L. Dung, Carbohydr. Polym., 75, 489 (2009).

    Article  Google Scholar 

  36. M. Sugimoto, M. Morimoto, H. Sashiwa, H. Saimoto, and Y. Shigemasa, Carbohydr. Polym., 36, 49 (1998).

    Article  CAS  Google Scholar 

  37. S. Tokura, N. Nishi, A. Tsutsumi, and O. Somorin, Polym. J., 15, 485 (1983).

    Article  CAS  Google Scholar 

  38. H. T. Pang, X. G. Chen, H. J. Park, D. S. Cha, and J. F. Kennedy, Carbohydr. Polym., 26, 419 (2007).

    Article  Google Scholar 

  39. P. R. Twentyman and M. Luscombe, Br. J. Cancer, 56, 279 (1987).

    Article  CAS  Google Scholar 

  40. S.-H. Park, S.-Y. Seo, H.-N. Na, K.-I. Kim, J.-W. Lee, H.-D. Woo, J.-H. Lee, H.-K. Seok, J.-G. Lee, S.-I. Chung, K. H. Chung, D. Han, Y. Ito, E. Jang, and T. Son, Macromol. Res., 19, 921 (2011).

    Article  CAS  Google Scholar 

  41. A.-P. Zhu and N. Fang, Biomacromolecules, 6, 2607 (2005).

    Article  CAS  Google Scholar 

  42. R.-N. Chen, G.-M. Wang, C.-H. Chen, H.-O. Ho, and M.-T. Sheu, Biomacromolecules, 7, 1058 (2006).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Tae-Il Son.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Na, HN., Park, SH., Kim, KI. et al. Photocurable O-carboxymethyl chitosan derivatives for biomedical applications: Synthesis, in vitro biocompatibility, and their wound healing effects. Macromol. Res. 20, 1144–1149 (2012). https://doi.org/10.1007/s13233-012-0167-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-012-0167-2

Keywords

Navigation