Drug Release Behavior of Poly($\varepsilon$-caprolactone )-b-Poly( acrylic acid) Shell Crosslinked Micelles below the Critical Micelle Concentration

  • Hong Sung Woo (Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University) ;
  • Kim Keon Hyeong (Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University) ;
  • Huh June (Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University) ;
  • Ahn Cheol-Hee (Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University) ;
  • Jo Won Ho (Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University)
  • Published : 2005.10.01

Abstract

To explore the potential of shell crosslinked micelle (SCM) as a drug carrier, the drug release behavior of poly($\varepsilon$-caprolactone)-b-poly(acrylic acid) (PCL-b-PAA) SCMs was investigated. PCL-b-PAA was synthesized by ring opening polymerization of $\varepsilon$-caprolactone and atom transfer radical polymerization of tert-butyl acrylate, followed by selective hydrolysis of tert-butyl ester groups to acrylic acid groups. The resulting amphiphilic polymer was used to prepare SCMs by crosslinking of PAA corona via amidation chemistry. The drug release behavior of the SCMs was studied, using pyrene as a model drug, and was compared with that of non-crosslinked micelles, especially below the critical micelle concentration (CMC). When the shell layers were crosslinked, the drug release behavior of the SCMs was successfully modulated at a controlled rate compared with that of the non-crosslinked micelles, which showed a burst release of drug within a short time.

Keywords

References

  1. Z. Tuzar and P. Kratochvil, Adv. Colloid Interface Sci., 6, 201 (1976) https://doi.org/10.1016/0001-8686(76)80009-7
  2. K. Kataoka, A. Harada, and Y. Nagasaki, Adv. Drug. Deliv. Rev., 47, 113 (2001) https://doi.org/10.1016/S0169-409X(00)00117-4
  3. G. Kwon, M. Naito, M. Yokoyama, T. Okano, Y. Sakurai, and K. Kataoka, J. Control. Rel., 48, 195 (1997) https://doi.org/10.1016/S0168-3659(97)00039-4
  4. S. Y. Kim, I. L. G. Shin, Y. M. Lee, C. S. Cho, and Y. K. Sung, J. Control. Rel., 51, 13 (1998) https://doi.org/10.1016/S0168-3659(97)00124-7
  5. V. Y. Alakhov, E. Y. Moskaleva, E. V. Batrakova, and A. V. Kabanov, Bioconj. Chem., 7, 209 (1996) https://doi.org/10.1021/bc950093n
  6. S. B. La, T. Okano, and K. Kataoka, J. Pharm. Sci., 85, 85 (1996) https://doi.org/10.1021/js950204r
  7. R. Gref, Y. Minamitake, M .T. Peracchia, V. Trubetskoy, V. Torchilin, and R. Langer, Science, 263, 1600 (1994) https://doi.org/10.1126/science.8128245
  8. M. T. Peracchia, R. Gref, Y. Minamitake, A. Domb, N. Lotan, and R. Langer, J. Control. Rel., 46, 223 (1997) https://doi.org/10.1016/S0168-3659(96)01597-0
  9. V. P. Torchilin, J. Control. Rel., 73, 137 (2001) https://doi.org/10.1016/S0168-3659(01)00247-4
  10. A. Rosler, Guido W. M. Vandermeulen, and H. Klok, Adv. Drug. Deliv. Rev., 53, 95 (2001) https://doi.org/10.1016/S0169-409X(01)00236-8
  11. H. Huang, E. E. Remsen, and K. L. Wooley, Chem. Comm., 1415 (1998)
  12. K. B. Thurmond II, H. Huang, C. G. Clark Jr., T. Kowalewski, and K. L. Wooley, Colloids Surf. B, 16, 45 (1999) https://doi.org/10.1016/S0927-7765(99)00060-0
  13. S. Liu and S. P. Armes, Curr. Opin. Colloid Interf. Sci., 6, 249 (2001) https://doi.org/10.1016/S1359-0294(00)00095-9
  14. H. Huang, T. Kowalewski, E. E. Remsen, R. Gerztmann, and K. L. Wooley, J. Am. Chem. Soc., 119, 11653 (1997) https://doi.org/10.1021/ja9717469
  15. K. Kalyanasundoram and J. K. Thomas, J. Am. Chem. Soc., 99, 2039 (1988)
  16. Q. Ma, E. E. Remsen, T. Kowalewski, J. Schaefer, and K. L. Wooley, Nano Lett., 1, 651 (2001) https://doi.org/10.1021/nl0001914
  17. E. Neagu and R. Neagu, Appl. Surf. Sci., 64, 231 (1993) https://doi.org/10.1016/0169-4332(93)90029-B
  18. K. S. Murthy, Q. Ma, C. G. Clark, Jr., E. E. Remsen, and K. L. Wooley, Chem. Comm., 773 (2001)