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

Sung Woo Hong; Keon Hyeong Kim; June Huh; Cheol-Hee Ahn; Won Ho Jo

Macromolecular Research, Vol.13, No.5, 397-402, October, 2005

Sung Woo Hong, Keon Hyeong Kim, June Huh, Cheol-Hee Ahn , and Won Ho Jo^†

Hyperstructured Organic Materials Research Center and School of Materials Science and Engineering, Seoul National University, Seoul 151-742, Korea

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To explore the potential of shell crosslinked micelle (SCM) as a drug carrier, the drug release behavior of poly( ε-caprolactone)-b-poly(acrylic acid) (PCL-b-PAA) SCMs was investigated. PCL-b-PAA was synthesized by ring opening polymerization of ε-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:PAA;PCL;release;shell crosslinked micelles

[References]

Tuzar Z, Kratochvil P, Adv. Colloid Interface Sci., 6, 201 (1976)
Kataoka K, Harada A, Nagasaki Y, Adv. Drug Deliv. Rev., 47, 113 (2001)
Kwon G, Naito M, Yokoyama M, Okano T, Sakurai Y, Kataoka K, J. Control. Release, 48, 195 (1997)
Kim SY, Shin ILG, Lee YM, Cho CS, Sung YK, J. Control. Release, 51, 13 (1998)
Alakhov VY, Moskaleva EY, Batrakova EV, Kabanov AV, Bioconjugate Chem., 7, 209 (1996)
La SB, Okano T, Kataoka K, J. Pharm. Sci., 85, 85 (1996)
Gref R, Minamitake Y, Peracchia MT, Trubetskoy V, Torchilin V, Langer R, Science, 263(5153), 1600 (1994)
Peracchia MT, Gref R, Minamitake Y, Domb A, Lotan N, Langer R, J. Control. Release, 46, 223 (1997)
Torchilin VP, J. Control. Release, 73, 137 (2001)
Rosler A, Vandermeulen GWM, Klok HA, Adv. Drug Deliv. Rev., 53, 95 (2001)
Huang H, Remsen EE, Wooley KL, Chem. Commun., 1415 (1998)
Thurmond II KB, Huang H, Clark CG, Kowalewski T, Wooley KL, Colloids Surf. B: Biointerfaces, 16, 45 (1999)
Liu S, Armes SP, Curr. Opin. Colloid Interface Sci., 6, 249 (2001)
Huang HY, Kowalewski T, Remsen EE, Gertzmann R, Wooley KL, J. Am. Chem. Soc., 119(48), 11653 (1997)
Kalyanasundoram K, Thomas JK, J. Am. Chem. Soc., 99, 2039 (1988)
Ma Q, Remsen EE, Kowalewski T, Schaefer J, Wooley KL, Nano Lett., 1, 651 (2001)
Neagu E, Neagu R, Appl. Surf. Sci., 64, 231 (1993)
Murthy KS, Ma Q, Clark CG, Remsen EE, Wooley KL, Chem. Commun., 773 (2001)

[Referenced By]

[Related Articles]

[1] Tuzar Z, Kratochvil P, Adv. Colloid Interface Sci., 6, 201 (1976)

[2] Kataoka K, Harada A, Nagasaki Y, Adv. Drug Deliv. Rev., 47, 113 (2001)

[3] Kwon G, Naito M, Yokoyama M, Okano T, Sakurai Y, Kataoka K, J. Control. Release, 48, 195 (1997)

[4] Kim SY, Shin ILG, Lee YM, Cho CS, Sung YK, J. Control. Release, 51, 13 (1998)

[5] Alakhov VY, Moskaleva EY, Batrakova EV, Kabanov AV, Bioconjugate Chem., 7, 209 (1996)

[6] La SB, Okano T, Kataoka K, J. Pharm. Sci., 85, 85 (1996)

[7] Gref R, Minamitake Y, Peracchia MT, Trubetskoy V, Torchilin V, Langer R, Science, 263(5153), 1600 (1994)

[8] Peracchia MT, Gref R, Minamitake Y, Domb A, Lotan N, Langer R, J. Control. Release, 46, 223 (1997)

[9] Torchilin VP, J. Control. Release, 73, 137 (2001)

[10] Rosler A, Vandermeulen GWM, Klok HA, Adv. Drug Deliv. Rev., 53, 95 (2001)

[11] Huang H, Remsen EE, Wooley KL, Chem. Commun., 1415 (1998)

[12] Thurmond II KB, Huang H, Clark CG, Kowalewski T, Wooley KL, Colloids Surf. B: Biointerfaces, 16, 45 (1999)

[13] Liu S, Armes SP, Curr. Opin. Colloid Interface Sci., 6, 249 (2001)

[14] Huang HY, Kowalewski T, Remsen EE, Gertzmann R, Wooley KL, J. Am. Chem. Soc., 119(48), 11653 (1997)

[15] Kalyanasundoram K, Thomas JK, J. Am. Chem. Soc., 99, 2039 (1988)

[16] Ma Q, Remsen EE, Kowalewski T, Schaefer J, Wooley KL, Nano Lett., 1, 651 (2001)

[17] Neagu E, Neagu R, Appl. Surf. Sci., 64, 231 (1993)

[18] Murthy KS, Ma Q, Clark CG, Remsen EE, Wooley KL, Chem. Commun., 773 (2001)