Abstract
pH-sensitive block copolymers were synthesized by coupling reaction of sulfamethazine and amphiphilic diblock copolymer, and their micellization-demicellization behavior was investigated. Sulfamethazine (SM), a derivative of sulfonamide, was introduced as a pH responsive moiety while methoxy poly(ethylene glycol)-poly(d,l-lactide) (MPEG-PDLLA) and methoxy poly(ethylene glycol)-poly(d,l-lactide-co-ε-caprolactone) (MPEG-PCLA) were used as biodegradable amphiphilic diblock copolymers. After the sulfamethazine was carboxylated by the reaction with succinic anhydride, the diblock copolymer was conjugated with sulfamethazine by coupling reaction in the presence of DCC. The critical micelle concentration (CMC) and mean diameter of the micelles were examined at various pH conditions through fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. For MPEG-PDLLA-SM and MPEG-PCLA-SM solutions, the pH-dependent micellization-demicellization was achieved within a narrow pH band, which was not observed in the MPEG-PDLLA and MPEG-PCLA solutions. The micelle showed a spherical morphology and had a very narrow size distribution. This pH-sensitive block copolymer shows potential as a site-targeted drug carrier.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
M. Tobio, R. Gref, A. Sanchez, R. Langer, and M. J. Alonso,Pharm. Res.,15, 270 (1998).
C. E. Soma, C. Dubernet, G. Barratt, F. Nemati, M. Appel, S. Benita, and P. Couvreur,Pharm. Res.,16, 1710 (1999).
S. Cammas, K. Suzuki, C. Sone, Y. Sakurai, K. Kataoka, and T. Okano,J. Control. Rel.,48, 157 (1997).
K. Kataoka, G. S. Kwon, M. Yokoyama, T. Okano, and Y. Sakurai,J. Control. Rel.,24, 119 (1993).
K. Kataoka,J. Macromol. Sci. Pure Appl. Chem.,A31, 1759 (1994).
M. Yokoyama, M. Miyauchi, N. Yamada, T. Okano, Y. Sakurai, K. Kataoka, and S. Inoue,J. Control. Rel.,11, 269 (1990).
Z. Ding, C. J. Long, Y. Hayashi, E. V. Bulmus, A. S. Hoffman, and P. S. Stayton,Bioconjug. Chem.,10, 395 (1999).
B. Jeong, Y. H. Bae, D. S. Lee, and S. W. Kim,Nature,338, 860 (1997).
K. S. Soppimath, A. R. Kulkarni, and T. M. Aminabhavi,J. Control. Rel.,75, 331 (2001).
M. Lugo and N. A. Peppas,Macromolecules,32, 6646 (1999).
L. Yao and S. Krause,Macromolecules,36, 2055 (2003).
G. Filipcsei, J. Feher, and M. Zrinyi,J. Mol. Struct.,554, 109 (2000).
M. Stubbs, P. M. McSheehy, J. R. Griffiths, and C. L. Bashford,Mol. Med. Today,6, 15 (2000).
I. F. Tannock and D. Rotin,Cancer Res.,49, 4373 (1989).
S. R. Tonge and B. J. Tighe,Adv. Drug Deliv. Rev.,53, 109 (2001).
N. Murthy, J. R. Robichaud, D. A. Tirrell, P. S. Stayton, and A. S. Hoffman,J. Control. Rel.,61, 137 (1999).
A. S. Lee, V. Butun, M. Vamvakaki, S. P. Armes, J. A. Pople, and A. P. Gast,Macromolecules,35, 8540 (2002).
J. Gohy, B. G. G. Lohmeijer, S. K. Varshney, B. Decamps, E. Leroy, S. Boileau, and U. S. Schubert,Macromolecules,35, 9748 (2002).
S. Y. Park and Y. H. Bae,Macromol. Rapid Commun.,20, 269 (1999).
S. I. Kang and Y. H. Bae,J. Control. Rel.,80, 145 (2002).
K. Kalyanasundaram and J. K. Thomas,J. Am. Chem. Soc.,99, 2039 (1977).
W. S. Shim and D. S. Lee, J. Control. Rel., submitted.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shim, W.S., Lee, J.S. & Lee, D.S. pH-induced micellization of biodegradable block copolymers containing sulfamethazine. Macromol. Res. 13, 344–351 (2005). https://doi.org/10.1007/BF03218464
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF03218464