- About this Journal ·
- Abstracting and Indexing ·
- Aims and Scope ·
- Annual Issues ·
- Article Processing Charges ·
- Articles in Press ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Reviewers Acknowledgment ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
International Journal of Polymer Science
Volume 2012 (2012), Article ID 564348, 11 pages
Poly(ester amide)-Poly(ethylene oxide) Graft Copolymers: Towards Micellar Drug Delivery Vehicles
1Biomedical Engineering Graduate Program, The University of Western Ontario, 1151 Richmond Street, London, ON, Canada N6A 5B7
2Department of Chemical and Biochemical Engineering, The University of Western Ontario, 1151 Richmond Street, London, ON, Canada N6A 5B7
3Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, ON, Canada N6A 5B7
Received 2 January 2012; Accepted 1 March 2012
Academic Editor: Kibret Mequanint
Copyright © 2012 Gregory J. Zilinskas et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- J. M. Terwogt, B. Nuijen, W. W. Huinink, and J. H. Beijnen, “Alternative formulations of paclitaxel,” Cancer Treatment Reviews, vol. 23, no. 2, pp. 87–95, 1997.
- J. L. Arias, “Drug targeting strategies in cancer treatment: an overview,” Mini-Reviews in Medicinal Chemistry, vol. 11, no. 1, pp. 1–17, 2011.
- L. H. Reddy, “Drug delivery to tumours: recent strategies,” Journal of Pharmacy and Pharmacology, vol. 57, no. 10, pp. 1231–1242, 2005.
- C. Oerlemans, W. Bult, M. Bos, G. Storm, J. F. Nijsen, and W. E. Hennink, “Polymeric micelles in anticancer therapy: targeting, imaging and triggered release,” Pharmaceutical Research, vol. 27, no. 12, pp. 2569–2589, 2010.
- V. P. Torchilin, “Polymeric micelles for therapeutic applications in medicine,” Nanoscience and Nanotechnology, vol. 9, pp. 261–299, 2010.
- A. S. Mikhail and C. Allen, “Block copolymer micelles for delivery of cancer therapy: transport at the whole body, tissue and cellular levels,” Journal of Controlled Release, vol. 138, no. 3, pp. 214–223, 2009.
- S. Cai, K. Vijayan, D. Cheng, E. M. Lima, and D. E. Discher, “Micelles of different morphologies—advantages of worm-like filomicelles of PEO-PCL in paclitaxel delivery,” Pharmaceutical Research, vol. 24, no. 11, pp. 2099–2109, 2007.
- F. Meng, Z. Zhong, and J. Feijen, “Stimuli-responsive polymersomes for programmed drug delivery,” Biomacromolecules, vol. 10, no. 2, pp. 197–209, 2009.
- D. A. Christian, S. Cai, D. M. Bowen, Y. Kim, J. D. Pajerowski, and D. E. Discher, “Polymersome carriers: from self-assembly to siRNA and protein therapeutics,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 71, no. 3, pp. 463–474, 2009.
- R. P. Brinkhuis, F. P. J. T. Rutjes, and J. C. M. van Hest, “Polymeric vesicles in biomedical applications,” Polymer Chemistry, vol. 2, no. 7, pp. 1449–1462, 2011.
- H. Maeda, J. Wu, T. Sawa, Y. Matsumura, and K. Hori, “Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review,” Journal of Controlled Release, vol. 65, no. 1-2, pp. 271–284, 2000.
- Y. Y. Diao, H. Y. Li, Y. H. Fu, et al., “Doxorubicin-loaded PEG-PCL copolymer micelles enhance ctyotoxicity and intracellular accumulation of doxorubicin in adriamycin-resistant tumor cells,” International Journal of Nanomedicine, vol. 6, pp. 1955–1962, 2011.
- W. Zhang, Y. Shi, Y. Chen, J. Hao, X. Sha, and X. Fang, “The potential of Pluronic polymeric micelles encapsulated with paclitaxel for the treatment of melanoma using subcutaneous and pulmonary metastatic mice models,” Biomaterials, vol. 32, no. 25, pp. 5934–5944, 2011.
- G. S. Kwon, S. Suwa, M. Yokoyama, T. Okano, Y. Sakurai, and K. Kataoka, “Enhanced tumor accumulation and prolonged circulation times of Micelle- forming poly(ethylene oxide-aspartate) block copolymer-adriamycin conjugates,” Journal of Controlled Release, vol. 29, no. 1-2, pp. 17–23, 1994.
- A. Rodriguez-Galan, L. Franco, and J. Puiggali, “Degradable poly(ester amide)s for biomedical applications,” Polymers, vol. 3, no. 1, pp. 65–99, 2011.
- K. M. Atkins, D. Lopez, D. K. Knight, K. Mequanint, and E. R. Gillies, “A versatile approach for the syntheses of Poly(ester amide)s with pendant functional groups,” Journal of Polymer Science A, vol. 47, no. 15, pp. 3757–3772, 2009.
- R. Katsarava, V. Beridze, N. Arabuli, D. Kharadze, C. C. Chu, and C. Y. Won, “Amino acid-based bioanalogous polymers. Synthesis, and study of regular poly(ester amide)s based on bis(alpha-amino acid) alpha,omega-alkylene diesters, and aliphatic dicarboxylic acids,” Journal of Polymer Science A, vol. 37, no. 4, pp. 391–407, 1999.
- K. Guo and C. C. Chu, “Synthesis, characterization, and biodegradation of copolymers of unsaturated and saturated poly(ester amide)s,” Journal of Polymer Science A, vol. 45, no. 9, pp. 1595–1606, 2007.
- J. Montane, E. Armelin, A. Rodriguez-Galan, and J. Puiggali, “Comparative degradation data of polyesters and related poly(ester amide)s derived from 1,4-butanediol, sebacic acid, and alpha-amino acids,” Journal of Applied Polymer Science, vol. 85, no. 9, pp. 1815–1824, 2002.
- E. Armelin, N. Paracuellos, A. Rodriguez-Galan, and J. Puiggali, “Study on the degradability of poly(ester amide)s derived from the alpha-amino acids glycine, and L-alanine containing a variable amide/ester ratio,” Polymer, vol. 42, no. 19, pp. 7923–7932, 2001.
- N. Paredes, A. Rodriguez-Galan, J. Puiggali, and C. Peraire, “Studies on the biodegradation and biocompatibility of a new poly (ester amide) derived from L-alanine,” Journal of Applied Polymer Science, vol. 69, no. 8, pp. 1537–1549, 1998.
- N. Paredes, A. Rodriguez-Galan, and J. Puiggali, “Synthesis and characterization of a family of biodegradable poly(ester amide)s derived from glycine,” Journal of Polymer Science A, vol. 36, no. 8, pp. 1271–1282, 1998.
- N. Paredes, M. T. Casas, and J. Puiggali, “Packing of sequential poly(ester amide)s derived from diols, dicarboxylic acids, and amino acids,” Macromolecules, vol. 33, no. 24, pp. 9090–9097, 2000.
- Y. Saotome, T. Miyazawa, and T. Endo, “Novel enzymatically degradable polymers comprising alpha -amino acid, 1,2-ethanediol, and adipic acid,” Chemistry Letters, pp. 21–24, 1991.
- M. A. DeWit, Z. Wang, K. M. Atkins, K. Mequanint, and E. R. Gillies, “Syntheses, characterization, and functionalization of poly(ester amide)s with pendant amine functional groups,” Journal of Polymer Science A, vol. 46, no. 19, pp. 6376–6392, 2008.
- D. K. Knight, E. R. Gillies, and K. Mequanint, “Strategies in functional poly(ester amide) syntheses to study human coronary artery smooth muscle cell interactions,” Biomacromolecules, vol. 12, no. 7, pp. 2475–2487, 2011.
- G. Jokhadze, M. Machaidze, H. Panosyan, C. C. Chu, and R. Katsarava, “Synthesis and characterization of functional elastomeric poly(ester amide) co-polymers,” Journal of Biomaterials Science, Polymer Edition, vol. 18, no. 4, pp. 411–438, 2007.
- V. Montserrat, L. Franco, and J. Puiggali, “Synthesis of poly (ester amide)s with lateral groups from a bulk polycondensation reaction with formation of sodium chloride salts,” Journal of Polymer Science A, vol. 46, no. 2, pp. 661–667, 2008.
- Z. Guan, “Supramolecular design in biopolymers and biomimetic polymers for advanced mechanical properties,” Polymer International, vol. 56, no. 4, pp. 467–473, 2007.
- D. A. Barrera, E. Zylstra, P. T. Lansbury, and P. T. Langer, “Synthesis and RGD peptide modification of a new biodegradable copolymer: poly(lactic acid-co-lysine),” Journal of the American Chemical Society, vol. 115, no. 23, pp. 11010–11011, 1993.
- M. Deng, J. Wu, C. A. Reinhart-King, and C. C. Chu, “Synthesis and characterization of biodegradable poly(ester amide)s with pendant amine functional groups and in vitro cellular response,” Biomacromolecules, vol. 10, no. 11, pp. 3037–3047, 2009.
- K. Guo and C. C. Chu, “Synthesis of biodegradable amino-acid-based poly(ester amide)s and poly(ether ester amide)s with pendant functional groups,” Journal of Applied Polymer Science, vol. 117, no. 6, pp. 3386–3394, 2010.
- K. Guo and C. C. Chu, “Biodegradable and injectable paclitaxel-loaded poly(ester amide)s microspheres: fabrication and characterization,” Journal of Biomedical Materials Researchc B, vol. 89, no. 2, pp. 491–500, 2008.
- T. Ouchi, A. Hamada, and Y. Ohya, “Biodegradable microspheres having reactive groups prepared from L-lactic acid-depsipeptide copolymers,” Macromolecular Chemistry and Physics, vol. 200, no. 2, pp. 436–441, 1999.
- S. H. Lee, I. Szinai, K. Carpenter et al., “In-vivo biocompatibility evaluation of stents coated with a new biodegradable elastomeric and functional polymer,” Coronary Artery Disease, vol. 13, no. 4, pp. 237–241, 2002.
- Y. Huang, L. Wang, S. Li et al., “Stent-based tempamine delivery on neointimal formation in a porcine coronary model,” Acute Cardiac Care, vol. 8, no. 4, pp. 210–216, 2006.
- K. M. Defife, K. Grako, G. Cruz-Aranda et al., “Poly(ester amide) co-polymers promote blood and tissue compatibility,” Journal of Biomaterials Science, Polymer Edition, vol. 20, no. 11, pp. 1495–1511, 2009.
- D. Wu, X. Zhang, and C. C. Chu, “Synthesis, characterization and drug release from three-arm poly(epsilon-caprolactone) maleic acid/poly(ethylene glycol) diacrylate hydrogels,” Journal of Biomaterials Science, Polymer Edition, vol. 14, no. 8, pp. 777–802, 2003.
- Y. D. Park, N. Tirelli, and J. A. Hubbell, “Photopolymerized hyaluronic acid-based hydrogels and interpenetrating networks,” Biomaterials, vol. 24, no. 6, pp. 893–900, 2003.
- X. Pang and C. C. Chu, “Synthesis, characterization and biodegradation of poly(ester amide)s based hydrogels,” Polymer, vol. 51, no. 18, pp. 4200–4210, 2010.
- D. Dai Yamanouchi, J. Wu, A. N. Lazar, K. C. Kent, C. C. Chu, and B. Liu, “Biodegradable arginine-based poly(ester-amide)s as non-viral gene delivery reagents,” Biomaterials, vol. 29, no. 22, pp. 3269–3277, 2008.
- J. A. Horwitz, K. M. Shum, J. C. Bodle, M. Deng, C. C. Chu, and C. A. Reinhart-King, “Biological performance of biodegradable amino acid-based poly(ester amide)s: endothelial cell adhesion and inflammation in vitro,” Journal of Biomedical Materials Research A, vol. 95, no. 2, pp. 371–380, 2010.
- P. Karimi, A. S. Rizkalla, and K. Mequanint, “Versatile biodegradable poly(ester amide)s derived from alpha-amino acids for vascular tissue engineering,” Materials, vol. 3, no. 4, pp. 2346–2368, 2010.
- C. J. Bettinger, J. P. Bruggeman, J. T. Borenstein, and R. S. Langer, “Amino alcohol-based degradable poly(ester amide) elastomers,” Biomaterials, vol. 29, no. 15, pp. 2315–2325, 2008.
- K. Breitenkamp and T. Emrick, “Novel polymer capsules from amphiphilic graft copolymers and cross-metathesis,” Journal of the American Chemical Society, vol. 125, no. 40, pp. 12070–12071, 2003.
- S. Verbrugghe, A. Laukkanen, V. Aseyev, H. Tenhu, F. M. Winnik, and F. E. Du Prez, “Light scattering and microcalorimetry studies on aqueous solutions of thermo-responsive PVCL-g-PEO copolymers,” Polymer, vol. 44, no. 22, pp. 6807–6814, 2003.
- D. Tang, J. Lin, S. Lin, S. Zhang, T. Chen, and X. Tian, “Self-assembly of poly(γ-benzyl L-glutamate)-graft(ethylene glycol) and its mixtures with poly(γ-benzyl L-glutamate) homopolymer,” Macromolecular Rapid Communications, vol. 25, no. 13, pp. 1241–1246, 2004.
- M. Shi and M. S. Shoichet, “Furan-functionalized co-polymers for targeted drug delivery: caracterization, self-assembly and drug encapsulation,” Journal of Biomaterials Science, Polymer Edition, vol. 19, no. 9, pp. 1143–1157, 2008.
- R. K. Iha, B. A. van Horn, and K. L. Wooley, “Complex, degradable polyester materials via ketoxime ether-based functionalization: amphiphilic, multifunctional graft copolymers and their resulting solution-state aggregates,” Journal of Polymer Science A, vol. 48, no. 16, pp. 3553–3563, 2010.
- J. M. Harris, N. E. Martin, and M. Modi, “Pegylation: a novel process for modifying pharmacokinetics,” Clinical Pharmacokinetics, vol. 40, no. 7, pp. 539–551, 2001.
- J. M. Harris and S. Zalipsky, “Poly(ethylene glycol) chemistry and biological applications,” in Proceedings of the American Chemical Society Symposium Series 680 (ACS '97), Amercan Chemical Society, Washington, DC, USA, 1997.
- R. B. Greenwald, C. D. Conover, and Y. H. Choe, “Poly(ethylene glycol) conjugated drugs and prodrugs: a comprehensive review,” Critical Reviews in Therapeutic Drug, vol. 17, no. 2, pp. 101–161, 2000.
- M. L. Nucci, R. Shorr, and A. Abuchowski, “The therapeutic value of poly(ethylene glycol)-modified proteins,” Advanced Drug Delivery Reviews, vol. 6, no. 2, pp. 133–151, 1991.
- B. H. Zimm and W. H. Stockmayer, “The dimensions of chain molecules containing branches and rings,” Journal of Chemical Physics, vol. 17, no. 12, pp. 1301–1314, 1949.
- S. P. Perrault and W. C. W. Chan, “In vivo assembly of nanoparticle components to improve targeted cancer imaging,” Proceedings of the National Academy of Sciences of the United States of America, vol. 107, no. 25, pp. 11194–11199, 2010.
- P. Greenspan, E. P. Mayer, and S. D. Fowler, “Nile red: a selective fluorescent stain for intracellular lipid droplets,” Journal of Cell Biology, vol. 100, no. 3, pp. 965–973, 1985.
- M. M. G. Krishna, “Excited-state kinetics of the hydrophobic probe Nile red in membranes and micelles,” Journal of Physical Chemistry A, vol. 103, no. 19, pp. 3589–3595, 1999.
- I. R. Freshney, Culture of Animal Cells: A Manual of Basic Technique, Wiley-Liss, New York, NY, USA, 4th edition, 2000.
- International Standard 10993-5 Biological Evaluation of Medical Devices—Tests for In vitro Cytotoxicity, 2009.