PEG-b-PPS diblock copolymer aggregates for hydrophobic drug solubilization and release: Cyclosporin A as an example

Molecular Pharmaceutics

Volumn 5, Issue 4, 2008, Pages 632-642

  Velluto, Diana ^a   Demurtas, Davide ^b   Hubbell, Jeffrey A ^a  

^a EPFL   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Block copolymer; Cyclosporin A; Nanoparticle; Poly(propylene sulfide); Polymer micelle

Indexed keywords

AMPHOPHILE; COPOLYMER; CYCLOSPORIN A; HOT WATER; MACROGOL B POLY(PROPYLENE SULFIDE) DIBLOCK COPOLYMER; SOLVENT;

AQUEOUS SOLUTION; COMPLEX FORMATION; CONFERENCE PAPER; CONTROLLED STUDY; DISPERSION; DRUG RELEASE; DRUG SOLUBILITY; DRUG SYNTHESIS; ENCAPSULATION; GLASS TRANSITION TEMPERATURE; HYDROPHOBICITY; MICELLE; POLYMERIZATION; PRIORITY JOURNAL; SOLUBILIZATION;

CAPSULES; CRYOELECTRON MICROSCOPY; CYCLOSPORINE; HYDROPHOBICITY; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; POLYMERS; SOLUBILITY; SOLVENTS; SULFIDES;

EID: 51049095142     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp7001297     Document Type: Conference Paper

References (53)

1. Eltayar, N.; Mark, A. E.; Vallat, P.; Brunne, R. M.; Testa, B.; Vangunsteren, W. F. Solvent-dependent conformation and hydrogenbonding capacity of cyclosporine-A - evidence from partition-coefficients and molecular-dynamics simulations. J. Med. Chem. 1993, 36, 3757-3764.
2. Cattaneo, D.; Perico, N.; Remuzzi, G. Generic cyclosporine formulations: More open questions than answers. Transplant Int. 2005, 18, 371-378.
3. Allen, C.; Maysinger, D.; Eisenberg, A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf., B 1999, 16, 3-27.
4. Discher, D. E.; Ahmed, F. Polymersomes. Annu. Rev. Biomed. Eng. 2006, 8, 323-341.
5. Kataoka, K.; Harada, A.; Nagasaki, Y. Block copolymer micelles for drug delivery: Design, characterization and biological significance. Adv. Drug Delivery Rev. 2001, 47, 113-131.
6. Kwon, G. S.; Kataoka, K. Block-copolymer micelles as long-circulating drug vehicles. Adv. Drug Delivery Rev. 1995, 16, 295-309.
7. Nishiyama, N.; Kataoka, K. Nanostructured devices based on block copolymer assemblies for drug delivery: Designing structures for enhanced drug function. Adv. Polym. Sci. 2006, 193, 67-101.
8. Sokolsky-Papkov, M.; Agashi, K.; Olaye, A.; Shakesheff, K.; Domb, A. J. Polymer carriers for drug delivery in tissue engineering. Adv. Drug Delivery Rev. 2007, 59, 187-206.
9. Aliabadi, H. M.; Mahmud, A.; Sharifabadi, A. D.; Lavasanifar, A. Micelles of methoxy poly(ethylene oxide)-b-poly(epsilon-caprolactone) as vehicles for the solubilization and controlled delivery of cyclosporine A. J. Controlled Release 2005, 104, 301-311.
10. Kabanov, A. V.; Nazarova, I. R.; Astafieva, I. V.; Batrakova, E. V.; Alakhov, V. Y.; Yaroslavov, A. A.; Kabanov, V. A. Micelle formation and solubilization of fluorescent-probes in poly(oxyethylene-b-oxypropylene-b-oxyethylene) solutions. Macromolecules 1995, 28, 2303-2314.
11. Nakanishi, T.; Fukushima, S.; Okamoto, K.; Suzuki, M.; Matsumura, Y.; Yokoyama, M.; Okano, T.; Sakurai, Y.; Kataoka, K. Development of the polymer micelle carrier system for doxorubicin. J. Controlled Release 2001, 74, 295-302.
12. Yasugi, K.; Nagasaki, Y.; Kato, M.; Kataoka, K. Preparation and characterization of polymer micelles from poly(ethylene glycol)poly(d,l-lactide) block copolymers as potential drug carrier. J. Controlled Release 1999, 62, 89-100.
13. Gref, R.; Minamitake, Y.; Peracchia, M. T.; Trubetskoy, V.; Torchilin, V.; Langer, R. Biodegradable long-circulating polymeric nanospheres. Science 1994, 263, 1600-1603.
14. Lee, J.; Martic, P. A.; Tan, J. S. Protein adsorption on Pluronic copolymer-coated polystyrene particles. J. Colloid Interface Sci. 1989, 131, 252-266.
15. Muller, R. H.; Wallis, K. H.; Troster, S. D.; Kreuter, J. In vitro characterization of poly (methyl-methacrylate) nanoparticles and correlation to their in vivo fate. J. Controlled Release 1992, 20, 237-246.
16. Ahmed, F.; Pakunlu, R. I.; Brannan, A.; Bates, F.; Minko, T.; Discher, D. E. Biodegradable polymersomes loaded with both paclitaxel and doxorubicin permeate and shrink tumors, inducing apoptosis in proportion to accumulated drug. J. Controlled Release 2006, 116, 150-158.
17. Ahmed, F.; Pakunlu, R. I.; Srinivas, G.; Brannan, A.; Bates, F.; Klein, M. L.; Minko, T.; Discher, D. E. Shrinkage of a rapidly growing tumor by drug-loaded polymersomes: pH-triggered release through copolymer degradation. Mol. Pharmaceutics 2006, 3, 340-350.
18. Yamamoto, Y.; Yasugi, K.; Harada, A.; Nagasaki, Y.; Kataoka, K. Temperature-related change in the properties relevant to drug delivery of poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles in aqueous milieu. J. Controlled Release 2002, 82, 359-371.
19. Kabanov, A. V.; Batrakova, E. V.; Alakhov, V. Y. Pluronic block copolymers as novel polymer therapeutics for drug and gene delivery. J. Controlled Release 2002, 82, 189-212.
20. Oh, K. T.; Bronich, T. K.; Kabanov, A. V. Micellar formulations for drug delivery based on mixtures of hydrophobic and hydrophilic Pluronic block copolymers. J. Controlled Release 2004, 94, 411-422.
21. Napoli, A.; Valentini, M.; Tirelli, N.; Muller, M.; Hubbell, J. A. Oxidation-responsive polymeric vesicles. Nat. Mater. 2004, 3, 183-189.
22. Nicol, E.; Nicolai, T.; Durand, D. Dynamics of poly(propylene sulfide) studied by dynamic mechanical measurements and dielectric spectroscopy. Macromolecules 1999, 32, 7530-7536.
23. Napoli, A.; Tirelli, N.; Wehrli, E.; Hubbell, J. A. Lyotropic behavior in water of amphiphilic aba triblock copolymers based on poly(propylene sulfide) and poly(ethylene glycol). Langmuir 2002, 18, 8324-8329.
24. Napoli, A.; Bermudez, H.; Hubbell, J. A. Interfacial reactivity of block copolymers: Understanding the amphiphile-to-hydrophile transition. Langmuir 2005, 21, 9149-9153.
25. Napoli, A.; Boerakker, M. J.; Tirelli, N.; Nolte, R. J. M.; Sommerdijk, N.; Hubbell, J. A. Glucose-oxidase based self-destructing polymeric vesicles. Langmuir 2004, 20, 3487-3491.
26. Napoli, A.; Tirelli, N.; Kilcher, G.; Hubbell, J. A. New synthetic methodologies for amphiphilic multiblock copelymers of ethylene glycol and propylene sulfide. Macromolecules 2001, 34, 8913-8917.
27. Kalyanasundaram, K.; Thomas, J. K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 1977, 99, 2039-2044.
28. Winnik, F. M.; Regismond, S. T. A. Fluorescence methods in the study of the interactions of surfactants with polymers. Colloids Surf., A 1996, 118, 1-39.
29. Winnik, F. M. Photophysics of preassociated pyrenes in aqueous polymer-solutions and in other organized media. Chem. Rev. 1993, 93, 587-614.
30. Cerritelli, S.; Fontana, A.; Velluto, D.; Adrian, M.; Dubochet, J.; De Maria, P.; Hubbell, L A. Thermodynamic and kinetic effects in the aggregation behavior of a poly(ethylene glycol-b-propylene sulfide-b-ethylene glycol) ABA triblock copolymer. Macromolecules 2005, 38, 7845-7851.
31. Zhao, C. L.; Winnik, M. A.; Riess, G.; Croucher, M. D. Fluorescence probe techniques used to study micelle formation in water-soluble block copolymers. Langmuir 1990, 6, 514-516.
32. Wang, Y. C.; Winnik, M. A. Onset of aggregation for water-soluble polymeric associative thickeners - a fluorescence study. Langmuir 1990, 6, 1437-1439.
33. Dong, D. C.; Winnik, M. A. The py scale of solvent polarities. Can. J. Chem. 1984, 62, 2560-2565.
34. Curtis, J. J. Experience with cyclosporine. Transplant. Proc. 2004, 36, 54S-58S.
35. Curtis, J. J. Posttransplant hypertension. Transplant. Proc. 1998, 30, 2009-2011.
36. Tibell, A.; Larsson, M.; Alvestrand, A. Dissolving intravenous cyclosporine-a in a fat emulsion carrier prevents acute renal side-effects in the rat. Transplant Int. 1993, 6, 69-72.
37. Peppas, N. A.; Langer, R. New challenges in biomaterials. Science 1994, 263, 1715-1720.
38. Tessmar, J. K.; Gopferich, A. M. Customized peg-derived copolymers for tissue-engineering applications. Macromol. Biosci. 2007, 7, 23-39.
39. Peracchia, M. T.; Fattal, E.; Desmaele, D.; Besnard, M.; Noel, J. P.; Gomis, J. M.; Appel, M.; d'Angelo, J.; Couvreur, P. Stealth PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting. J. Controlled Release 1999, 60, 121-128.
40. Yoncheva, K.; Lizarraga, E.; Irache, J. M. PEGylated nanoparticles based on poly(methyl vinyl ether-co-maleic anhydride): Preparation and evaluation of their bioadhesive properties. Eur. J. Pharm. Sci. 2005, 24, 411-419.
41. Bearinger, J. P.; Terrettaz, S.; Michel, R.; Tirelli, N.; Vogel, H.; Textor, M.; Hubbell, J. A. Chemisorbed poly(propylene sulphide)based copolymers resist biomolecular interactions. Nat. Mater. 2003, 2, 259-264.
42. Kataoka, K.; Matsumoto, T.; Yokoyama, M.; Okano, T.; Sakurai, Y.; Fukushima, S.; Okamoto, K.; Kwon, G. S. Doxorubicin-loaded poly(ethylene glycol)-poly(beta-benzyl-l-aspartate) copolymer micelles: Their pharmaceutical characteristics and biological significance. J. Controlled Release 2000, 64, 143-153.
43. Tosatti, S.; De Paul, S. M.; Askendal, A.; VandeVondele, S.; Hubbell, J. A.; Tengvall, P.; Textor, M. Peptide functionalized poly(l-lysine)-g-poly(ethylene glycol) on titanium: Resistance to protein adsorption in full heparinized human blood plasma. Biomaterials 2003, 24, 4949-4958.
44. Rehor, A.; Hubbell, J. A.; Tirelli, N. Oxidation-sensitive polymeric nanoparticles. Langmuir 2005, 21, 411-417.
45. Cerritelli, S.; O'Neal, C.; Fontana, A.; Adrian, M.; Dubochet, J.; Hubbell, J. A. Poly(ethylene glycol-bl-propylene sulfide) di- and triblock copolymers: Aggregation behavior in aqueous solution. Manuscript in preparation.
46. Francis, M. F.; Lavoie, L.; Winnik, F. M.; Leroux, J. C. Solubilization of cyclosporin a in dextran-g-polyethyleneglycolalkyl ether polymeric micelles. Eur. J. Pharm. Biopharm. 2003, 56, 337-346.
47. Aliabadi, H. M.; Elhasi, S.; Mahmud, A.; Gulamhusein, R.; Mahdipoor, P.; Lavasanifar, A. Encapsulation of hydrophobic drugs in polymeric micelles through co-solvent evaporation: The effect of solvent composition on micellar properties and drug loading. Int. J. Pharm. 2007, 329, 158-165.
48. Lee, M. K.; Choi, L.; Kim, M. H.; Kim, C. K. Pharmacokinetics and organ distribution of cyclosporin a incorporated in liposomes and mixed micelles. Int. J. Pharm. 1999, 191, 87-93.
49. Beauchesne, P. R.; Chung, N. S. C.; Wasan, K. M. Cyclosporine a: A review of current oral and intravenous delivery systems. Drug Dev. Ind. Pharm. 2007, 33, 211-220.
50. Francis, M. F.; Cristea, M.; Yang, Y. L.; Winnik, F. M. Engineering polysaccharide-based polymeric micelles to enhance permeability of cyclosporin A across caco-2 cells. Pharm. Res. 2005, 22, 209-219.
51. Molpeceres, J.; Aberturas, M. R., Guzman, M. Biodegradable nanoparticles as a delivery system for cyclosporine: Preparation and characterization. J. Microencapsulation 2000, 17, 599-614.
52. Varela, M. C.; Guzman, M.; Molpeceres, J.; Aberturas, M. D.; Rodriguez-Puyol, D.; Rodriguez-Puyol, M. Cyclosporine-loaded polycaprolactone nanoparticles: Immunosuppression and nephrotoxicity in rats. Eur. J. Pharm. Sci. 2001, 12, 471-478.
53. Zhang, Q. N.; Yie, G. Q.; Li, Y.; Yang, Q. S.; Nagai, Y. T. Studies on the cyclosporin a loaded stearic acid nanoparticles. Int. J. Pharm. 2000, 200, 153-159.