Amphiphilic Ionizable Polyphosphazenes for the Preparation of pH-Responsive Liposomes

Polyphosphazenes for Biomedical Applications

Volumn , Issue , 2008, Pages 225-247

  Ghattas, David ^a   Leroux, Jean Christophe ^a,b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b ETH ZURICH   (Switzerland)

Author keywords

Amphiphilic ionizable polyphosphazenes; Drug delivery systems; PH responsive liposome characterization

Indexed keywords

EID: 84864503638     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470478882.ch13     Document Type: Chapter

References (56)

1. Allcock, H.R. 1977. Poly(organophosphazenes): unusual new high polymers. Angew. Chem. Int. Ed., 16:147-156.
2. Allcock, H.R., Dudley, G.K. 1996. Lower critical solubility temperature study of alkyl ether based polyphosphazenes. Macromolecules, 29:1313-1319.
3. Allcock, H.R., Fuller, T.J., Mack, D.P., Matsumura, K., Smeltz, K.M. 1977. Synthesis of poly[(amino acid alkyl ester)phosphazenes]. Macromolecules, 10:824-830.
4. Allcock, H.R., Fuller, T.J., Matsumura, K. 1982. Hydrolysis pathways for aminophosphazenes. Inorg. Chem., 21:515-521.
5. Allcock, H.R., Pucher, S.R., Scopelianos, A.G. 1994. Poly[(amino acid ester)phosphazenes]: synthesis, crystallinity, and hydrolytic sensitivity in solution and the solid state. Macromolecules, 27:1071-1075.
6. Allcock, H.R., Crane, C.A., Morrissey, C.T., Nelson, J.M., Reeves, S.D., Honeyman, C.H., Manners, I. 1996. ''Living'' cationic polymerization of phosphoranimines as an ambient temperature route to polyphosphazenes with controlled molecular weights. Macromolecules, 29:7740-7747.
7. Allen, C., Dos Santos, N., Gallagher, R., Chiu, G.N.C., Shu, Y., Li, W.M., Johnstone, S.A., Janoff, A.S., Mayer, L.D., Webb, M.S., Bally, M.B. 2002. Controlling the physical behavior and biological performance of liposome formulations through use of surface grafted poly(ethylene glycol). Biosci. Rep., 22:225-250.
8. Bartlett, G.R. 1959. Phosphorus assay in column chromatography. J. Biol. Chem., 234:466-468.
9. Boomer, J.A., Inerowicz, H.D., Zhang, Z.Y., Bergstrand, N., Edwards, K., Kim, J.M., Thompson, D.H. 2003. Acid-triggered release from sterically stabilized fusogenic liposomes via a hydrolytic dePEGylation strategy. Langmuir, 19:6408-6415.
10. Brazel, C.S., Peppas, N.A. 1996. Pulsatile local delivery of thrombolytic and antithrombotic agents using poly(N-isopropylacrylamide-co-methacrylic acid) hydrogels. J. Control. Release, 39:57-64.
11. Chen, G., Hoffman, A.S. 1995. Graft copolymers that exhibit temperature-induced phase transitions over a wide range of pH. Nature, 373:49-52.
12. Connor, J., Yatvin, M.B., Huang, L. 1984. pH-sensitive liposomes: acid-induced liposome fusion. Proc. Natl. Acad. Sci. USA, 81:1715-1718.
13. Couffin-Hoarau, A.C., Leroux, J.C. 2004. Report on the use of poly(organophosphazenes) for the design of stimuli-responsive vesicles. Biomacromolecules, 5:2082-2087.
14. Crommen, J.H.L., Schacht, E.H., Mense, E.H.G. 1992a. Biodegradable polymers: I. Synthesis of hydrolysis-sensitive poly[(organo)phosphazenes]. Biomaterials, 13:511-520.
15. Crommen, J.H.L., Schacht, E.H., Mense, E.H.G. 1992b. Biodegradable polymers: II. Degradation characteristics of hydrolysis-sensitive poly[(organo)phosphazenes]. Biomaterials, 13:601-611.
16. Drummond, D.C., Zignani, M., Leroux, J.C. 2000. Current status of pH-sensitive liposomes in drug delivery. Prog. Lipid. Res., 39:409-460.
17. Feil, H., Bae, Y.H., Feijen, J., Kim, S.W. 1993. Effect of comonomer hydrophilicity and ionization on the lower critical solution temperature of N-isopropylacrylamide copolymers. Macromolecules, 26:2496-2500.
18. Francis, M.F., Dhara, G., Winnik, F.M., Leroux, J.C. 2001. In vitro evaluation of pH-sensitive polymer/niosome complexes. Biomacromolecules, 2:741-749.
19. Guo, X., Szoka, F.C. 2001. Steric stabilization of fusogenic liposomes by a low-pH sensitive PEG-diortho ester-lipid conjugate. Bioconjugate Chem., 12:291-300.
20. Han, H.D., Shin, B.C., Choi, H.S. 2006. Doxorubicin-encapsulated thermosensitive liposomes modified with poly(N-isopropylacrylamide-co-acrylamide): drug release behavior and stability in the presence of serum. Eur. J. Pharm. Biopharm., 62:110-116.
21. Harvie, P., Desormeaux, A., Bergeron, M.C., Tremblay, M., Beauchamp, D., Poulin, L., Bergeron, M.G. 1996. Comparative pharmacokinetics, distributions in tissue, and interactions with blood proteins of conventional and sterically stabilized liposomes containing 2u,3u-dideoxyinosine. Antimicrob. Agents Chemother., 40:225-229.
22. Hayashi, H., Kono, K., Takagishi, T. 1999. Temperature sensitization of liposomes using copolymers of N-isopropylacrylamide. Bioconjugate Chem., 10:412-418.
23. Heskins, M., Guillet, J.E. 1968. Solution properties of poly(N-isopropylacrylamide). J. Macromol. Sci. Pure Appl. Chem., 2:1441-1455.
24. Hirotsu, S., Hirokawa, Y., Tanaka, T. 1987. Volume-phase transitions of ionized N-isopropylacrylamide gels. J. Chem. Phys., 87:1392-1395.
25. Hong, M.-S., Lim, S.-J., Oh, Y.-K., Kim, C.-K. 2002. pH-sensitive, serum-stable and long-circulating liposomes as a new drug delivery system. J. Pharm. Pharmacol., 54:51-58.
26. Ishida, T., Okada, Y., Kobayashi, T., Kiwada, H. 2006. Development of pH-sensitive liposomes that efficiently retain encapsulated doxorubicin (DXR) in blood. Int. J. Pharm., 309:94-100.
27. Kamata, H., Yagisawa, H., Takahashi, S., Hirata, H. 1994. Amphiphilic peptides enhance the efficiency of liposome-mediated DNA transfection. Nucleic Acids Res., 22:536-537.
28. Karanth, H., Murthy, R.S.R. 2007. pH-Sensitive liposomes: principle and application in cancer therapy. J. Pharm. Pharmacol., 59:469-483.
29. Kichler, A., Mechtler, K., Behr, J.P., Wagner, E. 1997. Influence of membrane-active peptides on lipospermine/DNA complex mediated gene transfer. Bioconjugate Chem., 8:213-221.
30. Klibanov, A.L., Maruyama, K., Torchilin, V.P., Huang, L. 1990. Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes. FEBS Lett., 268:235-237.
31. Kono, K., Igawa, T., Takagishi, T. 1997. Cytoplasmic delivery of calcein mediated by liposomes modified with a pH-sensitive poly(ethylene glycol) derivative. Biochim. Biophys. Acta., 1325:143-154.
32. Kono, K., Nakai, R., Morimoto, K., Takagishi, T. 1999. Thermosensitive polymermodified liposomes that release contents around physiological temperature. Biochim. Biophys. Acta., 1416:239-250.
33. Laukkanen, A., Valtola, L., Winnik, F.M., Tenhu, H. 2005. Thermosensitive graft copolymers of an amphiphilic macromonomer and N-vinylcaprolactam: synthesis and solution properties in dilute aqueous solutions below and above the LCST. Polymer, 46:7055-7065.
34. Lee, S.B., Song, S.-C, Jin, J.I., Sohn, Y.S. 1999. A new class of biodegradable thermosensitive polymers: II. Hydrolytic properties and salt effect on the lower critical solution temperature of poly(organophosphazenes) with methoxypoly(ethylene glycol) and amino acid esters as side groups. Macromolecules, 32:7820-7827.
35. Lemmouchi, Y., Schacht, E., Dejardin, S. 1998. Biodegradable poly[(amino acid ester)phosphazenes] for biomedical applications. J. Bioact. Compat. Polym., 13:4-18.
36. Leroux, J.-C., Roux, E., Le Garrec, D., Hong, K., Drummond, D.C. 2001. N-Isopropylacrylamide copolymers for the preparation of pH-sensitive liposomes and polymeric micelles. J. Control. Release, 72:71-84.
37. Li, W., Nicol, F., Szoka, F.C. 2004. GALA: a designed synthetic pH-responsive amphipathic peptide with applications in drug and gene delivery. Adv. Drug Deliv. Rev., 56:967-985.
38. Li, X., Liu, W., Ye, G., Zhang, B., Zhu, D., Yao, K., Liu, Z., Sheng, X. 2005. Thermosensitive N-isopropylacrylamide-N-propylacrylamide-vinyl pyrrolidone terpolymers: synthesis, characterization and preliminary application as embolic agents. Biomaterials, 26:7002-7011.
39. Maeda, M., Kumano, A., Tirrell, D.A. 1988. H+-induced release of contents of phosphatidylcholine vesicles bearing surface-bound polyelectrolyte chains. J. Am. Chem. Soc., 110:7455-7459.
40. Malonne, H., Eeckmann, F., Fontaine, D., Otto, A., De Vos, L., Moeïs, A., Fontaine, J., Amighi, K. 2005. Preparation of poly(N-isopropylacrylamide) copolymers and preliminary assessment of their acute and subacute toxicity in mice. Eur. J. Pharm. Biopharm., 61:188-194.
41. Meier, W., Hotz, J., Guïnther-Ausborn, S. 1996. Vesicle and cell networks: interconnecting cells by synthetic polymers. Langmuir, 12:5028-5032.
42. Meyer, O., Papahadjopoulos, D., Leroux, J.C. 1998. Copolymers of N-isopropylacrylamide can trigger pH sensitivity to stable liposomes. FEBS Lett., 42:61-64.
43. Petriat, F., Roux, E., Leroux, J.C., Giasson, S. 2004. Study of molecular interactions between a phospholipidic layer and a pH-sensitive polymer using the Langmuir balance technique. Langmuir, 20:1393-1400.
44. Provoda, C.J., Stier, E.M., Lee, K-D. 2003. Tumor cell killing enabled by listeriolysin Oliposome-mediated delivery of the protein toxin gelonin. J. Biol. Chem., 278:35102-35108.
45. Roux, E., Francis, M., Winnik, F.M., Leroux, J.C. 2002a. Polymer based pH-sensitive carriers as a means to improve the cytoplasmic delivery of drugs. Int. J. Pharm., 242:25-36.
46. Roux, E., Stomp, R., Giasson, S., Pézolet, M., Moreau, P., Leroux, J.C. 2002b. Steric stabilization of liposomes by pH-responsive N-isopropylacrylamide copolymer. J. Pharm. Sci., 91:1795-1802.
47. Roux, E., Lafleur, M., Lataste, É., Moreau, P., Leroux, J.C. 2003. On the characterization of pH-sensitive liposome/polymer complexes. Biomacromolecules, 4:240-248.
48. Roux, E., Passirani, C., Scheffold, S., Benoit, J.P., Leroux, J.C. 2004. Serum-stable longcirculating, PEGylated, pH-sensitive liposomes. J. Control. Release, 94:447-451.
49. Schmaljohann, D. 2006. Thermo-and pH-responsive polymers in drug delivery. Adv. Drug Deliv. Rev., 58:1655-1670.
50. Simoes, S., Moreira, J.N., Fonseca, C., Duzgunes, N., Pedroso de Lima, M.C. 2004. On the formulation of pH-sensitive liposomes with long circulation times. Adv. Drug Deliv. Rev., 56:947-965.
51. Taillefer, J., Jones, M.C., Brasseur, N., van Lier, J.E., Leroux, J.C. 2000. Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs. J. Pharm. Sci., 89:52-62.
52. Wang, B., Rivard, E., Manners, I. 2002. A new high-yield synthesis of Cl3PQNSiMe3, a monomeric precursor for the controlled preparation of high molecular weight polyphosphazenes. Inorg. Chem., 41:1690-1691.
53. Winnik, F.M. 1990. Fluorescence studies of aqueous solutions of poly(N-isopropylacrylamide) below and above their LCST. Macromolecules, 23:233-242.
54. Yang, H., Cheng, R., Wang, Z. 2003. A quantitative analyses of the viscometric data of the coil-to-globule and globule-to-coil transition of poly(N-isopropylacrylamide) in water. Polymer, 44:7175-7180.
55. Yessine, M.A., Leroux, J.C. 2004. Membrane-destabilizing polyanions: interaction with lipid bilayers and endosomal escape of biomacromolecules. Adv. Drug Deliv. Rev., 56:999-1021.
56. Zignani, M., Drummond, D.C., Meyer, O., Hong, K., Leroux, J.-C. 2000. In vitro characterization of a novel polymeric-based pH-sensitive liposome system. Biochim. Biophys. Acta., 1463:383-394.