Polymeric micelles based on poly(methacrylic acid) block-containing copolymers with different membrane destabilizing properties for cellular drug delivery

International Journal of Pharmaceutics

Volumn 454, Issue 2, 2013, Pages 611-620

  Mebarek, Naila ^a   Aubert Pouëssel, Anne ^a   Gérardin, Corine ^a   Vicente, Rita ^a,b   Devoisselle, Jean Marie ^a   Bégu, Sylvie ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b INSERM   (France)

Author keywords

Cellular trafficking; Double hydrophilic block copolymers; Endosomal escape; Micelles; Model membrane; Poly(methacrylic acid) polymer

Indexed keywords

COPOLYMER; POLYMETHACRYLIC ACID;

ARTICLE; CELL ENGINEERING; CELL MIGRATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; HUMAN; HUMAN CELL; MEMBRANE MODEL; MICELLE; MOLECULAR WEIGHT; PH; PRIORITY JOURNAL; ZETA POTENTIAL;

8-HYDROXYPYRENE-1,3,6-TRISULFONIC ACID; CELLULAR TRAFFICKING; DHBC; DIPALMITOYL PHOSPHATIDYLCHOLINE; DLS; DOUBLE HYDROPHILIC BLOCK COPOLYMERS; DPPC; DPX; DYNAMIC LIGHT SCATTERING; ENDOSOMAL ESCAPE; HPTS; MICELLES; MODEL MEMBRANE; MOLECULAR WEIGHTS; MW; P-XYLENE-BIS-PYRIDINIUM BROMIDE; PDI; PEO; PIC; PMAA; POLY(ETHYLENE OXIDE); POLY(METHACRYLIC ACID) POLYMER; POLY(METHACRYLIC ACID) POLYMERS; POLYDISPERSITY INDICE; POLYION COMPLEX; RBC; RED BLOOD CELLS; TEM; TRANSMISSION ELECTRON MICROSCOPE;

ANIMALS; CELL MEMBRANE; CELL SURVIVAL; DRUG DELIVERY SYSTEMS; ERYTHROCYTES; HEK293 CELLS; HEMOGLOBINS; HUMANS; HYDROGEN-ION CONCENTRATION; LIPOSOMES; MEMBRANES, ARTIFICIAL; MICE; MICE, INBRED C57BL; MICELLES; MOLECULAR WEIGHT; POLYETHYLENE GLYCOLS; POLYMETHACRYLIC ACIDS;

EID: 84884164764     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2013.06.014     Document Type: Article

References (51)

1. Arendshorst, W.J., Navar, L.G., 1993. Renal circulation and glomerular hemodynamics. In: Schrier, R.W. (Ed.), Diseases of the Kidney. Little, Brown and Co., Boston, p. 65.
2. Bae, Y., Fukushima, S., Harada, A., Kataoka, K., 2003. Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew. Chem. Int. Ed. 42, 4640-4643. (Pubitemid 37271305)
3. Bangham, A.D., Standish, M.M., Watkins, J.C., 1965. Diffusion of univalent ions across the lamellae of swollen phospholipids. J. Mol. Biol. 13, 238-252.
4. Bednar, B., Trenena, J., Svoboda, P., Vajda, S., Fidler, V., Prochazka, K., 1991. Time-resolved fluorescence study of chain dynamics. I. Poly(methacrylic acid) in dilute water solutions. Macromolecules 24, 2054-2059.
5. Bontha, S., Kabanov, A.V., Bronich, T.K., 2006. Polymer micelles with cross-linked ionic cores for delivery of anticancer drugs. J. Control. Release 114, 163-174. (Pubitemid 44308502)
6. Boudier, A., Aubert-Pouessel, A., Gerardin, C., Devoisselle, J.M., Begu, S., 2009. pH-sensitive double-hydrophilic block copolymer micelles for biological applications. Int. J. Pharm. 379, 212-217.
7. Bronstein, L.M., Kostylev, M., Shtykova, E., Vlahu, T., Huang, X., Stein, B.D., Bykov, A., Remmes, N.B., Baxter, D.V., Svergun, D.I., 2008. Mixed Co/Fe oxide nanoparticles in block copolymer micelles. Langmuir 24, 12618-12626.
8. Burkhardt, M., Martinez-Castro, N., Tea, S., Drechsler, M., Babin, I., Grishagin, I., Schweins, R., Pergushov, D.V., Gradzielski, M., Zezin, A.B., Muller, A.H., 2007. Polyisobutylene-block-poly(methacrylic acid) diblock copolymers: selfassembly in aqueous media. Langmuir 23, 12864-12874.
9. Caliceti, P., Veronese, F.M., 2003. Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates. Adv. Drug Deliv. Rev. 55, 1261-1277. (Pubitemid 37464561)
10. Chung, J.C., 1996. pH-sensitive, cation-selective channels formed by a simple synthetic polyelectrolyte in artificial bilayer membranes. Macromolecules 29, 4636-4641. (Pubitemid 126520431)
11. Cui, Q., Wu, F., Wang, E., 2011. Thermosensitive behavior of poly(ethylene glycol)-based block copolymer (PEG-b-PADMO) controlled via self-assembled microstructure. J. Phys. Chem. B 115, 5913-5922.
12. Felber, A.E., Castagner, B., Elsabahy, M., Deleavey, G.F., Damha, M.J., Leroux, J.C., 2011. SiRNA nanocarriers based on methacrylic acid copolymers. J. Control. Release 152, 159-167.
13. Harada, A., Kataoka, K., 1999. Chain length recognition: core-shell supramolecular assembly from oppositely charged block copolymers. Science 283, 65-67. (Pubitemid 29044846)
14. He, E., Yue, C.Y., Tam, K.C., 2009. Binding and release studies of a cationic drug from a star-shaped four-arm poly(ethylene oxide)-b- poly(methacrylic acid). J. Pharm. Sci. 99, 782-793.
15. Holappa, S., 2003. Soluble polyelectrolyte complexes composed of poly(ethylene oxide)-block-poly(sodium methacrylate) and poly(methacryloyloxyethyl trimethylammonium chloride). Polymer 44, 7907-7916.
16. Huotari, J., Helenius, A., 2011. Endosome maturation. EMBO J. 30, 3481-3500.
17. Jorgensen, K.E., Moller, J.V., 1979. Use of flexible polymers as probes of glomerular pore size. Am. J. Physiol. 236, F103-F111. (Pubitemid 9166413)
18. Kabanov, A.V., Bronich, T.K., Kabanov, V.A., 1996. Soluble stoichiometric complexes from poly(N-ethyl-4-vinylpyridinium) cations and poly(ethylene oxide)-block-polymethacrylate anions. Macromolecules 29, 6797-6802. (Pubitemid 126536654)
19. Kim, J.O., Kabanov, A.V., Bronich, T.K., 2009. Polymer micelles with cross-linked polyanion core for delivery of a cationic drug doxorubicin. J. Control. Release 138, 197-204.
20. Kwon, G.S., Kataoka, K., 1995. Block copolymer micelles as long-circulating drug vehicles. Adv. Drug Deliv. Rev. 16, 295-309.
21. Li, Y., Bronich, T.K., Chelushkin, P.S., Kabanov, A.V., 2008. Dynamic properties of block ionomer complexes with polyion complex cores. Macromolecules 41, 5863-5868.
22. Li, Y., Ding, L.J., Nakamura, H., Nakashima, K., 2003. Preparation and characterization of nanoaggregates of poly(ethylene oxide)-b-polymethacrylate and poly-L-lysine. J. Colloid Interface Sci. 264, 561-564. (Pubitemid 36960001)
23. Lysenko, E.A., Bronich, T.K., Eisenberg, A., Kabanov, V.A., Kabanov, A.V., 1998. Block ionomer complexes from polystyrene-block-polyacrylate anions and N-cetylpyridinium cations. Macromolecules 31, 4511-4515. (Pubitemid 128567890)
24. Martin, T.J., Prochazka, K., Munk, P., Webber, S.E., 1996. pH-dependent micellization of poly(2-vinylpyridine)-block-poly(ethylene oxide). Macromolecules 29, 6071-6073.
25. Oishi, M., Kataoka, K., Nagasaki, Y., 2006. pH-responsive three-layered PEGylated polyplex micelle based on a lactosylated ABC triblock copolymer as a targetable and endosome-disruptive nonviral gene vector. Bioconjug. Chem. 17, 677-688. (Pubitemid 43794377)
26. Olea, A.F., Rosenbluth, H., Thomas, J.K., 1999. Effect of the molecular weight on the dynamics of the conformational transition of poly(methacrylic acid). Macromolecules 32, 8077-8083. (Pubitemid 30544940)
27. Park, J.S., Akiyama, Y., Yamasaki, Y., Kataoka, K., 2007. Preparation and characterization of polyion complex micelles with a novel thermosensitive poly(2-isopropyl-2-oxazoline) shell via the complexation of oppositely charged block ionomers. Langmuir 23, 138-146. (Pubitemid 46129716)
28. Reboul, J., 2009. Assemblages induits et réversibles de Copolymères à Blocs Double Hydrophiles: de la synthèse des copolymères à leur utilisation en tant qu'agents structurants de matériaux siliciques à porosité ordonnée. Université de Montpellier II, Montpellier, France.
29. Reboul, J., Nugay, T., Anik, N., Cottet, H., Ponsinet, V., In, M., Lacroix-Desmazes, P., Gérardin, C., 2011. Synthesis of double hydrophilic block copolymers and induced assembly with oligochitosan for the preparation of polyion complex micelles. Soft Matter 7, 5836-5846.
30. Sanson, N., Bouyer, F., Destarac, M., In, M., Gerardin, C., 2012. Hybrid polyion complex micelles formed from double hydrophilic block copolymers and multivalent metal ions: size control and nanostructure. Langmuir 28, 3773-3782.
31. Sanson, N., Bouyer, F., Gérardin, C., In, M., 2004. Nanoassemblies formed from hydrophilic block copolymers and multivalent ions. Phys. Chem. Chem. Phys. 6, 1463-1466.
32. Sevimli, S., Inci, F., Zareie, H.M., Bulmus, V., 2012. Well-defined cholesterol polymers with pH-controlled membrane switching activity. Biomacromolecules 13, 3064-3075.
33. Seymour, L.W., Duncan, R., Strohalm, J., Kopecek, J., 1987. Effect of molecular weight (Mw) of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal, and intravenous administration to rats. J. Biomed. Mater. Res. 21, 1341-1358.
34. Seymour, L.W., Miyamoto, Y., Maeda, H., Brereton, M., Strohalm, J., Ulbrich, K., Duncan, R., 1995. Influence of molecular weight on passive tumour accumulation of a soluble macromolecular drug carrier. Eur. J. Cancer 31A, 766-770.
35. Sibeko, B., Choonara, Y.E., du Toit, L.C., Modi, G., Naidoo, D., Khan, R.A., Kumar, P., Ndesendo, V.M., Iyuke, S.E., Pillay, V., 2012. Composite polylactic-methacrylic acid copolymer nanoparticles for the delivery of methotrexate. J. Drug Deliv. 2012, 579629.
36. Solomatin, S.V., Bronich, T.K., Bargar, T.W., Eisenberg, A., Kabanov, V.A., Kabanov, A.V., 2003. Environmentally responsive nanoparticles from block ionomer complexes: effects of pH and ionic strength. Langmuir 19, 8069-8076.
37. Soutar, I., Swanson, L., 1994. Luminescence studies of polyelectrolyte behavior in solution. 3. Time-resolved fluorescence anisotropy measurements of the conformational behavior of poly(methacrylic acid) in dilute aqueous solutions. Macromolecules 27, 4304-4311.
38. Stepanek, M., Kosovan, P., Prochazka, K., Janata, M., Netopilik, M., Plestil, J., Slouf, M., 2010. Self-assembly of poly(4-methylstyrene)-g- poly(methacrylic acid) graft copolymer in selective solvents for grafts: scattering and molecular dynamics simulation study. Langmuir 26, 9289-9296.
39. Tarasov, K., Houssein, D., Destarac, M., Marcotte, N., Gérardin, C., Tichit, D., 2013. Stable aqueous colloids of ZnS quantum dots prepared using double hydrophilic block copolymers. New J. Chem. 37, 508-514.
40. Teoh, S.K., Ravi, P., Dai, S., Tam, K.C., 2005. Self-assembly of stimuli-responsive water-soluble [60]fullerene end-capped ampholytic block copolymer. J. Phys. Chem. B 109, 4431-4438. (Pubitemid 40429300)
41. Uchman, M., Cigler, P., Gruner, B., Prochazka, K., Matejicek, P., 2010. Micelle-like nanoparticles of block copolymer poly(ethylene oxide)-block- poly(methacrylic acid) incorporating fluorescently substituted metallacarboranes designed as HIV protease inhibitor interaction probes. J. Colloid Interface Sci. 348, 129-136.
42. Voets, I.K., de Keizer, A., Cohen Stuart, M.A., 2009. Complex coacervate core micelles. Adv. Colloid Interface Sci. 147/148, 300-318.
43. Warnant, J., Marcotte, N., Reboul, J., Layrac, G., Aqil, A., Jerome, C., Lerner, D.A., Gerardin, C., 2012. Physicochemical properties of pH-controlled polyion complex (PIC) micelles of poly(acrylic acid)-based double hydrophilic block copolymers and various polyamines. Anal. Bioanal. Chem. 403, 1395-1404.
44. Yamaoka, T., Tabata, Y., Ikada, Y., 1994. Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. J. Pharm. Sci. 83, 601-606. (Pubitemid 24222392)
45. Yang, Y.Q., Zheng, L.S., Guo, X.D., Qian, Y., Zhang, L.J., 2011. pH-sensitive micelles self-assembled from amphiphilic copolymer brush for delivery of poorly water-soluble drugs. Biomacromolecules 12, 116-122.
46. Yessine, M.A., Dufresne, M.H., Meier, C., Petereit, H.U., Leroux, J.C., 2007. Proton-actuated membrane-destabilizing polyion complex micelles. Bioconjug. Chem. 18, 1010-1014. (Pubitemid 47010827)
47. Yessine, M.A., Lafleur, M., Meier, C., Petereit, H.U., Leroux, J.C., 2003. Characterization of the membrane-destabilizing properties of different pH-sensitive methacrylic acid copolymers. Biochim. Biophys. Acta 1613, 28-38. (Pubitemid 36776507)
48. 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.
49. Zhang, J., Peppas, N.A., 2000. Synthesis and characterization of pH- and temperature-sensitive poly(methacrylic acid)/poly(N-isopropylacrylamide) interpenetrating polymeric networks. Macromolecules 33, 102-107. (Pubitemid 32212698)
50. Zhao, Y., Luo, Y.W., Li, B.G., Zhu, S., 2011. pH responsivity and micelle formation of gradient copolymers of methacrylic acid and methyl methacrylate in aqueous solution. Langmuir 27, 11306-11315.
51. Zhu, Z., Sukhishvili, S.A., 2009. Temperature-induced swelling and small molecule release with hydrogen-bonded multilayers of block copolymer micelles. ACS Nano 3, 3595-3605.