Preparation and characterization of polyion complex micelles with phosphobetaine shells

Langmuir

Volumn 29, Issue 31, 2013, Pages 9651-9661

  Nakai, Keita ^a   Nishiuchi, Midori ^a   Inoue, Masamichi ^a   Ishihara, Kazuhiko ^b   Sanada, Yusuke ^c   Sakurai, Kazuo ^c   Yusa, Shin Ichi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c UNIVERSITY OF KITAKYUSHU   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE NEUTRALIZATION; CHARGED DIBLOCK COPOLYMERS; HYDRODYNAMIC SIZE; MACROCHAIN-TRANSFER AGENTS; POLYION COMPLEX MICELLES; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER; SPONTANEOUS FORMATION; STATIC LIGHT SCATTERING;

CHLORINE COMPOUNDS; DYNAMIC LIGHT SCATTERING; FREE RADICAL POLYMERIZATION; MIXING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

MICELLES;

EID: 84881460544     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la401063b     Document Type: Article

References (50)

1. Cui, H.; Chen, Z.; Zhong, S.; Wooley, K. L.; Pochan, D. J. Block copolymer assembly via kinetic control Science 2007, 317, 647-650
2. Zhang, L.; Eisenberg, A. Multiple morphologies of "crew-cut" aggregates of polystyrene- b -poly(acrylic acid) block copolymers Science 1995, 268, 1728-1731
3. Zhang, L.; Eisenberg, A. Multiple morphologies and characteristics of "crew-cut" micelle-like aggregates of polystyrene- b -poly(acrylic acid) diblock copolymers in aqueous solutions J. Am. Chem. Soc. 1996, 118, 3168-3181
4. Kataoka, K.; Kwon, G. S.; Yokoyama, M.; Okano, T.; Sakurai, Y. Block copolymer micelles as vehicles for drug delivery J. Controlled Release 1993, 24, 119-132
5. Hurter, P. N.; Hatton, T. A. Solubilization of polycyclic aromatic hydrocarbons by poly(ethylene oxide-propylene oxide) block copolymer micelles: effects of polymer structure Langmuir 1992, 8, 1291-1299
6. Michaels, A. S.; Miekka, R. G. Polycation-polyanion complexes: preparation and properties of poly-(vinylbenzyltrimethylammonium) poly-(styrenesulfonate) J. Phys. Chem. 1961, 65, 1765-1773
7. Kudlay, A.; de la Cruz, M. O. Precipitation of oppositely charged polyelectrolytes in salt solutions J. Chem. Phys. 2004, 120, 404-412
8. Cohen Stuart, M. A.; Besseling, N. A. M.; Fokkink, R. G. Formation of micelles with complex coacervate cores Langmuir 1998, 14, 6846-6849
9. Kabanov, A. V.; Bronich, T. K.; Kabanov, V. A.; Yu, K.; Eisenberg, A. Soluble stoichiometric complexes from poly(N -ethyl-4-vinylpyridinium) cations and poly(ethylene oxide)- block -polymethacrylate anions Macromolecules 1996, 29, 6797-6802
10. Gohy, J. F.; Varshney, S. K.; Jéroîme, R. Morphology of water-soluble interpolyelectrolyte complexes formed by poly(2-vinylpyridinium)- block -poly(ethylene oxide) diblocks and poly(4-styrenesulfonate) polyanions Macromolecules 2001, 34, 2745-2747
11. Kataoka, K.; Togawa, H.; Harada, A.; Yagusi, K.; Matsumoto, T.; Katayose, S. Spontaneous formation of polyion complex micelles with narrow distribution from antisense oligonucleotide and cationic block copolymer in physiological saline Macromolecules 1996, 29, 8556-8557
12. Harada, A.; Kataoka, K. Novel polyion complex micelles entrapping enzyme molecules in the core: preparation of narrowly-distributed micelles from lysozyme and poly(ethylene glycol)-poly(aspartic acid) block copolymer in aqueous medium Macromolecules 1998, 31, 288-294
13. Harada, A.; Kataoka, K. Chain length recognition: core-shell supramolecular assembly from oppositely charged block copolymers Science 1999, 283, 65-67
14. Sanson, N.; Bouyer, F.; Destarac, M.; In, M.; Gérardin, C. Hybrid polyion complex micelles formed from double hydrophilic block copolymers and multivalent metal ions: size control and nanostructure Langmuir 2012, 28, 3773-3782
15. Lindhoud, S.; Norde, W.; Cohen Stuart, M. A. Effects of polyelectrolyte complex micelles and their components on the enzymatic activity of lipase Langmuir 2010, 26, 9802-9808
16. Oishi, M.; Nagasaki, Y.; Itaka, K.; Nishiyama, N.; Kataoka, K. Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells J. Am. Chem. Soc. 2005, 127, 1624-1625
17. Kim, W.; Yamasaki, Y.; Jang, W.-D.; Kataoka, K. Thermodynamics of DNA condensation induced by poly(ethylene glycol)- block -polylysine through polyion complex micelle formation Biomacromolecules 2010, 11, 1180-1186
18. Katayose, S.; Kataoka, K. Water-soluble polyion complex associates of DNA and poly(ethylene glycol)-poly(L-lysine) block copolymer Bioconjugate Chem. 1997, 8, 702-707
19. Zhang, J.; Zhou, Y.; Zhu, Z.; Ge, Z.; Liu, S. Polyion complex micelles possessing thermoresponsive coronas and their covalent core stabilization via "click" chemistry Macromolecules 2008, 41, 1444-1454
20. Sotiropoulou, M.; Cincu, C.; Bokias, G.; Staikos, G. Water-soluble polyelectrolyte complexes formed by poly(diallyldimethylammonium chloride) and poly(sodium acrylate- co -sodium 2-acrylamido-2-methyl-1-propanesulphonate)- graft -poly(N,N -dimethylacrylamide) copolymers Polymer 2004, 45, 1563-1568
21. Shovsky, A.; Varga, I.; Makuška, R.; Claesson, P. M. Formation and stability of water-soluble, molecular polyelectrolyte complexes: effects of charge density, mixing ratio, and polyelectrolyte concentration Langmuir 2009, 25, 6113-6121
22. Lindhoud, S.; Norde, W.; Stuart, M. A. C. Reversibility and relaxation behavior of polyelectrolyte complex micelle formation J. Phys. Chem. B 2009, 113, 5431-5439
23. Voets, I. K.; Fokkink, R.; Hellweg, T.; King, S. M.; de Waard, P.; de Keizer, A.; Cohen-Stuart, M. A. Spontaneous symmetry breaking: formation of Janus micelles Soft Matter 2009, 5, 999-1005
24. Iwasaki, Y.; Ishihara, K. Cell membrane-inspired phospholipid polymers for developing medical devices with excellent biointerfaces Sci. Technol. Adv. Mater. 2012, 13, 064101
25. Ishihara, K.; Ueda, T.; Nakabayasi, N. Preparation of phospholipid polymers and their properties as hydrogel sheet Polym. J. 1990, 22, 355-360
26. Kakizawa, Y.; Harada, A.; Kataoka, K. Environment-sensitive stabilization of core-shell structured polyion complex micelle by reversible cross-linking of the core through disulfide bond J. Am. Chem. Soc. 1999, 121, 11247-11248
27. Mitsukami, Y.; Donovan, M. S.; Lowe, A. B.; McCormick, C. L. Water-soluble polymers. 81. Direct synthesis of hydrophilic styrenic-based homopolymers and block copolymers in aqueous solution via RAFT Macromolecules 2001, 34, 2248-2256
28. Yusa, S.; Fukuda, K.; Yamamoto, T.; Ishihara, K.; Morishima, Y. Synthesis of well-defined amphiphilic block copolymers having phospholipid polymer sequences as a novel biocompatible polymer micelle reagent Biomacromolecules 2005, 6, 663-670
29. Meiboom, S.; Gill, D. Modified spin-echo method for measuring nuclear relaxation times Rev. Sci. Instrum. 1958, 29, 688-691
30. Seki, M.; Morishima, Y.; Kamachi, M. Characterization of the complexes of amphiphilic polyanions and double-chain cationic surfactants Macromolecules 1992, 25, 6540-6546
31. Piotto, M.; Saudek, V.; Sklenář, V. Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions J. Biomol. NMR 1992, 2, 661-665
32. Söderman, O.; Stilbs, P.; Price, W. S. NMR studies of surfactants Concepts Magn. Res. Part A 2004, 23A, 121-135
33. Jakes, J. Regularized positive exponential sum (REPES) program-a way of inverting Laplace transform data obtained by dynamic light scattering Collect. Czech. Chem. Commun. 1995, 60, 1781-1797
34. Stockmayer, W. H.; Schmidt, M. Effects of polydispersity, branching and chain stiffness on quasielastic light scattering Pure Appl. Chem. 1982, 54, 407-414
35. Phillies, G. D. J. Quasielastic light scattering Anal. Chem. 1990, 62, 1049A-1057A
36. Ali, S. I.; Heuts, J. P. A.; van Herk, A. M. Controlled synthesis of polymeric nanocapsules by RAFT-based vesicle templating Langmuir 2010, 26, 7848-7858
37. Donovan, M. S.; Lowe, A. B.; Sumerlin, B. S.; McCormick, C. L. Raft polymerization of N,N -dimethylacrylamide utilizing novel chain transfer agents tailored for high reinitiation efficiency and structural control Macromolecules 2002, 35, 4123-4132
38. Yusa, S.; Konishi, Y.; Mitsukami, Y.; Yamamoto, T.; Morishima, Y. pH-Responsive micellization of amine-containing cationic diblock copolymers prepared by reversible addition-fragmentation chain transfer (RAFT) radical polymerization Polym. J. 2005, 37, 480-488
39. Wu, T.; Wu, Q.; Guan, S.; Su, H.; Cai, Z. Binding of the environmental pollutant naphthol to bovine serum albumin Biomacromolecules 2007, 8, 1899-1906
40. Yusa, S.; Shimada, Y.; Mitsukami, Y.; Yamamoto, T.; Morishima, Y. pH-Responsive micellization of amphiphilic diblock copolymers synthesized via reversible addition-fragmentation chain transfer polymerization Macromolecules 2003, 36, 4208-4215
41. Yusa, S.; Yokoyama, Y.; Morishima, Y. Synthesis of oppositely charged block copolymers of poly(ethylene glycol) via reversible addition-fragmentation chain transfer radical polymerization and characterization of their polyion complex micelles in water Macromolecules 2009, 42, 376-383
42. Quintana, J. R.; Jánez, M. D.; Villacampa, M.; Katime, I. Diblock copolymer micelles in solvent binary mixtures. 1. Selective solvent/precipitant Macromolecules 1995, 28, 4139-4143
43. Villacampa, M.; Apodaca, E. D.; Quintana, J. R.; Katime, I. Diblock copolymer micelles in solvent binary mixtures. 2. Selective solvent/good solvent Macromolecules 1995, 28, 4144-4149
44. Xu, R.; Winnik, M. A.; Hallett, F. R.; Riess, G.; Croucher, M. D. Light-scattering study of the association behavior of styrene-ethylene oxide block copolymers in aqueous solution Macromolecules 1991, 24, 87-93
45. Huber, K.; Bantle, S.; Lutz, P.; Burchard, W. Hydrodynamic and thermodynamic behavior of short-chain polystyrene in toluene and cyclohexane at 34.5.degree.C Macromolecules 1985, 18, 1461-1467
46. Akcasu, A. Z.; Han, C. C. Molecular weight and temperature dependence of polymer dimensions in solution Macromolecules 1979, 12, 276-280
47. Konishi, T.; Yoshizaki, T.; Yamakawa, H. On the "universal constants" ρ and Φ of flexible polymers Macromolecules 1991, 24, 5614-5622
48. De Santis, S.; Ladogana, R. D.; Diociaiuti, M.; Masci, G. Pegylated and thermosensitive polyion complex micelles by self-assembly of two oppositely and permanently charged diblock copolymers Macromolecules 2010, 43, 1992-2001
49. Solomatin, S. V.; Bronich, T. K.; Eisenberg, A.; Kabanov, V. A.; Kabanov, A. V. Colloidal stability of aqueous dispersions of block ionomer complexes: effects of temperature and salt Langmuir 2004, 20, 2066-2068
50. Park, J. S.; Akiyama, Y.; Yamasaki, Y.; Kataoka, K. 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 2007, 23, 138-146