We have synthesized macromonomers by mechanochemical reaction of poly(benzyl methacrylate) (PBzMA) and maleic anhydride (MA). The ESR spectrum of the fractured sample of PBzMA and MA showed a broad singlet, which was apparently different from the spectrum of PBzMA mechanoradical. The amphiphilic blockcopolymer was synthesized with macromonomer of PBzMA and amino-terminated polyethyleneglycol (a-methyl-w-aminopropoxy polyoxyethylene, MEPA). The number average molecular weight of the produced amphiphilic blockcopolymer was 33,000. Polymeric micelles were readily prepared from the present amphiphilic blockcopolymer by a dialysis method. The mean diameter of the micelles measured by dynamic light scattering was about 146 nm. It was shown that the present macromonomer mechanically produced can be used for the synthesis of amphiphilic bockcopolymer to form polymeric micelles.
Yokoyama M, Miyauchi M, Yamada N, Okano T, Kataoka K, Inoue S. Polymer micelles as novel drug carrier: adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer. J Control Rel 1990; 11: 269-78. http://dx.doi.org/10.1016/0168-3659(90)90139-K
Kohori F, Sakai K, Aoyagi T, Yokoyama M, Sakurai Y, Okano T. Preparation and characterization of thermally responsive block copolymer micelles comprising poly (N-isopropylacrylamide-b-DL-lactide). J Control Rel 1998; 55: 87-98. http://dx.doi.org/10.1016/S0168-3659(98)00023-6
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 Control Rel 1999; 62: 89-100. http://dx.doi.org/10.1016/S0168-3659(99)00028-0
Akiyoshi K, Kang E-C, Kurumada S, Sunamoto J, Principi T, Winnik FM. Controlled association of amphiphilic polymers in water: thermosensitive nanoparticles formed by self-assembly of hydrophobically modified pullulans and poly(N-isopropylacrylamides). Macromolecules 2000; 33: 3244-49. http://dx.doi.org/10.1021/ma991798d
Katayama Y, Sonoda T, Maeda M. A polymer micelle responding to the protein kinase a signal. Macromolecules 2001; 34: 8569-73. http://dx.doi.org/10.1021/ma010966a
Kataoka K, Harada A, Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 2001; 47: 113-31 and references cited therein.
Savic R, Luo L, Eisenberg A, Maysinger D. Micellar nanocontainers distribute to defined cytoplasmic organelles. Science 2003; 300: 615-18. http://dx.doi.org/10.1126/science.1078192
Francis MF, Cristea M, Winnik FM. Polymeric micelles for oral drug delivery: Why and how. Pure Appl Chem 2004; 76: 1321-35, and references cited therein.
Djordjevic J, Barch M, Uhrich KE. Polymeric micelles based on amphiphilic scorpion-like macromolecules: novel carriers for water-insoluble drugs. Pharm Res 2005; 22: 24-32. http://dx.doi.org/10.1007/s11095-004-9005-3
Bae Y, Nishiyama N, Fukushima S, Koyama H, Yasuhiro M, Kataoka K. Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy. Bioconjugate Chem 2005; 16: 122-30. http://dx.doi.org/10.1021/bc0498166
Ito K. Polymeric design by macromonomer technique. Prog Polym Sci 1998; 23: 581-20. http://dx.doi.org/10.1016/S0079-6700(97)00049-X
Ito K, Kawaguchi S. Poly(macromonomers): homo- and copolymerization . Adv Polym Sci 1999; 142: 129-78. http://dx.doi.org/10.1007/3-540-68310-0_3
Maniruzzaman M, Kawaguchi S, Ito K. Micellar copolymeri-zation of styrene with poly(ethylene oxide) macromonomer in water: approach to unimolecular nanoparticles via pseudo-liming radical polymerization. Macromolecules 2000; 33: 1583-92. http://dx.doi.org/10.1021/ma991272t
Kondo S, Tsukamoto M, Sasai Y, Yamauchi Y, Kuzuya M. Novel synthesis of macromonomers by mechanochemical reaction for the application to polymeric micelles. J Phar Nutrit Sci 2011; 1: 124-29.
Gao Z, Varshney SK, Wong S, Eisenberg A. Block copolymer "Crew-Cut" micelles in water. Macromolecules 1994; 27: 7923-27. http://dx.doi.org/10.1021/ma00104a058
Zhang L, Barlow RJ, Eisenberg A. Scaling relations and coronal dimensions in aqueous block polyelectrolyte micelles. Macromolecules 1995; 28: 6055-66. http://dx.doi.org/10.1021/ma00122a010
Zhang L, Eisenberg A. Multiple morphologies of "Crew-Cut" aggregates of polystyrene-b-poly(acrylic acid) block copolymers. Science 1995; 268: 1728-31. http://dx.doi.org/10.1126/science.268.5218.1728
Yu K, Zhang L, Eisenberg A. Novel morphologies of "Crew-Cut" aggregates of amphiphilic diblock copolymers in dilute solution. Langmuir 1996; 12: 5980-84. http://dx.doi.org/10.1021/la960894u
Zhang L, Yu K, Eisenberg A. Ion-induced morphological changes in "crew-cut" aggregates of amphiphilic block copolymers. Science 1996; 272: 1777-79. http://dx.doi.org/10.1126/science.272.5269.1777
Yu K, Zhang L, Eisenberg A. Multiple morphologies of Crew-Cut aggregates of polybutadiene-b-poly(acrylic acid) diblocks with low Tg cores. Langmuir 1997; 13: 2578-81. http://dx.doi.org/10.1021/la961058n
Yu K, Eisenberg A. Multiple morphologies in aqueous solutions of aggregates of polystyrene-block-poly(ethyleneoxide) diblock copolymers. Macromolecules 1996; 29: 6359-61. http://dx.doi.org/10.1021/ma960381u
Ding J, Liu G. Polyisoprene-block-poly(2-cinnamoylethyl methacrylate) vesicles and their aggregates. Macromolecules 1997; 30: 655-57. http://dx.doi.org/10.1021/ma961177+
Zhang L, Eisenberg A. Thermodynamic vs kinetic aspects in the formation and morphological transitions of crew-cut aggregates produced by self-assembly of polystyrene-b-poly(acrylic acid) block copolymers in dilute solution. Macromolecules 1999; 32: 2239-49. http://dx.doi.org/10.1021/ma981039f
Liang Y, Li Z, Li F. Multiple morphologies of molecular assemblies formed by polystyrene-block-poly[2-(?-D-glucopyranosyloxy)ethyl acrylate
Yokoyama M, Miyauchi M, Yamada N, Okano T, Sakurai Y, Kataoka K, Inoue S. Characterization and anticancer activity of the micelle-forming polymeric anticancer drug Adriamycin-conjugated poly(ethylene glycol)-(aspartic acid) block copolymer. Cancer Res 1990; 50: 1693-700.
Iijima M, Nagasaki Y, Okada T, Kato M, Kataoka K. Core-Polymerized Reactive Micelles from Heterotelechelic Amphiphilic Block Copolymers. Macromolecules 1999; 32: 1140-46. http://dx.doi.org/10.1021/ma9815962
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Copyright (c) 2014 Shin-ichi Kondo, Machi Omoto, Yuka Sawama, Yasushi Sasai, Kenjiro Tatematsu, Yukinori Yamauchi , Masayuki Kuzuya