Block copolymer micelles: Preparation, characterization and application in drug delivery

Journal of Controlled Release

Volumn 109, Issue 1-3, 2005, Pages 169-188

  Gaucher, Geneviève ^a   Dufresne, Marie Hélène ^a   Sant, Vinayak P ^a   Kang, Ning ^a   Maysinger, Dusica ^b   Leroux, Jean Christophe ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

Block copolymer micelles; Drug solubilization; Micelle stability; Polyion complex micelles; Targeting

Indexed keywords

CHEMOTHERAPY; DRUG PRODUCTS; HYDROPHOBICITY; MICELLES; SELF ASSEMBLY; TISSUE; TUMORS;

CORONA; DRUG SOLUBILIZATION; MICELLE STABILITY;

BLOCK COPOLYMERS;

COPOLYMER; DOCETAXEL; DRUG CARRIER; MACROGOL DERIVATIVE; POLY(ETHYLENE GLYCOL) B POLY(PROPYLENE OXIDE) B POLY(ETHYLENE GLYCOL) COPOLYMER; POLYAMINOACID; POLYASPARTIC ACID; POLYGLUTAMIC ACID; POLYHISTIDINE; POLYLYSINE; POLYMETHACRYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; CONFERENCE PAPER; DRUG DELIVERY SYSTEM; DRUG PENETRATION; DRUG RESEARCH; DRUG STABILITY; HUMAN; HYDROPHILICITY; HYDROPHOBICITY; MEDICAL RESEARCH; MICELLE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SOLUBILIZATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELLS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; DRUG STABILITY; HUMANS; LIGANDS; MICELLES; POLYMERS;

EID: 28544450961     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2005.09.034     Document Type: Conference Paper

References (113)

1. G.S. Kwon Polymeric micelles for delivery of poorly water-soluble compounds Crit. Rev. Ther. Drug Carr. Syst. 20 2003 357 403
2. Y. Nishiyama, Y. Kato, Y. Sugiyama, and K. Kataoka Cisplatin-loaded polymer-metal complex micelle with time-modulated decaying property as a novel drug delivery system Pharm. Res. 18 2001 1035 1041
3. N. Nishiyama, S. Okazaki, H. Cabral, M. Miyamoto, Y. Kato, Y. Sugiyama, K. Nishio, Y. Matsumura, and K. Kataoka Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice Cancer Res. 63 2003 8977 8983
4. L. Zhang, and A. Eisenberg Multiple morphologies of "crew-cut" aggregates of polystyrene-b-poly(acrylic acid) block copolymers Science 268 1995 1728 1731
5. M.H. Dufresne, E. Fournier, M.-C. Jones, M. Ranger, and J.C. Leroux Block copolymer micelles-engineering versatile carriers for drugs and biomacromolecules R. Gurny B.T. Gattefossé vol. 96 2003 Gattefossé Saint-Priest 87 102
6. A. Lavasanifar, J. Samuel, and G.S. Kwon Poly(ethylene oxide)-block-poly(l-amino acid) micelles for drug delivery Adv. Drug Deliv. Rev. 54 2002 169 190
7. A. Kabanov, E.V. Batrakova, and V.Y. Alakhov Pluronic block copolymers as novel polymer therapeutics for drug and gene delivery J. Control. Release 82 2002 189 212
8. A.V. Kabanov, T.K. Bronich, V.A. Kabanov, K. Yu, and A. Eisenberg Soluble stoichiometric complexes from poly(N-ethyl-4-vinylpyridinium) cations and poly(ethylene oxide)-block-polymethacrylate anions Macromolecules 29 1996 6797 6802
9. D. Wakebayashi, N. Nishiyama, Y. Yamasaki, K. Itaka, N. Kanayama, A. Harada, Y. Nagasaki, and K. Kataoka Lactose-conjugated polyion complex micelles incorporating plasmid DNA as a targetable gene vector system: their preparation and gene transfecting efficiency against cultured HepG2 cells J. Control. Release 95 2004 653 664
10. M. Oishi, S. Sasaki, Y. Nagasaki, and K. Kataoka pH-responsive oligodeoxynucleotide (ODN)-poly(ethylene glycol) conjugate through acid-labile β-thiopropionate linkage: preparation and polyion complex micelle formation Biomacromolecules 4 2003 1426 1432
11. M.H. Dufresne, and J.C. Leroux Study of the micellization behavior of different order amino block copolymers with heparin Pharm. Res. 21 2004 160 169
12. A. Harada, and K. Kataoka Pronounced activity of enzymes through the incorporation into the core of polyion complex micelles made from charged block copolymers J. Control. Release 72 2001 85 91
13. T. Govender, S. Stolnik, C. Xiong, S. Zhang, L. Illum, and S.S. Davis Drug-polyionic block copolymer interactions for micelle formation: physicochemical characterisation J. Control. Release 75 2001 249 258
14. J.K. Tessmar, A.G. Mikos, and A. Göpferich Amine-reactive biodegradable diblock copolymer Biomacromolecules 3 2002 194 200
15. Y. Nagasaki, M. Iijima, M. Kato, and K. Kataoka Primary amino-terminal heterobifunctional poly(ethylene oxide), facile synthesis of poly(ethylene oxide) with a primary amino group at one end and a hydroxyl group at the other end Bioconjug. Chem. 6 1995 702 704
16. S. Zhang, J. Qing, C. Xiong, and Y. Peng Synthesis of end-functionalized AB copolymers: II. Synthesis and characterization of carboxyl-terminated poly(ethylene glycol)-poly(amino acid) block copolymers J. Polym. Sci., Part A, Polym. Chem. 42 2004 3527 3536
17. Y. Nagasaki, T. Kutsuna, M. Iijima, M. Kato, and K. Kataoka Formyl-ended heterobifunctional poly(ethylene oxide): synthesis of a poly(ethylene oxide) with a formyl group at one end and a hydroxyl group at the other end Bioconjug. Chem. 6 1995 231 233
18. T. Nakamura, Y. Nagasaki, and K. Kataoka Synthesis of heterobifunctional poly(ethylene glycol) with a reducing monosaccharide residue at one end Bioconjug. Chem. 9 1998 300 303
19. A. Harada, and K. Kataoka Formation of polyion complex micelles in an aqueous milieu from a pair of oppositely-charged block copolymers with poly(ethylene glycol) segments Macromolecules 28 1995 5294 5299
20. A. Harada, and K. Kataoka Effect of charged segment length on physicochemical properties of core-shell type polyion complex micelles from block ionomers Macromolecules 36 2003 4995 5001
21. Y. Bae, N. Nishiyama, S. Fukushima, H. Koyama, M. Yasuhiro, and K. Kataoka 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 Bioconjug. Chem. 16 2005 122 130
22. A. Lavasanifar, J. Samuel, and G.S. Kwon Micelles of poly(ethylene oxide)-block-poly(N-alkyl stearate l-aspartamide): synthetic analogues of lipoproteins for drug delivery J. Biomed. Mater. Res. 52 2000 831 835
23. G.H. Van Domeselaar, G.S. Kwon, L.C. Andrew, and D.S. Wishart Application of solid phase peptide synthesis to engineering PEO-peptide block copolymers for drug delivery Colloids Surf., B 30 2003 323 334
24. W.-J. Lin, L.-W. Juang, and C.-C. Lin Stability and release performance of a series of pegylated copolymeric micelles Pharm. Res. 20 2003 668 673
25. H.M. Burt, X. Zhang, P. Toleikis, L. Embree, and W.L. Hunter Development of copolymers of poly(d,l-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel Colloids Surf., B 16 1999 161 171
26. N. Kang, and J.-C. Leroux Triblock and star-block copolymer of N-(2-hydroxypropyl)methacrylamide or N-vinyl-2-pyrrolidone and d,l-lactide: synthesis and self-assembling properties in water Polymer 45 2004 8967 8980
27. X. Shuai, T. Merdan, F. Unger, M. Wittmar, and T. Kissel Novel biodegradable ternary copolymers hy-PEI-g-PCL-b-PEG: synthesis, characterization, and potential as efficient nonviral gene delivery vectors Macromolecules 36 2003 5751 5759
28. H.S. Yoo, and T.G. Park Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA-PEG block copolymer J. Control. Release 70 2001 63 70
29. T. Riley, S. Stolnik, C.R. Heald, C.D. Xiong, M.C. Garnett, L. Illum, S.S. Davis, S.C. Purkiss, R.J. Barlow, and P.R. Gellert Physicochemical evaluation of nanoparticles assembled from poly(lactic acid)-poly(ethylene glycol) (PLA-PEG) block copolymer as drug delivery vehicles Langmuir 17 2001 3168 3174
30. N. Kang, M.E. Perron, R.E. Prud'homme, Y. Zhang, G. Gaucher, and J.C. Leroux Stereocomplex block copolymer micelles: core-shell nanostructures with enhanced stability Nano Lett. 5 2005 315 319
31. L. Piao, Z. Dai, M. Deng, X. Chen, and X. Jing Synthesis and characterization of PCL/PEG/PCL triblock copolymers by using calcium catalyst Polymer 44 2003 2025 2031
32. Y. Nagasaki, T. Okada, C. Scholz, M. Iijima, M. Kato, and K. Kataoka The reactive polymeric micelle based on an aldehyde-ended poly(ethylene glycol)/poly(lactide) block copolymer Macromolecules 31 1998 1473 1479
33. M. Ranger, M.C. Jones, M.A. Yessine, and J.C. Leroux From well-defined diblock copolymers prepared by a versatile atom transfer radical polymerization method to supramolecular assemblies J. Polym. Sci., Part A, Polym. Chem. 39 2001 3861 3874
34. M.H. Dufresne, D. Le Garrec, V. Sant, J.C. Leroux, and M. Ranger Preparation and characterization of water-soluble pH-sensitive nanocarriers for drug delivery Int. J. Pharm. 277 2004 81 90
35. V.P. Sant, D. Smith, and J.C. Leroux Novel pH-sensitive supramolecular assemblies for oral delivery of poorly water soluble drugs: preparation and characterization J. Control. Release 97 2004 301 312
36. M.H. Dufresne, and J.C. Leroux Study of the micellization behavior of different order amino block copolymers with heparin Pharm. Res. 21 2004 160 169
37. C.-Y. Hong, Y.-Z. You, and C.-Y. Pan Synthesis and characterization of well-defined diblock and triblock copolymers of poly(N-isopropylacrylamide) and poly(ethylene oxide) J. Polym. Sci., Part A, Polym. Chem. 42 2004 4873 4881
38. D. Neradovic, C.F. Van Nostrum, and W.E. Hennink Thermoresponsive polymeric micelles with controlled instability based on hydrolytically sensitive N-isopropylacrylamide copolymers Macromolecules 34 2001 7589 7591
39. O. Soga, C.F. Van Nostrum, A. Ramzi, T. Visser, F. Soulimani, P.M. Frederik, P.H.H. Bomans, and W.E. Hennink Physicochemical characterization of degradable thermosensitive polymeric micelles Langmuir 20 2004 9388 9395
40. A. Benahmed, M. Ranger, and J.C. Leroux Novel polymeric micelles based on the amphiphilic diblock copolymer poly(N-vinyl-pyrrolodone)-block-poly(d,l- lactide) Pharm. Res. 18 2001 323 328
41. L. Luo, M. Ranger, D.G. Lessard, D. Le Garrec, S. Gori, J.C. Leroux, S. Rimmer, and D. Smith Novel amphiphilic diblock copolymer of low molecular weight poly(N-vinylpyrrolidone)-block-poly(d,l-lactide): synthesis, characterization, and micellization Macromolecules 37 2004 4008 4013
42. M.J. Hwang, J.M. Suh, Y.H. Bae, S.W. Kim, and B. Jeong Caprolactonic poloxamer analog: PEG-PCL-PEG Biomacromolecules 6 2005 885 890
43. B.S. Lele, and J.-C. Leroux Synthesis of novel amphiphilic star-shaped poly(ε-caprolactone)-block-poly(N-(2-hydroxypropyl)methacrylamide) by combination of ring-opening and chain transfer polymerization Polymer 43 2002 5595 5606
44. B.S. Lele, and J.-C. Leroux Synthesis and micellar characterization of novel amphiphilic A-B-A triblock copolymers of N-(2-hydroxypropyl) methacrylamide) or N-vinyl-2-pyrrolidone with poly(ε-caprolactone) Macromolecules 35 2002 6714 6723
45. C. Allen, D. Maysinger, and A. Eisenberg Nano-engineering block copolymer aggregates for drug delivery Colloids Surf., B 16 1999 3 27
46. D.L. Taegarden, and D.S. Baker Practical aspects of lyophilization using non-aqueous co-solvent systems Eur. J. Pharm. Sci. 15 2002 115 133
47. E. Fournier, M.H. Dufresne, D.C. Smith, M. Ranger, and J.C. Leroux A novel one-step drug-loading procedure for water-soluble amphiphilic nanocarriers Pharm. Res. 21 2004 962 968
48. P. Vangeyte, S. Gautier, and R. Jérôme About the methods of preparation of poly(ethylene oxide)-b-poly(ε-caprolactone) nanoparticles in water. Analysis by dynamic light scattering Colloids Surf., A 242 2004 203 211
49. C. Allen, J. Han, Y. Yu, D. Maysinger, and A. Eisenberg Polycaprolactone-b-poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosterone J. Control. Release 63 2000 275 286
50. X. Shuai, H. Ai, N. Nasongkla, S. Kim, and J. Gao Micellar carriers based on block copolymers of poly(ε-caprolactone) and poly(ethylene glycol) for doxorubicin delivery J. Control. Release 98 2004 415 426
51. J. Liu, Y. Xiao, and C. Allen Polymer-drug compatibility: a guide to the development of delivery systems for the anticancer agent, ellipticine J. Pharm. Sci. 93 2004 132 143
52. V. Toncheva, E. Schacht, S.Y. NG, J. Barr, and J. Heller Use of block copolymers of poly(ortho esters) and poly(ethylene glycol) micellar carriers as potential tumour targeting systems J. Drug Target. 11 2003 345 353
53. J. Liu, F. Zeng, and C. Allen Influence of serum protein on polycarbonate-based copolymer micelles as a delivery system for a hydrophobic anti-cancer agent J. Control. Release 103 2005 481 497
54. K.K. Jette, D. Law, E.A. Schmitt, and G.S. Kwon Preparation and drug loading of poly(ethylene glycol)-block-poly(ε-caprolactone) micelles through the evaporation of a cosolvent azeotrope Pharm. Res. 21 2004 1184 1191
55. M.L. Adams, D.R. Andes, and G.S. Kwon Amphotericin B encapsulated in micelles based on poly(ethylene oxide)-block-poly(l-amino acid) derivatives exerts reduced in vitro hemolysis but maintains potent in vivo antifungal activity Biomacromolecules 4 2003 750 757
56. M.L. Adams, and G.S. Kwon Relative aggregation state and hemolytic activity of amphotericin B encapsulated by poly(ethylene oxide)-block-poly(N- hexyl-l-aspartamide)-acyl conjugate micelles: effects of acyl chain length J. Control. Release 87 2003 23 32
57. P. Opanasopit, M. Yokoyama, M. Watanabe, K. Kawano, Y. Maitani, and T. Okano Block copolymer design for camptothecin incorporation into polymeric micelles for passive tumor targeting Pharm. Res. 21 2004 2001 2008
58. Y. Yamamoto, K. Yasugi, A. Harada, Y. Nagasaki, and K. Kataoka 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. Control. Release 82 2002 359 371
59. J. Slager, and A.J. Domb Biopolymer stereocomplexes Adv. Drug Deliv. Rev. 55 2003 549 583
60. K.B. Thurmond II, H. Huang, C.G. Clark Jr., T. Kowalewski, and K.L. Wooley Shell cross-linked polymer micelles: stabilized assemblies with great versatility and potential Colloids Surf., B 16 1999 45 54
61. X. Shuai, T. Merdan, A.K. Schaper, F. Xi, and T. Kissel Core-cross-linked polymeric micelles as paclitaxel carriers Bioconjug. Chem. 15 2004 441 448
62. M. Jaturanpinyo, A. Harada, X. Yuan, and K. Kataoka Preparation of bionanoreactor based on core-shell structured polyion complex micelles entrapping trypsin in the core cross-linked with glutaraldehyde Bioconjug. Chem. 15 2004 344 348
63. J. Lee, E.C. Cho, and K. Cho Incorporation and release behavior of hydrophobic drug in functionalized poly(d,l-lactide)-block-poly(ethylene oxide) micelles J. Control. Release 94 2004 323 335
64. Y. Li, and G.S. Kwon Methotrexate esters of poly(ethylene oxide)-block-poly(2-hydroxyethyl-l-aspartamide): Part 1. Effects of the level of methotrexate conjugation on the stability of micelles and on drug delivery Pharm. Res. 17 2000 607 611
65. H.S. Yoo, and T.G. Park Folate receptor targeted biodegradable polymeric doxorubicin micelles J. Control. Release 96 2004 273 283
66. M. Oishi, Y. Nagasaki, K. Itaka, N. Nishiyama, and K. Kataoka 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. 127 2005 1624 1625
67. M. Hruby, C. Konak, and K. Ulbrich Polymeric micellar pH-sensitive drug delivery system for doxorubicin J. Control. Release 103 2005 137 148
68. H.S. Yoo, E.A. Lee, and T.G. Park Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages J. Control. Release 82 2002 17 27
69. D.V. Pergushov, E.K. Remizova, M. Gradzielski, P. Lindner, J. Feldthusen, A.B. Zezin, A.H.E. Muller, and V.A. Kabanov Micelles of polyisobutylene-block- poly(methacrylic acid) diblock copolymers and their water-soluble interpolyelectrolyte complexes formed with quaternized poly(4-vinylpyridine) Polymer 45 2004 367 378
70. A. Harada, T. Hideyuki, and K. Kataoka Physicochemical properties and nuclease resistance of antisense-oligodeoxynucleotides entrapped in the core of polyion complex micelles composed of PEG-poly(l-lysine) block copolymers Eur. J. Pharm. Sci. 13 2001 35 42
71. K. Greish, J. Fang, T. Inutsuka, A. Nagamitsu, and H. Maeda Macromolecular therapeutics: advantages and prospects with special emphasis on solid tumour targeting Clin. Pharmacokinet. 42 2003 1089 1105
72. M.L. Adams, A. Lavasanifar, and G.S. Kwon Amphiphilic block copolymers for drug delivery J. Pharm. Sci. 92 2003 1343 1355
73. H. Otsuka, Y. Nagasaki, and K. Kataoka PEGylated nanoparticles for biological and pharmaceutical applications Adv. Drug Deliv. Rev. 55 2003 403 419
74. 1H NMR spectroscopy Biomaterials 18 1997 27 30
75. M. Kursa, G.F. Walker, V. Roessler, M. Ogris, W. Roedl, R. Kircheis, and E. Wagner Novel shielded transferrin-polyethylene glycol-polyethyleneimine/DNA complexes for systemic tumor-targeted gene transfer Bioconjug. Chem. 14 2003 222 231
76. V.P. Torchilin Structure and design of polymeric surfactant-based drug delivery systems J. Control. Release 73 2001 137 172
77. M.T. Peracchia, C. Vauthier, C. Passirani, P. Couvreur, and D. Labarre Complement consumption by poly(ethylene glycol) in different conformations chemically coupled to poly(isobutyl 2-cyanoacrylate) nanoparticles Life Sci. 61 1997 749 761
78. Y. Yamamoto, Y. Nagasaki, Y. Kato, Y. Sugiyama, and K. Kataoka Long-circulating poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles with modulated surface charge J. Control. Release 77 2001 27 38
79. D. Maysinger, O. Berezovska, R. Savic, P.L. Soo, and A. Eisenberg Block copolymers modify the internalization of micelle-incorporated probes into neural cells Biochim. Biophys. Acta 1539 2001 205 217
80. 44 block copolymer micelles Biochim. Biophys. Acta 1421 1999 32 38
81. L. Luo, J. Tam, D. Maysinger, and A. Eisenberg Cellular internalization of poly(ethylene oxide)-b-poly(ε-caprolactone) diblock copolymer micelles Bioconjug. Chem. 13 2002 1259 1265
82. R. Savic, L. Luo, A. Eisenberg, and D. Maysinger Micellar nanocontainers distribute to defined cytoplasmic organelles Science 300 2003 615 618
83. S. Vinogradov, E. Batrakova, S. Li, and A. Kabanov Polyion complex micelles with protein-modified corona for receptor-mediated delivery of oligonucleotides into cells Bioconjug. Chem. 10 1999 851 860
84. E. Jule, Y. Nagasaki, and K. Kataoka Surface plasmon resonance study on the interaction between lactose-installed poly(ethylene glycol)-poly(d,l- lactide) block copolymer micelles and lectins immobilized on a gold surface Langmuir 18 2002 10334 10339
85. E.S. Lee, K. Na, and Y.H. Bae Polymeric micelle for tumor pH and folate-mediated targeting J. Control. Release 91 2003 103 113
86. Y. Tang, S.Y. Liu, S.P. Armes, and N.C. Billingham Solubilization and controlled release of a hydrophobic drug using novel micelle-forming ABC triblock copolymers Biomacromolecules 4 2003 1636 1645
87. E.S. Lee, K. Na, and Y.H. Bae Super pH-sensitive multifunctional polymeric micelle Nano Lett. 5 2005 325 329
88. J.C. Leroux, E. Roux, D. Le Garrec, K. Hong, and D.C. Drummond N-isopropylacrylamide copolymers for the preparation of pH-sensitive liposomes and polymeric micelles J. Control. Release 72 2001 71 84
89. J. Taillefer, N. Brasseur, J.E. van Lier, V. Lenaerts, D. Le Garrec, and J.C. Leroux In-vitro and in-vivo evaluation of pH-responsive polymeric micelles in a photodynamic cancer therapy model J. Pharm. Pharmacol. 53 2001 155 166
90. Y. Kakizawa, A. Harada, and K. Kataoka Glutathione-sensitive stabilization of block copolymer micelles composed of antisense DNA and thiolated poly(ethylene glycol)-block-poly(l-lysine): a potential carrier for systemic delivery of antisense DNA Biomacromolecules 2 2001 491 497
91. E.R. Gillies, and J.M.J. Fréchet A new approach towards acid sensitive copolymer micelles for drug delivery Chem. Commun. 2003 1640 1641
92. M.C. Jones, M. Ranger, and J.C. Leroux pH-sensitive unimolecular polymeric micelles: synthesis of a novel drug carrier Bioconjug. Chem. 14 2003 774 781
93. V.P. Sant, D. Smith, and J.C. Leroux Enhancement of oral bioavailability of poorly water-soluble drugs by poly(ethylene glycol)-block-poly(alkyl acrylate-co-methacrylic acid) self-assemblies J. Control. Release 104 2005 289 300
94. N.Y. Rapoport, D.A. Christensen, H.D. Fain, L. Barrows, and Z. Gao Ultrasound-triggered drug targeting of tumors in vitro and in vivo Ultrasonics 42 2004 943 950
95. N. Rapoport, W.G. Pitt, H. Sun, and J.L. Nelson Drug delivery in polymeric micelles: from in vitro to in vivo J. Control. Release 91 2003 85 95
96. N. Rapoport Combined cancer therapy by micellar-encapsulated drug and ultrasound Int. J. Pharm. 277 2004 155 162
97. J.E. Chung, M. Yokoyama, T. Aoyagi, Y. Sakurai, and T. Okano Thermo-responsive drug delivery from polymeric micelles constructed using block copolymers of poly(N-isopropylacrylamide) and poly(butylmethacrylate) J. Control. Release 62 1999 115 127
98. J.E. Chung, M. Yokoyama, and T. Okano Inner core segment design for drug delivery control of thermo-responsive polymeric micelles J. Control. Release 65 2000 93 103
99. H. Gelderblom, J. Verweij, K. Nooter, and A. Sparreboom Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation Eur. J. Cancer 37 2001 1590 1598
100. R.T. Liggins, and H.M. Burt Polyether-polyester diblock copolymers for the preparation of paclitaxel loaded polymeric micelle formulations Adv. Drug Deliv. Rev. 54 2002 191 202
101. S.C. Kim, D.W. Kim, Y.H. Shim, J.S. Bang, H.S. Oh, S.W. Kim, and M.H. Seo In vivo evaluation of polymeric micellar paclitaxel formulation: toxicity and efficacy J. Control. Release 72 2001 191 202
102. T.Y. Kim, D.W. Kim, J.Y. Chung, S.G. Shin, S.C. Kim, D.S. Heo, N.K. Kim, and Y.J. Bang Phase I and pharmacokinetic study of Genexol-PM, a Cremophor-free, polymeric micelle-formulated paclitaxel, in patients with advanced malignancies Clin. Cancer Res. 10 2004 3708 3716
103. D. Le Garrec, S. Gori, L. Luo, D. Lessard, D.C. Smith, M.A. Yessine, M. Ranger, and J.C. Leroux Poly(N-vinylpyrrolidone)-block-poly(d,l-lactide) as a new polymeric solubilizer for hydrophobic anticancer drugs: in vitro and in vivo evaluation J. Control. Release 99 2004 83 101
104. D. Le Garrec, S. Gori, D. Karkan, L. Luo, D. Lessard, D. Smith, M. Ranger, M.A. Yessine, and J.C. Leroux Preparation, characterization, cytotoxicity and biodistribution of docetaxel-loaded polymeric micelle formulations J. Drug Deliv. Tech. 15 2005 115 120
105. K. Yasugi, T. Nakamura, Y. Nagasaki, M. Kato, and K. Kataoka Sugar-installed polymer micelles: synthesis and micellization of poly(ethylene glycol)-poly(d,l-lactide) block copolymers having sugar groups at the PEG chain end Macromolecules 32 1999 8024 8032
106. Y. Nagasaki, K. Yasugi, Y. Yamamoto, A. Harada, and K. Kataoka Sugar-installed block copolymer micelles: their preparation and specific interaction with lectin molecules Biomacromolecules 2 2001 1067 1070
107. D.W. Lim, Y.I. Yeom, and T.G. Park Poly(DMAEMA-NVP)-b-PEG-galactose as gene delivery vector for hepatocytes Bioconjug. Chem. 11 2000 688 695
108. M.J. Joralemon, K.S. Murthy, E.E. Remsen, M.L. Becker, and K.L. Wooley Synthesis, characterization and bioavailability of mannosylated shell cross-linked nanoparticles Biomacromolecules 5 2004 903 913
109. E. Jule, Y. Nagasaki, and K. Kataoka Lactose-installed poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles exhibit fast-rate binding and high affinity toward a protein bed simulating a cell surface. A surface plasmon resonance study Bioconjug. Chem. 14 2003 177 186
110. E.K. Park, S.B. Lee, and Y.M. Lee Preparation and characterization of methoxy poly(ethylene glycol)/poly(ε-caprolactone) amphiphilic block copolymeric nanospheres for tumor-specific folate-mediated targeting of anticancer drugs Biomaterials 26 2005 1053 1061
111. M. Ogris, G. Walker, T. Blessing, R. Kircheis, M. Wolschek, and E. Wagner Tumor-targeted gene therapy: strategies for the preparation of ligand-polyethylene glycol-polyethylenimine/DNA complexes J. Control. Release 91 2003 173 181
112. M.L. Becker, E.E. Remsen, D. Pan, and K.L. Wooley Peptide-derivatized shell-cross-linked nanoparticles: 1. Synthesis and characterization Bioconjug. Chem. 15 2004 699 709
113. T. Merdan, J. Callahan, H. Petersen, K. Kunath, U. Bakowsky, P. Kopecková, T. Kissel, and J. Kopecek Pegylated polyethylenimine-Fab' antibody fragment conjugates for targeted gene delivery to human ovarian carcinoma cells Bioconjug. Chem. 14 2003 989 996