Triggered destabilisation of polymeric micelles and vesicles by changing polymers polarity: An attractive tool for drug delivery

Journal of Controlled Release

Volumn 120, Issue 3, 2007, Pages 131-148

  Rijcken, C J F ^a   Soga, O ^a   Hennink, W E ^a   Nostrum, C F van ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Controlled release; Polymeric micelles; Responsive; Stimulus sensitive; Vesicles

Indexed keywords

CONTROLLED RELEASE; POLYMERIC MICELLES; STIMULUS SENSITIVE; VESICLES;

BLOCK COPOLYMERS; CONTROLLED DRUG DELIVERY; DRUG PRODUCTS; HYDROPHOBICITY; LIPOSOMES; POLYMERS;

MICELLES;

2,4,6 TRIMETHOXYBENZALDEHYDE; 6 [4 DEOXY 4 (2,4 TETRADECADIENOYLGLYCYLAMINO) GLYCERO BETA MANNOHEPTOPYRANOSYLAMINO] 9H PURINE; AMPHOTERICIN B; AZOBENZENE; BENZALDEHYDE DERIVATIVE; CISPLATIN; COPOLYMER; DOXORUBICIN; DRUG CARRIER; FENOFIBRATE; INDOMETACIN; MACROGOL; NANOPARTICLE; PHOTOSENSITIZING AGENT; POLYMER; UNCLASSIFIED DRUG;

BIODEGRADABILITY; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; HYDROLYSIS; HYDROPHOBICITY; ISOMERIZATION; MICELLE; MICELLIZATION; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW; TEMPERATURE; ULTRAVIOLET IRRADIATION;

DELAYED-ACTION PREPARATIONS; DENDRIMERS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; DRUG STABILITY; HEAT; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; INFRARED RAYS; LIGHT; MICELLES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NANOSTRUCTURES; POLYMERS; ULTRAVIOLET RAYS;

EID: 34447302274     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2007.03.023     Document Type: Review

References (194)

1. Crommelin D.J.A., Scherphof G., and Storm G. Active targeting with particulate carrier systems in the blood compartment. Adv. Drug Deliv. Rev. 17 (1995) 49-60
2. Gros L., Ringsdorf H., and Schupp H. Polymeric antitumor agents on a molecular and on a cellular level?. Angew. Chem., Int. Ed. Engl. 20 (1981) 305-325
3. Moses M.A., Brem H., and Langer R. Advancing the field of drug delivery: taking aim at cancer. Cancer Cells 4 (2003) 337-341
4. Duncan R. The dawning era of polymer therapeutics. Nat. Rev. Drug Discovery 2 (2003) 347-360
5. Crommelin D.J.A., Storm G., Jiskoot W., Stenekes R., Mastrobattista E., and Hennink W.E. Nanotechnological approaches for the delivery of macromolecules. J. Control. Release 87 (2003) 81-88
6. Crommelin D.J.A., and Storm G. Liposomes: from the bench to the bed. J. Liposome Res. 13 (2003) 33-36
7. Drummond D.C., Meyer O., Hong K., Kirpotin D.B., and Papahadjopoulos D. Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors. Pharmacol. Rev. 51 (1999) 691-743
8. Yamaguchi T., and Mizushima Y. Lipid microspheres for drug delivery from the pharmaceutical viewpoint. Crit. Rev. Ther. Drug Carr. Syst. 11 (1994) 215-229
9. Tamilvanan S. Oil-in-water lipid emulsions: implications for parenteral and ocular delivering systems. Prog. Lipid Res. 43 (2004) 489-533
10. Bala I., Hariharan S., and Kumar M.N. PLGA nanoparticles in drug delivery: the state of the art. Crit. Rev. Ther. Drug Carr. Syst. 21 (2004) 387-422
11. Panyam J., and Labhasetwar V. Biodegradable nanoparticles for drug and gene delivery to cells and tissue. Adv. Drug Deliv. Rev. 55 (2003) 329-347
12. Haag R. Supramolecular drug-delivery systems based on polymeric core-shell architectures. Angew. Chem., Int. Ed. Engl. 43 (2004) 278-282
13. Kataoka K., Harada A., and Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv. Drug Deliv. Rev. 47 (2001) 113-131
14. Kwon G.S. Polymeric micelles for delivery of poorly water-soluble compounds. Crit. Rev. Ther. Drug Carr. Syst. 20 (2003) 357-403
15. Discher D.E., and Eisenberg A. Polymer vesicles. Science 297 (2002) 967-973
16. Ahmed F., and Discher D.E. Self-porating polymersomes of PEG-PLA and PEG-PCL: hydrolysis-triggered controlled release vesicles. J. Control. Release 96 (2004) 37-53
17. Nori A., and Kopecek J. Intracellular targeting of polymer-bound drugs for cancer chemotherapy. Adv. Drug Deliv. Rev. 57 (2005) 609-636
18. Satchi-Fainaro R., Puder M., Davies J.W., Tran H.T., Sampson D.A., Greene A.K., Corfas G., and Folkman J. Targeting angiogenesis with a conjugate of HPMA copolymer and TNP-470. Nat. Med. 10 (2004) 255-261
19. Gillies E.R., and Frechet J.M.J. Dendrimers and dendritic polymers in drug delivery. Drug Discov. Today 10 (2005) 35-43
20. Aulenta F., Hayes W., and Rannard S. Dendrimers: a new class of nanoscopic containers and delivery devices. Eur. Polym. J. 39 (2003) 1741-1771
21. Zamboni W.C. Liposomal, nanoparticle and conjugated formulations of anticancer agents. Clin. Cancer Res. 11 (2005) 8230-8234
22. Torchilin V.P. Micellar nanocarriers: pharmaceutical perspectives. Pharm. Res. 24 (2007) 1-16
23. Forster S., and Plantenberg T. From self-organizing polymers to nanohybrid and biomaterials. Angew. Chem., Int. Ed. Engl. 41 (2002) 689-714
24. Riess G. Micellization of block copolymers. Prog. Polym. Sci. 28 (2003) 1107-1170
25. Harada A., and Kataoka K. Chain length recognition: core-shell supramolecular assembly from oppositely charged block copolymers. Science 283 (1999) 65-67
26. Kang N., Perron M.E., Prud'homme R.E., Zhang Y.B., Gaucher G., and Leroux J.C. Stereocomplex block copolymer micelles: core-shell nanostructures with enhanced stability. Nano Lett. 5 (2005) 315-319
27. Discher D.E., and Eisenberg A. Polymer vesicles. Science 297 (2002) 967-973
28. Bader H., Ringsdorf H., and Schmidt B. Water soluble polymers in medicine. Angew. Makromol. Chem. 123/124 (1984) 457-485
29. Yokoyama M., Kwon G.S., Okano T., Sakurai Y., Seto T., and Kataoka K. Preparation of micelle-forming polymer-drug conjugates. Bioconjug. Chem. 3 (1992) 295-301
30. Kabanov A.V., Chekhonin V.P., Alakhov V.Y., Batrakova E.V., Lebedev A.S., Melik-Nubarov N.S., Arzhakov S.A., Levashov A.V., Morozov G.V., Severin E.S., and Kabanov V.A. The neuroleptic activity of haloperidol increases after its solubilization in surfactant micelle. Micelles as microcontainers for drug targeting. FEBS Lett. 258 (1989) 343-345
31. Allen C., Maysinger D., and Eisenberg A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf., B Biointerface 16 (1999) 3-27
32. Adams M.L., Lavasanifar A., and Kwon G.S. Amphiphilic block copolymers for drug delivery. J. Pharm. Sci. 92 (2003) 1343-1355
33. Lavasanifar A., Samuel J., and Kwon G.S. Poly(ethylene oxide)-block-poly(l-amino acid) micelles for drug delivery. Adv. Drug Deliv. Rev. 54 (2002) 169-190
34. Jones M.C., and Leroux J.C. Polymeric micelles - a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 48 (1999) 101-111
35. Torchilin V.P. Structure and design of polymeric surfactant-based drug delivery systems. J. Control. Release 73 (2001) 137-172
36. Mathot F., van Beijsterveldt L., Preat V., Brewster M., and Arien A. Intestinal uptake and biodistribution of novel polymeric micelles after oral administration. J. Control. Release 111 (2006) 47-55
37. Sant V.P., Smith D., and Leroux J.-C. 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
38. Matsumura Y., and Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res. 46 (1986) 6387-6392
39. Maeda H., Wu J., Sawa T., Matsumura Y., and Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J. Control. Release 65 (2000) 271-284
40. Metselaar J.M., Bruin P., de Boer L.W., de Vringer T., Snel C., Oussoren C., Wauben M.H., Crommelin D.J.A., Storm G., and Hennink W.E. A novel family of L-amino acid-based biodegradable polymer-lipid conjugates for the development of long-circulating liposomes with effective drug-targeting capacity. Bioconjug. Chem. 14 (2003) 1156-1164
41. Stolnik S., Illum L., and Davis S.S. Long circulating microparticulate drug carriers. Adv. Drug Deliv. Rev. 16 (1995) 195-214
42. Kwon G., Suwa S., Yokoyama M., Okano T., Sakurai Y., and Kataoka K. Enhanced tumor accumulation and prolonged circulation times of micelle-forming poly (ethylene oxide-aspartate) block copolymer-adriamycin conjugates. J. Control. Release 29 (1994) 17-23
43. Avgoustakis K., Beletsi A., Panagi Z., Klepetsanis P., Livaniou E., Evangelatos G., and Ithakissios D.S. Effect of copolymer composition on the physicochemical characteristics, in vitro stability, and biodistribution of PLGA-mPEG nanoparticles. Int. J. Pharm. 259 (2003) 115-127
44. D. Neradovic, O. Soga, C.J. Snel, C. Oussoren, C.F. Van Nostrum, G. Storm, W.E. Hennink, Thermoresponsive Polymeric Nanoparticles with Controlled Instability, Thesis (2003) Chapter 6.
45. Sun X., Rossin R., Turner J.L., Becker M.L., Joralemon M.J., Welch M.J., and Wooley K.L. An assessment of the effects of shell cross linked nanoparticle size, core composition and surface pegylation on in vivo distribution. Biomacromolecules 6 (2005) 2541-2554
46. Yamamoto Y., Nagasaki Y., Kato Y., Sugiyama Y., and Kataoka K. Long-circulating poly(ethylene glycol)-poly(-lactide) block copolymer micelles with modulated surface charge. J. Control. Release 77 (2001) 27-38
47. Moghimi S.M., Hunter A.C., and Murray J.C. Long-circulating and target specific nanoparticles: theory to practice. Pharmacol. Rev. 53 (2001) 283-318
48. Savic R., Luo L., Eisenberg A., and Maysinger D. Micellar nanocontainers distribute to defined cytoplasmic organelles. Science 300 (2003) 615-618
49. Shuai X., Merdan T., Schaper A.K., Xi F., and Kissel T. Core-cross-linked polymeric micelles as paclitaxel carriers. Bioconjug. Chem. 15 (2004) 441-448
50. Rapoport N. Combined cancer therapy by micellar-encapsulated drug and ultrasound. Int. J. Pharm. 277 (2004) 155-162
51. Allen T.M. Ligand-targeted therapeutics in anticancer therapy. Nat. Rev., Cancer 2 (2002) 750-763
52. Seymour L.W., Duncan R., Strohalm J., and Kopecek J. 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 (1987) 1341-1358
53. Kabanov A.V., Lemieux P., Vinogradov S., and Alakhov V. Pluronic block copolymers: novel functional molecules for gene therapy. Adv. Drug Deliv. Rev. 54 (2002) 223-233
54. Francis M.F., Lavoie L., Winnik F.M., and Leroux J.C. Solubilization of cyclosporin A in dextran-g-polyethyleneglycolalkyl ether polymeric micelles. Eur. J. Pharm. Biopharm. 56 (2003) 337-346
55. Kakizawa Y., and Kataoka K. Block copolymer micelles for delivery of gene and related compounds. Adv. Drug Deliv. Rev. 54 (2002) 203-222
56. Woodle M.C., and Lasic D.D. Sterically stabilized liposomes. Biochim. Biophys. Acta 1113 (1992) 171-199
57. Molineux G. Pegylation: engineering improved pharmaceuticals for enhanced therapy. Cancer Treat. Rev. 28 (2002) 13-16
58. Lee J.H., Lee H.B., and Andrade J.D. Blood compatibility of polyethylene oxide surfaces. Prog. Polym. Sci. 20 (1995) 1043-1079
59. Benahmed A., Ranger M., and Leroux J.C. Novel polymeric micelles based on the amphiphilic diblock copolymer poly(N-vinyl-2-pyrrolidone)-block-poly(d,l-lactide). Pharm. Res. 18 (2001) 323-328
60. Inoue T., Chen G., Nakamae K., and Hoffman A.S. An AB block copolymer of oligo(methyl methacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drugs. J. Control. Release 51 (1998) 221-229
61. Kabanov A.V., Batrakova E.V., and Alakhov V.Y. Pluronic block copolymers as novel polymer therapeutics for drug and gene delivery. J. Control. Release 82 (2002) 189-212
62. Yokoyama M., Fukushima S., Uehara R., Okamoto K., Kataoka K., Sakurai Y., and Okano T. Characterization of physical entrapment and chemical conjugation of adriamycin in polymeric micelles and their design for in vivo delivery to a solid tumor. J. Control. Release 50 (1998) 79-92
63. Kwon G.S., Naito M., Yokoyama M., Okano T., Sakurai Y., and Kataoka K. Physical entrapment of adriamycin in AB block-copolymer micelles. Pharm. Res. 12 (1995) 192-195
64. Hagan S.A., Coombes A.G.A., Garnett M.C., Dunn S.E., Davis M.C., Illum L., Davis S.S., Harding S.E., Purkiss S., and Gellert P.R. Polylactide-poly(ethylene glycol) copolymers as drug delivery systems. 1. Characterization of water dispersible micelle-forming systems. Langmuir 12 (1996) 2153-2161
65. Liggins R.T., and Burt H.M. Polyether-polyester diblock copolymers for the preparation of paclitaxel loaded polymeric micelle formulations. Adv. Drug Deliv. Rev. 54 (2002) 191-202
66. Allen C., Han J., Yu Y., Maysinger D., and Eisenberg A. Polycaprolactone-b-poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosterone. J. Control. Release 63 (2000) 275-286
67. Letchford K., Zastre J., Liggins R., and Burt H. Synthesis and micellar characterization of short block length methoxy poly(ethylene glycol)-block-poly(caprolactone) diblock copolymers. Colloids Surf., B Biointerface 35 (2004) 81-91
68. Zhang Z., Grijpma D.W., and Feijen J. Thermo-sensitive transition of monomethoxy poly(ethylene glycol)-block-poly(trimethylene carbonate) films to micellar-like nanoparticles. J. Controlled. Release 112 (2006) 57-63
69. Nakanishi T., Fukushima S., Okamoto K., Suzuki M., Matsumura Y., Yokoyama M., Okano T., Sakurai Y., and Kataoka K. Development of the polymer micelle carrier system for doxorubicin. J. Control. Release 74 (2001) 295-302
70. Lee E.S., Na K., and Bae Y.H. Super pH-sensitive multifunctional polymeric micelle. Nano Lett. 5 (2005) 325-329
71. Hruby M., Konak C., and Ulbrich K. Polymeric micellar pH-sensitive drug delivery system for doxorubicin. J. Control. Release 103 (2005) 137-148
72. Kabanov A.V., Batrakova E.V., and Alakhov V.Y. Pluronic block copolymers for overcoming drug resistance in cancer. Adv. Drug Deliv. Rev. 54 (2002) 759-779
73. Gillies E.R., and Frechet J.M. pH-Responsive copolymer assemblies for controlled release of doxorubicin. Bioconjug. Chem. 16 (2005) 361-368
74. Kim S.C., Kim D.W., Shim Y.H., Bang J.S., Oh H.S., Wan Kim S., and Seo M.H. In vivo evaluation of polymeric micellar paclitaxel formulation: toxicity and efficacy. J. Control. Release 72 (2001) 191-202
75. Torchilin V.P., Lukyanov A.N., Gao Z., and Papahadjopoulos-Sternberg B. Immunomicelles: targeted pharmaceutical carriers for poorly soluble drugs. Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 6039-6044
76. Krishnadas A., Rubinstein I., and Onyuksel H. Sterically stabilized phospholipid mixed micelles: in vitro evaluation as a novel carrier for water-insoluble drugs. Pharm. Res. 20 (2003) 297-302
77. Cavallaro G., Licciardi M., Giammona G., Caliceti P., Semenzato A., and Salmaso S. Poly(hydroxyethylaspartamide) derivatives as colloidal drug carrier systems. J. Control. Release 89 (2003) 285-295
78. Hamaguchi T., Matsumura Y., Suzuki M., Shimizu K., Goda R., Nakamura I., Nakatomi I., Yokoyama M., Kataoka K., and Kakizoe T. NK105, a paclitaxel-incorporating micellar nanoparticle formulation, can extend in vivo antitumour activity and reduce the neurotoxicity of paclitaxel. Br. J. Cancer 92 (2005) 1240-1246
79. Huh K.M., Lee S.C., Cho Y.W., Lee J., Jeong J.H., and Park K. Hydrotropic polymer micelle system for delivery of paclitaxel. J. Control. Release 101 (2005) 59-68
80. Kim T.Y., Kim D.W., Chung J.Y., Shin S.G., Kim S.C., Heo D.S., Kim N.K., and Bang Y.J. 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
81. Nishiyama N., Okazaki S., Cabral H., Miyamoto M., Kato Y., Sugiyama Y., Nishio K., Matsumura Y., and Kataoka K. Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res. 63 (2003) 8977-8983
82. Nishiyama N., Kato Y., Sugiyama Y., and Kataoka K. Cisplatin-loaded polymer-metal complex micelle with time-modulated decaying property as a novel drug delivery system. Pharm. Res. 18 (2001) 1035-1041
83. Lavasanifar A., Samuel J., Sattari S., and Kwon G.S. Block copolymer micelles for the encapsulation and delivery of amphotericin B. Pharm. Res. 19 (2002) 418-422
84. Lin W.J., Juang L.W., and Lin C.C. Stability and release performance of a series of pegylated copolymeric micelles. Pharm. Res. 20 (2003) 668-673
85. Djordjevic J., Barch M., and Uhrich K.E. Polymeric micelles based on amphiphilic scorpion-like macromolecules: novel carriers for water-insoluble drugs. Pharm. Res. 22 (2005) 24-32
86. van Nostrum C.F. Polymeric micelles to deliver photosensitizers for photodynamic therapy. Adv. Drug Deliv. Rev. 56 (2004) 9-16
87. Zhang G.D., Harada A., Nishiyama N., Jiang D.L., Koyama H., Aida T., and Kataoka K. Polyion complex micelles entrapping cationic dendrimer porphyrin: effective photosensitizer for photodynamic therapy of cancer. J. Control. Release 93 (2003) 141-150
88. Le Garrec D., Taillefer J., Van Lier J.E., Lenaerts V., and Leroux J.C. Optimizing pH-responsive polymeric micelles for drug delivery in a cancer photodynamic therapy model. J. Drug Target. 10 (2002) 429-437
89. Yokoyama M., Satoh A., Sakurai Y., Okano T., Matsumura Y., Kakizoe T., and Kataoka K. Incorporation of water-insoluble anticancer drug into polymeric micelles and control of their particle size. J. Control. Release 55 (1998) 219-229
90. Matsumura Y., Yokoyama M., Kataoka K., Okano T., Sakurai Y., Kawaguchi T., and Kakizoe T. Reduction of the side effects of an antitumor agent, KRN5500, by incorporation of the drug into polymeric micelles. Jpn. J. Cancer Res. 90 (1999) 122-128
91. Taillefer J., Jones M.C., Brasseur N., van Lier J.E., and Leroux J.C. Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs. J. Pharm. Sci. 89 (2000) 52-62
92. Zhang X., Jackson J.K., and Burt H.M. Development of amphiphilic diblock copolymers as micellar carriers of taxol. Int. J. Pharm. 132 (1996) 195-206
93. Teng Y., Morrison M.E., Munk P., Webber S.E., and Prochazka K. Macromolecules 31 (1998) 3578-3587
94. Kim S.Y., Shin I.G., Lee Y.M., Cho C.S., and Sung Y.K. Methoxy poly(ethylene glycol) and epsilon-caprolactone amphiphilic block copolymeric micelle containing indomethacin. II. Micelle formation and drug release behaviours. J. Control. Release 51 (1998) 13-22
95. Kabanov A.V., Nazarova I.R., Astafieva I.V., Batrakova E.V., Alakhov V.Y., Yaroslavov A.A., and Kabanov V.A. Macromolecules 28 (1995) 2303-2314
96. Kwon G.S., Naito M., Kataoka K., Yokoyama M., Sakurai Y., and Okano T. Block copolymer micelles as vehicles for hydrophobic drugs. Colloids Surf., B Biointerface 2 (1994) 429-434
97. Wilhelm M., Zhao C.L., Wang Y.C., Xu R.L., Winnik M.A., Mura J.L., Riess G., and Croucher M.D. Polymer micelle formation. 3. Poly(styrene-ethylene oxide) block copolymer micelle formation in water - a fluorescence probe study. Macromolecules 24 (1991) 1033-1040
98. Zhao J.X., Allen C., and Eisenberg A. Partitioning of pyrene between "crew cut" block copolymer micelles and H2O/DMF solvent mixtures. Macromolecules 30 (1997) 7143-7150
99. Burt H.M., Zhang X.C., Toleikis P., Embree L., and Hunter W.L. Development of copolymers of poly(d,l-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel. Colloids Surf., B Biointerface 16 (1999) 161-171
100. Le Garrec D., Gori S., Luo L., Lessard D., Smith D.C., Yessine M.A., Ranger M., and Leroux J.C. 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
101. Lavasanifar A., Samuel J., and Kwon G.S. The effect of fatty acid substitution on the in vitro release of amphotericin B from micelles composed of poly(ethylene oxide)-block-poly(N-hexyl stearate-l-aspartamide). J. Control. Release 79 (2002) 165-172
102. Lavasanifar A., Samuel J., and Kwon G.S. The effect of alkyl core structure on micellar properties of poly(ethylene oxide)-block-poly(l-aspartamide) derivatives. Colloids Surf., B Biointerface 22 (2001) 115-126
103. Prompruk K., Govender T., Zhang S., Xiong C.D., and Stolnik S. Synthesis of a novel PEG-block-poly(aspartic acid-stat-phenylalanine) copolymer shows potential for formation of a micellar drug carrier. Int. J. Pharm. 297 (2005) 242-253
104. Yokoyama M., Okano T., Sakurai Y., and Kataoka K. Improved synthesis of adriamycin-conjugated poly (ethylene oxide)-poly (aspartic acid) block copolymer and formation of unimodal micellar structure with controlled amount of physically entrapped adriamycin. J. Control. Release 32 (1994) 269-277
105. Lee J., Lee S.C., Acharya G., Chang C.J., and Park K. Hydrotropic solubilization of paclitaxel: analysis of chemical structures for hydrotropic property. Pharm. Res. 20 (2003) 1022-1030
106. Jeong B., Bae Y.H., Lee D.S., and Kim S.W. Biodegradable block copolymers as injectable drug-delivery systems. Nature 388 (1997) 860-862
107. Chilkoti A., Dreher M.R., Meyer D.E., and Raucher D. Targeted drug delivery by thermally responsive polymers. Adv. Drug Deliv. Rev. 54 (2002) 613-630
108. Hoffman A.S., Stayton P.S., Volga B., Chen G., Chen J., Cheung C., Chilkoti A., Ding Z., Dong L., Fong R., Lackey C.A., Long C.J., Miura M., Morris J.E., Murthy N., Nabeshima Y., Park T.G., Press O.W., Shimoboji T., Shoemaker S., Yang H.J., Monji N., Nowinski R.C., Cole C.A., Priest J.H., Harris J.M., Nakamae K., Nishino T., and Miyata T. Really smart bioconjugates of smart polymers and receptor proteins. J. Biomed. Mater. Res. 52 (2000) 577-586
109. Pelton R. Temperature-sensitive aqueous microgels. Adv. Colloid Interface Sci. 85 (2000) 1-33
110. Schild H.G. Poly (N-isopropylacrylamide) - experiment, theory and application. Prog. Polym. Sci. 17 (1992) 163-249
111. Heskins M., and Guillet J.E. J. Macromol. Sci., Chem. A2 (1968) 1441-1455
112. Jeong B., Kim S.W., and Bae Y.H. Thermosensitive sol-gel reversible hydrogels. Adv. Drug Deliv. Rev. 54 (2002) 37-51
113. Huang X., and Lowe T.L. Biodegradable thermoresponsive hydrogels for aqueous encapsulation and controlled release of hydrophilic model drugs. Biomacromolecules 6 (2005) 2131-2139
114. Mori T., and Maeda M. Temperature-responsive formation of colloidal nanoparticles from poly(N-isopropylacrylamide) grafted with single-stranded DNA. Langmuir 20 (2004) 313-319
115. Kavanagh C.A., Gorelova T.A., Selezneva, Rochev Y.A., Dawson K.A., Gallagher W.M., Gorelov A.V., and Keenan A.K. Poly(N-isopropylacrylamide) copolymer films as vehicles for the sustained delivery of proteins to vascular endothelial cells. J. Biomed. Mater. Res. A 72 (2005) 25-35
116. Kono K. Thermosensitive polymer-modified liposomes. Adv. Drug Deliv. Rev. 53 (2001) 307-319
117. Leroux J., Roux E., Le Garrec D., Hong K., and Drummond D.C. N-isopropylacrylamide copolymers for the preparation of pH-sensitive liposomes and polymeric micelles. J. Control. Release 72 (2001) 71-84
118. Feil H., You H., Bae, Feijen J., Sung W., and Kim. Effect of comonomer hydrophilicity and ionization on the lower critical solution temperature of N-isopropylacrylamide copolymers. Macromolecules 26 (1993) 2496-2500
119. Shibayama M., Mizutani S., and Nomura S. Thermal properties of copolymer gels containing N-isopropylacrylamide. Macromolecules 29 (1996) 2019-2024
120. Chung J.E., Yokoyama M., and Okano T. Inner core segment design for drug delivery control of thermo-responsive polymeric micelles. J. Control. Release 65 (2000) 93-103
121. Kohori F., Sakai K., Aoyagi T., Yokoyama M., Yamato M., Sakurai Y., and Okano T. Control of adriamycin cytotoxic activity using thermally responsive polymeric micelles composed of poly(N-isopropylacrylamide-co-N,N-dimethylacrylamide)-b-poly(d,l-lactide). Colloids Surf., B Biointerface 16 (1999) 195-205
122. Zhang Y., Juang M., Zhao J., Ren X., Chen D., and Zhang G. A novel route to thermosensitive polymeric core-shell aggregates and hollow spheres in aqueous media. Adv. Funct. Mater. 15 (2005) 695-699
123. Topp M.D.C., Dijkstra P.J., Talsma H., and Feijen J. Thermosensitive micelle-forming block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide). Macromolecules 30 (1997) 8518-8520
124. Zhu P.W., and Napper D.H. Effect of heating rate on nanoparticle formation of poly(N-isopropylacrylamide)-poly(ethylene glycol) block copolymer microgels. Langmuir 16 (2000) 8543-8545
125. Qiu X.P., and Wu C. Study of the core-shell nanoparticle formed through the "coil-to-globule" transition of poly(N-isopropylacrylamide) grafted with poly(ethylene oxide). Macromolecules 30 (1997) 7921-7926
126. Neradovic D., Soga O., Van Nostrum C.F., and Hennink W.E. The effect of the processing and formulation parameters on the size of nanoparticles based on block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide) with and without hydrolytically sensitive groups. Biomaterials 25 (2004) 2409-2418
127. Sershen S.R., Westcott S.L., Halas N.J., and West J.L. Temperature-sensitive polymer-nanoshell composites for photothermally modulated drug delivery. J. Biomed. Mater. Res. 5 (2000) 293-298
128. Engin K., Leeper D.B., Cater J.R., Thistlethwaite A.J., Tupchong L., and McFarlane J.D. Extracellular pH distribution in human tumours. Int. J. Hypertherm. 11 (1995) 211-216
129. Ulbrich K., and Subr V. Polymeric anticancer drugs with pH-controlled activation. Adv. Drug Deliv. Rev. 56 (2004) 1023-1050
130. Gillies E.R., and Frechet J.M.J. Development of acid-sensitive copolymer micelles for drug delivery. Pure Appl. Chem. 78 (2004) 1295-1307
131. Dufresne M.-H., Garrec D.L., Sant V., Leroux J.-C., and Ranger M. Preparation and characterization of water-soluble pH-sensitive nanocarriers for drug delivery. Int. J. Pharm. 277 (2004) 81-90
132. Bronich T.K., Keifer P.A., Shlyakhtenko L.S., and Kabanov A.V. Polymer micelle with cross-linked ionic core. J. Am. Chem. Soc. 127 (2005) 8236-8237
133. Lee E.S., Shin H.J., Na K., and Bae Y.H. Poly(L-histidine)-PEG block copolymer micelles and pH-induced destabilization. J. Control. Release 90 (2003) 363-374
134. Lee E.S., Na K., and Bae Y.H. Polymeric micelle for tumor pH and folate-mediated targeting. J. Control. Release 91 (2003) 103-113
135. Martin T.J., Prochazka K., Munk P., and Webber S.E. pH-dependent micellization of poly(2-vinylpyridine)-block-poly(ethylene oxide). Macromolecules 29 (1996) 6071-6073
136. Lee A.S., Gast A.P., Butun V., and Armes S.P. Characterizing the structure of pH dependent polyelectrolyte block copolymer micelles. Macromolecules 32 (1999) 4302-4310
137. Tang Y., Liu S.Y., Armes S.P., and Billingham N.C. Solubilization and controlled release of a hydrophobic drug using novel micelle-forming ABC triblock copolymers. Biomacromolecules 4 (2003) 1636-1645
138. Borchert U., Lipprandt U., Bilang M., Kimpfler A., Rank A., Peschka R., Schubert R., Lindner P., and Forster S. pH-Induced release from P2VP-PEO block copolymer vesicles. Langmuir 22 (2006) 5843-5847
139. Bellomo E.G., Wyrsta M.D., Pakstis L., Pochan D.J., and Deming T.J. Stimuli-responsive polypeptide vesicles by conformation-specific assembly. Nat. Mater. 3 (2004) 244-248
140. Licciardi M., Giammona G., Du J., Armes S.P., Tang Y., and Lewis A.L. New folate-functionalized biocompatible block copolymer micelles as potential anti-cancer drug delivery systems. Polymer 47 (2006) 2946-2955
141. Giacomelli C., Le Men L., Borsali R., Lai-Kee-Him J., Brisson A., Armes S.P., and Lewis A.L. Phosphorylcholine-based pH-responsive diblock copolymer micelles as drug delivery vehicles: light scattering, electron microscopy, and fluorescence experiments. Biomacromolecules 7 (2006) 817-828
142. Jones M.C., Ranger M., and Leroux J.C. pH-sensitive unimolecular polymeric micelles: synthesis of a novel drug carrier. Bioconjug. Chem. 14 (2003) 774-781
143. Sant V.P., Smith D., and Leroux J.-C. Novel pH-sensitive supramolecular assemblies for oral delivery of poorly water soluble drugs: preparation and characterization. J. Control. Release 97 (2004) 301-312
144. Taillefer J., Jones M.C., Brasseur N., van Lier J.E., and Leroux J.C. Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs. J. Pharm. Sci. 89 (2000) 52-62
145. Taillefer J., Brasseur N., van Lier J.E., Lenaerts V., Le Garrec D., and Leroux J.C. In-vitro and in-vivo evaluation of pH-responsive polymeric micelles in a photodynamic cancer therapy model. J. Pharm. Pharmacol. 53 (2001) 155-166
146. Soppimath K.S., Tan D.C.-W., and Yang Y.-Y. pH-triggered thermally responsive polymer core-shell nanoparticles for drug delivery. Adv. Mater. 17 (2005) 318-323
147. Na K., and Bae K.H. Self-assembled hydrogel nanoparticles responsive to tumor extracellular pH from pullulan derivative/sulfonamide conjugate: characterization, aggregation, and adriamycin release in vitro. Pharm. Res. 19 (2002) 681-688
148. Na K., Lee K.H., and Bae Y.H. pH-sensitivity and pH-dependent interior structural change of self-assembled hydrogel nanoparticles of pullulan acetate/oligo-sulfonamide conjugate. J. Control. Release 97 (2004) 513-525
149. Kumar N., Ravikumar M.N., and Domb A.J. Biodegradable block copolymers. Adv. Drug Deliv. Rev. 53 (2001) 23-44
150. Lescure F., Seguin C., Breton P., Bourrinet P., Roy D., and Couvreur P. Preparation and characterization of novel poly(methylidene malonate 2.1.2.)-made nanoparticles. Pharm. Res. 11 (1994) 1270-1277
151. Shah S.S., Wertheim J., Wang C.T., and Pitt C.G. Polymer-drug conjugates: manipulating drug delivery kinetics using model LCST systems. J. Control. Release 45 (1997) 95-101
152. Neradovic D., Hinrichs W.L.J., Kettenes-van den Bosch J.J., van Nostrum C.F., and Hennink W.E. Poly(N-isopropylacrylamide) with hydrolyzable lactic acid ester side groups: a new type of thermosensitive polymer. Macromol. Rapid Commun. 20 (1999) 577-581
153. Lee B.H., and Vernon B. Copolymers of N-isopropylacrylamide HEMA-lactate and acrylic acid with time-dependent lower critical solution temperature as a bioresorbable carrier. Polym. Int. 54 (2005) 418-422
154. Neradovic D., Van Nostrum C.F., and Hennink W.E. Thermoresponsive polymeric micelles with controlled instability based on hydrolytically sensitive N-isopropylacrylamide copolymers. Macromolecules 34 (2001) 7589-7591
155. Soga O., Van Nostrum C.F., and Hennink W.E. Poly(N-2-hydroxylpropyl) methacrylamide mono/di lactate): a new class of biodegradable polymers with tuneable thermosensitivity. Biomacromolecules 5 (2004) 818-821
156. Soga O., Van Nostrum C.F., Ramzi A., Visser T., Soulimani F., Frederik P.M., Bomans P.H.H., and Hennink W.E. Physicochemical characterization of degradable thermosensitive polymeric micelles. Langmuir 20 (2004) 9388-9395
157. Soga O., Van Nostrum C.F., Fens M., Rijcken C.J.F., Schiffelers R.M., Storm G., and Hennink W.E. Thermosensitive and biodegradable polymeric micelles for paclitaxel delivery. J. Control. Release 103 (2005) 341-353
158. Rijcken C.J.F., Veldhuis T.F.J., Ramzi A., Meeldijk J.D., Van Nostrum C.F., and Hennink W.E. Novel fast degradable thermosensitive polymeric micelles based on PEG-block-poly(N-(2-hydroxyethyl)methacrylamide-oligolactates). Biomacromolecules 6 (2005) 2343-2351
159. Gillies E.R., and Frechet J.M. A new approach towards acid sensitive copolymer micelles for drug delivery. Chem. Commun. (Cambridge) 14 (2003) 1640-1641
160. Gillies E.R., Jonsson T.B., and Frechet J.M. Stimuli-responsive supramolecular assemblies of linear-dendritic copolymers. J. Am. Chem. Soc. 126 (2004) 11936-11943
161. Gillies E.R., and Frechet J.M. pH-Responsive copolymer assemblies for controlled release of doxorubicin. Bioconjug. Chem. 16 (2005) 361-368
162. Bae Y., Nishiyama N., Fukushima S., Koyama H., Yasuhiro M., and 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. Bioconjug. Chem. 16 (2005) 122-130
163. Bae Y., Fukushima S., Harada A., and Kataoka K. Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew. Chem., Int. Ed. Engl. 42 (2003) 4640-4643
164. Bae Y., Nishiyama N., Fukushima S., Koyama H., Yasuhori M., and Kataoka K. Preparation and biological characterization of polymeric micell 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
165. Napoli A., Valentini M., Tirelli N., Muller M., and Hubbell J.A. Oxidation-responsive polymeric vesicles. Nat. Mater. 3 (2004) 183-189
166. Napoli A., Boerakker M.J., Tirelli N., Nolte R.J., Sommerdijk N.A., and Hubbell J.A. Glucose-oxidase based self-destructing polymeric vesicles. Langmuir 20 (2004) 3487-3491
167. Katayama Y., Sonoda T., and Maeda M. Macromolecules 34 (2001) 8569-8573
168. Anton P., Heinze J., and Laschewsky A. Redox-active monomeric and polymeric surfactants. Langmuir 9 (1993) 77-85
169. Takeoka Y., Aoki T., Sanui K., Ogata N., Yokoyama M., Okano T., Sakurai Y., and Watanabe M. Electrochemical control of drug release from redox-active micelles. J. Control. Release 33 (1995) 79-87
170. Power-Billard K.N., and Manners S.R.J.I. Redox-active organometallic vesicles: aqueous self-assembly of a diblock copolymer with a hydrophilic polyferrocenylsilane polyelectrolyte block. Angew. Chem., Int. Ed. Engl. 43 (2004) 1260-1264
171. Säily V.M.J., Fyhänen S.J., Lankinen H., Luciani P., Mancini G., Parry M.J., and Kinnunen P.K.J. Impact of reductive cleavage of an intramolecular disulfide bond containing cationic gemini surfactant in monolayers and bilayers. Langmuir 22 (2006) 956-962
172. Mart R.J., Osborne R.D., Stevens M.M., and Ulijn R.V. Peptide-based stimuli-responsive biomaterials. Soft Matter 2 (2006) 822-835
173. Jiang J., Tong, and Zhao. A new design for light-breakable polymer micelles. J. Am. Chem. Soc. 127 (2005) 8290-8291
174. Jiang J., Tong X., Morris D., and Zhao Y. Toward photocontrolled release using light-dissociable block copolymer micelles. Macromolecules 39 (2006) 4633-4640
175. Goodwin A.P., Mynar J.L., Ma Y., Fleming G.R., and Frechet J.M.J. Synthetic micelle sensitive to IR light via a two-photon process. J. Am. Chem. Soc. 127 (2005) 9952-9953
176. Wang G., and Wang X. A novel hyperbranched polyester functionalized with azo chromophore: synthesis and photoresponsive properties. Polym. Bull. 49 (2002) 1-8
177. Pieroni O., Fissi A., and Popova G. Photochromic polypeptides. Prog. Polym. Sci. 23 (1998) 81-123
178. Minoura N., Higuchi M., and Kinoshita T. Stimuli-responsive formation of helical polypeptide rod assemblies. Mater. Sci. Eng., C, Biomim. Mater., Sens. Syst. 4 (1997) 249-254
179. Wang G., Tong X., and Zhao Y. Preparation of azobenzene-containing amphiphilic diblock copolymers for light-responsive micellar aggregates. Macromolecules 37 (2004) 8911-8917
180. Tong X., Wang G., Soldera A., and Zhao Y. How can azobenzene block copolymer vesicles be dissociated and reformed by light. J. Phys. Chem. B 109 (2005) 20281-20287
181. Liu X., and Jiang M. Optical switching of self-assembly: micellization and micelle-hollow-sphere transition of hydrogen-bonded polymers. Angew. Chem., Int. Ed. Engl. 45 (2006) 3846-3850
182. Han M.R., and Hara M. Chain length-dependent photoinduced formation of azobenzene aggregates. New J. Chem. 30 (2006) 223-227
183. Li Y., Deng Y., Tong X., and Wang X. Formation of photoresponsive uniform colloidal spheres from an amphiphilic azobenzen-containing random copolymer. Macromolecules 39 (2006) 1108-1115
184. Sugiyama K., and Sono K. Characterization of photo- and thermoresponsible amphiphilic copolymers having azobenzene moieties as side groups. J. Appl. Polym. Sci. 81 (2000) 3056-3063
185. Desponds A., and Freitag R. Synthesis and characterization of photoresponsive N-isopropylacrylamide cotelomers. Langmuir 19 (2003) 6261-6270
186. Ravi P., Sin S.L., Gan L.H., Gan Y.Y., Tam K.C., Xia X.L., and Hu X. New water soluble azobenzene-containing diblock copolymers: synthesis and aggregation behavior. Polymer 46 (2005) 137-146
187. Laschewsky A., and Rekai E.D. Photochemical modification of the lower critical solution temperature of cinnamoylated poly(N-2-hydropropylmethacrylamide) in water. Macromol. Rapid Commun. 21 (2000) 937-940
188. Szczubialka K., Moczek L., Blaskiewicz S., and Nowakowska M. Photocrosslinkable smart terpolymers responding to pH, temperature and ionic strength. J. Polym. Sci., Polym. Chem. Ed. 43 (2004) 3879-3886
189. Yuan Z., Fischer K., and Schärtl W. Photocleavable microcapsules built from photoreactive nanospheres. Langmuir 21 (2005) 9374-9380
190. Kono K., Nishihara Y., and Takagishi T. Photoresponsive permeability of polyelectrolyte complex capsule membrane containing triphenylmethane leucohydroxide residues. J. Appl. Polym. Sci. 56 (1995) 707-713
191. Konak C., Rathi R.C., Kopeckova P., and Kopecek J. Photoregulated association of water-soluble copolymers with spirobenzopyran-containing side chains. Macromolecules 30 (1997) 5553-5556
192. Konak C., Rathi R.C., Kopeckova P., and Kopecek J. Photoassociation of water-soluble copolymers containing photochromic spirobenzopyran moieties. Polym. Adv. Technol. 9 (1998) 641-648
193. Ivanov A.E., Eremeev N.L., Wahlund P.-O., Galaev I.Y., and Mattiasson B. Photosensitive copolymer of N-isopropylacrylamide and methacryloyl derivative of spyrobenzopyran. Polymer 43 (2002) 3819-3823
194. De Geest B.G., Jonas A.M., Demeester J., and De Smedt S.C. Glucose-responsive polyelectrolyte capsules. Langmuir 22 (2006) 5070-5074