Polymeric micelles from poly(ethylene glycol)-poly(amino acid) block copolymer for drug and gene delivery

Journal of the Royal Society Interface

Volumn 6, Issue SUPPL. 3, 2009, Pages

  Osada, Kensuke ^a   Christie, R James ^a   Kataoka, Kazunori ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Block copolymer; Cancer therapy; Drug delivery systems; Nanomedicine; Non viral gene delivery; Polymeric micelle

Indexed keywords

AMINES; AMINO ACIDS; BIOMATERIALS; BLOCK COPOLYMERS; COPOLYMERIZATION; DRUG DELIVERY; ETHYLENE; ETHYLENE GLYCOL; FUNCTIONAL POLYMERS; GENE TRANSFER; MEDICAL NANOTECHNOLOGY; MICELLES; NANOBIOTECHNOLOGY; ORGANIC ACIDS; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES;

CANCER THERAPY; DRUG DELIVERY SYSTEMS; NANOMEDICINE; NON-VIRAL GENE DELIVERY; POLYMERIC MICELLE;

POLYMERS;

AMINO ACID DERIVATIVE; BIOMATERIAL; COPOLYMER; MACROGOL; POLYMER;

BIOTECHNOLOGY; CANCER THERAPY; DRUG DELIVERY SYSTEM; GENE TARGETING; JAPAN; LYSOSOME; MEDICAL RESEARCH; MICELLE; PH; REVIEW;

EID: 67049134437     PISSN: 17425689     EISSN: 17425662     Source Type: Journal    
DOI: 10.1098/rsif.2008.0547.focus     Document Type: Review

References (129)

1. Aiuti, A. et al. 2002 Correction of ADA-SCID by stem cell gene therapy combined with nonmyeloablative conditioning. Science 296, 2410-2413. (doi:10.1126/science.1070104) (Pubitemid 34734219)
2. Akagi, D., Oba, M., Koyama, H., Nishiyama, N., Fukushima, S., Miyata, T., Nagawa, H. & Kataoka, K. 2007 Biocompatible micellar nanovectors achieve efficient gene transfer to vascular lesions without cytotoxicity and thrombus formation. Gene Ther. 14, 1029-1038. (doi:10.1038/sj.gt.3302945) (Pubitemid 46965272)
3. Arnida, Nishiyama, N., Kanayama, N., Jang, W. D., Yamasaki, Y. & Kataoka, K. 2006 PEGylated gene nanocarriers based on block catiomers bearing ethylene-diamine repeating units directed to remarkable enhancement of photochemical transfection. J. Control. Release 115, 208-215. (doi:10.1016/j.jconrel.2006.07.014) (Pubitemid 44537495)
4. Bader, H. R., Ringsdorf, H. & Schmidt, B. 1984 Watersoluble polymers in medicine. Angew. Makromol. Chem. 123/124, 457-485.
5. Bae, Y., Fukushima, S., Harada, A. & Kataoka, K. 2003a 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. (doi:10.1002/anie.200250653)
6. Bae, Y., Fukushima, S., Harada, A. & Kataoka, K. 2003b Preparation and characterization of pH responsive adriamycin-loaded polymeric micelles: drug release profile and in vitro cytotoxicity on human lung cancer SBC-3. J. Control. Release 91, 237-239.
7. Bae, Y., Jang, W. D., Nishiyama, N., Fukushima, S. & Kataoka, K. 2005a Multifunctional polymeric micelles with folate-mediated cancer cell targeting and pH-triggered drug releasing properties for active intracellular drug delivery. Mol. Biosyst. 1, 242-250. (doi:10.1039/b500266d)
8. Bae, Y., Nishiyama, N., Fukushima, S., Koyama, H., Yasuhiro, M. & Kataoka, K. 2005b 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, 122-130. (doi:10.1021/bc0498166)
9. Bogdanov, A., Wright, S. C., Marecos, E. M., Bogdanova, A., Martin, C., Petherick, P. & Weissleder, R. 1997 A long-circulating co-polymer in 'passive targeting' to solid tumors. J. Drug Target. 4, 321-330. (doi:10.3109/10611869708995848)
10. Boussif, O., Lezoualch, F., Zanta, M. A., Mergny, M. D., Scherman, D., Demeneix, B. & Behr, J. P. 1995 A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo - polyethylenimine. Proc. Natl Acad. Sci. USA 92, 7297-7301. (doi:10.1073/pnas.92.16.7297)
11. Brooks, P. C., Clark, R. A. F. & Cheresh, D. A. 1994 Requirement of vascular integrin alpha(V)beta(3) for angiogenesis. Science 264, 569-571. (doi:10.1126/science.7512751)
12. Cabral, H., Nishiyama, N., Okazaki, S., Koyama, H. & Kataoka, K. 2005 Preparation and biological properties of dichloro(1,2-diaminocyclohexane) platinum(II) (DACHPt)-loaded polymeric micelles. J. Control. Release 101, 223-232. (doi:10.1016/j.jconrel.2004.08.022) (Pubitemid 39600985)
13. Cabral, H., Nishiyama, N. & Kataoka, K. 2007 Optimization of (1,2-diamino-cyclohexane)platinum(II )-loaded polymeric micelles directed to improved tumor targeting and enhanced antitumor activity. J. Control. Release 121, 146-155. (doi:10.1016/j.jconrel.2007.05.024) (Pubitemid 47212536)
14. Cavazzana-Calvo, M. et al. 2000 Gene therapy of human severe combined immunodeficiency (SCID)-X1 disease. Science 288, 669-672. (doi:10.1126/science. 288.5466.669) (Pubitemid 30241569)
15. Christie, R. J. & Grainger, D. W. 2003 Design strategies to improve soluble macromolecular delivery constructs. Adv. Drug Deliv. Rev. 55, 421-437. (doi:10.1016/S0169-409X(02)00229-6)
16. Davis, M. E., Chen, Z. & Shin, D. M. 2008 Nanoparticle therapeutics: an emerging treatment modality for cancer. Nat. Rev. Drug Discov. 7, 771-782. (doi:10.1038/nrd2614)
17. Duncan, R. 2003 The dawning era of polymer therapeutics. Nat. Rev. Drug Discov. 2, 347-360. (doi:10.1038/nrd1088)
18. Folkman, J. et al. 1971 Tumor angiogenesis - therapeutic implications. N. Engl. J. Med. 285, 1182-1186.
19. Fukushima, S., Miyata, K., Nishiyama, N., Kanayama, N., Yamasaki, Y. & Kataoka, K. 2005 PEGylated polyplex micelles from triblock catiomers with spatially ordered layering of condensed pDNA and buffering units for enhanced intracellular gene delivery. J. Am. Chem. Soc. 127, 2810-2811. (doi:10.1021/ja0440506)
20. Gebhart, C. L. & Kabanov, A. V. 2001 Evaluation of polyplexes as gene transfer agents. J. Control. Release 73, 401-416. (doi:10.1016/S0168-3659(01) 00357-1)
21. Gianasi, E., Wasil, M., Evagorou, E. G., Keddle, A., Wilson, G. & Duncan, R. 1999 HPMA copolymer platinates as novel antitumour agents: in vitro properties, pharmacokinetics and antitumour activity in vivo. Eur. J. Cancer 35, 994-1002. (doi:10.1016/S0959-8049(99)00030-1) (Pubitemid 29277137)
22. Glover, D. J., Lipps, H. J. & Jans, D. A. 2005 Towards safe, non-viral therapeutic gene expression in humans. Nat. Rev. Genet. 6, 299-310. (doi:10.1038/nrg1577)
23. Gref, R., Minamitake, Y., Peracchia, M. T., Trubetskoy, V., Torchilin, V. & Langer, R. 1994 Biodegradable long-circulating polymeric nanospheres. Science 263, 1600-1603. (doi:10.1126/science.8128245) (Pubitemid 24128361)
24. Haag, R. 2004 Supramolecular drug-delivery systems based on polymeric core-shell architectures. Angew. Chem. Int. Ed. 43, 278-282. (doi:10.1002/anie.200301694)
25. Hacein-Bey-Abina, S. et al. 2003 LMO2-associated clonal T cell proliferation in two patients after gene therapy for SCID-X1. Science 302, 415-419. (doi:10.1126/science.1088547) (Pubitemid 37296260)
26. Hamaguchi, T. et al. 2005 NK105, a paclitaxel-incorporating micellar nanoparticle formulation, can extend in vivo antitumour activity and reduce the neurotoxicity of paclitaxel. Br. J. Cancer 92, 1240-1246. (doi:10.1038/sj.bjc. 6602479) (Pubitemid 40604398)
27. Hamaguchi, T. et al. 2007 A phase I and pharmacokinetic study of NK105, a paclitaxel-incorporating micellar nanoparticle formulation. Br. J. Cancer 97, 170-176. (doi:10.1038/sj.bjc.6603855) (Pubitemid 47057476)
28. Han, M., Bae, Y., Nishiyama, N., Miyata, K., Oba, M. & Kataoka, K. 2007 Transfection study using multicellular tumor spheroids for screening non-viral polymeric gene vectors with low cytotoxicity and high transfection efficiencies. J. Control. Release 121, 38-48. (doi:10.1016/j.jconrel.2007.05. 012) (Pubitemid 47126063)
29. Harada, A. & Kataoka, K. 1995 Formation of polyion complex micelles in an aqueous milieu from a pair of oppositely-charged block-copolymers with poly(ethylene glycol) segments. Macromolecules 28, 5294-5299. (doi:10.1021/ma00119a019)
30. Harada, A. & Kataoka, K. 1999 Chain length recognition: core-shell supramolecular assembly from oppositely charged block copolymers. Science 283, 65-67. (doi:10.1126/science.283.5398.65) (Pubitemid 29044846)
31. Harada-Shiba, M., Yamauchi, K., Harada, A., Takamisawa, I., Shimokado, K. & Kataoka, K. 2002 Polyion complex micelles as vectors in gene therapy - pharmacokinetics and in vivo gene transfer. Gene Ther. 9, 407-414. (doi:10.1038/sj.gt.3301665) (Pubitemid 34414039)
32. Hood, J. D., Bednarski, M., Frausto, R., Guccione, S., Reisfeld, R. A., Xiang, R. & Cheresh, D. A. 2002 Tumor regression by targeted gene delivery to the neovasculature. Science 296, 2404-2407. (doi:10.1126/science.1070200) (Pubitemid 34734217)
33. Ideta, R. et al. 2005 Nanotechnology-based photodynamic therapy for neovascular disease using a supramolecular nanocarrier loaded with a dendritic photosensitizer. Nano Lett. 5, 2426-2431. (doi:10.1021/nl051679d) (Pubitemid 43088890)
34. Imai, Y., Kaneko, E., Asano, T., Kumagai, M., Ai, M., Kawakami, A., Kataoka, K. & Shimokado, K. 2007 A novel contrast medium detects increased permeability of rat injured carotid arteries in magnetic resonance T2 mapping imaging. J. Atheroscler. Thromb. 14, 65-71.
35. Itaka, K., Yamauchi, K., Harada, A., Nakamura, K., Kawaguchi, H. & Kataoka, K. 2003 Polyion complex micelles from plasmid DNA and poly(ethylene glycol)-poly(L-lysine) block copolymer as serum-tolerable polyplex system: physicochemical properties of micelles relevant to gene transfection efficiency. Biomaterials 24, 4495-4506. (doi:10.1016/S0142-9612(03)00347-8) (Pubitemid 36960144)
36. a directed to enhance intracellular gene silencing. J. Am. Chem. Soc. 126, 13 612-13 613. (doi:10.1021/ja047174r)
37. Itaka, K., Ohba, S., Miyata, K., Kawaguchi, H., Nakamura, K., Takato, T., Chung, U. I. & Kataoka, K. 2007 Bone regeneration by regulated in vivo gene transfer using biocompatible polyplex nanomicelles. Mol. Ther. 15, 1655-1662. (doi:10.1038/sj.mt.6300218)
38. Jang, W. D. et al. 2005 Supramolecular nanocarrier of anionic dendrimer porphyrins with cationic block copolymers modified with polyethylene glycol to enhance intracellular photodynamic efficacy. Angew. Chem. Int. Ed. 44, 419-423. (doi:10.1002/anie.200461603)
39. Jang, W. D., Nakagishi, Y., Nishiyama, N., Kawauchi, S., Morimoto, Y., Kikuchi, M. & Kataoka, K. 2006 Polyion complex micelles for photodynamic therapy: incorporation of dendritic photosensitizer excitable at long wavelength relevant to improved tissue-penetrating property. J. Control. Release 113, 73-79. (doi:10.1016/j.jconrel.2006.03.009) (Pubitemid 43818161)
40. Jang, W. D., Nishiyama, N. & Kataoka, K. 2007 Supramolecular assembly of photofunctional dendrimers for biomedical nano-devices. Supramol. Chem. 19, 309-314. (doi:10.1080/10610270701324089)
41. Jaturanpinyo, M., Harada, A., Yuan, X. F. & Kataoka, K. 2004 Preparation of bionanoreactor based on core-shell structured polyion complex micelles entrapping trypsin in the core cross-linked with glutaraldehyde. Bioconjug. Chem. 15, 344-348. (doi:10.1021/bc034149m)
42. Jeon, S. I., Lee, J. H., Andrade, J. D. & Degennes, P. G. 1991 Protein surface interactions in the presence of polyethylene oxide; 1. Simplified theory. J. Colloid Interface Sci. 142, 149-158. (doi:10.1016/0021- 9797(91)90043-8)
43. Jeong, Y. I., Seo, S. J., Park, I. K., Lee, H. C., Kang, I. C., Akaike, T. & Cho, C. S. 2005 Cellular recognition of paclitaxel-loaded polymeric nanoparticles composed of poly(γ-benzyl L-glutamate) and poly(ethylene glycol) diblock copolymer endcapped with galactose moiety. Int. J. Pharm. 296, 151-161. (doi:10.1016/j.ijpharm.2005.02.027)
44. Jones, M. C. & Leroux, J. C. 1999 Polymeric micelles - a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 48, 101-111. (doi:10.1016/S0939-6411(99)00039-9)
45. Kabanov, A. V., Bronich, T. K., Kabanov, V. A., Yu, K. & Eisenberg, A. 1996 Soluble stoichiometric complexes from poly(N-ethyl-4-vinylpyridinium) cations and poly(ethylene oxide)-block-polymethacrylate anions. Macromolecules 29, 6797-6802. (doi:10.1021/ma960120k) (Pubitemid 126536654)
46. Kabanov, A. V., Lemieux, P., Vinogradov, S. & Alakhov, V. 2002 Pluronic((R)) block copolymers: novel functional molecules for gene therapy. Adv. Drug Deliv. Rev. 54, 223-233. (doi:10.1016/S0169-409X(02)00018-2)
47. Kakizawa, Y., Harada, A. & Kataoka, K. 1999 Environment-sensitive stabilization of core-shell structured polyion complex micelle by reversible cross-linking of the core through disulfide bond. J. Am. Chem. Soc. 121, 11 247-11 248. (doi:10.1021/ja993057y)
48. Kakizawa, Y., Furukawa, S., Ishii, A. & Kataoka, K. 2006 Organic-inorganic hybrid-nanocarrier of siRNA constructing through the self-assembly of calcium phosphate and PEG-based block aniomer. J. Control. Release 111, 368-370. (doi:10.1016/j.jconrel.2006.01.004)
49. Kanayama, N., Fukushima, S., Nishiyama, N., Itaka, K., Jang, W. D., Miyata, K., Yamasaki, Y., Chung, U. I. & Kataoka, K. 2006 A PEG-based biocompatible block catiomer with high buffering capacity for the construction of polyplex micelles showing efficient gene transfer toward primary cells. ChemMedChem 1, 439-444. (doi:10.1002/cmdc.200600008)
50. Kano, M. R. et al. 2007 Improvement of cancer-targeting therapy, using nanocarriers for intractable solid tumors by inhibition of TGF-beta signaling. Proc. Natl Acad. Sci. USA 104, 3460-3465. (doi:10.1073/pnas.0611660104)
51. Kataoka, K., Kwon, G. S., Yokoyama, M., Okano, T. & Sakurai, Y. 1993 Block-copolymer micelles as vehicles for drug delivery. J. Control. Release 24, 119-132. (doi:10.1016/0168-3659(93)90172-2) (Pubitemid 23161325)
52. Kataoka, K., Togawa, H., Harada, A., Yasugi, K., Matsumoto, T. & Katayose, S. 1996 Spontaneous formation of polyion complex micelles with narrow distribution from antisense oligonucleotide and cationic block copolymer in physiological saline. Macromolecules 29, 8556-8557. (doi:10.1021/ma961217C)
53. Kataoka, K., Ishihara, A., Harada, A. & Miyazaki, H. 1998 Effect of the secondary structure of poly(L-lysine) segments on the micellization in aqueous milieu of poly (ethylene glycol)-poly(L-lysine) block copolymer partially substituted with a hydrocinnamoyl group at the N-epsilon-position. Macromolecules 31, 6071-6076. (doi:10.1021/ma971838i) (Pubitemid 128563383)
54. Kataoka, K., Harada, A., Wakebayashi, D. & Nagasaki, Y. 1999 Polyion complex micelles with reactive aldehyde groups on their surface from plasmid DNA and end-functionalized charged block copolymers. Macromolecules 32, 6892-6894. (doi:10.1021/ma990973n)
55. Katayose, S. & Kataoka, K. 1997 Water-soluble polyion complex associates of DNA and poly(ethylene glycol)-poly(L-lysine) block copolymer. Bioconjug. Chem. 8, 702-707. (doi:10.1021/bc9701306)
56. Katayose, S. & Kataoka, K. 1998 Remarkable increase in nuclease resistance of plasmid DNA through supramolecular assembly with poly(ethylene glycol)-poly(L-lysine) block copolymer. J. Pharm. Sci. 87, 160-163. (doi:10.1021/js970304s)
57. Kawamura, A., Harada, A., Kono, K. & Kataoka, K. 2007 Self-assembled nano-bioreactor from block ionomers with elevated and stabilized enzymatic function. Bioconjug. Chem. 18, 1555-1559. (doi:10.1021/bc070029t)
58. Kawano, T., Okuda, T. & Niidome, T. 2004 Biodistribution of DNA-complex of dendritic poly(L-lysine) after intravenous injection. Mol. Ther. 9, S315. (doi:10.1016/j.ymthe.2004.06.732)
59. Khalil, I. A., Kogure, K., Akita, H. & Harashima, H. 2006 Uptake pathways and subsequent intracellular trafficking in nonviral gene delivery. Pharmacol. Rev. 58, 32-45. (doi:10.1124/pr.58.1.8)
60. Kidani, Y., Inagaki, K., Saito, R. & Tsukagoshi, S. 1977 Synthesis and anti-tumor activities of platinum(II) complexes of 1,2-diaminocyclohexane isomers and their related derivatives. J. Clin. Hematol. Oncol. 7, 197-202.
61. Kidani, Y., Inagaki, K., Iigo, M., Hoshi, A. & Kuretani, K. 1978 Anti-tumor activity of 1,2-diaminocyclohexaneplatinum complexes against sarcoma-180 ascites form. J. Med. Chem. 21, 1315-1318. (doi:10.1021/jm00210a029)
62. Kim, W. J., Yockman, J. W., Lee, M., Jeong, J. H., Kim, Y. H. & Kim, S. W. 2005 Soluble Flt-1 gene delivery using PEI-g-PEG-RGD conjugate for anti-angiogenesis. J. Control. Release 106, 224-234. (doi:10.1016/j.jconrel. 2005.04.016) (Pubitemid 41140097)
63. Kim, W. J., Yockman, J. W., Jeong, J. H., Christensen, L. V., Lee, M., Kim, Y. H. & Kim, S. W. 2006 Anti-angiogenic inhibition of tumor growth by systemic delivery of PEI-g-PEG-RGD/pCMV-sFlt-1 complexes in tumor-bearing mice. J. Control. Release 114, 381-388. (doi:10.1016/j.jconrel.2006.05.029) (Pubitemid 44310812)
64. Kogure, K., Akita, H., Yamada, Y. & Harashima, H. 2008 Multifunctional envelope-type nano device (MEND) as a non-viral gene delivery system. Adv. Drug Deliv. Rev. 60, 559-571. (doi:10.1016/j.addr.2007.10.007)
65. Koizumi, F., Kitagawa, M., Negishi, T., Onda, T., Matsumoto, S., Hamaguchi, T. & Matsumura, Y. 2006 Novel SN-38-incorporating polymeric micelles, NK012, eradicate vascular endothelial growth factor-secreting bulky tumors. Cancer Res. 66, 10 048-10 056. (doi:10.1158/0008-5472.CAN-06-1605) (Pubitemid 44672058)
66. Kumagai, M. et al. 2007 Iron hydroxide nanoparticles coated with poly(ethylene glycol)-poly(aspartic acid) block copolymer as novel magnetic resonance contrast agents for in vivo cancer imaging. Colloids Surf. B Biointerfaces 56, 174-181. (doi:10.1016/j.colsurfb.2006.12.019) (Pubitemid 46467334)
67. Kwon, G., Naito, M., Yokoyama, M., Okano, T., Sakurai, Y.& Kataoka, K. 1993 Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl L-aspartate). Langmuir 9, 945-949. (doi:10.1021/la00028a012)
68. Kwon, G. S., Suwa, S., Yokoyama, M., Okano, T., Sakurai, Y. & Kataoka, K. 1994 Enhanced tumor accumulation and prolonged circulation times of micelle-forming poly (ethylene oxide-aspartate) block copolymer-adriamycin conjugates. J. Control. Release 29, 17-23. (doi:10.1016/0168-3659(94)) (Pubitemid 24104093)
69. Lavasanifar, A., Samuel, J. & Kwon, G. S. 2002 Poly(ethylene oxide)-block-poly(L-amino acid) micelles for drug delivery. Adv. Drug Deliv. Rev. 54, 169-190. (doi:10.1016/S0169-409X(02)00015-7)
70. Lee, E. S., Na, K. & Bae, Y. H. 2003 Polymeric micelle for tumor pH and folate-mediated targeting. J. Control. Release 91, 103-113. (doi:10.1016/S0168-3659(03)00239-6) (Pubitemid 37288881)
71. Lehrman, S. 1999 Virus treatment questioned after gene therapy death. Nature 401, 517-518. (doi:10.1038/43977)
72. Mann, A., Richa, R. & Ganguli, M. 2008 DNA condensation by poly-L-lysine at the single molecule level: role of DNA concentration and polymer length. J. Control. Release 125, 252-262. (doi:10.1016/j.jconrel.2007. 10.019)
73. Marshall, E. 1999 Clinical trials - gene therapy death prompts review of adenovirus vector. Science 286, 2244-2245. (doi:10.1126/science.286.5448.2244)
74. Masago, K., Itaka, K., Nishiyama, N., Chung, U. I. & Kataoka, K. 2007 Gene delivery with biocompatible cationic polymer: pharmacogenomic analysis on cell bioactivity. Biomaterials 28, 5169-5175. (doi:10.1016/j.biomaterials.2007. 07.019) (Pubitemid 47488486)
75. Mastrobattista, E., van der Aa, M. A. E. M., Hennink, W. E. & Crommelin, D. J. A. 2006 Artificial viruses: a nanotechnological approach to gene delivery. Nat. Rev. Drug Discov. 5, 115-121. (doi:10.1038/nrd1960)
76. Matsumoto, S., Christie, R. J., Nishiyama, N., Miyata, K., Ishii, A., Oba, M., Koyama, H., Yamasaki, Y. & Kataoka, K. 2009 Environment-responsive block copolymer micelles with a disulfide cross-linked core for enhanced siRNA delivery. Biomacromolecules 10, 119-127. (doi:10.1021/bm800985e)
77. Matsumura, Y. 2008 Poly (amino acid) micelle nanocarriers in preclinical and clinical studies. Adv. Drug Deliv. Rev. 60, 899-914. (doi:10.1016/j.addr. 2007.11.010)
78. Matsumura, Y. & Maeda, H. 1986 A new concept for macromolecular therapeutics in cancer-chemotherapy - mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res. 46, 6387-6392. (Pubitemid 17221789)
79. Meister, A. & Anderson, M. E. 1983 Glutathione. Annu. Rev. Biochem. 52, 711-760. (doi:10.1146/annurev.bi.52.070183.003431)
80. Merdan, T., Kopecek, J. & Kissel, T. 2002 Prospects for cationic polymers in gene and oligonucleotide therapy against cancer. Adv. Drug Deliv. Rev. 54, 715-758. (doi:10.1016/S0169-409X(02)00046-7)
81. Miyata, K., Kakizawa, Y., Nishiyama, N., Harada, A., Yamasaki, Y., Koyama, H. & Kataoka, K. 2004 Block catiomer polyplexes with regulated densities of charge and disulfide cross-linking directed to enhance gene expression. J. Am. Chem. Soc. 126, 2355-2361. (doi:10.1021/ja0379666)
82. Miyata, K., Kakizawa, Y., Nishiyama, N., Yamasaki, Y., Watanabe, T., Kohara, M. & Kataoka, K. 2005 Freeze-dried formulations for in vivo gene delivery of PEGylated polyplex micelles with disulfide crosslinked cores to the liver. J. Control. Release 109, 15-23. (doi:10.1016/j.jconrel.2005.09.043) (Pubitemid 41737249)
83. Nagasaki, Y., Yasugi, K., Yamamoto, Y., Harada, A. & Kataoka, K. 2001 Sugar-installed block copolymer micelles: their preparation and specific interaction with lectin molecules. Biomacromolecules 2, 1067-1070. (doi:10.1021/bm015574q) (Pubitemid 34026879)
84. Nah, J. W., Yu, L., Han, S. O., Ahn, C. H. & Kim, S. W. 2002 Artery wall binding peptide-poly (ethylene glycol)-grafted-poly(L-lysine)-based gene delivery to artery wall cells. J. Control. Release 78, 273-284. (doi:10.1016/S0168-3659(01)00499-0) (Pubitemid 34081872)
85. Nakanishi, M., Park, J. S., Jang, W. D., Oba, M. & Kataoka, K. 2007 Study of the quantitative aminolysis reaction of poly(β-benzyl L-aspartate) (PBLA) as a platform polymer for functionality materials. React. Funct. Polym. 67, 1361-1372. (doi:10.1016/j.reactfunctpolym.2007.08.009)
86. Nasongkla, N., Shuai, X., Ai, H., Weinberg, B. D., Pink, J., Boothman, D. A. & Gao, J. M. 2004 cRGD-functionalized polymer micelles for targeted doxorubicin delivery. Angew. Chem. Int. Ed. 43, 6323-6327. (doi:10.1002/anie. 200460800)
87. Niidome, T. & Huang, L. 2002 Gene therapy progress and prospects: nonviral vectors. Gene Ther. 9, 1647-1652. (doi:10.1038/sj.gt.3301923) (Pubitemid 36104607)
88. Nishiyama, N. & Kataoka, K. 2006 Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol. Ther. 112, 630-648. (doi:10.1016/j.pharmthera.2006.05.006)
89. Nishiyama, N., Yokoyama, M., Aoyagi, T., Okano, T., Sakurai, Y. & Kataoka, K. 1999 Preparation and characterization of self-assembled polymer-metal complex micelle from cis-dichlorodiammineplatinum(II ) and poly (ethylene glycol)-poly(α,β-aspartic acid) block copolymer in an aqueous medium. Langmuir 15, 377-383. (doi:10.1021/la980572l)
90. Nishiyama, N., Kato, Y., Sugiyama, Y. & Kataoka, K. 2001 Cisplatin-loaded polymer-metal complex micelle with time-modulated decaying property as a novel drug delivery system. Pharm. Res. 18, 1035-1041. (doi:10.1023/A:1010908916184)
91. Nishiyama, N., Okazaki, S., Cabral, H., Miyamoto, M., Kato, Y., Sugiyama, Y., Nishio, K., Matsumura, Y. & Kataoka, K. 2003 Novel cisplatin- incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res. 63, 8977-8983. (Pubitemid 38064079)
92. Nishiyama, N. et al. 2005 Light-induced gene transfer from packaged DNA enveloped in a dendrimeric photosensitizer. Nat. Mater. 4, 934-941. (doi:10.1038/nmat1524)
93. Nishiyama, N., Arnida, Jang, W. D., Date, K., Miyata, K. & Kataoka, K. 2006 Photochemical enhancement of transgene expression by polymeric micelles incorporating plasmid DNA and dendrimer-based photosensitizer. J. Drug Target. 14, 413-424. (doi:10.1080/10611860600834508) (Pubitemid 44207826)
94. Nishiyama, N., Jang, W. D. & Kataoka, K. 2007 Supramolecular nanocarriers integrated with dendrimers encapsulating photosensitizers for effective photodynamic therapy and photochemical gene delivery. N. J. Chem. 31, 1074-1082. (doi:10.1039/b616050f)
95. 5 integrins. Bioconjug. Chem. 18, 1415-1423. (doi:10.1021/bc0700133)
96. Osada, K. & Kataoka, K. 2006 Drug and gene delivery based on supramolecular assembly of PEG-polypeptide hybrid block copolymers. Pept. Hybrid Polym. 202, 113-153. (doi:10.1007/12-084)
97. Osada, K., Yamasaki, Y., Katayose, S. & Kataoka, K. 2005 A synthetic block copolymer regulates S1 nuclease fragmentation of supercoiled plasmid DNA. Angew. Chem. Int. Ed. 44, 3544-3548. (doi:10.1002/anie.200500201)
98. Otsuka, H., Nagasaki, Y. & Kataoka, K. 2001 Self-assembly of poly(ethylene glycol)-based block copolymers for biomedical applications. Curr. Opin. Colloid Interface Sci. 6, 3-10. (doi:10.1016/S1359-0294(00)00082-0)
99. Oupicky, D., Konak, C., Ulbrich, K., Wolfert, M. A. & Seymour, L. W. 2000 DNA delivery systems based on complexes of DNA with synthetic polycations and their copolymers. J. Control. Release 65, 149-171. (doi:10.1016/S0168- 3659(99)00249-7) (Pubitemid 30122923)
100. Pack, D. W., Hoffman, A. S., Pun, S. & Stayton, P. S. 2005 Design and development of polymers for gene delivery. Nat. Rev. Drug Discov. 4, 581-593. (doi:10.1038/nrd1775)
101. Rixe, O., Ortuzar, W., Alvarez, M., Parker, R., Reed, E., Paull, K. & Fojo, T. 1996 Oxaliplatin, tetraplatin, cisplatin, and carboplatin: spectrum of activity in drug-resistant cell lines and in the cell lines of the National Cancer Institute's Anticancer Drug Screen panel. Biochem. Pharmacol. 52, 1855-1865. (doi:10.1016/S0006-2952(97)81490-6)
102. Rosenber, B., Vancamp, L., Trosko, J. E. & Mansour, V. H. 1969 Platinum compounds - a new class of potent antitumour agents. Nature 222, 385-386. (doi:10.1038/222385a0)
103. Schiffelers, R. M. et al. 2004 Cancer siRNA therapy by tumor selective delivery with ligand-targeted sterically stabilized nanoparticle. Nucleic Acids Res. 32, e149. (doi:10.1093/nar/gnh140)
104. Schmidt, J. A., Marshall, J., Hayman, M. J., Ponka, P. & Beug, H. 1986 Control of erythroid-differentiation - possible role of the transferrin cycle. Cell 46, 41-51. (doi:10.1016/0092-8674(86)90858-5) (Pubitemid 16027825)
105. Sorokin, L. M., Morgan, E. H. & Yeoh, G. C. T. 1989 Transformation-induced changes in transferrin and iron-metabolism in myogenic cells. Cancer Res. 49, 1941-1947. (Pubitemid 19106494)
106. Sumitomo, M., Koizumi, F., Asano, T., Horiguchi, A., Ito, K., Asano, T., Kakizoe, T., Hayakawa, M. & Matsumura, Y. 2008 Novel SN-38-incorporated polymeric micelle, NK012, strongly suppresses renal cancer progression. Cancer Res. 68, 1631-1635. (doi:10.1158/0008-5472.CAN-07-6532)
107. Sutton, D., Nasongkla, N., Blanco, E. & Gao, J. M. 2007 Functionalized micellar systems for cancer targeted drug delivery. Pharm. Res. 24, 1029-1046. (doi:10.1007/s11095-006-9223-y)
108. Torchilin, V. P. 2001 Structure and design of polymeric surfactant-based drug delivery systems. J. Control. Release 73, 137-172. (doi:10.1016/S0168- 3659(01)00299-1)
109. Torchilin, V. P. 2007 Micellar nanocarriers: pharmaceutical perspectives. Pharm. Res. 24, 1-16. (doi:10.1007/s11095-006-9132-0)
110. Torchilin, V. P., Lukyanov, A. N., Gao, Z. G. & Papahadjopoulos- Sternberg, B. 2003 Immunomicelles: targeted pharmaceutical carriers for poorly soluble drugs. Proc. Natl Acad. Sci. USA 100, 6039-6044. (doi:10.1073/pnas. 0931428100)
111. Uchino, H. et al. 2005 Cisplatin-incorporating polymeric micelles (NC-6004) can reduce nephrotoxicity and neurotoxicity of cisplatin in rats. Br. J. Cancer 93, 678-687. (doi:10.1038/sj.bjc.6602772) (Pubitemid 41486459)
112. Wagner, E. & Kloeckner, J. 2006 Gene delivery using polymer therapeutics. Polym. Ther. I Polym. Drugs Conjug. Gene Deliv. Syst. 192, 135-173. (doi:10.1007/12-023)
113. Wakebayashi, D., Nishiyama, N., Yamasaki, Y., Itaka, K., Kanayama, N., Harada, A., Nagasaki, Y. & Kataoka, K. 2004 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, 653-664. (doi:10.1016/j.jconrel.2004.01.003) (Pubitemid 38340512)
114. Weitman, S. D., Lark, R. H., Coney, L. R., Fort, D. W., Frasca, V., Zurawski, V. R. & Kamen, B. A. 1992 Distribution of the folate receptor Gp38 in normal and malignant-cell lines and tissues. Cancer Res. 52, 3396-3401.
115. Wermuth, J., Goodman, S. L., Jonczyk, A. & Kessler, H. 1997 Stereoisomerism and biological activity of the selective and superactive avb3 integrin inhibitor cyclo (-RGDfV-) and its retro-inverso peptide. J.Am. Chem. Soc. 119, 1328-1335. (doi:10.1021/ja961908l)
116. Wickham, T. J. 2003 Ligand-directed targeting of genes to the site of disease. Nat. Med. 9, 135-139. (doi:10.1038/nm0103-135)
117. Wu, G. Y. & Wu, C. H. 1988 Receptor-mediated gene delivery and expression in vivo. J. Biol. Chem. 263, 14 621-14 624.
118. Yamamoto, Y., Nagasaki, Y., Kato, M. & Kataoka, K. 1999 Surface charge modulation of poly(ethylene glycol)-poly (D,L-lactide) block copolymer micelles: conjugation of charged peptides. Colloids Surf. B Biointerfaces 16, 135-146. (doi:10.1016/S0927-7765(99)) (Pubitemid 29486801)
119. Yasugi, K., Nakamura, T., Nagasaki, Y., Kato, M. & Kataoka, K. 1999 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, 8024-8032. (doi:10.1021/ma991066l) (Pubitemid 30544933)
120. Yokoyama, M., Inoue, S., Kataoka, K., Yui, N. & Sakurai, Y. 1987 Preparation of adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer - a new type of polymeric anticanceragent. Makromol. Chem. Rapid Commun. 8, 431-435. (doi:10.1002/marc.1987.030080903)
121. Yokoyama, M., Inoue, S., Kataoka, K., Yui, N., Okano, T. & Sakurai, Y. 1989 Molecular design for missile drug - synthesis of adriamycin conjugated with immunoglobulin-G using poly(ethylene glycol)-block-poly (aspartic acid) as intermediate carrier. Makromol. Chem. Macromol. Chem. Phys. 190, 2041-2054.
122. Yokoyama, M., Miyauchi, M., Yamada, N., Okano, T., Sakurai, Y., Kataoka, K. & Inoue, S. 1990 Polymer micelles as novel drug carrier - adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer. J. Control. Release 11, 269-278. (doi:10.1016/0168-3659(90)90139-K) (Pubitemid 20070104)
123. Yokoyama, M., Okano, T., Sakurai, Y., Ekimoto, H., Shibazaki, C. & Kataoka, K. 1991 Toxicity and antitumor activity against solid tumors of micelle-forming polymeric anticancer drug and its extremely long circulation in blood. Cancer Res. 51, 3229-3236.
124. Yokoyama, M., Sugiyama, T., Okano, T., Sakurai, Y., Naito, M. & Kataoka, K. 1993 Analysis of micelle formation of an adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer by gel permeation chromatography. Pharm. Res. 10, 895-899. (doi:10.1023/A:1018921513605)
125. Yokoyama, M., Okano, T., Sakurai, Y., Suwa, S. & Kataoka, K. 1996 Introduction of cisplatin into polymeric micelle. J. Control. Release 39, 351-356. (doi:10.1016/0168-3659(95)00165-4) (Pubitemid 26195838)
126. Yokoyama, M., Okano, T., Sakurai, Y., Fukushima, S., Okamoto, K. & Kataoka, K. 1999 Selective delivery of adiramycin to a solid tumor using a polymeric micelle carrier system. J. Drug Target. 7, 171-186. (Pubitemid 30028961)
127. Yoo, H. S. & Park, T. G. 2004 Folate receptor targeted biodegradable polymeric doxorubicin micelles. J. Control. Release 96, 273-283. (doi:10.1016/j.jconrel.2004.02.003)
128. Yuan, X. F., Yamasaki, Y., Harada, A. & Kataoka, K. 2005 Characterization of stable lysozyme-entrapped polyion complex (PIC) micelles with crosslinked core by glutaraldehyde. Polymer 46, 7749-7758. (doi:10.1016/j.polymer.2005.02.121) (Pubitemid 41125236)
129. Zhang, C. X. & Lippard, S. J. 2003 New metal complexes as potential therapeutics. Curr. Opin. Chem. Biol. 7, 481-489. (doi:10.1016/S1367-5931(03) 00081-4)