Intelligent polymeric micelles from functional poly(ethylene glycol)-poly(amino acid) block copolymers

Atkins, 2002, Selective anticancer drugs, Nat. Rev. Cancer, 1, 645, 10.1038/nrc900 Duncan, 2003, The dawning era of polymer therapeutics, Nat. Rev. Drug. Discov., 2, 347, 10.1038/nrd1088 Maeda, 1989, Tumoritropic and lymphotropic principles of macromolecular drugs, Crit. Rev. Ther. Drugs, 6, 193 Putnam, 1995, Polymer conjugates with anticancer activity, Adv. Polym. Sci., 122, 55, 10.1007/3540587888_14 Kratz, 1999, Drug–polymer conjugates containing acid-cleavable bonds, Crit. Rev. Ther. Drugs, 16, 245, 10.1615/CritRevTherDrugCarrierSyst.v16.i3.10 Kataoka, 1993, Block copolymer micelles as vehicles for drug delivery, J. Control. Release, 24, 119, 10.1016/0168-3659(93)90172-2 Lian, 2001, Trends and developments in liposome drug delivery systems, J. Pharm. Sci., 90, 667, 10.1002/jps.1023 Kataoka, 2001, Block copolymer micelles for drug delivery: design, characterization and biological significance, Adv. Drug Deliv. Rev., 47, 113, 10.1016/S0169-409X(00)00124-1 Allen, 1999, Nano-engineering block copolymer aggregates for drug delivery, Colloids Surf. B: Biointerfaces, 16, 3, 10.1016/S0927-7765(99)00058-2 Nishiyama, 2005, Smart polymeric micelles for gene and drug delivery, Drug Discov. Today: Technol., 2, 21, 10.1016/j.ddtec.2005.05.007 Cabral, 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, 10.1016/j.jconrel.2007.05.024 Nishiyama, 1999, Preparation and characterization of self-assembled polymer–metal complex micelle from cis-dichlorodiammineplatinum (II) and poly(ethylene glycol)-poly(aspartic acid) block copolymer in an aqueous medium, Langmuir, 15, 377, 10.1021/la980572l Bae, 2005, Polymer assemblies: intelligent block copolymer micelles for the programmed delivery of drugs and genes, vol. 148, 491 Nagasaki, 2001, Sugar-installed block copolymer micelles: their preparation and specific interaction with lectin molecules, Biomacromolecules, 2, 1067, 10.1021/bm015574q Allen, 2002, Ligand-targeted therapeutics in anticancer therapy, Nat. Rev. Drug Discov., 2, 750, 10.1038/nrc903 Otsuka, 2003, PEGylated nanoparticles for biological and pharmaceutical applications, Adv. Drug Deliv. Rev., 55, 403, 10.1016/S0169-409X(02)00226-0 Nishiyama, 2006, Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery, Pharmacol. Ther., 112, 630, 10.1016/j.pharmthera.2006.05.006 Adams, 2003, Amphiphilic block copolymers for drug delivery, J. Pharm. Sci., 92, 1343, 10.1002/jps.10397 Gao, 1993, A model of micellization for block copolymers in solutions, Macromolecules, 26, 7353, 10.1021/ma00078a035 Webber, 1996, vol. 327, 383 Kabanov, 1992, A new class of drug carriers: micelles of poly(oxyethylene)-poly(oxypropylene) block copolymers as microcontainers for drug targeting from blood in brain, J. Control. Release, 22, 141, 10.1016/0168-3659(92)90199-2 Lavasanifar, 2002, Poly(ethylene oxide)-block-poly(l-amino acid) micelles for drug delivery, Adv. Drug. Deliv. Rev., 54, 169, 10.1016/S0169-409X(02)00015-7 Yamaoka, 1994, Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice, J. Pharm. Sci., 83, 601, 10.1002/jps.2600830432 Kwon, 1995, Block copolymer micelles as long-circulating drug vehicles, Adv. Drug. Deliv. Rev., 16, 295, 10.1016/0169-409X(95)00031-2 Yokoyama, 1990, Polymer micelles as novel drug carriers: adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer, J. Control. Release, 11, 269, 10.1016/0168-3659(90)90139-K Kwon, 1993, Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl l-aspartate), Langmuir, 9, 945, 10.1021/la00028a012 Cammas, 1996, Poly(ethylene oxide-co-β-benzyl l-aspartate) block copolymers: influence of the poly(ethylene oxide) block on the conformation of the poly(β-benzyl l-aspartate) segment in organic solvents, Macromolecules, 29, 3227, 10.1021/ma951025z Harada, 1996, Stabilized α-helix structure of poly(l-lysine)-block-poly(ethylene glycol) in aqueous medium through supramolecular assembly, Macromolecules, 29, 6183, 10.1021/ma960487p Yokoyama, 1994, Improved synthesis of adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer and formation of unimodal micellar structure with controlled amount of physically entrapped adriamycin, J. Control. Release, 32, 269, 10.1016/0168-3659(94)90237-2 Cammas, 1995, Functional poly (ethylene oxide)-co-(β-benzyl-l-aspartate) polymeric micelles: block copolymer synthesis and micelles formation, Macromol. Chem. Phys., 196, 1899, 10.1002/macp.1995.021960609 Yokoyama, 1994, Influencing factors on in vitro micelle stability of adriamycin–block copolymer conjugates, J. Control. Release, 28, 59, 10.1016/0168-3659(94)90153-8 Yamamoto, 2002, 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, 359, 10.1016/S0168-3659(02)00147-5 Kwon, 1994, Block copolymer micelles as vehicles for hydrophobic drugs, Colloids Surf., B Biointerfaces, 2, 429, 10.1016/0927-7765(94)80007-3 Kataoka, 2000, Doxorubicin-loaded poly(ethylene glycol)-poly(β-benzyl-l-aspartate) copolymer micelles: their pharmaceutical characteristics and biological significance, J. Control. Release, 64, 143, 10.1016/S0168-3659(99)00133-9 Jule, 2004, Thermal characterization of poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles based on pyrene excimer formation, J. Control. Release, 97, 407 Yokoyama, 1990, Characterization and anticancer activity of the micelle-forming polymeric anticancer drug adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer, Cancer Res., 50, 1693 Yokoyama, 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, 10.1023/A:1018921513605 Yokoyama, 1998, 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, 79, 10.1016/S0168-3659(97)00115-6 Fukushima, 1999, Roles of adriamycin and adriamycin dimer in antitumor activity of the polymeric micelle carrier system, Colloids Surf., B Biointerfaces, 16, 227, 10.1016/S0927-7765(99)00073-9 Yokoyama, 1998, Incorporation of water-insoluble anticancer drug into polymeric micelles and control of their particle size, J. Control. Release, 55, 219, 10.1016/S0168-3659(98)00054-6 Kwon, 1997, Block copolymer micelles for drug delivery: loading and release of doxorubicin, J. Control. Release, 48, 195, 10.1016/S0168-3659(97)00039-4 Harada, 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, 10.1021/ma00119a019 Bae, 2005, Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy, Bioconjugate Chem., 16, 122, 10.1021/bc0498166 Bae, 2003, 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, 10.1002/anie.200250653 Harada, 2001, Physicochemical properties and nuclease resistance of antisense-oligodeoxynucleotides entrapped in the core of polyion complex micelles composed of poly(ethylene glycol)-poly(l-lysine) block copolymers, Eur. J. Pharm. Sci., 13, 35, 10.1016/S0928-0987(00)00205-0 Kaneko, 1991, New hydrazone derivatives of adriamycin and their immunoconjugates — a correlation between acid stability and cytotoxicity, Bioconjugate Chem., 2, 133, 10.1021/bc00009a001 West, 2005, Reversible covalent chemistry in drug delivery, Curr. Drug Discov Technol., 2, 123, 10.2174/1570163054866882 Kanayama, 2006, A PEG-based biocompatible block catiomer with high buffering capacity for the construction of polyplex micelles showing efficient gene transfer toward primary cells, Med. Chem., 1, 439 Jones, 2003, Understanding endocytic pathways and intracellular trafficking: a prerequisite for effective design of advanced drug delivery systems, Adv. Drug. Del. Rev., 55, 1353, 10.1016/j.addr.2003.07.002 Matsumura, 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 Takakura, 1990, Distribution characteristics of macromolecules in tumor-bearing mice, Pharm. Res., 7, 339, 10.1023/A:1015807119753 Takakura, 1996, Macromolecular carrier systems for targeted drug delivery: pharmacokinetic considerations on biodistribution, Pharm. Res., 13, 820, 10.1023/A:1016084508097 Jain, 2002, Dissecting tumour pathophysiology using intravital microscopy, Nat. Rev. Cancer, 2, 266, 10.1038/nrc778 Sutherland, 1988, Cell and environment interactions in tumor microregions: the multicell spheroid model, Science, 240, 177, 10.1126/science.2451290 Hamilton, 1998, Multicellular spheroids as an in vitro tumor model, Cancer Lett., 131, 29, 10.1016/S0304-3835(98)00198-0 Tsukioka, 2002, Pharmaceutical and biomedical differences between micellar doxorubicin (NK911) and liposomal doxorubicin (Doxil), Jpn. J. Cancer Res., 93, 1145, 10.1111/j.1349-7006.2002.tb01217.x Seymour, 1987, 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, 1341, 10.1002/jbm.820211106 Yasugi, 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, 10.1021/ma991066l Suzuki, 1996, Design of a drug delivery system for targeting based on pharmacokinetic consideration, Adv. Drug. Del. Rev., 19, 335, 10.1016/0169-409X(96)00008-7 Garin-Chesa, 1993, Trophoblast and ovarian cancer antigen LK26. Sensitivity and specificity in immunopathology and molecular identification as a folate-binding protein, Am. J. Pathol., 142, 557 Weitman, 1992, Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues, Cancer Res., 52, 3396 Bae, 2007, In vivo antitumor activity of the folate-conjugated pH-sensitive polymeric micelle selectively releasing adriamycin in the intracellular acidic compartments, Bioconjugate Chem., 18, 1131, 10.1021/bc060401p Stella, 2000, Design of folic acid-conjugated nanoparticles for drug targeting, J. Pharm. Sci., 89, 1452, 10.1002/1520-6017(200011)89:11<1452::AID-JPS8>3.0.CO;2-P Yamamoto, 2001, Long-circulating poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles with modulated surface charge, J. Control. Release, 77, 27, 10.1016/S0168-3659(01)00451-5 Bae, 2005, Multifunctional polymeric micelles with folate-mediated cancer cell targeting and pH-triggered drug releasing properties for active intracellular drug delivery, Mol. Biosyst., 1, 242, 10.1039/b500266d Leamon, 2003, Folate-liposome-mediated antisense oligodeoxynucleotide targeting to cancer cells: evaluation in vitro and in vivo, Bioconjugate Chem., 14, 738, 10.1021/bc020089t Ringsdorf, 1975, Structure and properties of pharmacologically active polymers, J. Polym. Sci. Polym. Symp., 51, 135, 10.1002/polc.5070510111 Yokoyama, 1993, Composition-dependent in vivo antitumor activity of adriamycin-conjugated polymeric micelle against murine colon adenocarcinoma 26, Drug Deliv., 1, 11, 10.3109/10717549309031336 Kwon, 1993, Biodistribution of micelle-forming polymer–drug conjugates, Pharm. Res., 10, 970, 10.1023/A:1018998203127 Yokoyama, 1999, Selective delivery of adriamycin to a solid tumor using a polymeric micelle carrier system, J. Drug. Target., 7, 171, 10.3109/10611869909085500 Kwon, 1994, Enhanced tumor accumulation and prolonged circulation times of micelle-forming poly(ethylene oxide-aspartate) block copolymers–adriamycin conjugates, J. Control. Release, 29, 17, 10.1016/0168-3659(94)90118-X Nishiyama, 2003, Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice, Cancer Res., 63, 8977 Nakanishi, 2001, Development of the polymer micelle carrier system for doxorubicin, J. Control. Release, 74, 295, 10.1016/S0168-3659(01)00341-8 Yokoyama, 1994, In vivo antitumor activity of polymeric micelle anticancer drug against murine C 26 tumor, J. Control. Release, 28, 336, 10.1016/0168-3659(94)90204-6 Matsumura, 1999, Reduction of the side effects of an antitumor agent KRN5500, by incorporation of the drug into polymeric micelles, Jpn. J. Cancer Res., 90, 122, 10.1111/j.1349-7006.1999.tb00675.x Yokoyama, 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 Kano, 2007, Improvement of cancer-targeting therapy, using nanocarriers for intractable solid tumors by inhibition of TGF-beta signaling, PNAS, 104, 3460, 10.1073/pnas.0611660104 Jain, 1997, Delivery of molecular and cellular medicine to solid tumors, Adv. Drug. Del. Rev., 26, 71, 10.1016/S0169-409X(97)00027-6 Scripture, 2006, Drug interactions in cancer therapy, Nat. Rev. Cancer, 6, 546, 10.1038/nrc1887 Smalley, 2006, Multiple signaling pathways must be targeted to overcome drug resistance in cell lines derived from melanoma metastases, Mol. Cancer Ther., 5, 1136, 10.1158/1535-7163.MCT-06-0084 Bae, 2007, Mixed polymeric micelles for combination cancer chemotherapy through the concurrent delivery of multiple chemotherapeutic agents, J. Control. Release, 122, 324, 10.1016/j.jconrel.2007.05.038 Chen, 2008, Release of hydrophobic molecules from polymer micelles into cell membranes revealed by Förster resonance energy transfer imaging, PNAS, 105, 6596, 10.1073/pnas.0707046105