Block copolymer micelles for drug delivery: design, characterization and biological significance

Advanced Drug Delivery Reviews - Tập 47 Số 1 - Trang 113-131 - 2001
Kazunori Kataoka1, Atsushi Harada, Yukio Nagasaki
1Department of Materials Science, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan. [email protected]

Tóm tắt

Từ khóa


Tài liệu tham khảo

Moffitt, 1996, Micellization of ionic block copolymers, Acc. Chem. Res., 29, 95, 10.1021/ar940080

Tuzar, 1976, Block and graft copolymer micelles in solution, Adv. Colloid Interface Sci., 6, 201, 10.1016/0001-8686(76)80009-7

Munk, 1998, Exploiting polymer micelle technology, CHEMTECH, 28, 20

Talingting, 1999, Onion-type micelles from polystyrene-block–poly(2-vinylpyridine) and poly(2-vinylpyridine)-block–poly(ethylene oxide), Macromolecules, 32, 1593, 10.1021/ma981269u

Kwon, 1995, Block copolymer micelles as long-circulating drug vehicles, Adv. Drug Deliv. Rev., 16, 295, 10.1016/0169-409X(95)00031-2

Kreuter, 1994, Nanoparticles, 219

Scholes, 1997, Particle engineering of biodegradable colloids for site-specific drug delivery, 73

Cammas, 1996, Site specific drug-carriers: Polymeric micelles as high potential vehicles for biologically active molecules, Vol. 327, 83

Kwon, 1996, Polymeric micelles as new drug carriers, Adv. Drug Deliv. Rev., 21, 107, 10.1016/S0169-409X(96)00401-2

Kataoka, 1993, Block copolymer micelles as vehicles for drug delivery, J. Controlled Release, 24, 119, 10.1016/0168-3659(93)90172-2

Bader, 1984, Water soluble polymers in medicine, Ang. Makromol. Chem., 123/124, 457, 10.1002/apmc.1984.051230121

Yokoyama, 1990, Polymer micelles as novel drug carrier: adriamycin-conjugated poly(ethylene glycol)–poly(aspartic acid) block copolymer, J. Controlled Release, 11, 269, 10.1016/0168-3659(90)90139-K

Kabanov, 1989, The neuroleptic activity of haloperidol increases after its solubilization in surfactant micelles, FEBS Lett., 258, 343, 10.1016/0014-5793(89)81689-8

Kwon, 1993, Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl l-aspartate), Langmuir, 9, 945, 10.1021/la00028a012

Bazile, 1995, PEG–PLA nanoparticles avoid uptake by the mononuclear phagocytes system, J. Pharm. Sci., 84, 493, 10.1002/jps.2600840420

Hagan, 1996, Polylactide–poly(ethylene glycol) copolymers as drug delivery systems. 1. Characterization of water dispersible micelle-forming systems, Langmuir, 12, 2153, 10.1021/la950649v

Gref, 1994, Biodegradable long-circulating polymeric nanosphere, Science, 263, 1600, 10.1126/science.8128245

Zhang, 1996, Development of amphiphilic diblock copolymers as micellar carriers of taxol, Int. J. Pharm., 132, 195, 10.1016/0378-5173(95)04386-1

Yasugi, 1999, Preparation and characterization of polymer micelles from poly(ethylene glycol)–poly(d,l-lactide) block copolymer as potential drug carrier, J. Controlled Release, 62, 89, 10.1016/S0168-3659(99)00028-0

Harada, 1995, Formation of polyion complex micelles in aqueous milieu from a pair of oppositely-charged block copolymers with poly(ethylene glycol) segments, Macromolecules, 28, 5294, 10.1021/ma00119a019

Harada, 1996, Formation of stable and monodispersive polyion complex micelles in aqueous medium from poly(l-lysine) and poly(ethylene glycol)–poly(aspartic acid) block copolymer, J. Macromol. Sci., Pure Appl. Chem., A34, 2119

Kataoka, 1996, Spontaneous formation of polyion complex micelles with narrow distribution from antisense oligonucleotide and cationic block copolymer in physiological saline, Macromolecules, 29, 8556, 10.1021/ma961217+

Harada, 1999, Chain length recognition: core–shell supramolecular assembly from oppositely charged block copolymers, Science, 283, 65, 10.1126/science.283.5398.65

Kabanov, 1995, Water-soluble block polycations as carriers for oligonucleotide delivery, Bioconjug. Chem., 6, 639, 10.1021/bc00036a001

Kabanov, 1996, Soluble stoichiometric complexes from poly(N-ethyl-4-vinylpyridinium) cations and poly(ethylene oxide)-block–polymethacrylate anions, Macromolecules, 29, 6797, 10.1021/ma960120k

Bronich, 1997, Soluble complexes from poly(ethylene oxide)-block–polymethacrylate anions and N-alkylpyridinium cations, Macromolcules, 30, 3519, 10.1021/ma970197o

Lysenko, 1998, Block ionomer complexes from polystyrene-block–polyacrylate anions and N-cetylpyridinium cations, Macromolecules, 31, 4511, 10.1021/ma980366k

Yokoyama, 1996, Introduction of cisplatin into polymeric micelle, J. Controlled Release, 39, 351, 10.1016/0168-3659(95)00165-4

Nishiyama, 1999, Preparation and characterization of self-assembled polymer–metal complex micelle from cis-dichlorodiamine platinum (II) and poly(ethylene glycol)–poly(α,β-aspartic acid) block copolymer in an aqueous medium, Langmuir, 15, 377, 10.1021/la980572l

Kataoka, 1998, Effect of secondary structure of poly(l-lysine) segments on the micellization of poly(ethylene glycol)–poly(l-lysine) block copolymer partially substituted with hydrocinnamoyl-group at the Nε-position in aqueous milieu, Macromolecules, 31, 6071, 10.1021/ma971838i

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

Yokoyama, 1987, Preparation of adriamycin-conjugated poly(ethylene glycol)–poly(aspartic acid) block copolymer: A new type of polymeric anticancer agent, Makromol. Chem., Rapid Commun., 8, 431, 10.1002/marc.1987.030080903

Yokoyama, 1990, Characterization and anti-cancer activity of micelle-forming polymeric anticancer drug, adriamycin-conjugated poly(ethylene glycol)–poly(aspartic acid) block copolymer, Cancer Res., 50, 1693

Yokoyama, 1994, 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. Controlled Release, 32, 269, 10.1016/0168-3659(94)90237-2

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. Controlled Release, 50, 79, 10.1016/S0168-3659(97)00115-6

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 copolymer–adriamycin conjugate, J. Controlled Release, 29, 17, 10.1016/0168-3659(94)90118-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

Yokoyaxna, 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, 1995, Physical entrapment of adriamycin in AB block copolymer micelles, Pharm. Res., 12, 200

Kwon, 1997, Block copolymer micelles for drug delivery: loading and release of doxorubicin, J. Controlled Release, 48, 195, 10.1016/S0168-3659(97)00039-4

Cammas, 1997, Design of functional polymeric micelles as site-specific drug vehicles based on poly(α-hydroxy ethylene oxid-co-b-benzyl l-aspartate) block copolymers, Materials Science & Engineering C: Biomimetic Materials, Sensors and Systems, 4, 241, 10.1016/S0928-4931(97)00007-6

Kataoka, 2000, Doxorubicin-loaded poly(ethylene glycol)–poly(β-benzyl-l-aspartate) copolymer micelles: their pharmaceutical characteristics and biological significance, J. Controlled Release, 64, 143, 10.1016/S0168-3659(99)00133-9

Rosenberg, 1969, Platinum compounds: A new class of potent antitumor agents, Nature, 222, 385, 10.1038/222385a0

Takahara, 1995, Crystal-structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin, Nature, 377, 649, 10.1038/377649a0

Pinzani, 1994, Cisplatin-induced renal toxicity and toxicity-modulating strategies—a review, Cancer Chemother. Pharmacol., 35, 1, 10.1007/BF00686277

Siddik, 1987, The comparative pharmacokinetics of carboplatin and cisplatin in mice and rats, Biochem. Pharmacol., 36, 1925, 10.1016/0006-2952(87)90490-4

Howe-Grant, 1980, Aqueous platinum(II) chemistry: binding to biological molecules, Vol. 11, 63

Schechter, 1989, Soluble polymers as carriers of cis-platinum, J. Controlled Release, 10, 75, 10.1016/0168-3659(89)90019-9

Ohya, 1996, Synthesis and cytotoxic activity of dextran carrying cis-dichloro(cyclohexane-trans-l-1,2-diamine) platinum(II) complex, J. Biomater. Sci. Polym. Ed., 7, 1085, 10.1163/156856296X00570

Bogdanov, 1997, A long-circulating copolymer in ‘passive targeting’ to solid tumors, J. Drug Target., 4, 321, 10.3109/10611869708995848

Han, 1992, Synthesis, characterization, and biological activity of polyanion-cis-diamineplatinum(II) complexes as antitumor agents, J. Bioact. Compat. Polym., 7, 358, 10.1177/088391159200700405

Perez-Soler, 1994, Lipophilic platinum complexes entrapped in liposomes: Improved stability and preserved antitumor activity with complexes containing linear alkyl carboxylato leaving groups, Cancer Chemother. Pharmcol., 33, 378, 10.1007/BF00686266

Y. Mizumura, Y. Matsumura, T. Hamaguchi, N. Nishiyama, K. Kataoka, T. Kawaguchi, M. Kawaguchi, T. Saito, T. Kakizoe, Cisplatin-incorporated polymeric micelles reducing nephrotoxicity, while maintaining antitumor activity. Jap. J. of Cancer Res. Submitted for publication.

Yokoyama, 1992, Synthesis of poly(ethylene oxide) with heterobifunctional reactive groups at its terminals by an anionic initiator, Bioconjug. Chem., 3, 275, 10.1021/bc00016a003

Kim, 1994, Heterobifunctional poly(ethylene oxide)—One pot synthesis of poly(ethylene oxide) with a primary amino group at one end and a hydroxyl group at the other end, Polym. Bull., 33, 1, 10.1007/BF00313466

Cammas, 1995, Heterobifunctional poly(ethylene oxide)(PEO): Synthesis of α-methoxy-ω-amino and α-hydroxy-ω-amino PEOs with the same molecular weights, Bioconjug. Chem., 6, 226, 10.1021/bc00032a011

Nagasaki, 1995, Formyl-ended heterobifunctional poly(ethylene oxide)—A synthesis of poly(ethylene oxide) with a formyl group at one end and a hydroxyl group at the other end, Bioconjug. Chem., 6, 231, 10.1021/bc00032a012

Nagasaki, 1995, 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, 702, 10.1021/bc00036a007

Nakamura, 1998, Synthesis of heterobifunctional PEG with a reducing monosaccharide residue at one end, Bioconjug. Chem., 9, 300, 10.1021/bc970179b

Scholz, 1995, A novel reactive polymeric micelles. Polymeric micelle with aldehyde groups on its surface, Macromolecules, 28, 7295, 10.1021/ma00125a040

Nagasaki, 1998, The reactive polymeric micelle based on an aldehyde-ended poly(ethylene glycol)/poly(lactide) block copolymer, Macromolecules, 31, 1473, 10.1021/ma971294k

Nagasaki, 1999, A reactive polymeric micelle as drug vehicle for active targeting, Polymer Preprints, 40, 286

Yasugi, 1999, Sugar-installed polymer micelles: Synthesis and micellization of poly(ethylene glycol)–poly(d,l-lactide) block copolymers having sugar groups at PEG chain end, Macromolecules, 32, 8024, 10.1021/ma991066l

Dowling, 1990, A novel micellar synthesis and photophysical characterization of water-soluble acrylamide–styrene block copolymers, Macromolecules, 23, 1059, 10.1021/ma00206a025

Zhao, 1990, Fluorescence probe techniques used to study micelle formation in water-soluble block copolymers, Langmuir, 6, 514, 10.1021/la00092a038

Yasugi, 1999, Preparation and characterization of polymer micelles from poly(ethylene glycol)–poly(d,l-lactide) block copolymer as potential drug carrier, J. Controlled Release, 62, 89, 10.1016/S0168-3659(99)00028-0

Yamamoto, 1999, Surface charge modulation of poly(ethylene glycol)–poly(d,l-lactide) block copolymer micelles: conjugation of charged peptides, Colloids and Surfaces B: Biointerfaces, 16, 135, 10.1016/S0927-7765(99)00065-X

A. Harada, K. Kataoka, Manuscript in preparation.

Kabanov, 1998, Interpolyelectrolyte and block ionomer complexes for gene delivery: physicochemical aspects, Adv. Drug Deliv. Rev., 30, 49, 10.1016/S0169-409X(97)00106-3

A. Harada, H. Togawa, K. Kataoka, 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., in press.

Katayose, 1997, Water-soluble polyion complex associates of DNA and poly(ethylene glycol)–poly(l-lysine) block copolymer, Bioconjug. Chem., 8, 702, 10.1021/bc9701306

Katayose, 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, 10.1021/js970304s

Wolfert, 1996, Characterization of vectors for gene therapy formed by self-assembly of DNA with synthetic block co-polymers, Hum. Gene Ther., 7, 2123, 10.1089/hum.1996.7.17-2123

Dash, 1997, Synthetic polymers for vectorial delivery of DNA: characterisation of polymer–DNA complexes by photon correlation spectroscopy and stability to nuclease degradation and disruption by polyanions in vitro, J. Controlled Release, 48, 269, 10.1016/S0168-3659(97)00043-6

Toncheva, 1998, Novel vectors for gene delivery formed by self-assembly of DNA with poly(l-lysine) grafted with hydrophilic polymers, Biochem. Biophys. Acta, 1380, 354, 10.1016/S0304-4165(98)00004-X

Oupicky, 1999, Effect of albumin and polyanion on the structure of DNA complexes with polycation containing hydrophilic nonionic block, Bioconjug. Chem., 10, 764, 10.1021/bc990007+

Seymour, 1998, Cationic block copolymers as self-assembling vectors for gene delivery, 219

Harada, 1998, Novel polyion complex micelles entrapping enzyme molecules in the core: Preparation of narrowly-distributed micelles from lysozyme and poly(ethylene glycol)–poly(aspartic acid) block copolymer in aqueous medium, Macromolecules, 31, 288, 10.1021/ma971277v

Harada, 1999, Novel polyion complex micelles entrapping enzyme molecules in the core. [II]: Characterization of the micelles prepared at non-stoichiometric mixing ratios, Langmuir, 15, 4208, 10.1021/la981087t

Harada, 1999, On–off control of enzymatic activity synchronizing with reversible formation of supramolecular assembly from enzyme and charged block copolymers, J. Am. Chem. Soc., 121, 9241, 10.1021/ja9919175

A. Harada, K. Kataoka, Pronounced activity of enzymes through the incorporation into the core of polyion complex micelles made from charged block copolymers. J. Controlled Release (submitted).

Kataoka, 1999, Polyion complex micelles with reactive aldehyde groups on their surface from plasmid DNA and end-functionalized charged block copolymers, Macromolecules, 32, 6892, 10.1021/ma990973n

Boussif, 1996, Optimized galenics improve in vitro gene transfer with cationic molecules up to 1000-fold, Gene Ther., 3, 1074

Boussif, 1995, A versatile vector for gene and oligonucleotide transfer into cells in culture and in-vivo-polyethyleneimine, Proc. Natl. Acad. Sci. USA, 92, 7297, 10.1073/pnas.92.16.7297

Behr, 1996, The proton sponge, a means to enter cells viruses never thought of, M/S-Med. Sci., 12, 56

Vinogradov, 1998, Self-assembly of polyamine–poly(ethylene glycol) copolymers with phosphorothioate oligonucleotides, Bioconjug. Chem., 9, 805, 10.1021/bc980048q

Vinogradov, 1999, Polyion complex micelles with protein-modified corona for receptor-mediated delivery of oligonucleotides into cells, Bioconjug. Chem., 10, 851, 10.1021/bc990037c

Akiyama, 2000, Synthesis of poly(ethylene glycol)-block–poly(ethyleneimine) possessing an acetal group at the PEG end, Macromolecules, 33, 5841, 10.1021/ma000167c

Guo, 1996, Star polymers and nanospheres from cross-linkable diblock copolymers, Macromolecules, 29, 2487, 10.1021/ma951354r

Thurmond, 1996, Water-soluble knedel-like structures: the preparation of shell-cross-linked small particles, J. Am. Chem. Soc., 118, 7239, 10.1021/ja961299h

Kakizawa, 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, 11247, 10.1021/ja993057y

Meister, 1979, Glutathione deficiency produced by inhibition of its synthesis, and its reversal; applications in research and therapy, Ciba Found. Symp., 72, 135

Meister, 1991, Glutathione deficiency produced by inhibition of its synthesis, and its reversal; applications in research and therapy, Pharmacol. Ther., 51, 155, 10.1016/0163-7258(91)90076-X