Self-assembly and cellular uptake of degradable and water-soluble polyperoxides

Bioconjugate Chemistry

Volumn 20, Issue 10, 2009, Pages 1879-1887

  Fujioka, Tamami ^a   Taketani, Shuji ^a   Nagasaki, Takeshi ^a   Matsumoto, Akikazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 ANILINO 1 NAPHTHALENESULFONIC ACID; EPIRUBICIN; FLUORESCENT DYE; POLYMER; POLYPEROXIDE DERIVATIVE; SORBIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; ENDOCYTOSIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; PARTICLE SIZE; POLYMERIZATION; TRANSITION TEMPERATURE;

TETRA;

ANILINO NAPHTHALENESULFONATES; CELL LINE, TUMOR; CELL SURVIVAL; DRUG CARRIERS; ENDOCYTOSIS; EPIRUBICIN; HUMANS; MICELLES; OXYGEN; PEROXIDES; POLYMERS; SOLUBILITY; SPECTROMETRY, FLUORESCENCE;

EID: 70350343805     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9001618     Document Type: Article

References (61)

1. Kwon, G. S., and Kataoka, K. (1995) Block copolymer micelles as long-circulating drug vehicles. Adv. Drug Delivery Rev. 16, 295-309.
2. Kwon, G. S., and Okano, T. (1996) Polymeric micelles as new drug carriers. Adv. Drug Delivery Rev. 21, 107-116.
3. Torchilin, V. P. (2001) Structure and design of polymeric surfactant-based drug delivery systems. J. Controlled Release 73, 137-172. (Pubitemid 32544594)
4. Kakizawa, Y., and Kataoka, K. (2002) Block copolymer micelles for delivery of gene and related compounds. Adv. Drug Delivery Rev. 54, 203-222. (Pubitemid 34230442)
5. Ladmiral, V., Melia, E., and Haddleton, D. M. (2004) Synthetic glycopolymers: an overview. Eur. Polym. J. 40, 431-449.
6. Hawker, C. J., and Wooley, K. L. (2005) The convergence of synthetic organic and polymer chemistries. Science 309, 1200-1205.
7. Harada, A., and Kataoka, K. (2006) Supramolecular assemblies of block copolymers in aqueous media as nanocontainers relevant to biological applications. Prog. Polym. Sci. 31, 949-982. (Pubitemid 44738012)
8. Rapoport, N. (2007) Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery. Prog. Polym. Sci. 32, 962-990. (Pubitemid 47198285)
9. Park, K., Shalaby, W. S. W., Park, H. (1993) Biodegradable Hydrogels for Drug Delivery, Technomic, Lancaster.
10. Uhrich, K. E., Cannizzaro, S. M., Langer, R. S., and Shakesheff, K. M. (1999) Polymeric systems for controlled drug release. Chem. Rev. 99, 3181-3191.
11. Miyata, T., Uragami, T., and Nakamae, K. (2002) Biomolecule-sensitive hydrogels. Adv. Drug Delivery Rev. 54, 79-98.
12. Langer, R., and Tirrell, D. A. (2004) Designing materials for biology and medicine. Nature 428, 487-492.
13. Schmaljohann, D. (2006) Thermo- and pH-responsive polymers in drug delivery. Adv. Drug Delivery Rev. 58, 1655-1670. (Pubitemid 44830149)
14. Nagasaki, T., and Shinkai, S. (2007) The concept of molecular machinery is useful for design of stimuli-responsive gene delivery systems in the mammalian cell. J. Inclusion Phenom. Macrocyclic Chem. 58, 205-219.
15. Oh, J. K., Drumright, R., Siegwert, D. J., and Matyjaszewski, K. (2008) The development of microgels/nanogels for drug delivery applications. Prog. Polym. Sci. 33, 448-477.
16. Ganta, S., Devalapally, H., and Amiji, M. (2008) A review of stimuli-responsive nanocarriers for drug and gene delivery. J. Controlled Release 126, 187-204.
17. Maeda, H. (2001) SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy. Adv. Drug Delivery Rev. 46, 169-185.
18. Katayama, Y., Fujii, K., Ito, E., Sakakihara, S., Sonoda, T., Murata, M., and Maeda, M. (2002) Intracellular signal-responsive artificial gene regulation for novel gene delivery. Biomacromolecules 3, 905-909.
19. Murthy, N., Campbell, J., Fausto, N., and Hoffman, A. S. (2003) Bioinspired pH-responsive polymers for the intracellular delivery of biomolecular drugs. Bioconjugate Chem. 14, 412-419. (Pubitemid 36348665)
20. You, J., Hu, F., Du, Y., and Yuan, H. (2007) Polymeric micelles with glycolipid-like structure and multiple hydrophobic domains for mediating molecular target delivery of paclitaxel. Biomacromolecules 8, 2450-2456. (Pubitemid 47316985)
21. Jung, J., Lee, I. H., Park, J., and Jon, S. (2007) pH-sensitive polymer nanospheres for use as a potential drug delivery vehicle. Biomacromolecules 8, 3401-3407. (Pubitemid 350193739)
22. Irie, M., and Kunwatchakun, D. (1986) Photoresponsive polymers. 8 Reversible photostimulated dilation of polyacrylamide gels having triphenylmethane leuco derivatives. Macromolecules 19, 2476-2480.
23. Patnaik, S., Sharma, A. K., Garg, B. S., Gandhi, R. P., and Gupta, K. C. (2007) Photoregulation of drug release in azodextran nanogels. Int. J. Pharm. 342, 184-193. (Pubitemid 47259316)
24. Vivero-Escoto, J. L., Slowing, I. I., Wu, C. W., and Lin, V. S. (2009) Photoinduced intracellular controlled release drug delivery in human cells by gold-capped mesoporous silica nanosphere. J. Am. Chem. Soc. 131, 3462-3463.
25. Kono, K., Murakami, T., Yoshida, T., Haba, Y., Kanaoka, S., Takagishi, T., and Aoshima, S. (2005) Temperature sensitization of liposomes by use of thermosensitive block copolymers synthesized by living cationic polymerization: Effect of copolymer chain length. Bioconjugate Chem. 16, 1367-1374. (Pubitemid 41681502)
26. Lo, C., Huang, C., Lin, K., and Hsiue, G. (2007) Mixed micelles formed from graft and diblock copolymers for application in intracellular drug delivery. Biomaterials 28, 1225-1235. (Pubitemid 44809411)
27. Jeong, B., Bae, Y. H., and Kim, S. W. (1999) Thermoreversible gelation of PEG-PLGA-PEG triblock copolymer aqueous solutions. Macromolecules 32, 7064-7069. (Pubitemid 32079730)
28. Dumitriu, S., Ed. (2002) Polymeric Biomaterials, 2nd ed, Marcel Dekker, New York.
29. Domb, A. J., Kost, J., Wiseman, D. M. (1997) Handbook of Biodegradable Polymers, Harwood Academic, Amsterdam.
30. Kumar, N., Ravikumar, M. N. V., and Domb, A. J. (2001) Biodegradable block copolymers. Adv. Drug Delivery Rev. 53, 23-44.
31. Li, Y., and Kissel, T. (1998) Synthesis, characteristics and in vitro degradation of star-block copolymers consisting of L-lactide, glycolide and branched multi-arm poly(ethylene oxide). Polymer 39, 4421-4427. (Pubitemid 128369020)
32. Liu, M., Kono, K., and Fréchet, M. J. (2000) Water-soluble dendritic unimolecular micelles: Their potential as drug delivery agents. J. Controlled Release 65, 121-131. (Pubitemid 30122921)
33. Goodwin, A. P., Lam, S. S., and Fréchet, M. J. (2007) Rapid, efficient synthesis of heterobifunctional biodegradable dendrimers. J. Am. Chem. Soc. 129, 6994-6995. (Pubitemid 46903254)
34. Ozalp, Y., Ozdemir, N., Kocagöz, S., and Hasirci, V. (2001) Controlled release of vancomycin from biodegradable microcapsules. J. Microencapsul. 18, 89-110. (Pubitemid 32058684)
35. Zhang, Z., and Feng, S. S. (2006) The drug encapsulation efficiency, in vitro drug release, cellular uptake and cytotoxicity of paclitaxel-loaded poly(lactide)-tocopheryl polyethylene glycol succinate nanoparticles. Biomaterials 27, 4025-4033.
36. Zhao, Q., and Li, B. (2008) pH-controlled drug loading and release from biodegradable microcapsules. Nanomedicine 4, 302-310.
37. Stenekes, R. J. H., Loebis, A. E., Fernandes, C. M., Crommelin, D. J. A., and Hennink, W. E. (2001) Degradable dextran microspheres for the controlled release of liposomes. Int. J. Pharm. 214, 17-30.
38. Yokoyama, M., Miyauchi, M., Yamada, N., Okano, T., Sakurai, Y., Kataoka, K., and Inoue, S. (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, 1963-11700 (Pubitemid 20098806)
39. Hagan, S. A., Coombes, A. G. A., Garnett, M. C., Dunn, S. E., Davies, M. C., Illum, L. L., and Davis, S. S. (1996) Polylactidepoly(ethylene glycol) copolymers as drug delivery systems. 1. Characterization of water dispersible micelle-forming systems. Langmuir 12, 2153-2161.
40. Allen, C., Yu, Y., Myasinger, D., and Eisenberg, A. (1998) Polycaprolactone-b-poly(ethylene oxide) block copolymer micelles as a novel drug delivery vehicle for neurotrophic agents FK506 and L-685, 818. Bioconjugate Chem. 9, 564-572. (Pubitemid 28437000)
41. Bovey, F. A., and Kolthoff, I. M. (1948) Inhibition and retardation of vinyl polymerization. Chem. Rev. 42, 491-525.
42. Mukundan, T., and Kishore, K. (1990) Synthesis, characterization and reactivity of polymeric peroxides. Prog. Polym. Sci. 15, 475-505. (Pubitemid 20735875)
43. Matsumoto, A., Ishizu, Y., and Yokoi, K. (1998) Solid-state photopolymerization of octadecyl sorbate to yield an alternating copolymer with oxygen. Macromol. Chem. Phys. 199, 2511-2516. (Pubitemid 128491891)
44. Matsumoto, A., and Higashi, H. (2000) Convenient synthesis of polymers containing labile bonds in the main chain by radical alternating copolymerization of alkyl sorbates with oxygen. Macromolecules 33, 1651-1655. (Pubitemid 30589123)
45. Sugimoto, Y., Taketani, S., Kitamura, T., Uda, D., and Matsumoto, A. (2006) Regiospecific structure, degradation, and functionalization of polyperoxides prepared from sorbic acid derivatives with oxygen. Macromolecules 39, 9112-9119. (Pubitemid 46101983)
46. Kitamura, T., and Matsumoto, A. (2007) Synthesis of poly(lactic acid) with branched and network structures containing thermally degradable junctions. Macromolecules 40, 509-517. (Pubitemid 46266486)
47. Sato, E., Kitamura, T., and Matsumoto, A. (2008) In-situ collapse of phase-separated structure by covalent bond cleavage at a branching point upon heating. Macromol. Rapid Commun. 29, 1950-1953.
48. Matsumoto, A., and Taketani, S. (2006) Regiospecific radical polymerization of a tetra-substituted ethylene monomer with molecular oxygen for the synthesis of a new degradable polymer. J. Am. Chem. Soc. 128, 4566-4567.
49. Matsumoto, A., and Taketani, S. (2004) Fabrication and degradation of polyperoxides by a radical chain process under mild conditions. Chem. Lett. 33, 732-733. (Pubitemid 39163705)
50. Taketani, S., and Matsumoto, A. (2006) Synthesis of degradable polymer exhibiting LCST-type phase separation by radical copolymerization of sorbic esters and molecular oxygen. Chem. Lett. 35, 104-105.
51. Nanda, A. K., Ganesh, K., Kishore, K., and Surinaranyanan, M. (2000) End-group analysis of vinyl polyperoxides by MALDI- TOF-MS, FT-IR technique and thermochemical calculations. Polymer 41, 9063-9072.
52. Schild, H. G. (1992) Poly(N-isopropylacrylamide): experiment, theory and application. Prog. Polym. Sci. 17, 163-249.
53. Aoshima, S., and Kanaoka, S. (2008) Synthesis of stimuli-responsive polymers by living polymerization: Poly(N-isopropylacrylamide) and poly(vinyl ether)s. Adv. Polym. Sci. 210, 169-208.
54. Kim, S. C., Kim, D. W., Shim, Y. H., Bang, J. S., Oh, H. S., Kim, S. W., and Seo, M. H. (2001) In vivo evaluation of polymeric micellar paclitaxel formulation: toxicity and efficacy. J. Controlled Release 72, 191-202.
55. Akimura, H., Ohya, Y., and Ouchi, T. (2005) Formation of core-shell type biodegradable polymeric micelles from amphiphilic poly(aspartic acid)-block-polylactide diblock copolymer. Biomacromolecules 6, 720-725. (Pubitemid 40467813)
56. Huhtala, A., Pohjonen, T., Saiminen, L., Saiminen, A., Kaarniranta, K., and Uusitalo, H. (2007) In vitro biocompatibility of degradable biopolymers in cell line cultures from various ocular tissues: Direct contact studies. J. Biomed. Mater. Res. A 83A, 407-413. (Pubitemid 47557390)
57. Rejman, J., Bragonzi, A., and Conese, M. (2005) Role of clathrin- and caveolae-mediated endocytosis in gene transfer mediated by lipo- and polyplexes. Mol. Ther. 12, 468-474. (Pubitemid 41150132)
58. Karinaga, R., Koumoto, K., Mizu, M., Anada, T., Shinkai, S., and Sakurai, K. (2005) PEG-appended β-(1→3)-D-glucan schizophyllan to deliver antisense-oligonucleotides with avoiding lysosomal degradation. Biomaterials 26, 4866-4873. (Pubitemid 40343034)
59. Taketani, S., and Matsumoto, A. (2004) Facile synthesis of a degradable gel by radical copolymerization of vinyl sorbate and molecular oxygen. Macromol. Chem. Phys. 205, 2451-2456. (Pubitemid 40083016)
60. Matsumoto, A., Horie, A., and Otsu, T. (1991) Synthesis and thermal properties of poly(adamantyl sorbate). Makromol. Chem., Rapid Commun. 12, 681-685.
61. Goldin, A., Venditti, J. M., and Geran, R. (1985) The effectiveness of the anthhracycline analog 4′-epidoxorubicin in the treatment of experimental-tumors: A review. Invest. New Drugs 3, 3-21. (Pubitemid 15138598)