Cellular internalization of poly(ethylene oxide)-b-poly(ε-caprolactone) diblock copolymer micelles

Bioconjugate Chemistry

Volumn 13, Issue 6, 2002, Pages 1259-1265

  Luo, Laibin ^a   Tam, Joseph ^b   Maysinger, Dusica ^b   Eisenberg, Adi ^a  

^a MCGILL UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BLOCK COPOLYMERS; DRUG DELIVERY; DYNAMIC LIGHT SCATTERING; ETHYLENE; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; MOLECULAR BIOLOGY; POLYETHYLENE OXIDES; SOLUTIONS;

BLOCK CO POLYMERS; CELLULAR INTERNALIZATION; DIBLOCK COPOLYMER MICELLES; HYDROPHOBICS; IN-VITRO; P19 CELLS; POLY(Ε CAPROLACTONE); RHODAMINE; SELF-ASSEMBLE; TETRAMETHYL;

MICELLES;

ANIMALIA;

EID: 0036860748     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc025524y     Document Type: Article

References (54)

1. Kabanov, A. V., and Alakhov, V. Y. (1997) Micelles of amphiphilic block copolymers as vehicles for drug delivery. Amphiphilic Block Copolymers: Self-Assembly and Applications (P. Alexamdris, and B. Lindman, Eds.) Elsevier, Netherlands.
2. Allen, C., Eisenberg, A., and Maysinger, D. (1999) Copolymer drug carriers: Conjugates, micelles and microspheres. S. T. P. Pharma Sci. 9, 139-151.
3. Kataoka, K., Harada, A., and Nagasaki, Y. (2001) Block copolymer micelles for drug delivery: Design, characterization and biological significance. Adv. Drug Delivery Rev. 47, 113-131.
4. Bader, H., Ringsdorf, H., and Schmidt, B. (1984) Water soluble polymers in medicine. Angew. Makromol. Chem. 123-124, 457-485.
5. 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. (1989) The neuroleptic activity of haloperidol increases after its solubilization in surfactant micelles. Micelles as microcontainers for drug targeting. FEBS Lett. 258, 343-345.
6. 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, 1693-1700.
7. Yokoyama, M., Okano, T., Sakurai, Y., Ekimoto, H., Shibazaki, C., and 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, 3229-3336.
8. Muller, R. H. (1991) Colloidal Carriers for Controlled Drug Delivery and Targeting: Modification, Characterization and In Vivo Distribution, CRC Press Inc., Boca Raton, FL.
9. Kabanov, A. V., Batrakova, E. V., Melik-Nubarov, N. S., Fedoseev, N. A., Dorodnich, T. Y., Alakhov, V. Y., Chekhonin, V. P., Nazarova, I. R., and Kabanov, V. A. (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. Controlled Release 22, 141-158.
10. Kwon, G., Suwa, S., Yokoyama, M., Okano, T., Sakurai, Y., and Kataoka, K. (1994) Enhanced tumor accumulation and prolonged circulation times of micelle-forming poly(ethylene oxide-aspartate) block copolymer-adriamycin conjugate. J. Controlled Release 29, 17-23.
11. Hagan, S. A., Coombes, A. G. A., Garnett, M. C., Dunn, S. E., Davies, M. C., Illum, L., Davis, S. S., Harding, S. E., Purkiss, S., and Gellert, P. R. (1996) Polylactide-poly(ethylene glycol) copolymers as drug delivery systems. 1. Characterization of water dispersible micelle-forming system. Langmuir 7, 2153-2161.
12. Ramaswamy, M., Zhang, X., Burt, H. M., and Wasan, K. M. (1997) Human plasma distribution of free paclitaxel and paclitaxel associated with diblock copolymers. J. Pharm. Sci. 86, 460-464.
13. Yokoyama, M., Fukushima, S., Uehara, R., Okamoto, K., Kataoka, K., Sakurai, Y., and Okano, T. (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, 79-92.
14. Shin, IL G., Kim, S. Y., Lee, Y. M., Cho, C. S., and Sung, Y. K. (1998) Methoxy poly(ethylene glycol)/∈-caprolactone amphiphilic block copolymeric micelle containing indomethacin. I. Preparation and characterization. J. Controlled Release 51, 1-11.
15. Inoue, T., Chen, G., Nakamae, K., and Hoffman, A. S. (1998) An AB block copolymer of oligo(methyl methacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drugs. J. Controlled Release 51, 221-229.
16. Allen, C., Yu, Y., Maysinger, 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.
17. Allen, C., Han, J., Yu, Y., Maysinger, D., and Eisenberg, A. (2000) Polycaprolactone-b-poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosterone. J. Controlled Release 63, 275-286.
18. Walter, E., Dreher, D., Kok, M., Thiele, L., Kiama, S. G., Gehr, P., and Merkle, H. P. (2001) Hydrophilic poly(D, L-lactide-co-glycolide) microspheres for the delivery of DNA to human-derived macrophages and dendritic cells. J. Controlled Release 76, 149-168.
19. Yoo, H. S., and Park, T. G. (2001)Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA-PEG block copolymer. J. Controlled Release 70, 63-70.
20. Yamamoto, Y., Nagasaki, Y., Kato, Y., Sugiyama, Y., and Kataoka, K. (2001) Long-circulating poly(ethylene glycol)-poly(D,L-lactide) block copolymer micelles with modulated surface charge. J. Controlled Release 77, 27-38.
21. Benahmed, A., Ranger, M. and Leroux, J.-C. (2001) Novel polymeric micelles based on the amphiphilic diblock copolymer poly(N-vinyl-2-pyrrolidone)-block-poly(D,L-lactide). Pharm. Res. 18, 323-328.
22. Nishiyama, N., Yokoyama, M., Aoyagi, T., Okano, T., Sakurai, Y., and Kataoka, K. (1999) Preparation and characterization of self-assembled polymer-metal complex micelles from cis-dichlorodiammineplatinum(II) and poly(ethylene glycol)-poly(αβ-aspartic acid) block copolymer in an aqueous medium. Langmuir 15, 377-383.
23. Kabanov, A. V., Vinogradov, S. V., Suzdaltseva, Yu. G., and Alakhov, V. Yu. (1995) Water-soluble block polycations for oligonucleotide delivery. Bioconjugate Chem. 6, 639-643.
24. Katayose, S., and Kataoka, K. (1997) Water-soluble polyion complex associates of DNA and poly(ethylene glycol)-poly-(L-lysine) block copolymer. Bioconjugate Chem. 8, 702-707.
25. Harada, A. and Kataoka, K. (1999) Chain length recognition: Core-shell supramolecular assembly from oppositely charged block copolymers. Science 283, 65-67.
26. Higashi, N., and Sunamoto, J. (1995) Endocytosis of poly-(ethylene oxide)-modified liposome by human lymphoblastoid cells. Biochim. Biophys. Acta 1243, 386-92.
27. Vittaz, M., Bazile, D., Spenlehauer, G., Verrecchia, T., Veillard, M., Puisieux, F., and Labarre, D. (1996) Effect of PEO surface density on long-circulating PLA-PEO nanoparticles which are very low complement activators. Biomaterials 17, 1575-81.
28. Higashi, N., Yamauchi, M., Okumura, Y., Nakanishi, M., and Sunamoto, J. (1996) Fusion between Jurkat cell and PEO-lipid modified liposome. Biochim. Biophys. Acta 1285, 183-91.
29. Liaw, J., Aoyagi, T., Kataoka, K., Sakurai, Y., and Okano, T. (1999) Permeation of PEO - PBLA-FITC polymeric micelles in aortic endothelial cells. Pharm. Res. 16, 213-20.
30. De Jaeghere, F., Allemann, E., Leroux, J. C., Stevels, W., Feijen, J, Doelker, E., and Gurny, R. (1999) Formulation and lyoprotection of poly(lactic acid-co-ethylene oxide) nanoparticles: Influence on physical stability and in vitro cell uptake. Pharm. Res. 16, 859-66.
31. Kabanov, A. V., Slepnev, V. I., Kuznetsova, L. E., Batrakova, E. V., Alakhov, V. Y., Melik-Nubarov, N. S., Sveshnikov, P. G., and Kabanov, V. A. (1992) Pluronic micelles as a tool for low-molecular compound vector delivery into a cell: Effect of Staphylococcus aureus enterotoxin B on cell loading with micelle incorporated fluorescent dye. Biochem. Int. 26, 1035-1042.
32. Venne, A., Li, S., Mandeville, R., Kabanov, A. V., and Alakhov, V. Yu. (1996) Hypersensitizing effects of Pluronic L61 on cytotoxic activity, transport, and subcellular distribution of doxorubicin in multiple drug-resistant cells. Cancer Res. 56, 3626-3629.
33. Alakhov, V. Y., Moskaleva, E. Y., Batrakova, E. V., and Kabanov, A. V. (1996) Hypersensitization of multidrug resistant human ovarian carcinoma cells by Pluronic P85 block copolymer. Bioconjugate Chem. 7, 209-216.
34. Miller, D. W., Batrakova, E. V., Waltner, T. O., Alakhov, V. Y., and Kabanov, A. V. (1997)Interactions of Pluronic block copolymers with brain microvessel endothelial cells: Evidence of two potential pathways for drug absorption. Bioconjugate Chem. 8, 649-657.
35. Batrakova, E. V., Li, S., Elmquist, W. F., Miller, D. W., Alakhov, V. Y.; Kabanov. A. V. (2001) Mechanism of sensitization of MDR cancer cells by Pluronic block copolymers: Selective energy depletion. Br. J. Cancer 85, 1987-1997.
36. Allen, C., Yu, Y., Eisenber, A., and Maysinger, D. (1999) Biochim. Biophys. Acta 1421, 32-38.
37. Maysinger, D., Berezovska, O., Savic, R., Lim Soo, P., and Eisenberg, A. (2001) Block copolymers modified the internalization of micelle-incorporated probes into neural cells. Biochim. Biophys. Acta 1539, 205-217.
38. Mcburney, M. W., Jones-Villeneuve, E. M. V., Edwards, M. K. S., and Anderson, P. J. (1982) Control of muscle and neuronal differentiation in a cultured embryonal carcinoma cell line. Nature 299, 165-167.
39. Is, S. (1999) Cardiac and skeletal muscle development in P19 embryonal carcinoma cells. Trends Cardiovasc. Med. 9, 139-143.
40. Ventura, C., and Maioli, M. (2000) Opioid peptide gene expression primes cardiogenesis in embryonal pluripotent stem cells. Circ. Res. 87, 189-194.
41. Bogdanov, B., Vidts, A., Bulcke, A. V. D., Verbeeck, R., and Schacht, E. (1998) Synthesis and thermal properties of poly-(ethylene glycol)-poly(∈-caprolactone) copolymers. Polymer 39, 1631-1636.
42. Balestrieri, C., Camussi, G., Giovane, A., Iorio, E. L., Quagliuolo, L., and Servillo, L (1996) Measurement of platelet-activating factors acetylhydrolase activity by quantitative high-performance liquid chromatography determination of coumarin-derivatized 1-O-alkyl-2-sn-lysoglyceryl-3-phosphorylcholine. Anal. Biochem. 233, 145-150.
43. Beutner, D., Voets, T., Neher, E., and Moser, T. (2001) Calcium dependence of exocytosis and endocytosis at the cochlear inner hair cell afferent synapse. Neuron 29, 681-90.
44. Sankaranarayanan, S., and Ryan, T. A. (2001) Calcium accelerates endocytosis of vSNAREs at hippocampal synapse. Nat. Neurosci. 4, 129-36.
45. Lai, M. M., Hong, J. J., Ruggiero, A. M., Burnett, P. E., Slepnev, V. I., De Camilli, P., and Snyder, S. H. (1999) The calcineurin-dynamin 1 complex as a calcium sensor for synaptic vesicle endocytosis. J. Biol. Chem. 274, 25963-6.
46. 2+/calmodulin-binding proteins are involved in Tetrahymena thermophila. Cell Struct. Funct. 25, 243-51.
47. Lai, M. M., Luo, H. R., Burnett P. E., Hong, J. J., and Snyder, S. H. (2000) The calcineurin-binding protein cain is a negative regulator of synaptic vesicle endocytosis. J. Biol. Chem. 275, 34017-20.
48. Yuan, A, Siu, C. H, and Chia, C. P. (2001) Calcium requirement for efficient phagocytosis by Dictyostelium discoideum. Cell Calcium 29, 229-38.
49. Steinman, R. M., Mellman, I. S., Muller, W. A., and Cohn, Z. A. (1983) Endocytosis and the recycling of plasma membrane. J. Cell Biol. 96, 1-27.
50. Davoust, J., Gruenberg, J., and Howell, J. E. (1987) Two threshold values of low pH block endocytosis at different stages. EMBO J. 6, 3601-3609.
51. Sandvig, K., Olsnes, S., Petersen, O. W., and Van Deurs, B. (1987) Acidification of the cytosol inhibits endocytosis form coated pits. J. Cell Biol. 105, 679-689.
52. Heuser, J. E., and Anderson, R. G. W. (1989) Hypertonic media inhibit receptor-mediated endocytosis by blocking clathrin coated pit formation. J. Cell Biol. 108, 389-400.
53. Heuser, J. E. (1989) Effects of cytoplasmic acidification on clathrin lattice morphology. J. Cell Biol. 108, 401-411.
54. Hansen, S. H., Sandvig, K., and Van Deurs, B. (1993) Clathrin and HA2 adaptors: effects of potassium depletion, hypertonic medium and cytosol acidification. J. Cell Biol. 121, 61-72.