Development of acid-sensitive copolymer micelles for drug delivery

Pure and Applied Chemistry

Volumn 76, Issue 7-8, 2004, Pages 1295-1307

  Gillies, Elizabeth R ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER; DOXORUBICIN; DRUG CARRIER; LIPOSOME; MACROGOL; POLY(2 ETHYLACRYLIC ACID); POLY(2 VINYLPYRIDINE) BLOCK POLY(ETHYLENE DIOXIDE) COPOLYMER; POLY(AMIDOAMINE); POLY(ETHYL METHACRYLATE); POLY(ETHYLENE OXIDE) BLOCK POLY(ASPARTIC ACID); POLY(ETHYLENE OXIDE) BLOCK POLY(LACTIC ACID); POLY(ETHYLENE OXIDE) BLOCK POLY(ORTHO ESTER); POLY(HISTIDINE) BLOCK POLY(ETHYLENE OXIDE) COPOLYMER; POLY(LACTIC ACID) BLOCK POLY(ETHYLENE OXIDE) BLOCK POLYSUFADIMETHOXINE; POLY(ORTHO ESTER); POLY(SODIUM 4 STYRENESULFONATE) BLOCK POLY(SODIUM 4 VINYLBENZOATE); POLYASPARTIC ACID; POLYBUTADIENE BLOCK POLY(GLUTAMIC ACID); POLYLACTIC ACID; POLYMER; POLYMETHACRYLIC ACID; POLYPEPTIDE; POLY[2 (DIMETHYLAMINO)ETHYL METHACRYLATE] BLOCK POLY[2 (DIETHYLAMINO)ETHYL METHACRYLATE] COPOLYMER; POLY[SODIUM 2 (ACRYLAMIDO) 2 METHYLPROPANESULFONATE BLOCK POLY(SODIUM 6 ACRYLAMIDOHEXANOATE)]; UNCLASSIFIED DRUG;

ACIDITY; CONFERENCE PAPER; DEGRADATION; DRUG BINDING; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STRUCTURE; ENDOSOME; INFLAMMATION; MICELLE; PARTICLE SIZE; PH MEASUREMENT; PROTON TRANSPORT; SUPRAMOLECULAR CHEMISTRY; TUMOR;

EID: 4644299417     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200476071295     Document Type: Conference Paper

References (82)

1. A. K. Singla, A. Garg, D. Aggarwal. Int. J. Pharm. 235, 179-192 (2002).
2. R. S. Benjamin. Cancer Chemother. Rep. 58, 271-273 (1974).
3. K. Kataoka, A. Harada, Y. Nagasaki. Adv. Drug Delivery Rev. 47, 113-131 (2001).
4. A. Lavasanifar, J. Samuel, G. S. Kwon. Adv. Drug Delivery Rev. 54, 169-190 (2002).
5. A. V. Kabanov, E. V. Batrakova, V. Y. Alakhov. J. Controlled Release 82, 189-212 (2002).
6. G. S. Kwon and T. Okano. Adv. Drug Delivery Rev. 21, 107-116 (1996).
7. H. Maeda and Y. Matsumura. Cancer Res. 46, 6387-9392 (1986).
8. K. Kataoka, G. S. Kwon, M. Yokoyama, T. Okano, Y. Sakurai. J. Controlled Release 24, 119-132 (1993).
9. S. Cammas, K. Suzuki, C. Sone, Y. Sakurai, K. Kataoka, T. Okano. J. Controlled Release 48, 157-164 (1997).
10. J. E. Chung, M. Yokoyama, T. Okano. J. Controlled Release 65, 93-103 (2000).
11. G. A. Husseini, G. D. Myrup, W. G. Pitt, D. A. Christensen, N. Y. Rapoport. J. Controlled Release 69, 43-52 (2000).
12. N. Rapoport, W. G. Pitt, H. Sun, J. L. Nelson. J. Controlled Release 91, 85-95 (2003).
13. K. Engin, D. B. Leeper, J. R. Cater, A. J. Thistlethwaite, L. Tupchong, J. D. McFarlane. Int. J. Hypertherm. 11, 211-216 (1995).
14. R. van Sluis, Z. M. Bhujwalla, P. Ballerteros, J. Alverez, S. Cerdan, J. P. Galons, R. J. Gillies. Magn. Reson. Med. 41, 743-750 (1999).
15. A. S. E. Ojugo, P. M. J. Mesheehy, D. J. O. McIntyre, C. McCoy, M. Stubbs, M. O. Leach, I. R. Judson, J. R. Griffiths. NMR Biomed. 12, 495-504 (1999).
16. L. Luo, J. Tam, D. Maysinger, A. Eisenberg. Bioconjugate Chem. 13, 1259-1265 (2002).
17. A. V. Kabanov, V. I. Slepnev, L. E. Kuznetsova, E. V. Batrakova, V. Y. Alakhov, N. S. Melik-Nubarov, P. G. Sveshnikov. Biochem. Int. 26, 1035-1042 (1992).
18. I. Mellman, R. Fuchs, A. Helenius. Annu. Rev. Biochem. 55, 773-700 (1986).
19. T. J. Martin, K. Prochazka, P. Munk, S. E. Webber. Macromolecules 29, 6071-6073 (1996).
20. J.-F. Gohy, B. G. G. Lohmeijer, S. K. Varshney, B. Décamps, E. Leroy, S. Boileau, U. S. Schubert. Macromolecules 35, 9748-9755 (2002).
21. J.-F. Gohy, N. Willet, S. Varshney, J.-X. Zhang, R. Jérome. Angew. Chem., Int. Ed. 40, 3214-3216 (2001).
22. A. S. Lee, A. P Gast, V. Bütün, S. P. Armes. Macromolecules 32, 4302-4310 (1999).
23. M. V. de Paz Bánez, K. L. Robinson, V. Bütün, S. P. Armes. Polymer 42, 29-37 (2001).
24. V. Bütün, S. P. Armes, N. C. Billingham, Z. Tuzar, A. Rankin, J. Eastoe, R. K. Heenan. Macromolecules 34, 1503-1511 (2001).
25. A. S. Lee, V. Bütün, M. Vamvakaki, S. P. Armes, J. A. Pople, A. P. Gast. Macromolecules 35, 8540-8551 (2002).
26. S. Lui, J. V. M. Weaver, Y. Tang, N. C. Billingham, S. P Armes. Macromolecules 35, 6121-6131 (2002).
27. S.-I. Yusa, Y. Shimada, Y. Mitsukami, T. Yamamoto, Y. Morishima. Macromolecules 36, 4208-4215 (2003).
28. Y. Mitsukami, M. S. Donovan, A. B. Lowe, C. L. McCormick. Macromolecules 34, 2248-2256 (2001).
29. H. Dou, M. Jiang, H. Peng, D. Chen, Y. Hong. Angew. Chem., Int. Ed. 42, 1516-1519 (2003).
30. S. Cammas-Marion, M.-M. Béar, A. Harada, P Guérin, K. Kataoka. Macromol. Chem. Phys. 201, 355-364 (2000).
31. F. Chécot, S. Lecommandoux, Y. Gnanou, H.-A. Klok. Angew. Chem. Int. Ed. 41, 1340-1343 (2002).
32. S. Lui and S. P. Armes. Angew. Chem., Int. Ed. 41, 1413-1416 (2002).
33. E. S. Lee, H. J. Shin, K. Na, Y. H. Bae. J. Controlled Release 90, 363-374 (2003).
34. E. S. Lee, K. Na, Y. H. Bae. J. Controlled Release 91, 103-113 (2003).
35. S. K. Han, K. Na, Y. H. Bae. Colloids Surf., A 214, 49-59 (2003).
36. J. Taillefer, M.-C. Jones, N. Brasseur, J. E. Van Lier, J.-C. Leroux. J. Pharm. Sci. 89, 52-62 (2000).
37. J. Leroux, E. Roux, D. Garrec, K. Hong, D. C. Drummond. J. Controlled Release 72, 71-84 (2001).
38. M.-C. Jones, M. Ranger, J.-C. Leroux. Bioconjugate Chem. 14, 774-781 (2003).
39. A. Harada and K. Kataoka. Macromolecules 28, 5294-5299 (1995).
40. A. Harada and K. Kataoka. Science 283, 65-67 (1999).
41. A. V. Kabanov, T. K. Bronich, V. A. Kabanov, K. Yu, A. Eisenberg. Macromolecules 29, 6797-6802 (1996).
42. A. V. Kabanov, S. V. Vinogradov, Y. G. Suzdaltseva, V. Y. Alakhov. Bioconjugate Chem. 6, 639-643 (1995).
43. K. Kataoka, H. Togawa, A. Harada, K. Yasugi, T. Matsumoto, S. Katayose. Macromolecules 29, 8556-8557 (1996).
44. S. Katayose and K. Kataoka. Bioconjugate Chem. 8, 702-707 (1997).
45. G.-D. Zhang, N. Nishiyama, A. Harada, D.-L. Jiang, T. Aida, K. Kataoka. Macromolecules 36, 1304-1309 (2003).
46. M. C. Woodle. Adv. Drug Delivery Rev. 13, 139-152 (1998).
47. T. M. Allen. Adv. Drug Delivery Rev. 13, 285-309 (1994).
48. D. D. Lasic, M. C. Woodle, D. J. Papahadjopoulos. J. Liposome Res. 2, 335-353 (1992).
49. D. D. Lasic and D. Needham. Chem. Rev. 95, 2601-2628 (1995).
50. K. Hong, F. Schuber, D. Papahadjopoulos. Biochim. Biophys. Acta 732, 469-472 (1983).
51. A. Walter, C. Steer, R. Blumenthal. Biochim. Biophys. Acta 861, 319-330 (1986).
52. A. E. Gad, B. L. Silver, G. D. Eytan. Biochim. Biophys. Acta 690, 124-132 (1982).
53. C.-Y. Wang and L. Huang. Biochemistry 23, 4409-4416 (1984).
54. P. S. Uster and D. W. Deamer. Biochemistry 24, 1-8 (1985).
55. R. Epand and W. Lim. Biosci. Rep. 15, 151-160 (1995).
56. S. Richardson, P. Ferruti, R. Duncan. J. Drug Target. 6, 391-404 (1999).
57. R. Duncan, P. Ferruti, D. Sgouras, A. Tuboku-Metzger, E. Ranucci, F. Bignotti. J. Drug Target. 2, 341-347 (1994).
58. A. V. Kabanov. PSTT 2, 365-372 (1999).
59. N. Oku, S. Shibamoto, F. Ito, H. Gondo, M. Nango. Biochemistry 26, 8145-8150 (1987).
60. K. Seki and D. A. Tirrell. Macromolecules 17, 1692-1698 (1984).
61. I. M. Pinilla, M. B. Martinez, D. A. Tirrell. Macromolecules 27, 2671-2674 (1994).
62. J. L. Thomas, H. You, D. A. Tirrell. J. Am. Chem. Soc. 117, 2949-2950 (1995).
63. J. L. Thomas and D. A. Tirrell. Acc. Chem. Res. 25, 336-342 (1992).
64. K. Kono, K.-I. Zenitani, T. Takagishi. Biochim. Biophys. Acta 1193, 1-9 (1994).
65. K. Kono, H. Hayashi, T. Takagishi. J. Controlled Release 30, 69-75 (1994).
66. J. C. Kim, S. K. Bae, J. D. Kim. J. Biochem. 121, 15-19 (1997).
67. H. Hayashi, K. Kono, T. Takagishi. Biochim. Biophys. Acta 1280, 127-134 (1996).
68. O. Meyer, D. Papahadjopoulos, J.-C. Leroux. FEBS Lett. 421, 61-64 (1998).
69. E. Roux, M. Lafleur, E. Lataste, P. Moreau, J.-C. Leroux. Biomacromolecules 4, 240-248 (2003).
70. J.-C. Leroux, E. Roux, D. Le Garrec, K. Hong, D. C. Drummond. J. Controlled Release 72, 71-84 (2001).
71. M. Spafford, A. Polozova, F. M. Winnik. Macromolecules 31, 7099-7102 (1998).
72. M. F. Francis, G. Dhara, F. M. Winnik, J.-C. Leroux. Biomacromolecules 2, 741-749 (2001).
73. D. C. Drummond, M. Zignani, J.-C. Leroux. Prog. Lipid Res. 39, 409-460 (2000).
74. H. S. Yoo, E. A. Lee, T. G. Park. J. Controlled Release 82, 17-27 (2002).
75. Y. Bae, S. Fukushima, A. Harada, K. Kataoka. Angew. Chem., Int. Ed. 42, 4640-4643 (2003).
76. M. Krämer, J.-F. Stumbé, H. Turk, S. Krause, A. Komp, L. Delineau, S. Prokhorova, H. Kautz, R. Haag. Angew. Chem., Int. Ed. 41, 4252-4256 (2002).
77. J. Heller, J. Barr, S. Y. Ng, K. S. Abdellauoi, R. Gurny. Adv. Drug Delivery Rev. 54, 1015-1039 (2002).
78. S. Y. Ng and J. Heller. U.S. Patent 2003152630, Filed 2 May, 2002, Issued 14 August 2003.
79. E. R. Gillies and J. M. J. Fréchet. Chem. Commun. 14, 1640-1641 (2003).
80. T. Fife and L. Jao. J. Org. Chem. 30, 1492-1495 (1965).
81. P. Greenspan, E. P. Mayer, S. D. Fowler. J. Cell Biol. 100, 965-973 (1985).
82. M. M. G. Krishna. J. Phys. Chem. A 103, 3589-3595 (1999).