The synthesis and in vitro biodegradation of poly(ethylene glycol) modified poly[N-2-hydroxyethyl)L-glutamine] are described. Poly(ethylene glycol) (PEG) with terminal amino endgroup was coupled onto 4-nitrophenyl chloroformate activated poly[N-2-hydroxyethyl-L-glutamineI (PHEG). The influence of the degree of substitution and the molecular weight of PEG side groups on the degradability of the PHEG backbone exposed to isolated rat liver lysosomal enzymes was determined. These data indicate that substitution of PHEG with PEG side-chains only slightly alters the degradability of the carrier. The PEG-grafted polymers showed potential tensioactive properties. DSC analysis demonstrated phase separation of the PEG side-groups in solid state.
Get full access to this article
View all access options for this article.
References
1.
1. Davis, S. and L. Illum. 1986. Colloidal Delivery Systems—Opportunities and Challenges, Site Specific Drug Delivery. E. Tomlinson and S. Davis, eds., Lancing, Sussex, UK: J. Wiley and Sons Ltd., p. 93.
2.
2. Gregoriadis, G., J. Senior, B. Wolff and C. Kirby. 1984. Fate of Liposomes in vivo: Control Leading to Targeting. Receptor Mediated Targeted Drugs. G. Gregoriadis, G. Poste, J. Senior and A. Trouet, eds., New York: Plenum Press, p. 243.
3.
3. Ringsdorf, H.1975. J. Polymer Science Symp., 51:135.
4.
4. Endo, N., N. Unemoto, Y. Kato, Y. Takeda and T. Hara. 1987. J. Immunol. Methods, 104:253.
5.
5. Duncan, R., P. Rejmanova, J. Strohalm, I. Hume, H. Cable, J. Pohl and J. Kopecek. 1987. Br. J. Cancer, 59:165.
6.
6. Bader, H., H. Ringsdorf, B. Schmidt. 1984. Angew. Chemie, 124:457.
7.
7. Yokoyama, M.1992. Critical Reviews in Therapeutic Drug Carrier Systems, 9:213.
8.
8. Delgado, C., G. Francis and D. Fisher. 1992. Critical Reviews in Therapeutic Drug Carrier Systems, 9(3,4):249-304.
9.
9. Matsushima, A., H. Nishimura, Y. Ashihara, Y. Yokota and Y. Inada. 1980. Chem. Lett., 773.
10.
10. Ashihara Y, T. Kono, S. Yamazaki and Y. Inada. 1978. Biochem. Biophys. Res. Coomun., 89:385.
11.
11. Kartre, N., M. Knauf and W. Kaird. 1987. Proc. Natl. Acad. Sci. USA, 84:1487.
12.
12. Kamisaki, Y., H. Wada, T. Yagura, A. Matsushima and Y. Inada. 1981. J. Pharmacol. Exp. Ther., 216:410.
13.
13. Abuchowski, A., T. van Es, N. Palczuk and F. Davis. 1977. J. Biol. Chem., 252:3578.
14.
14. Savoca, A., A. Abuchowski, T. van Es, F. Davis and N. Palczuk. 1979. Biochim. Biophys. Acta, 578:47.
15.
15. Lisi, P., T. van Es, A. Abuchowski, N. Palczuk and F. Davis. 1982. J. Appl. Biochem., 4:19.
16.
16. Illum, L., L. Jacobsen, R. Muller, E. Mak and S. Davis. 1987. Biomaterials, 8:113.
17.
17. Yokoyama, M., M. Miyauchi, N. Yamada, T. Okano, Y. Sakurai, K. Kataoka and S. Inoue. 1990. Cancer Res., 50:1693.
18.
18. Yokoyama M., T. Okano, Y. Sakrai, H. Ekimoto, C. Shibazaki and K. Kataoka. 1991. Cancer Res., 51:3229.
19.
19. De Marre, A., H. Soyez and E. Schacht. 1994. J. Controlled Release, 32:129.
20.
20. De Marre, A., L. Seymour and E. Schacht. 1994. J. Contr. Rel., 31:89.
21.
21. De Marre, A., H. Soyez, E. Schacht, M. Shoaibi, L. Seymour and B. Rihova. 1995. J. Controlled Release, 36:87.
22.
22. Neri, P., G. Antoni, F. Benvenuti and F. Concola. 1973. J. Med. Chem., 16:893.
23.
23. Dinckinson, H. and A. Hiltner. 1981. J. Biomat. Res., 15:591.
24.
24. Hayashi, T., Y. Tabata and A. Nakajima. 1983. Reports on Progress in Polymer Phys. Jap, 25:591.
25.
25. Rypacek, F., V. Saudek, J. Pytela and V. Skarda. 1985. Makromol. Chem. Suppl., 9:129.
26.
26. Pytela, J., V. Skarda, J. Drobnik and F. Rypacek. 1989. J. Contr. Rel., 10:17.
27.
27. Pytela, J., R. Kotva, M. Metalova and F. Rypacek. 1990. Int. J. Biol. Macromol., 12:241.
28.
28. Loccufier, J., J. Crommen, J. Vandorpe and E. Schacht. 1991. Makromol. Chemie, Rapid Commun., 12:159.
29.
29. Loccufier, J., M. Van Bos and E. Schacht. 1991. Polymer Bulletin (Berlin), 27:201.
30.
30. Block, H.1983. Polymer Monographs Volume 9: Poly(y-benzyl-L-glutamate) and Other Glutamic Acid Containing Polymers. M. Huglin, ed., Gordon and Breach Science Publishers, pp. 30-31.
31.
31. De Marre, A., H. Soyez, J. Pytela and E. Schacht. 1994. Polymer, 11:2443.
32.
32. De Marre, A. and E. Schacht. 1992. Makromol. Chemie, 193:3023.
33.
33. Trouet, A.1974. Meths. Enzymol., 31:323.
34.
34. Benoit, H., Z. Grubisic, R. Rempp, D. Decker and J. Zilliox. 1966. J. Chim. Phys., 63:1507.
35.
35. Grubisic, Z., P. Rempp and H. Benoit. 1967. Polymer Letters, 5:753.
36.
36. Hoste, K., D. Bruneel, A. De Marre, F. De Schrijver and E. Schacht. 1994. Makromol. Chemie, Rapid Commun., 15:697.
