High-molecular weight HPMA copolymer-adriamycin conjugates

Journal of Controlled Release

Volumn 60, Issue 2-3, 1999, Pages 321-332

  Dvorak M ^a   Kopeckova P ^a   Kopecek J ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Adriamycin (doxorubicin); Degradation; Drug release; HPMA copolymer; Lysosomal enzymes; Polymeric anticancer drugs; Prodrugs

Indexed keywords

COPOLYMER; DOXORUBICIN DERIVATIVE; N (2 HYDROXYPROPYL)METHACRYLAMIDE;

ARTICLE; DRUG DEGRADATION; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL;

3-MERCAPTOPROPIONIC ACID; ANIMALS; ANTINEOPLASTIC AGENTS; BIODEGRADATION, ENVIRONMENTAL; CROSS-LINKING REAGENTS; DOXORUBICIN; LIVER; LYSOSOMES; METHACRYLATES; ORNITHINE; POLYMERS; RATS;

EID: 0041461026     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-3659(99)00087-5     Document Type: Article

References (29)

1. Marecos E., Weissleder R., Bogdanov A. Jr. Antibody-mediated versus nontargeted delivery in a human small cell lung carcinoma model. Bioconj. Chem. 9:1998;184-191.
2. Matsumura Y., Maeda H. A new concept for macromolecular therapeutics in cancer therapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent SMANCS. Cancer Res. 46:1986;6387-6392.
3. Noguchi Y., Wu J., Duncan R., Strohalm J., Ulbrich K., Akaike T., Maeda H. Early phase tumor accumulation of macromolecules: a great difference in clearance rate between tumor and normal tissues. Jpn. J. Cancer Res. 89:1998;307-314.
4. Šprincl L., Exner J., Štěrba O., Kopeček J. New types of synthetic infusion solutions. III. Elimination and retention of poly[N-(2-hydroxypropyl)methacrylamide] in a test organism. J. Biomed. Mater. Res. 10:1976;953-963.
5. Rejmanová P., Pohl J., Baudyš M., Kostka V., Kopaček J. Polymers containing enzymatically degradable bonds. 8. Degradation of oligopeptide sequencers in N-(2-hydroxypropyl)methacrylamide copolymers by bovine spleen cathepsin B. Makromol. Chem. 184:1983;2009-2020.
6. Kopeček J., Cífková I., Rejmanová P., Strohalm J., Obereigner B., Ulbrich K. Polymers containing enzymatically degradable bonds. 4. Preliminary experiments in vivo. Makromol. Chem. 182:1981;2941-2949.
7. Cartlidge S.A., Duncan R., Lloyd J.B., Rejmanová P., Kopeček J. Soluble, crosslinked N-(2-hydroxypropyl)methacrylamide copolymers as potential drug carriers. 1. Pinocytosis by rat visceral yolk sacs and rat intestine cultured in vitro. Effect of molecular weight on uptake and intracellular degradation. J. Control. Release. 3:1986;55-66.
8. Cartlidge S.A., Duncan R., Lloyd J.B., Kopečková-Rejmanová P., Kopeček J. Soluble, crosslinked N-(2-hydroxypropyl)methacrylamide copolymers as potential drug carriers. 3. Targeting by incorporation of galactosamine residues. Effect of route of administration. J. Control. Release. 4:1987;253-264.
9. Cartlidge S.A., Duncan R., Lloyd J.B., Kopečková-Rejmanová P., Kopeček J. Soluble, crosslinked N-(2-hydroxypropyl)methacrylamide copolymers as potential drug carriers. 2. Effect of molecular weight on blood clearance and body distribution in the rat after intraveneous administration. Distribution of unfractionated copolymer after intraperitoneal, subcutaneous or oral administration. J. Control. Release. 4:1987;253-264.
10. Dvořák M., Kopečková P., Kopeček J. Novel synthesis of long-circulating HPMA copolymer-adriamycin conjugates. Proc. Int. Symp. Control. Release Bioact. Mater. 25:1998;884-885.
11. Trouet A. Isolation of rat liver lysosomal enzymes. Methods Enzymol. 31:1974;323-329.
12. Kopeček J., Bažilová H. Poly[N-(2-hydroxypropyl)methacrylamide]. I. Radical polymerization and copolymerization. Eur. Polym. J. 9:1973;7-14.
13. J. Kopeček, P. Rejmanová, J. Strohalm, K. Ulbrich, B. Říhová, V. Chytrý, J.B. Lloyd, R. Duncan, Synthetic Polymeric Drugs, US Pat. 5 037 883, Aug. 6, 1991.
14. Ulbrich K., Šubr V., Podpěrová P., Burešová M. Synthesis of novel hydrolytically degradable hydrogels for controlled drug release. J. Control. Release. 34:1995;155-165.
15. Lu Z.-R., Kopečková P., Wu Z., Kopeček J. Functionalized semitelechelic poly[N-(2-hydroxypropyl)methacrylamide] for protein modification. Bioconj. Chem. 9:1998;793-804.
16. Ulbrich K., Zacharieva E.I., Obereigner B., Kopeček J. Polymers containing enzymatically degradable bonds. 5. Hydrophilic polymers degradable by papain. Biomaterials. 1:1980;199-204.
17. Kopeček J., Bažilová H. Poly[N-(2-hydroxypropyl)methacrylamide]. III. Crosslinking copolymerization. Eur. Polym. J. 10:1974;465-470.
18. Seymour L.W., Duncan R., Strohalm J., Kopeček J. Effect of molecular weight of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal and intravenous administration to rats. J. Biomed. Mater. Res. 21:1987;1341-1358.
19. Cartlidge S.A., Rejmanová P., Duncan R., Kopeček J., Lloyd J.B. Targeting of soluble cross-linked N-(2-hydroxypropyl)methacrylamide copolymers in vivo. A potential drug delivery system. Biochem. Soc. Trans. 12:1984;1064-1065.
20. 14C-labelled polyvinylpyrrolidone with a relatively low mean molecular weight after intraveneous administration. Drug Res. 27:1997;1158-1162.
21. Kopeček J. Reactive copolymers of N-(2-hydroxypropyl)methacrylamide with N-methacryloylated derivatives of L-leucine and L-phenylalanine. I. Preparation, characterization and reaction with diamines. Makromol. Chem. 178:1977;2169-2183.
22. Kopeček J., Rejmanová P. Reactive copolymers of N-(2-hydroxypropyl)methacrylamide with N-methacryloylated derivatives of L-leucine and L-phenylalanine. II. Reaction with the polymeric amine and stability of crosslinks towards chymotrypsin in vitro. J. Polym. Sci. Polym. Symp. 66:1979;15-32.
23. Musil D., Zucic D., Turk D., Engh R.A., Mayr I., Huber R., Popovic T., Turk V., Towatari T., Katunuma N., Bode W. The refined 2.15 Å X-ray crystal structure of human liver cathepsin B: the structural basis for its specificity. EMBO J. 10:1991;2321-2330.
24. Šubr V., Duncan R., Kopeček J. Release of macromolecules and daunomycin from hydrophilic gels containing enzymatically degradable bonds. J. Biomat. Sci. Polym. Ed. 1:1990;261-278.
25. Kopeček J., Rejmanová P. Enzymatically degradable bonds in synthetic polymers. Bruck S.D. Controlled Drug Delivery. I:1983;81-124 CRC Press, Boca Raton, FL.
26. Dušek K., Prins W. Structure and elasticity of non-crystalline polymer networks. Adv. Polym. Sci. 6:1969;1-102.
27. Kopeček J. Controlled degradability of polymers: a key to drug delivery systems. Biomaterials. 5:1984;19-25.
28. Krinick N.L., Kopeček J. Soluble polymers as targetable drug carriers. Juliano R.L. Handbook of Experimental Pharmacology. Targeted Drug Delivery. 100:1991;105-179 Springer, New York.
29. Putnam D.A., Kopeček J. Polymer conjugates with anticancer activity. Adv. Polym. Sci. 122:1995;55-123.