Enantioselective Release of 5-Fluorouracil from N-(2-Hydroxypropyl)Methacrylamide-Based Copolymers via Lysosomal Enzymes

Bioconjugate Chemistry

Volumn 6, Issue 4, 1995, Pages 483-492

  Putnam, David ^a   Kopeček, Jindřich ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSOL AMINOPEPTIDASE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUOROURACIL; GLYCINE; HYDROXYPROPYL METHACRYLATE; METHACRYLIC ACID DERIVATIVE; OLIGOPEPTIDE; PRODRUG; PROTEINASE;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; CHEMISTRY; COMPARATIVE STUDY; ENZYMOLOGY; KINETICS; LYSOSOME; MATHEMATICS; METABOLISM; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; THEORETICAL MODEL;

AMINO ACID SEQUENCE; ANIMAL; COMPARATIVE STUDY; ENDOPEPTIDASES; FLUOROURACIL; GLYCINE; INDICATORS AND REAGENTS; KINETICS; LEUCYL AMINOPEPTIDASE; LYSOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; MATHEMATICS; METHACRYLATES; MODELS, THEORETICAL; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PRODRUGS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0029339453     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc00034a019     Document Type: Article

References (32)

1. Putnam, D., and Kopeček, J. (1995) Polymer conjugates with anticancer activity. Adv. Polym. Sci. 122, 55-123.
2. Ringsdorf, H. (1975) Structure and properties of pharmacologically active polymers. J. Polym. Sci.: Polym. Symp. 51, 135-153.
3. Ozaki, S., Ohnishi, J., Watanabe, Y., Nohda, T., Nagase, T., Akiyama, T., Uehara, N., and Hoshi, A. (1989) Preparation of potentially antitumor-active vinyl polymers having 5-fluo-rouracil unit as a component. Polym. J. 21, 955-958.
4. Ouchi, T., Hagita, K, Kwashima, M., Inoi, T., and Tahiro, T. (1988) Synthesis and anti-tumor activity of vinyl polymers containing 5-fluorouracils attached via carbamoyl bonds to organosilicon groups. J. Controlled Release 8, 141-150.
5. Ohya, Y., Inosaka, K., and Ouchi, T. (1992) Synthesis and antitumor activity of 6-O-carboxymethyl chitin fixing 5-fluo-rouracils through pentamethylene, monomethylene spacer groups via amide, ester bonds. Chem. Pharm. Bull. 40, 559-561.
6. Yang, F., and Zhuo, R. (1990) Synthesis and antitumor activity of poly(L-cysteine) bonded covalently 5-fluorouracil. Polym. J. 22, 572-577.
7. Ohya, Y., Huang, T. Z., Ouchi, T., Hasegawa, K., Tamura, J., Kadowaki, K, Matumoto, T., Suzuki, S., and Suzuki, M. (1991) Synthesis and antitumor activity of α-l, 4-polygalac-tosamine and N-acetyl-α-l, 4-polygalactosamine immobilized 5-fluorouracils through hexamethylene spacer groups via urea, urea bonds. J. Controlled Release 17, 259-266.
8. Rejmanová, P., Kopeček, J., Duncan, R., and Lloyd, J. B. (1985) Stability in rat plasma and serum of lysosomally degradable oligopeptide sequences in N-(2-hydroxypropyl)-methacrylamide copolymers. Biomaterials 6, 45-48.
9. Rejmanová, P., Kopeček, J., Pohl, J., Baudyš, M., and Kostka, V. (1983) Polymers containing enzymatically degradable bonds, 8. Degradation of oligopeptide sequences in N-(2-hydroxypropyl)methacrylamide copolymers by bovine spleen cathepsin B. Makromol. Chem. 184, 2009-2020.
10. Kingsbury, W. D., Boehm, J. C., Mehta, R. J., Grappel, S. F., and Gilvarg, C. (1984) A novel peptide delivery system involving peptidase activated prodrugs as antimicrobial agents. Synthesis and biological activity of peptidyl derivatives of 5-fluorouracil. J. Med. Chem. 27, 1447-1451.
11. Nichifor, M., and Schacht, E. H. (1994) Synthesis of peptide derivatives of 5-fluorouracil. Tetrahedron 50, 3747-3760.
12. Strohalm, J., and Kopeček, J. (1978) Poly[N-(2-hydrox-ypropyl) methacrylamide] IV. Heterogeneous Polymerization. Angeui. Makromol. Chem. 70, 109-118.
13. Kopeček, J. (1977) Reactive copolymers of N-(2-hydrox-ypropyl)methacrylamide with N-methacryloylated derivatives of L-leucine and L-phenylalanine I. Preparation, characterization and reaction with diamines. Makromol. Chem. 178, 2169-2183.
14. Rejmanová, P., Obereigner, B., and Kopeček, J. (1981) Polymers containing enzymatically degradable bonds 2. Poly-[N-(2-hydroxypropyl)methacrylamide] chains connected by oligopeptide sequences cleavable by chymotrypsin. Makromol. Chem. 182, 1899-1915.
15. Řihová, B., Bilej, M., Vetvička, V., Ulbrich, K., Strohalm, J., Kopeček, J., and Duncan, R. (1989) Biocompatibility of N-(2-hydroxypropyl)methacrylamide copolymers containing adriamycin. Biomaterials 10, 335-342.
16. Trouet, A. (1974) Isolation of modified liver lysosomes. Methods Enzymol. 31, 323-329.
17. Apitz, G., and Steglich, W. (1991) Conversion of serine and threonine residues into α-acyloxy-, α-alkylthio-, and α-halo-genoglycine moieties: a new strategy for the modification of peptides. Tetrahedron Lett. 32, 3163-3166.
18. Schwartz, W. N., and Barrett, A. J. (1980) Human Cathepsin H. Biochem. J. 191, 487-497.
19. Friberger, P. (1982) Chromogenic peptide substrates: their use for the assay of factors in the fibrinolytic and the plasma kallikrein-kinin systems. Scand. J. Clin. Lab. Invest. 42, 1-98.
20. Bodanszky, and Bodanszky, A. (1984) Hydrolysis: Base catalyzed hydrolysis of alkyl esters (saponification with alkali). The Practice of Peptide Synthesis, pp 177-178, Springer-Verlag, Berlin.
21. Nollet, A. J., and Pandit, U. K. (1969) Michael addition of 4-O-ethyluracil: a method for specific Ni1-alkylation of hydroxypyrimidines. Tetrahedron Lett. 53, 4605-4606.
22. Garrett, E. R., Nestler, H. J., and Somodi A. (1968) Kinetics and mechanism of hydrolysis of 5-halouracils. J. Org. Chem. 33, 3460-3468.
23. Rich, D. H., Moon, B. J., and Harbeson, S. (1984) Inhibition of aminopeptidases by amastatin and bestatin derivatives. Effect of inhibitor structure on slow binding processes. J. Med. Chem. 27, 417-422.
24. Borissova, R., Stjarnkvist, P., Karlsson, M., and Sjöholm, I. (1995) Biodegradable microspheres. 17. Lysosomal degradation of primaquine-peptide spacer arms. J. Pharm. Sci. 84, 256-262.
25. Krinick, N. L., and Kopeček, J. (1991) Soluble Polymers as Targetable Drug Carriers. Handbook of Experimental Pharmacology, Vol. 100, Targeted Drug Delivery (R. L. Juliano, Ed.) pp 130-131, Springer-Verlag, Berlin.
26. Rothe, M., Zichner, A., Auerswald, E. A., and Dodt, J. (1994) Structure/function implications for the aminopeptidase specificity of aleurain. Eur. J. Biochem. 224, 559-565.
27. Takahashi, T., Dehdarani, A. H., and Tang, J. (1988) Porcine spleen cathepsin H hydrolyzes oligopeptides solely by aminopeptidase activity. J. Biol. Chem. 263, 10952-10957.
28. Greenstein, J. P., and Winitz, M. (1961) Chemistry of the Amino Acids, Vol. 2, p 1514, John Wiley and Sons, New York.
29. Duncan, R., Hume, I., Kopečková, P., Ulbrich, K, Strohalm, J., and Kopeček, J. (1989) Anticancer agents coupled to N-[2-hydroxypropyljmethacrylamide copolymers. 3. Evaluation of adriamycin conjugates against mouse leukaemia L1210 in vivo. J. Controlled. Release 10, 51-63.
30. Kopeček, J. (1984) Controlled biodegradability of polymers—a key to drug delivery systems. Biomaterials 5, 19-25.
31. Musil, D., Zucic, D., Turk, D., Engh, R. A., Mayr, I., Huber, R., Popovic, T., Turk, V., Towatari, T., Katunuma, N., and Bode, W. (1991) The refined 2.15 Å X-ray crystal structure of human liver cathepsin B: the structural basis for its specificity. EMBO J. 10, 2321-2330.
32. Calabresi, P., and Parks, R. E. (1985) Antiproliferative Agents and Drugs Used for Immunosuppression. Goodman and Gillman's: The Pharmacological Basis of Therapeutics (A. G. Gilman, L. S. Goodman, T. W. Rail, and F. Murak, Eds.) pp 1268-1271, MacMillan Publishing Co., New York.