Modification of physico-chemical and biopharmaceutical properties of superoxide dismutase by conjugation to the co-polymer of divinyl ether and maleic anhydride

Journal of Controlled Release

Volumn 39, Issue 1, 1996, Pages 27-34

  Caliceti, Paolo ^a   Schiavon, Oddone ^a   Hirano, Takashi ^b   Ohashi, Shinichi ^b   Veronese, Francesco M ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

DIVEMA; Polymer protein conjugate; Superoxide dismutase; Therapeutical enzyme

Indexed keywords

COPPER; DIMETHYLMALEIC ACID ANHYDRIDE; ENZYME ANTIBODY; POLYCLONAL ANTIBODY; PYRAN COPOLYMER; RADIOISOTOPE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIGENICITY; ARTICLE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG ELIMINATION; ENZYME MODIFICATION; IMMUNOPRECIPITATION; INTRAVENOUS DRUG ADMINISTRATION; MALE; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN STRUCTURE; RAT; THERMOSTABILITY;

EID: 0029926692     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/0168-3659(95)00130-1     Document Type: Article

References (35)

1. T. Hirano, T. Todoroki, S. Kato, H. Yamamoto, P. Caliceti, F.M. Veronese, H. Maeda and S. Ohashi, Synthesis of the conjugate of superoxide dismutase with the copolymer of divinyl ether and maleic anhydride retaining enzymatic activity, J. Control. Release 28 (1994) 203-209.
2. P. Caliceti, F.M. Veronese and O. Schiavon, Controlled release of protein peptides from hydrogels synthesised by gamma ray-induced polymerisation, Farmaco 47 (1992) 275-286.
3. T. Kitao, and K. Hattorui, Urokinase immobilised on erythrocytes, Thromb. Haemost. 43 (1980) 70.
4. R.V. Padmanabhan, R. Gudapaty, I.E. Liener, B.A. Schwartz and J.R. Hoidal, Protection against pulmonary oxygen toxicity in rats by the intratracheal administration of liposome-encapsuled superoxide dismutase or catalase, Am. Rev. Respir. Dis. 132 (1985) 164-167.
5. J.P. McGee, S.S. Davis and D.T. O'Hagaan, The immunogenicity of a model protein entrapped in poly (lactide-co-glycolide) microparticles prepared by a novel phase separation technique, J. Control. Release, 31 (1994) 55-60.
6. H.K. Sah, R. Toddywala and Y.W. Chien, The influence of biodegradable microcapsule formulations on the controlled release of protein, J. Control. Release, 30 (1994) 201-211.
7. F.M. Veronese, P. Caliceti, O. Schiavon and L. Sartore, Preparation and properties of monomethoxy poly(ethylene glycol) modified enzymes for therapeutic application, in: J.M. Harris (Ed.), Poly(ethylene glycol): Chemistry, Biochemical and Biomedical Application, Plenum Press, New York, 1992, pp.127-137.
8. N.K. Kartre, The conjugation of proteins with polyethylene glycol and other polymers, Adv. Drug Deliv. Rev. 10 (1993) 91-114.
9. C. Delgado, G.E. Francis and D. Fisher, The uses and properties of PEG-linked proteins, Crit. Rev. Ther. Drugs Carrier Syst. 9 (1992) 249-304.
10. M.L. Nucci, Shorr, R. and A. Abuchowski, The therapeutic nature of poly(ethylene glycol) modified proteins, Adv. Drug Deliv. Rev. 6 (1991) 133-155.
11. F. Fuertges and A. Abuchowski, The clinical efficacy of polyethylene glycol) modified proteins,. J. Control. Release 11 (1990) 139-148.
12. Y. Yasuda, T. Fujita, Y. Takakura, M. Hashida and H. Sezaki, Biochemical and biopharmaceutical properties of macromolecular conjugates of uricase with dextran and polyethylene glycol, Chem. Pharm. Bull. 38 (1990) 2053-2056.
13. B.U. Von Specht and W. Brendel, Preparation and properties of trypsin and chymotrypsin coupled covalently to poly(N-vinyl pyrrolidone), Biochim. Biophys. Acta 484 (1977) 109-114.
14. P. Caliceti, O. Schiavon, M. Morpurgo, L. Sartore, E. Ranucci, P. Ferruti and F.M., Veronese, Physico-chemical and biological properties of monofunctional hydroxy terminating poly(N-vinyl pyrrolidone) conjugated superoxide dismutase, J. Bioact. Comp. Polym. 10 (995) 103-120.
15. J.R. Uren and R.C. Ragin, Improvement in the therapeutic, immunological and clearance properties of Escherichia coli and Erwinia carotovora L-asparaginases by attachment of poly-DL-alanyl peptides, Cancer Res. 39 (1979) 1927-1933.
16. K. Wong, L.G. Cleland and M.J. Poznasky, Enhanced anti-inflammatory effect and reduced immunogenicity of bovine liver superoxide dismutase by conjugation with homologous albumin, Agents Actions 10 (1980) 231-239.
17. F.M. Veronese, L. Sartore, P. Caliceti and O. Schiavon, Hydroxyl-terminated polyvinylpyrrolidone for the modification of polypeptides, J. Bioact. Comp. Polym. 5 (1990) 167-178.
18. P.A. Flanagan, P. Kopeckova, J. Kopecek and R. Duncan, Evaluation of protein-N-(2-hydroxypropyl)methacrylamide copolymer conjugates as targetable drug carriers, Biochim. Biophys. Acta 993 (1989) 83-91.
19. C. Monfardini C., O. Schiavon, P. Caliceti, M. Morpurgo, J.M. Harris and F.M. Veronese, A branched monomethoxypoly(ethylene glycol) for protein modification, J. Bioconj. Chem. 6 (1995) 62-69.
20. T. Fujita, Y. Yasuda, Y. Takakura, M. Hashida and H. Sezaki, Alteration of biopharmaceutical properties of drugs by their conjugation with water-soluble macromolecules: uricase-dextran conjugate, J. Control. Release 11 (1990) 149-156.
21. I. Fuke, T. Hayashi, Y. Tabata and Y. Ikada, Synthesis of poly(ethylene glycol) derivatives with different branchings and their use for protein modification, J. Control. Release 30 (1994) 27-34.
22. T. Oda, T. Akaike, T. Hamamoto, S. Fujio, T. Hirano and H. Maeda, Oxygen radicals in influenza induced pathogenesis and treatment with pyran polymer-conjugated SOD, Science 244 (1989) 974-976.
23. T. Hirano, S. Ohashi, S. Morimoto, K. Tsuda, T. Kobayashi and S. Tsuksgoshi, Synthesis of antitumor-active conjugates of adriamicyn or daunomicyn with the copolymer of divinyl ether and maleic anhydride, Makromol. Chem. 187 (1986) 2815-2824.
24. D.S. Breslow, E.I. Edwards and N.R. Newborg, Divinyl ethermaleic anhydride (pyran) copolymer used to demonstrate the effect of molecular weight on biological activity, Nature 246 (1973) 160-162.
25. D.S. Breslow, Biologically active synthetic polymers, Pure Appl. Chem. 46 (1976) 103-113.
26. A.G. Gornall, C.J. Bardawill and M.M. Cavid, Determination of serum protein by means of biuret reaction, J. Biol. Chem. 177 (1949) 751-766.
27. A.F.S.A. Habeeb, Determination of free amino groups in protein by trinitrobenzensulphonic acid, Anal. Biochem. 14 (1966) 328-336.
28. F. Paoletti, D. Aldinucci, A. Mocali and A. Capanini, A sensitive spectrophotometric method for the determination of superoxide dismutase activity in tissue extracts, Anal. Biochem. 154 (1986) 536-541.
29. S.L. Snyder and P.Z. Sobocinsky, An improved 2,4,6-trinitrobenzensulfonic acid method for the determination of amines, Anal. Biochem. 64 (1975) 284-288.
30. S.E. Zale and A.M. Klibanov, Why does ribonuclease irreversibly inactivate at high temperatures? Biochemistry 25 (1986) 5432-5444.
31. J.J. Marshall and M.L. Rabinowitz, Enzyme stabilisation by covalent attachment of carbohydrate, Arch. Biochem. Biophys. 167 (1975) 777-779.
32. J.A. Fee, Studies on the reconstitution of bovine erythrocytes superoxide dismutase, Biochim. Biophys. Acta 295 (1973) 87-95.
33. J.A. Fee, R. Natter and G.S.T. Baker, Studies on the reconstitution of bovine erythrocyte superoxide dismutase, Biochim. Biophys. Acta 295 (1973) 96-106.
34. H. Maeda, Smancs and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy, Adv. Drug Deliv. Rev. 6 (1991) 181-202.
35. 111In-labelled uricase conjugated with charged dextrans and polyethylene glycol, J. PharmacobioDyn. 14 (1991) 623-629.