Extending insulin action in Vivo by conjugation to carboxymethyl dextran

Bioconjugate Chemistry

Volumn 9, Issue 2, 1998, Pages 176-183

  Baudyš, Miroslav ^a   Letourneur, Didier ^b   Liu, Feng ^a   Mix, Don ^a   Jozefonvicz, Jacqueline ^b   Kim, Sung Wan ^a  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITÉ PARIS 13   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD; CHAINS; DEXTRAN; GLUCOSE; MOLECULES; PROTEINS;

BIOACTIVE PEPTIDES; BIOACTIVE PROTEINS; BIOCHEMICAL PROPERTIES; BLOOD GLUCOSE; CARBOXYMETHYL; IN-VIVO; INSULIN ACTION; INSULIN MOLECULES; PHARMACOLOGICAL PROPERTIES; SITE-SPECIFIC;

INSULIN;

EID: 0032030858     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970180a     Document Type: Article

References (38)

1. Hixson, H. F. (1973) Water-soluble enzyme-polymer grafts: Thermal stabilization of glucose oxidase. Biotechnol. Bioeng. 15, 1011-1016.
2. Abuchowski, A., McCoy, J., Palczuk, N. C., van Es, T., and Davis, F. F. (1977) Effect of covalent attachment of polyethylene glycol on immunogenecity and circulating life of bovine liver catalase. J. Biol. Chem. 252, 3582-3586.
3. Marshall, J., Humphreys, J. D., and Abramson, L. (1977) Attachment of carbohydrate to enzymes increases their circulatory lifetimes. FEBS Lett. 83, 249-251.
4. Mikolajczyk, S. D., Meyer, D. L., Fagnani, R., Hagan, M. S., Law, K. L., and Starling, J. J. (1996) Dextran modification of a Fab′-β-lactamase conjugate modulated by variable pretreatment of Fab′ with amine-blocking reagents. Bioconjugate Chem. 7, 150-158.
5. Takakura, Y., Mahato, R. I., Nishikawa, M., and Hashida, M. (1996) Control of pharmacokinetic profiles of drug-macromolecule conjugates. Adv. Drug Delivery Rev. 19, 377-399.
6. Fujita, T., Nishikawa, M., Tamaki, C., Takakura, Y., Hashida, M., and Sezaki, H. (1992) Targeted delivery of human recombinant superoxide dismutase by chemical modification with mono and polysaccharide derivatives. J. Pharmacol. Exp. Ther. 263, 971-978.
7. Kobayashi, M., Yanagihara, S., and Ichishima, E. (1989) Preparation and characterization of Taka-amylase A attached to carboxymethyl dextran by water-soluble carbodiimide. Agric. Biol. Chem. 53, 3133-3138.
8. Hattori, M., Nagasawa, K., Ametani, A., Kaminogawa, S., and Takahashi, K. (1994) Functional changes in β-lactoglobulin by conjugation with carboxymethyl dextran. J. Agric. Food Chem. 42, 2120-2125.
9. Hattori, M., Imamura, S., Nagasawa, K., and Takahashi, K (1994) Functional changes of lysozyme by conjugating with carboxymethyl dextran. Biosci., Biotechnol., Biochem. 58, 174-177.
10. Heindel, N. D., Kauffman, M. A., Akyea, E. K., Engel, S. A., Frey, M. F., Lacey, C. J., and Egolf, R. A. (1994) Carboxymethyl dextran lactone: A preactivated polymer for amine conjugations. Bioconjugate Chem. 5, 98-100.
11. Banting, F. G., and Best, C. H. (1922) Pancreatic extracts. J. Lab. Clin. Med. 7, 464-472.
12. Schilling, R. J., and Mitra, A. K. (1992) Pharmacodynamics of insulin following intravenous and enteral administrations of porcine zinc insulin in rats. Pharm. Res. 9, 1003-1009.
13. Howey, D. C., Bowsher, R. R., Brunelle, R. L., and Woodworth, J. R. (1994) [Lys(B28), Pro(B29)]-human insulin; A rapidly absorbed analogue of human insulin. Diabetes 43, 396-402.
14. Brange, J. (1987) Galenics of Insulin, Springer-Verlag, Berlin and Heidelberg.
15. Kagedal, L., and Akerstrom, S. (1971) Binding of covalent proteins to polysaccharides by cyanogen bromide and organic cyanates. I. Preparation of soluble glycine-, insulin-, and ampicillin-dextran. Acta Chem. Scand. 25, 1855-1859.
16. Suzuki, F., Daikuhara, Y., Ono, M., and Takeda, Y. (1972) Studies on the mode of action of insulin: Properties and biological activity of an insulin-dextran complex. Endocrinology 90, 1220-1230.
17. Molteni, L., and Scrollini, F. (1974) Methode pour prolonger l'action des medicaments par la formation de composes macromoleculaires. Eur. J. Med. Chem. 9, 618-620.
18. Sakamoto, Y., Akanuma, Y., Kosaha, K., and Jeanrenaud, B. (1977) Comparative effects of native insulin and insulin-dextran complexes on the metabolism of adipose tissue. Biochim. Biophys. Acta 498, 102-113.
19. Armstrong, K. J., Noall, N. W., and Stouffer, J. E. (1972) Dextran-linked insulin: A soluble high molecular weight derivative with biological activity in vivo and in vitro. Biochem. Biophys. Res. Commun. 47, 354-360.
20. Takakura, Y., Fujita, T., Hashida, M., and Sezaki, H. (1990) Disposition characteristics of macromolecules in tumor-bearing mice. Pharm. Res. 7, 339-346.
21. Baudys, M., Uchio, T., Mix, D., Wilson, D., and Kim, S. W. (1995) Physical stabilization of insulin by glycosylation. J. Pharm. Sci. 84, 28-33.
22. Mauzac, M., and Jozefonvicz, J. (1984) Anticoagulant activity of dextran derivatives. Part I: Synthesis and characterization. Biomaterials 5, 301-304.
23. Baudys, M., and Kostka, V. (1983) Covalent structure of chicken pepsinogen. Eur. J. Biochem. 136, 89-99.
24. Blundell, T. L., Dodson, G. G., Hodgkin, D. C., and Mercola, D. (1972) Insulin: The structure in the crystal and its reflection in chemistry and biology. Adv. Protein Chem. 26, 279-402.
25. Letourneur, D., Logeart, D., Avramoglou, T., and Jozefonvicz, J. (1993) Antiproliferative capacity of synthetic dextrans on smooth muscle cell growth. The model of derivatized dextrans as heparin-like polymers. J. Biomater. Sci., Polym. Ed. 4, 431-444.
26. Chytry, V., Letourneur, D., Baudys, M., and Jozefonvicz, J. (1996) Conjugates of insulin with copolymers of N-(2-hydroxypropyl) methacrylamide: Effects on smooth muscle cell proliferation. J. Biomed. Mater. Res. 31, 265-272.
27. Skalli, O., Rapraz, P., Trzeciak, A., Benzonana, G., Gillssen, D., and Gabbiani, G. (1986) A monoclonal antibody against a smooth muscle actin. A new probe for smooth muscle cell differentiation. J. Cell. Biol. 103, 2783-2796.
28. Baudys, M., Uchio, T., Hovgaard, L., Zhu, E. F., Avramoglou, T., Jozefowicz, M., Ríhová, B., Park, J. Y., Lee, H. K., and Kim, S. W. (1995) Glycosylated insulins. J. Controlled Release 36, 151-156.
29. Dahlquist, F. W. (1978) The meaning of Scatchard and Hill plots. Methods Enzymol. 48, 270-299.
30. Gabaldi, M., and Perrier, D. (1982) Pharmacokinetics, pp 409-417, Marcel Decker, New York.
31. Gammeltoft, S. (1984) Insulin receptors: Binding kinetics and structure-function relationship of insulin. Physiol. Rev. 64, 1321-1378.
32. Schäffer, L. (1994) A model for insulin binding to the insulin receptor. Eur. J. Biochem. 227, 1127-1132.
33. Murray-Rust, J., McLeod, A. N., Blundell, T. L., and Wood. S. P. (1992) Structure and evolution of insulins: Implications for receptor binding. BioEssays 14, 325-330.
34. Sato, H., Terasaki, T., Okumura, K., and Tsuji, A. (1991) Effect of receptor up-regulation on insulin pharmacokinetics in streptozotocin-treated diabetic rats. Pharm. Res. 8, 563-569.
35. Torchilin, V. P., Il'ina, E. V., Mazaev, A. V., Lebedev, B. S., Smirnov, V. N., and Chazov, E. I. (1977) Study of modified Sephadex-bound insulin in animal experiments. J. Solid-Phase Biochem. 2, 187-193.
36. Spector, W. S. (1956) Handbook of Biological Data, p 258, W. B. Saunders, Philadelphia and London.
37. Kurtzhals, P., Havelund, S., Jonassen, I., Kiehr, B., Larsen, U. D., Ribel, U., and Markussen, J. (1995) Albumin binding of insulins acylated with fatty acids: Characterization of the ligand-protein interaction and correlation between binding affinity and timing of the insulin effect in vivo. Biochem. J. 312, 725-731.
38. Markussen, J., Havelund, S., Kurtzhals, P., Andersen, A. S., Halstrøm, J., Hasselager, E., Larsen, U. D., Ribel, U., Schäffer, L., Vad, K., and Jonassen, I. (1996) Soluble fatty acid acylated insulins bind to albumin and show protracted action in pigs. Diabetologia 39, 281-288.