Synthesis and characterization of poly(ethylene glycol)-insulin conjugates

Bioconjugate Chemistry

Volumn 11, Issue 2, 2000, Pages 195-201

  Hinds, Ken ^a   Koh, Jae Joon ^a   Joss, Lisa ^a   Liu, Feng ^a   Baudyš, Miroslav ^a   Kim, Sung Wan ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMALIA;

EID: 0343527961     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9901189     Document Type: Article

References (41)

1. Banting, F. G., and Best, C. M. (1922) Pancreatic extracts. J. Lab. Clin. Med. 7, 464-472.
2. Brange, J., and Volund, A. (1999) Insulin analogues with improved pharmacokinetic profiles. Adv. Drug Delivery Rev. 35, 307-335.
3. Binder, C. (1969) Absorption of injected insulin. Acta Pharmacol. Toxicol. 2 (Suppl.), 1-87.
4. Brange, J. (1987) Galenics of Insulin, Springer-Verlag, New York.
5. Brange, J., Owens, D. R., Kang, S., and Volund, A. (1990) Monomeric insulins and their experimental and clinical implications. Diabetes Care 13, 923-954.
6. Kang, S., Brange, J., Burch, A., Volund, A., and Owens, D. R. (1991) Subcutaneous insulin absorption explained by insulin's physicochemical properties. Evidence from absorption studies of soluble human insulin and insulin analogues in humans. Diabetes Care 14, 942-948.
7. Ribel, U., Jorgensen, K., Brange, J., and Henriksen, U. (1986) The pig as a model for subcutaneous insulin absorption in man in Diabetes (M. Serrano-Rios and P. Lefebvre, Eds.), pp 891-896, Elsevier, Amsterdam.
8. Blundell, T., Dodson, G., Hodgkin, D., and Mercola, D. (1972) Insulin: the structure in the crystal and its reflection in chemistry and biology. Adv. Protein Chem. 26, 279-402.
9. Derwenda, U., Derwenda, Z., Dodson, G. G., Hubbard, R. E., and Korber, F. (1989) Molecular structure of insulin: the insulin monomer and its assembly. Br. Med. Bull. 45, 4-18.
10. Mark, A. E., and Jeffrey, P. D. (1990) The self-association of zinc-free bovine insulin. Biol. Chem. Hoppe-Seyler 371, 1165-1174.
11. Brems, D. N., Alter, A. A., Beckage, M. J., Chance, R. E., DiMarchi, R. D., Green, L. K., Long, H. B., Pekar, A. H., Shields, J. E., and Frank, B. H. (1992) Altering the association properties of insulin by amino acid replacement. Protein Eng. 5, 527-533.
12. Brange, J., Dodson, G. G., Edwards, D. J., Holden, P. H., and Whittingham, J. L. (1997) A model of insulin fibrils derived from the X-ray crystal structure of monomeric insulin (despentapeptide insulin). Proteins: Struct., Funct., Genet. 27, 507-516.
13. Brange, J., Anderson, L., Laursen, E. D., Meyn, G., and Rasmussen, E. (1997) Toward understanding insulin fibrillation. J. Pharm. Sci. 86, 517-525.
14. Abuchowski, A., McCoy, J. R., Palczuk, N. C., van Es, T., and Davis, F. F. (1977) Effect of covalent attachment of poly-(ethylene glycol) on immunogenicity and circulating life of bovine liver catalase. J. Biol. Chem. 252, 3582-3586.
15. Beauchamp, C. O., Gonias, S. L., Menapace, D. P., and Pizzo, S. V. (1983) A new proceedure for the synthesis of poly-(ethylene glycol)-protein adducts; effects on function, receptor recognition, and clearance of superoxide dismutase, lactoferrin, and alpha 2-macroglobulin. Anal. Biochem. 131, 25-33.
16. Davis, S., Abuchowski, A., Park, Y. K., and Davis, F. F. (1981) Alteration of the circulating life and antigenic properties of bovine adenosine deamidase in mice by attachment of poly(ethylene glycol). Clin. Exp. Immunol. 46, 649-652.
17. Delgado, C., Francis, G. M., and Fisher, D. (1992) The uses and properties of PEG-linked proteins. CRC Crit. Rev. Ther. Drug Carrier Sys. 9, 249-304.
18. Nucci, M. L., and Abuchowski, A. (1991) The therapeutic value of poly(ethylene glycol)-modified proteins. Adv. Drug Delivery Rev. 6, 133-151.
19. Wieder, K. J., Palczuk, N. C., van Es, T., and Davis, F. F. (1979) Some properties of poly(ethylene glycol): phenylalanine ammonia-lyase adducts J. Biol. Chem. 254, 12579-12587.
20. Zalipsky, S., and Lee, C. (1992) Use of functionalized poly-(ethylene glycol)s for modification of polypeptides. In Poly (ethylene glycol) Chemistry: Biotechnical and Biomedical Applications (J. M. Harris, Ed.), Plenum Press, New York.
21. Monfardini, C., and Veronese, F. M. (1998) Stabilization of substances in circulation. Bioconjugate Chem. 9, 418-450.
22. Gliemann, J., and Gammeltoft, S. (1974) The biological activity and the binding affinity of modified insulins determined on isolated rat fat cells. Diabetologia 10, 105-113.
23. Hashimoto, M., Takada, K., Kiso, Y., and Muranishi, S. (1989) Synthesis of palmitoyl derivatives of insulin and their biological activities. Pharm. Res. 6, 171-176.
24. 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, 325-331.
25. Liu, F., Song, S. C., Mix, D., Baudyš, M., and Kim, S. W. (1997) Glucose-induced release of glycosylpoly(ethylene glycol) insulin bound to a soluble conjugate of concavalin A. Bioconjugate Chem. 8, 664-672.
26. Uchio, T., Baudyš, M., Liu, F., and Kim, S. W. (1999) Novel site-specific insulin conjugates with enhanced stability and extended action profile for parenteral delivery. Adv. Drug Delivery Rev. 35, 289-306.
27. Ehrat, M., and Luisi, P. L. (1983) Synthesis and spectroscopic characterization of insulin derivatives containing one or two poly(ethylene glycol) chains at specific positions. Biopolymers 22, 569-573.
28. Hinds, K. D., Liu, F., Koh, J. J., Baudyš, M., and Kim, S. W. (1999) Poly(ethylene glycol) conjugation to improve the physical and biological properties of insulin. Proc. Int. Symp. Controlled Release Bioactive Mater. 26, 6424-6425.
29. Caliceti, P., and Veronese, F. M. (1998) Successful insulin delivery by PEG conjugation. Proc. Int. Symp. Controlled Release Bioactive Mater. 25, 263-264.
30. Neubauer, H. P., Obermeier, R., and Schone, H. H. (1983) Influence of poly(ethylene glycol) insulin on the lipid tissues of experimental animals. Diabetes 32, 953-958.
31. Baudyš, M., Uchio, T., Mix, D., Wilson, D., and Kim, S. W. (1995) Physical stabilization of insulin by glycosylation. J. Pharm. Sci. 84, 28-33.
32. Myers, S. R., Yakubu-Madus, F. E., Johnson, W. T., Baker, J. E., Cusick, T. S., Williams, V. K., Tinsley, F. C., Kriauciunas, A., Manetta, J., and Chen, V. J. (1997) Acylation of human insulin with palmitic acid extends the time action of human insulin in diabetic dogs. Diabetes 46, 637-642.
33. Johnson, M. L., Correia, J. J., Yphantis, D. A., and Halvorson, H. R. (1981) Analysis of data from the analytical ultracentrifuge by nonlinear least squares techniques. Biophys. J. 36, 575-588.
34. Yphantis, D. A. (1964) Equilibrium ultracentrifugation of dilute solutions. Biochemistry 3, 297-317.
35. Goldman, J., and Carpenter, F. H. (1974) Zinc binding, circular dichroism, and equilibrium sedimentation studies in insulin (bovine) and several of its derivatives. Biochemistry 13, 4566-4574.
36. Melberg, S. G., and Johnson, W. C. (1990) Changes in secondary structure follow the dissociation of human insulin hexamers: A circular dichroism study. Proteins: Struct., Funct., Genet. 8, 280-286.
37. Mercola, D. A., Morris, J. W. S., Arquilla, E. R., and Bromer, W. W. (1967) The ultraviolet circular dichroism of bovine insulin and desoctapeptide insulin. Biochim. Biophys. Acta 133, 224-232.
38. Morris, J. W. S., Mercola, D., and Arquilla, E. R. (1968) An analysis of the near-ultraviolet circular dichroism of insulin. Biochim. Biophys. Acta 160, 145-150.
39. Pocker, Y., and Biswas, S. B. (1980) Conformational dynamics of insulin in solution. Circular dichroic studies. Biochemistry 19, 5043-5049.
40. Wood, S. P., Blundell, T. L., Wollmer, A., and Lazarus, N. R. (1975) The relation of conformation and association of insulin to receptor binding; X-ray and circular-dichroism studies on bovine and hystricomorph insulins. Eur. J. Biochem. 55, 531-542.
41. Bakaysa, D. L., Radziuk, J., Havel, H. A., Brader, M. L., Li, S., Dodd, S. W., Beals, J. M., Pekar, A. H., and Brems, D. N. (1996) Physicochemical basis for the rapid time-action of LysB28ProB29-insulin: dissociation of a protein-ligand complex. Protein Sci. 5, 2521-2531.