NB1-C16-insulin: Site-specific synthesis, purification, and biological activity

Pharmaceutical Research

Volumn 16, Issue 11, 1999, Pages 1680-1686

  Mei, Hong ^a   Yu, X Christopher ^a   Chan, Kenneth K ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Hypoglycemic effect; Lipid modified insulin; Site specific synthesis

Indexed keywords

INSULIN DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; DIABETES MELLITUS; DRUG DETERMINATION; DRUG EFFECT; DRUG FORMULATION; DRUG PURIFICATION; DRUG PURITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HYPOGLYCEMIA; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY;

ALKYLATION; ANIMALS; BINDING, COMPETITIVE; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIABETES MELLITUS, EXPERIMENTAL; HUMANS; HYDROGEN-ION CONCENTRATION; HYPOGLYCEMIC AGENTS; INSULIN; LIPIDS; MALE; MASS SPECTROMETRY; RADIOLIGAND ASSAY; RATS; RECEPTOR, INSULIN; TUMOR CELLS, CULTURED;

EID: 0032734541     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1018993629553     Document Type: Article

References (23)

1. 1. P. Kurtzhals, S. Havelund, I. Jonassen, B. Kiehr, U. D. Larsen, and J. Markussen. Albumin binding of insulins acylated with fatty acids: characterization of the ligand-protein interaction and correlation between binding and timing of insulin effect in vivo. Biochem. J. 312:725-31 (1995).
2. 2. J. Markussen, S. Havelund, P. Kurtzhal, A. S. Anderson, J. Halstom, U. D. Larsen, E. Hasselager, U. Ribel, L. Schaffer, K. Vad, and I. Jonassen. Soluble, fatty acid acylated insulins bind to albumin and show protracted action in pigs. Diabetologia 39:281-288 (1996).
3. 3. H. Asada, T. Douen, Y. Mizokoshi, T. Fujita, M. Murakami, A. Yamamoto, and S. Muranishi. Stability of acyl derivatives of insulin in the small intestine: relative importance of insulin association characteristics in aqueous solution. Pharm. Res. 11:1115-1120 (1994).
4. 4. H. Asada, T. Douen, M. Waki, S. Adachi, T. Fujita, T. Yamamoto, and S. Muranishi. Absorbtion charateristics of chemically modified-insulin derivatives with various fatty acids in the small and large intestine. J. Pharm. Sci. 84:682-687 (1995).
5. 5. S. R. Myers, F. E. Yakubu-Madus, W. T. Johnson, J. E. Baker, T. S. Cusick, V. K. Williams, F. C. Tinsley, A. Kriauciunas, J. Manetta, and V. J. Chen. Acylation of human insulin with palmitic acid extends the time action of human insulin in diabetic dogs. Diabetes 46:637-642 (1997).
6. 6. D. G. Lindsay and H. Shall. The acetylation of insulin. Biochem. J. 121:737-745 (1971).
7. 7. M. Hashimoto, K. Takada, Y. Kiso, and S. Muranishi. Synthesis of Palmitoyl derivatives of insulin and their biological activities. Pharm. Res. 6:171-76 (1989).
8. 8. T. J. Tsai, A. Rottero, D. D Chow, K. J. Hwang, V. H. L. Lee, G. Zhu, and K. K. Chan. Synthesis and purification of NBI-palmitoyl insulin. J. Pharm. Sci. 86:1264-1268 (1997).
9. 9. O. B. Kinstler, D. N. Brems, S. L. Lauren, A. G. Paige, J. B. Hamburger, and M. J. Treuheit. Characterization and Stability of N-terminally PEGylated rhG-CSF. Pharm. Res. 13:996-1002 (1996).
10. 10. R. M. Young. Incorporation of insulin into a liposomal membrane. Master thesis. The Ohio State University. 1982.
11. 11. R. L. Lundblad. Site-specific chemical modification of proteins. In R. L. Lundblad (ed), Techiniques in Protein Modification, CRC Press, New York, 1995. pp. 1-14.
12. 12. M. Crettaz. Hepatoma cells in culture as a tool for the study of insulin receptor and insulin action. In C. R. Kahn and L. C. Harrison (eds). Insulin Receptors, Part A: Methods For The Study Of Structure And Function, Alan R. Liss, Inc., New York, 1988, pp. 221-233.
13. 13. K. Waxman, H. M. Soliman, and K. H. Nguyen. Absorbtion of insulin in the peritoneal cavity in a diabetic animal model. Artificial Organs 17:925-928 (1993).
14. 14. B. Ahren, J. S. Stern, R. L. Gingerrich, D. L. Curley, and P. J. Havel. Glucagon secretary response to hypoglycemia, adrenaline and carbachol in streptozotocin-diabetic rats. Acta Physio. Scand. 155:215-21 (1995).
15. 15. T. Blundell, G. Dodson, and D. Hodgkin, and D. Mercola. Insulin: the structure in the crystal and its reflection in chemistry and biology. Adv. Protein Chem. 26:279-402 (1972)
16. 16. J. H. Bradbury and L. R. Brown. Nuclear-magnetic-resonance-spectroscopic studies of the amino groups of insulin. Eur. J. Biochem 76:573-82 (1977).
17. 2+ to the Glu(B13) site drives hexamer assembly and induces a conformation change. Biochemistry 27:3387-97 (1988).
18. 18. W. E. Choi, D. Borchardt, N. C. Kaarsholm, P. S. Brzovic, and M. F. Dunn. Spectroscopic evidence for preexisting T-and R-state insulin hexamer conformations. Proteins: structure, function and genetics 26:377-390 (1996).
19. 19. J. L. Whittingham, S. Havelund, and I. Jonassen. Crystal structure of a prolonged-acting-insulin with albumin-binding properties. Biochemistry 36: 2826-31 (1997).
20. 20. W. Touitou, A. P. Fisher, A. Memoli, F. M. Riccieri, and E. Santucci. Prevention of molecular self association by sodium salicylate: effect on insulin and 6-carboxyfluorecein. J. Pharm. Sci. 76:791-793 (1987).
21. 21. M. Roy, M. L. Brader, R. W.-K Lee, N. C. Kaarsholm, J. F. Hansen, and M. F. Dunn. Spectroscopic signitures of the T to R conformational transition in the insulin hexamer. J. Biol. Chem. 264:19081-19085 (1989).
22. 22. Y. Tsai. Palmitoyl insulin as a homing ligand for targeting liposomes to hepatocytes. Ph.D dissertation. University of Southern California. 1992.
23. 23. A. Kurtaran, S. Li, M. Raderer, M. Leimer, C. Muller, J. Pidlich, N. Neuhold, P. Hubsch, P. Angelberger, W. Scheithauer, and I. Virgolini. Technetium-99m-Galactosyl-Neoglycoalbumin combined with Iodine-123-Tyr-(A14)-Insulin visualizes human hepatocellular carcinomas J. Nucl. Med. 36:1875-1881 (1995).