Soluble, fatty acid acylated insulins bind to albumin and show protracted action in pigs

Diabetologia

Volumn 39, Issue 3, 1996, Pages 281-288

  Markussen, J ^a,b   Havelund, S ^a   Kurtzhals, P ^a   Andersen, A S ^a   Halstrom J ^a   Hasselager, E ^a   Larsen, U D ^a   Ribel, U ^a   Schaffer L ^a   Vad, K ^a   Jonassen, I ^a  

^a Novo Research Institute   (Denmark)

^b NOVO NORDISK A S   (Denmark)

Author keywords

Acylation; Albumin binding; Basal insulin; Fatty acids; Insulin analogues; Lysine(B29); Myristic acid; Prolonged action; Receptor affinity; Tetradecanoic acid

Indexed keywords

INSULIN DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DIABETES MELLITUS; NONHUMAN; PRIORITY JOURNAL; SUBCUTANEOUS DRUG ADMINISTRATION; SWINE;

EID: 9044226136     PISSN: 0012186X     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00418343     Document Type: Article

References (28)

1. The Diabetes Control and Complications Trial Research Group (1993) The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus. N Engl J Med 329: 977-986
2. Krayenbühl C, Rosenberg T (1946) Crystalline protamine insulin. Rep Steno Mem Hosp Nord Insulinlab 1: 60-73
3. Hallas-Møller K (1956) The Lente insulins. Diabetes 5: 7-14
4. Frid A, Östman J, Linde B (1990) Hypoglycemia risk during exercise after intramuscular injection of insulin in thigh in IDDM. Diabetes Care 13: 473-477
5. Thow JC, Johnson AB, Antsiferov M, Home PD (1989) Effect of raising injection-site skin temperature on Isophane (NPH) insulin crystal dissociation. Diabetes Care 12: 432-434
6. Markussen J, Hougaard P, Ribel U, Sørensen AR, Sørensen E (1987) Soluble, prolonged-acting insulin derivatives. I. Degree of protraction and crystallizability of insulins substituted in the termini of the B-chain. Protein Engineering 1: 205-213
7. Markussen J, Diers I, Engesgaard A et al. (1987) Soluble, prolonged-acting insulin derivatives. II. Degree of protraction and crystallizability of insulins substituted in positions A17, B8, B13, B27 and B30. Protein Engineering 1: 215-223
8. Markussen J, Diers I, Hougaard P et al. (1988) Soluble, prolonged-acting insulin derivatives. III. Degree of protraction, crystallizability and stability of insulins substituted in positions A21, B13, B23, B27 and B30. Protein Engineering 2: 157-166
9. Jørgensen S, Vaag A, Langkjær L, Hougaard P, Markussen J (1989) NovoSol Basal: pharmacokinetics of a novel soluble long acting insulin analogue. BMJ 299: 415-419
10. Holman RR, Steemson J (1989) OPID 174: a novel long-acting insulin preparation. Diabet Med 6[Suppl 1]1:A41 (Abstract)
11. Spector AA (1975) Fatty acid binding to plasma albumin. J Lipid Res 16: 165-179
12. Peters T (1985) Serum albumin. Adv Protein Chem 17: 161-245
13. Gliemann J, Gammeltoft S (1974) The biological activity and the binding affinity of modified insulins determined on isolated rat fat cells. Diabetologia 10: 105-113
14. Geiger R, Obermeier R, Teetz V et al. (1980) Biological activity of insulin analogues substituted at the amino group of B1-phenylalanine. In: Brandenburg D, Wollmer A (eds) Insulin: chemistry, structure and function of insulin and related hormones. Walter de Gruyter, Berlin New York, pp 409-415
15. Hashimoto M, Takada K, Kiso Y, Muranishi S (1989) Synthesis of palmitoyl derivatives of insulin and their biological activities. Pharm Res 6: 171-176
16. 2+. Diabet Med 3: 532-536
17. Havelund S, Halstrøm JB, Jonassen I, Andersen AS, Markussen J (1995) Acylated insulin. Patent application PCT/ DK94/00347. International publication number: WO 95/ 07931
18. Drejer K, Kruse V, Larsen UD, Hougaard P, Bjørn S, Gammeltoft S (1991 ) Receptor binding and tyrosine kinase activation by insulin analogues with extreme affinities studied in human hepatoma HepG2 cells. Diabetes 40: 1488-1495
19. Reed RG, Gates T, Peters T (1975) Albumin immobilized on agarose as a tool for measuring ligand binding by proteins or peptides. Anal Biochem 69: 361-371
20. Markussen J, Halstrøm JB, Wiberg FC, Schäffer L (1991) Immobilized insulin for high capacity affinity chromatography of insulin receptors. J Biol Chem 266: 18814-18818
21. Kristensen C, Andersen AS, Hach M, Wiberg FC, Schäffer L, Kjeldsen T (1995) A single-chain insulin-like growth factor I/insulin hybrid binds with high affinity to the insulin receptor. Biochem J 305: 981-986
22. Baadegaard N (1993) Measurements of drug absorption patterns. An Industrial Research Project EF 340, Ph. D. Thesis, the Technical University of Denmark, June 1993
23. th Congress of the International Diabetes Federation, Madrid 1985. Excerpta Medica, Amsterdam, pp 891-896
24. 125I-labelled neutral insulin solutions. Diabetologia 27[Suppl 2]:325A (Abstract)
25. Ribel U, Hougaard P, Drejer K, Sørensen AR (1990) Equivalent in vivo biological activity of insulin analogues and human insulin despite different in vitro potencies. Diabetes 39: 1033-1039
26. He XM, Carter DC (1992) Atomic structure and chemistry of human serum albumin. Nature 358: 209-215
27. Carter DC, Ho JX (1994) Structure of serum albumin. Adv Protein Chem 45: 153-203
28. Pullen RA, Lindsay DG, Wood SP et al. (1976) Receptor-binding region of insulin. Nature 259: 369-373