Dipeptidyl peptidase IV resistant analogues of glucagon-like peptide-1 which have extended metabolic stability and improved biological activity

Diabetologia

Volumn 41, Issue 3, 1998, Pages 271-278

  Deacon, C F ^a   Knudsen, L B ^b   Madsen, K ^b   Wiberg, F C ^b   Jacobsen, O ^a   Holst, J J ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

Author keywords

Analogue; Dipeptidyl peptidase IV; Glucagon like peptide 1; Non insulin dependent diabetes mellitus; Therapy

Indexed keywords

DIPEPTIDYL PEPTIDASE IV; GLUCAGON LIKE PEPTIDE 1; GLYCINE; SERINE; THREONINE;

AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ARTICLE; DIABETES MELLITUS; GLUCAGON RELEASE; GLUCOSE METABOLISM; HUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIGENS, CD26; CROSS REACTIONS; DRUG STABILITY; GLUCAGON; GLUCAGON-LIKE PEPTIDE 1; GLUCAGON-LIKE PEPTIDES; INSULIN; PANCREAS; PEPTIDE FRAGMENTS; PERFUSION; PROTEIN BINDING; PROTEIN PRECURSORS; RECEPTORS, GLUCAGON; SWINE;

EID: 0031782440     PISSN: 0012186X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s001250050903     Document Type: Article

References (42)

1. Holst JJ (1983) Gut glucagon, enteroglucagon, gut glucagonlike immunoreactivity, glicentin: current status. Gastroenterology 84: 1602-1613
2. Ørskov C (1992) Glucagon-like peptide-1, a new hormone of the entero-insular axis. Diabetologia 35: 701-711
3. Ørskov C, Rabenhøj L, Wettergren A, Kofod H, Holst JJ (1994) Tissue and plasma concentrations of amidated and glycine-extended glucagon-like peptide-1 in humans. Diabetes 43: 535-539
4. Ørskov C, Holst JJ, Nielsen OV (1988) Effect of truncated glucagon-like peptide-1 [proglucagon-(78-107) amide] on endocrine secretion from pig pancreas, antrum and non-antral stomach. Endocrinology 123: 2009-2013
5. Kreymann B, Williams G, Ghatei MA, Bloom SR (1987) Glucagon-like peptide 17-36: a physiological incretin in man. Lancet ii: 1300-1304
6. Nathan DM, Schreiber E, Fogel H, Mojsov S, Habener JF (1992) Insulinotropic action of glucagonlike peptide-1-(7-37) in diabetic and nondiabetic subjects. Diabetes Care 15: 270-276
7. Weir GC, Mojsov S, Hendrick GK, Habener JF (1989) Glucagon-like peptide 1 (7-37) actions on endocrine pancreas. Diabetes 38: 338-342
8. Gutniak M, Ørskov C, Holst JJ, Ahrén B, Efendic S (1992) Anti-diabetogenic effect of glucagon-like peptide-1 (7-36) amide in normal subjects and patients with diabetes mellitus. N Engl J Med 326: 1316-1322
9. Nauck MA, Heimsaat MM, Ørskov C, Holst JJ, Ebert R, Creutzfeldt W (1993) Preserved incretin activity of glucagon-like peptide-1 [7-36 amide] but not of synthetic gastric inhibitory polypeptide in patients with type-2 diabetes mellitus. J Clin Invest 91: 301-307
10. Holz GG, Kühtreiber WM, Habener JF (1993) Pancreatic beta cells are rendered glucose-competent by the insulinotropic hormone glucagon-like peptide-1 (7-36). Nature 361: 362-365
11. Thorens B, Waeber G (1993) Glucagon-like peptide-1 and the control of insulin secretion in the normal state and in NIDDM. Diabetes 42: 1219-1225
12. Mentlein R, Gallwitz B, Schmidt WE (1993) Dipeptidyl peptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1 (7-36) amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem 214: 829-835
13. Deacon CF, Johnsen AH, Holst JJ (1995) Degradation of glucagon-like peptide-1 by human plasma in vitro yields an N-terminally truncated peptide which is a major endogenous metabolite in vivo. J Clin Endocrinol Metab 80: 952-957
14. Kieffer TJ, McIntosh CHS, Pederson RA (1995) Degradation of glucose-dependent insulinotropic polypeptide (GIP) and truncated glucagon-like peptide 1 (tGLP-1) in vitro and in vivo by dipeptidyl peptidase IV. Endocrinology 136: 3585-3596
15. Grandt B, Sieburg B, Sievert J et al. (1994) Is GLP-1 (9-36) amide an endogenous antagonist at GLP-1 receptors? Digestion 55: 302A (Abstract)
16. Knudsen LB, Pridal L (1996) Glucagon-like peptide-1 (9-36) amide is a major metabolite of glucagon-like peptide-1 (7-36) amide after in vivo administration to dogs, and it acts as an antagonist on the pancreatic receptor. Eur J Pharmacol 318: 429-435
17. 2-terminus in type II diabetic patients and in healthy subjects. Diabetes 44: 1126-1131
18. Heins J, Neubert K, Barth A, Canizaro PC, Behal FJ (1984) Kinetic investigation of the hydrolysis of aminoacyl p-nitroanilides by dipeptidyl peptidase IV from human and pig kidney. Biochim Biophys Acta 785: 30-35
19. Rahfeld J, Schutkowski M, Faust J, Neubert K, Barth A, Heins J (1991) Extended investigation of the substrate specificity of dipeptidyl peptidase IV from pig kidney. Biol Chem Hoppe-Seyler 372: 313-318
20. Martin RA, Cleary DL, Guido DM, Zurcher-Neely HA, Kubiak TM (1993) Dipeptidyl peptidase IV (DPP IV) from pig kidney cleaves analogs of bovine growth hormone-releasing factor (bGRF) modified at position 2 with Ser, Thr or Val. Extended DPP-IV substrate specificity? Biochim Biophys Acta 1164: 252-260
21. Southern PJ, Berg P (1982) Transformation of mammalian cells to antibiotic resistance with a bacterial gene under the control of the SV40 early region promoter. J Mol Appl Genet 1: 327-341
22. Chen C, Okayama H (1987) High-efficiency transformation of mammalian cells by plasmid DNA. Mol Cell Biol 7: 2745-2752
23. 125I to high specific activity. Biochim Biophys Acta 251: 363-369
24. 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
25. Holst JJ, Fahrenkrug J, Knuhtsen SL, Poulsen SS, Nielsen OV (1984) Vasoactive intestinal polypeptide (VIP) in pig pancreas: role of VIPergic nerves in control of fluid and bicarbonate secretion. Regul Pept 8: 245-259
26. Ørskov C, Holst JJ, Seier Poulsen S, Kirkegaard P (1987) Pancreatic and intestinal processing of proglucagon in man. Diabetologia 30: 874-881
27. Ørskov C, Jeppesen J, Madsbad S, Holst JJ (1991) Proglucagon products in the plasma of non-insulin dependent diabetics and nondiabetic controls in the fasting state and following oral glucose and intravenous arginine. J Clin Invest 87: 415-423
28. Gutniak MK, Larsson H, Heiber SJ, Juneskans OT, Holst JJ. Ahrén B (1996) Potential therapeutic levels of glucagon-like peptide I achieved in humans by a buccal tablet. Diabetes Care 19: 843-848
29. Hvidberg A, Nielsen MT, Hilstead J, Ørskov C, Holst JJ (1994) Effect of glucagon-like peptide-1 (proglucagon 78-107 amide) on hepatic glucose production in healthy man. Metab Clin Exp 43: 104-108
30. Holst JJ (1980) Evidence that glicentin contains the entire sequence of glucagon. Biochem J 187: 337-343
31. Pauly RP, Rosche F, Wermann M, McIntosh CH, Pederson RA, Demuth HU (1996) Investigation of glucose-dependent insulinotropic polypeptide-(l-42) and glucagon-like peptide-1-(7-36) degradation in vitro by dipeptidyl peptidase IV using matrix-assisted laser desorption/ionization-time of flight mass spectrometry. A novel kinetic approach. J Biol Chem 271: 23222-23229
32. Pridal L, Deacon CF, Kirk O, Christensen JV, Carr RD, Holst JJ (1996) Glucagon-like peptide-1 (7-37) has a larger volume of distribution than glucagon-like peptide-1 (7-36) amide in dogs and is degraded more quickly in vitro by dog plasma. Eur J Drug Metab Pharmacokinet 21: 51-59
33. Deacon CF, Pridal L, Klarskov L, Olesen M, Holst JJ (1996) Glucagon-like peptide 1 undergoes differential tissue-specific metabolism in the anesthetized pig. Amer J Physiol 271: E458-E464
34. Thorens B, Porret A, Bühler L, Deng S-P, Morel P, Widmann C (1993) Cloning and functional expression of the human islet GLP-1 receptor. Demonstration that exendin-4 is an agonist and exendin-(9-39) an antagonist of the receptor. Diabetes 42: 1678-1682
35. Kubiak TM, Friedman AR, Martin RA et al. (1993) Position 2 and position 2/Ala 15-substituted analogs of bovine growth hormone-releasing factor (bGRF) with enhanced metabolic stability and improved in vivo bioactivity. J Med Chem 36: 888-897
36. Rachman J, Gribble FM, Barrow BA, Levy JC, Buchanan KD, Turner RC (1996) Normalization of insulin responses to glucose by overnight infusion of glucagon-like peptide 1 (7-36) amide in patients with NIDDM. Diabetes 45: 1524-1530
37. Rachman J, Barrow BA, Levy JC, Turner RC (1997) Nearnormalisation of diurnal glucose concentrations by continuous administration of glucagon-like peptide-1 (GLP-1) in subjects with NIDDM. Diabetologia 40: 205-211
38. Larsen J, Jallad N, Damsbo P (1996) One-week continuous infusion of GLP-1 (7-37) improves the glycaemic control in NIDDM. Diabetes 45 [Suppl 2]: 233A (Abstract)
39. Larsen J, Damsbo P (1997) GLP-1 must be present continuously in order to obtain good glycaemic control in NIDDM. Diabetes 46 [Suppl 1]: 186A (Abstract)
40. Juntti-Berggren L, Pigon J, Karpe F et al. (1996) The antidiabetogenic effect of GLP-1 is maintained during a 7-day treatment period and improves diabetic dyslipoproteinemia in NIDDM patients. Diabetes Care 19: 1200-1206
41. Gutniak MK, Linde B, Holst JJ, Efendic S (1994) Subcutaneous injection of the incretin hormone glucagon-like peptide 1 abolishes postprandial glycemia in NIDDM. Diabetes Care 17: 1039-1044
42. Todd JF, Wilding JPH, Edwards CMB, Khan FA, Ghatei MA, Bloom SR (1997) Glucagon like peptide 1 (GLP-1): a trial of treatment in noninsulin dependent diabetes mellitus. Eur J Clin Invest 27: 533-536