Taspoglutide, an analog of human glucagon-like peptide-1 with enhanced stability and in vivo potency

Endocrinology

Volumn 151, Issue 6, 2010, Pages 2474-2482

  Sebokova, Elena ^a   Christ, Andreas D ^a   Wang, Haiyan ^a   Sewing, Sabine ^a   Dong, Jesse Z ^b   Taylor, John ^b   Cawthorne, Michael A ^c   Culler, Michael D ^b  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b Biomeasure Inc   (United States)

^c UNIVERSITY OF BUCKINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDIABETIC AGENT; CYCLIC AMP; DIPEPTIDYL PEPTIDASE IV; EXENDIN 4; GLUCAGON LIKE PEPTIDE 1; GLUCAGON LIKE PEPTIDE 1 RECEPTOR; GLUCOSE; INSULIN; IODINE 125; TASPOGLUTIDE; UNCLASSIFIED DRUG; DPP4 PROTEIN, HUMAN; DRUG DERIVATIVE; GLUCAGON LIKE PEPTIDE RECEPTOR; GLUCAGON RECEPTOR; GLUCAGON-LIKE PEPTIDE RECEPTOR; PEPTIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CHO CELL; CONCENTRATION (PARAMETERS); CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG HALF LIFE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STABILITY; ENZYME INHIBITION; FEMALE; GENE OVEREXPRESSION; INCUBATION TIME; INSULIN BLOOD LEVEL; INSULIN RELEASE; INSULINOMA; LIGAND BINDING; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CLEAVAGE; RAT; ROOM TEMPERATURE; ANIMAL; BLOOD; CHEMISTRY; CRICETULUS; ENZYME LINKED IMMUNOSORBENT ASSAY; HAMSTER; HUMAN; METABOLISM; PROTEIN BINDING; SPRAGUE DAWLEY RAT; TUMOR CELL LINE;

ANIMALS; ANTIGENS, CD26; CELL LINE, TUMOR; CHO CELLS; CRICETINAE; CRICETULUS; CYCLIC AMP; DRUG STABILITY; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLUCAGON-LIKE PEPTIDE 1; HUMANS; INSULIN; PEPTIDES; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, GLUCAGON;

EID: 77951293658     PISSN: 00137227     EISSN: 00137227     Source Type: Journal    
DOI: 10.1210/en.2009-1459     Document Type: Article

References (58)

1. Drucker DJ 2005 Biologic actions and therapeutic potential of the proglucagon-derived peptides. Nat Clin Pract Endocrinol Metab 1:22-31
2. Orskov C, Wettergren A, Holst JJ 1993 Biological effects and metabolic rates of glucagon-like peptide-1 7-36 amide and glucagon-like peptide-1 7-37 in healthy subjects are indistinguishable. Diabetes 42:658-661 (Pubitemid 23127154)
3. Fehmann HC, Habener JF 1992 Insulinotropic glucagon-like peptide-I(7-37)/(7-36) amide A new incretin hormone. Trends Endocrinol Metab 3:158-163
4. Holz 4th GG, Kühtreiber WM, Habener JF 1993 Pancreatic β-cells are rendered glucose-competent by the insulinotropic hormone glucagon-like peptide-1(7-37). Nature 361:362-365
5. Kreymann B, Williams G, Ghatei MA, Bloom SR 1987 Glucagon-like peptide-1 7-36: a physiological incretin in man. Lancet 2:1300-1304 (Pubitemid 17156636)
6. Brubaker PL, Anini Y 2003 Direct and indirect mechanisms regulating secretion of glucagon-like peptide-1 and glucagon-like peptide-2. Can J Physiol Pharmacol 81:1005-1012 (Pubitemid 38045829)
7. Kieffer TJ, Habener JF 1999 The glucagon-like peptides. Endocr Rev 20:876-913
8. McIntyre N, Holdsworth CD, Turner DS 1964 New interpretation of oral glucose tolerance. Lancet 2:20-21
9. Buteau J, El-Assaad W, Rhodes CJ, Rosenberg L, Joly E, Prentki M 2004 Glucagon-like peptide-1 prevents beta cell glucolipotoxicity. Diabetologia 47:806-815 (Pubitemid 38756992)
10. Drucker DJ 2003 Glucagon-like peptide-1 and the islet β-cell: augmentation of cell proliferation and inhibition of apoptosis. Endocrinology 144:5145-5148 (Pubitemid 37476039)
11. Drucker DJ, Philippe J, Mojsov S, Chick WL, Habener JF 1987 Glucagon-like peptide I stimulates insulin gene expression and increases cyclic AMP levels in a rat islet cell line. Proc Natl Acad Sci USA 84:3434-3438 (Pubitemid 17085418)
12. Farilla L, Bulotta A, Hirshberg B, Li Calzi S, Khoury N, Noushmehr H, Bertolotto C, Di Mario U, Harlan DM, Perfetti R 2003 Glucagon-like peptide 1 inhibits cell apoptosis and improves glucose responsiveness of freshly isolated human islets. Endocrinology 144: 5149-5158 (Pubitemid 37476040)
13. Flint A, Raben A, Astrup A, Holst JJ 1998 Glucagon-like peptide 1 promotes satiety and suppresses energy intake in humans. J Clin Invest 101:515-520 (Pubitemid 28084232)
14. Nauck MA, Heimesaat MM, Behle K, Holst JJ, Nauck MS, Ritzel R, Hüfner M, Schmiegel WH 2002 Effects of glucagon-like peptide 1 on counterregulatory hormone responses, cognitive functions, and insulin secretion during hyperinsulinemic, stepped hypoglycemic clamp experiments in healthy volunteers. J Clin Endocrinol Metab 87:1239-1246 (Pubitemid 36121094)
15. Turton MD, O'Shea D, Gunn I, Beak SA, Edwards CM, Meeran K, Choi SJ, Taylor GM, Heath MM, Lambert PD, Wilding JP, Smith DM, Ghatei MA, Herbert J, Bloom SR 1996 A role for glucagon-like peptide-1 in the central regulation of feeding. Nature 379:69-72 (Pubitemid 26008136)
16. Kawai K, Suzuki S, Ohashi S, Mukai H, Ohmori H, Murayama Y, Yamashita K 1989 Comparison of the effects of glucagon-like peptide-1-(1-37) and -(7-37) and glucagon on islet hormone release from isolated perfused canine and rat pancreases. Endocrinology 124:1768-1773 (Pubitemid 19105444)
17. Orskov 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 nonantral stomach. Endocrinology 123:2009-2013
18. Wettergren A, Schjoldager B, Mortensen PE, Myhre J, Christiansen J, Holst JJ 1993 Truncated GLP-1 (proglucagon 78-107-amide) inhibits gastric and pancreatic functions in man. Dig Dis Sci 38:665-673 (Pubitemid 23121274)
19. Gutniak M, Orskov C, Holst JJ, Ahrén B, Efendic S 1992 Antidiabetogenic effect of glucagon-like peptide-1 (7-36)amide in normal subjects and patients with diabetes mellitus. N Engl J Med 326: 1316-1322
20. Meneilly GS, Greig N, Tildesley H, Habener JF, Egan JM, Elahi D 2003 Effects of 3 months of continuous subcutaneous administration of glucagon-like peptide 1 in elderly patients with type 2 diabetes. Diabetes Care 26:2835-2841 (Pubitemid 37205555)
21. Rachman J, Barrow BA, Levy JC, Turner RC 1997 Near-normalisation of diurnal glucose concentrations by continuous administration of glucagon-like peptide-1 (GLP-1) in subjects with NIDDM. Diabetologia 40:205-211 (Pubitemid 27060294)
22. Vilsbøll T, Knop FK, Krarup T, Johansen A, Madsbad S, Larsen S, Hansen T, Pedersen O, Holst JJ 2003 The pathophysiology of diabetes involves a defective amplification of the late-phase insulin response to glucose by glucose-dependent insulinotropic polypeptide-regardless of etiology and phenotype. J Clin Endocrinol Metab 88:4897-4903
23. Zander M, Madsbad S, Madsen JL, Holst JJ 2002 Effect of 6-week course of glucagon-like peptide 1 on glycaemic control, insulin sensitivity, and β-cell function in type 2 diabetes: a parallel-group study. Lancet 359:824-830
24. Kjems LL, Holst JJ, Vølund A, Madsbad S 2003 The influence of GLP-1 on glucose-stimulated insulin secretion: effects on β-cell sensitivity in type 2 and nondiabetic subjects. Diabetes 52:380-386
25. Kieffer TJ, McIntosh CH, Pederson RA 1995 Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV. Endocrinology 136:3585-3596
26. Toft-Nielsen MB, Madsbad S, Holst JJ 1999 Continuous subcutaneous infusion of glucagon-like peptide 1 lowers plasma glucose and reduces appetite in type 2 diabetic patients. Diabetes Care 22:1137-1143
27. 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
28. Deacon CF, Johnsen AH, Holst JJ 1995 Degradation of glucagon-like peptide-1 by human plasma in vitro yields an N-terminally truncated peptide that is a major endogenous metabolite in vivo. J Clin Endocrinol Metab 80:952-957
29. Dong JZ, Shen Y, Zhang J, Taylor JE, Woon C-W, Morgan B, Skinner S, Cawthorne M, Culler M, Moreau J-P 2004 Design and synthesis of novel GLP-1 analogs that have significantly improved in vivo activities. Peptides: peptide revolution: genomics, proteomics &therapeutics. Proc 18th American Peptide Symposium, Chorev M and Sawyer TK, eds., KLUWER, 625-627 (Abstract)
30. 2) is cleaved by plasma enzymes not only at the N terminus but also at the C terminus: development of novel GLP-1 analogs which are highly resistant to enzymatic degradation. Benedetti, Eand Pedone C, eds. Peptides 2002: Proc 27th European Peptide Symposium 2002, Edizioni Ziino, 88-89 (Abstract)
31. Al-Sabah S, Donnelly D 2003 A model for receptor-peptide binding at the glucagon-like peptide-1 (GLP-1) receptor through the analysis of truncated ligands and receptors. Br J Pharmacol 140:339-346
32. Runge S, Schimmer S, Oschmann J, Schiødt CB, Knudsen SM, Jeppesen CB, Madsen K, Lau J, Thøgersen H, Rudolph R 2007 Differential structural properties of GLP-1 and exendin-4 determine their relative affinity for the GLP-1 receptor N-terminal extracellular domain. Biochemistry 46:5830-5840
33. Richter B, Bandeira-Echtler E, Bergerhoff K, Lerch C 2008 Emerging role of dipeptidyl peptidase-4 inhibitors in the management of type 2 diabetes. Vasc Health Risk Manag 4:753-768
34. Lautar SL, Rojas C, Slusher BS, Wozniak KM, Wu Y, Thomas AG, Waldon D, Li W, Ferraris D, Belyakov S 2005 DPP IV inhibitor blocks mescaline-induced scratching and amphetamine-induced hyperactivity in mice. Brain Res 1048:177-184
35. Aytac U, Dang NH 2004 CD26/dipeptidyl peptidase IV: a regulator of immune function and a potential molecular target for therapy. Curr Drug Targets Immune Endocr Metab Disord 4:11-18
36. Schnölzer M, Alewood P, Jones A, Alewood D, Kent SB 1992 In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences. Int J Pept Protein Res 40:180-193
37. 1989 Transfection of coprecipitates of calcium phosphate and DNA. In: Sambrook J, Fritsch EF, Maniatis T, eds. Molecular cloning - a laboratory manual. 2nd ed. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press; 16.32-16.40
38. Göke R, Conlon JM 1988 Receptors for glucagon-like peptide-1(7-36) amide on rat insulinoma-derived cells. J Endocrinol 116: 357-362
39. Thoma R, Löffler B, Stihle M, Huber W, Ruf A, Hennig M 2003 Structural basis of proline-specific exopeptidase activity as observed in human dipeptidyl peptidase-IV. Structure 11:947-959
40. Kim D, Wang L, Beconi M, Eiermann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio F, McCann ME, Patel RA, Petrov A, Scapin G, Patel SB, Roy RS, Wu JK, Wyvratt MJ, Zhang BB, Zhu L, Thornberry NA, Weber AE 2005 (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3- a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem 48:141-151
41. Graziano MP, Hey PJ, Strader CD 1996 The amino terminal domain of the glucagon-like peptide-1 receptor is a critical determinant of subtype specificity. Receptors Channels 4:9-17
42. van Eyll B, Lankat-Buttgereit B, Bode HP, Göke R, Göke B 1994 Signal transduction of the GLP-1-receptor cloned from a human insulinoma. FEBS Lett 348:7-13
43. Hareter A, Hoffmann E, Bode HP, Göke B, Göke R 1997 The positive charge of the imidazole side chain of histidine7 is crucial for GLP-1 action. Endocr J 44:701-705
44. Hjorth SA, Adelhorst K, Pedersen BB, Kirk O, Schwartz TW 1994 Glucagon and glucagon-like peptide 1: selective receptor recognition via distinct peptide epitopes. J Biol Chem 269:30121-30124
45. Thorens B 1992 Expression cloning of the pancreatic β cell receptor for the gluco-incretin hormone glucagon-like peptide 1. Proc Natl Acad Sci USA 89:8641-8645
46. Graziano MP, Hey PJ, Borkowski D, Chicchi GG, Strader CD 1993 Cloning and functional expression of a human glucagon-like peptide-1 receptor. Biochem Biophys Res Commun 196:141-146
47. Holst JJ 1999 Glucagon-like peptide-1, a gastrointestinal hormone with a pharmaceutical potential. Curr Med Chem 6:1005-1017
48. 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
49. Toniolo C 1993 Cα, α-Symmetrically disubstituted glycines: useful building blocks in the design of conformationally restricted peptides. Janssen Chim Acta 11:10-16
50. Mahalakshmi R, Balaram P 2006 Non-protein amino acids in the design of secondary structure scaffolds. Methods Mol Biol 340: 71-94
51. Knudsen LB, Nielsen PF, Huusfeldt PO, Johansen NL, Madsen K, Pedersen FZ, Thøgersen H, Wilken M, Agersø H 2000 Potent derivatives of glucagon-like peptide-1 with pharmacokinetic properties suitable for once daily administration. J Med Chem 43:1664-1669
52. Lambeir AM, Durinx C, Scharpé S, De Meester I 2003 Dipeptidylpeptidase IV from bench to bedside: an update on structural properties, functions, and clinical aspects of the enzyme DPP IV. Crit Rev Clin Lab Sci 40:209-294
53. de Meester I, Lambeir AM, Proost P, Scharpé S 2003 Dipeptidyl peptidase IV substrates. An update on in vitro peptide hydrolysis by human DPPIV. Adv Exp Med Biol 524:3-17
54. Mentlein R 1999 Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides. Regul Pept 85:9-24
55. Ritzel U, Leonhardt U, Ottleben M, Rühmann A, Eckart K, Spiess J, Ramadori G 1998 A synthetic glucagon-like peptide-1 analog with improved plasma stability. J Endocrinol 159:93-102
56. Nauck MA, Ratner RE, Kapitza C, Berria R, Boldrin M, Balena R 2009 Treatment with the human once-weekly glucagon-like peptide-1 analog taspoglutide in combination with metformin improves glycemic control and lowers body weight in patients with type 2 diabetes inadequately controlled with metformin alone: a double-blind placebo-controlled study. Diabetes Care 32:1237-1243
57. Kapitza C, Heise T, Birman P, Jallet K, Ramis J, Balena R 2009 Pharmacokinetic and pharmacodynamic properties of taspoglutide, a once-weekly, human GLP-1 analogue, after single-dose administration in patients with type 2 diabetes. Diabet Med 26:1156-1164
58. Sebokova E, Benardeau A, Sprecher U, Sewing S, Tobalina L, Migliorini C, 3 February 2010 Taspoglutide, a novel human onceweekly analogue of glucagon-like peptide-1, improves glucose homeostasis and body weight in the ZDF rat. Diabetes Obes Metab; doi: 10.1111/j.1463-1326.2010.01207.x