Design, synthesis, and biological activity of novel dicoumarol glucagon-like peptide 1 conjugates

Journal of Medicinal Chemistry

Volumn 56, Issue 24, 2013, Pages 9955-9968

  Han, Jing ^a   Sun, Lidan ^a   Chu, Yingying ^a   Li, Zheng ^a   Huang, Dandan ^a   Zhu, Xiaoyun ^a   Qian, Hai ^a   Huang, Wenlong ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

12 (2,5 DIOXO 2H PYRROL 1(5H) YL) N [4 [(4 HYDROXY 2 OXO 2H CHROMEN 3 YL)(4 HYDROXY 2 OXOCHROMAN 3 YL)METHYL]PHENYL]DODECANAMIDE; 3 (2,5 DIOXO 2H PYRROL 1(5H) YL) N [4 [(4 HYDROXY 2 OXO 2H CHROMEN 3 YL)(4 HYDROXY 2 OXOCHROMAN 3 YL)METHYL]PHENYL]PROPANAMIDE; 6 (2,5 DIOXO 2H PYRROL 1(5H) YL) N [4 [(4 HYDROXY 2 OXO 2H CHROMEN 3 YL)(4 HYDROXY 2 OXOCHROMAN 3 YL)METHYL]PHENYL]HEXANAMIDE; 8 GLYCINE GLUCAGON LIKE PEPTIDE 1 [7-36] AMIDE; ALBUMIN; DICOUMAROL DERIVATIVE; DICOUMAROL GLUCAGON LIKE PEPTIDE 1 CONJUGATE; EXENDIN 4; GLUCAGON LIKE PEPTIDE 1; GLUCAGON LIKE PEPTIDE 1 [7-36] AMIDE; GLUCOSE; HEMOGLOBIN A1C; LIRAGLUTIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTICOAGULATION; ANTIDIABETIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DESIGN; DRUG EFFICACY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG RECEPTOR BINDING; DRUG STABILITY; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; GLUCOSE TOLERANCE TEST; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; RAT; TIME TO MAXIMUM PLASMA CONCENTRATION;

EID: 84891293068     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4017448     Document Type: Article

References (49)

1. Wild, S.; Roglic, G.; Green, A.; Sicree, R.; King, H. Global prevalence of diabetes: estimates for the year 2000 and projections for 2030 Diabetes Care 2004, 27, 1047-1053
2. Kahn, S. E. The relative contributions of insulin resistance and β-cell dysfunction to the pathophysiology of type 2 diabetes Diabetologia 2003, 46, 13-19
3. Pratley, R. E.; Weyer, C. The role of impaired early insulin secretion in the pathogenesis of type II diabetes mellitus Diabetologia 2001, 44, 929-945
4. Baggio, L. L.; Drucker, D. J. Therapeutic approaches to preserve islet mass in type 2 diabetes Annu. Rev. Med. 2006, 57, 265-281
5. Amori, R. E.; Lau, J.; Pittas, A. G. Efficacy and safety of incretin therapy in type 2 diabetes JAMA, J. Am. Med. Assoc. 2007, 298, 194-206
6. Sinclair, E. M.; Drucker, D. J. Glucagon-like peptide 1 receptor agonists and dipeptidyl peptidase IV inhibitors: new therapeutic agents for the treatment of type 2 diabetes Curr. Opin. Endocrinol., Diabetes Obes. 2005, 12, 146-151
7. Orskov, C.; Rabenhoj, L.; Wettergren, A.; Kofod, H.; Holst, J. J. Tissue and plasma concentrations of amidated and glycine-extended glucagon-like peptide I in humans Diabetes 1994, 43, 535-539
8. Meier, J. J.; Nauck, M. A. Glucagon-like peptide 1 (GLP-1) in biology and pathology Diabetes Metab. Res. 2005, 21, 91-117
9. Drucker, D. J. The biology of incretin hormones Cell Metab. 2006, 3, 153-165
10. Zhao, T.; Parikh, P.; Bhashyam, S.; Bolukoglu, H.; Poornima, I.; Shen, Y. T.; Shannon, R. P. Direct effects of glucagon-like peptide-1 on myocardial contractility and glucose uptake in normal and postischemic isolated rat hearts J. Pharmacol. Exp. Ther. 2006, 317, 1106-1113
11. Mentlein, R.; Gallwitz, B.; Schmidt, W. E. 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. 2005, 214, 829-835
12. Raz, I.; Hanefeld, M.; Xu, L.; Caria, C.; Williams-Herman, D.; Khatami, H. Efficacy and safety of the dipeptidyl peptidase-4 inhibitor sitagliptin as monotherapy in patients with type 2 diabetes mellitus Diabetologia 2006, 49, 2564-2571
13. Fonseca, V.; Schweizer, A.; Albrecht, D.; Baron, M. A.; Chang, I.; Dejager, S. Addition of vildagliptin to insulin improves glycaemic control in type 2 diabetes Diabetologia 2007, 50, 1148-1155
14. Briones, M.; Bajaj, M. Exenatide: a GLP-1 receptor agonist as novel therapy for type 2 diabetes mellitus Expert Opin. Pharmacother. 2006, 7, 1055-1064
15. DeFronzo, R. A.; Ratner, R. E.; Han, J.; Kim, D. D.; Fineman, M. S.; Baron, A. D. Effects of exenatide (exendin-4) on glycemic control and weight over 30 weeks in metformin-treated patients with type 2 diabetes Diabetes Care 2005, 28, 1092-1100
16. Lee, S.; Youn, Y.; Lee, S.; Byun, Y.; Lee, K. PEGylated glucagon-like peptide-1 displays preserved effects on insulin release in isolated pancreatic islets and improved biological activity in db/db mice Diabetologia 2006, 49, 1608-1611
17. Chi, Y.; Zhang, H.; Huang, W.; Zhou, J.; Zhou, Y.; Qian, H.; Ni, S. Microwave-assisted solid phase synthesis, PEGylation, and biological activity studies of glucagon-like peptide-1 (7-36) amide Bioorg. Med. Chem. 2008, 16, 7607-7614
18. Madsen, K.; Knudsen, L. B.; Agersoe, H.; Nielsen, P. F.; Thøgersen, H.; Wilken, M.; Johansen, N. L. Structure-activity and protraction relationship of long-acting glucagon-like peptide-1 derivatives: importance of fatty acid length, polarity, and bulkiness J. Med. Chem. 2007, 50, 6126-6132
19. Kim, J. G.; Baggio, L. L.; Bridon, D. P.; Castaigne, J. P.; Robitaille, M. F.; Jetté, L.; Benquet, C.; Drucker, D. J. Development and characterization of a glucagon-like peptide 1-albumin conjugate the ability to activate the glucagon-like peptide 1 receptor in vivo Diabetes 2003, 52, 751-759
20. Soltani, N.; Kumar, M.; Glinka, Y.; Prud'Homme, G. J.; Wang, Q. In vivo expression of GLP-1/IgG-Fc fusion protein enhances beta-cell mass and protects against streptozotocin-induced diabetes Gene Ther. 2007, 14, 981-988
21. Kim, D.; MacConell, L.; Zhuang, D.; Kothare, P. A.; Trautmann, M.; Fineman, M.; Taylor, K. Effects of once-weekly dosing of a long-acting release formulation of exenatide on glucose control and body weight in subjects with type 2 diabetes Diabetes Care 2007, 30, 1487-1493
22. Seino, Y. Safety, tolerability, pharmacokinetics and pharmacodynamics of albiglutide, a long-acting GLP-1-receptor agonist, in Japanese subjects with type 2 diabetes mellitus Curr. Med. Res. Opin. 2009, 25, 3049-3057
23. Glaesner, W. Engineering and characterization of the long-acting glucagon-like peptide-1 analogue LY2189265, an Fc fusion protein Diabetes 2010, 26, 287-296
24. Barrington, P. LY2189265, a long-acting glucagon-like peptide-1 analogue, showed a dose-dependent effect on insulin secretion in healthy subjects Diabetes, Obes. Metab. 2011, 13, 434-438
25. Meier, J. J. GLP-1 receptor agonists for individualized treatment of type 2 diabetes mellitus Nat. Rev. Endocrinol. 2012, 8, 728-742
26. Chae, S. Y.; Choi, Y. G.; Son, S.; Jung, S. Y.; Lee, D. S.; Lee, K. C. The fatty acid conjugated exendin-4 analogs for type 2 antidiabetic therapeutics J. Controlled Release 2010, 144, 10-16
27. Chae, S. Y.; Jin, C. H.; Shin, J. H.; Son, S.; Kim, T. H.; Lee, S.; Youn, Y. S.; Byun, Y.; Lee, M. S.; Lee, K. C. Biochemical, pharmaceutical and therapeutic properties of long-acting lithocholic acid derivatized exendin-4 analogs J. Controlled Release 2010, 142, 206-213
28. Léger, R.; Thibaudeau, K.; Robitaille, M.; Quraishi, O.; van Wyk, P.; Bousquet-Gagnon, N.; Carette, J.; Castaigne, J. P.; Bridon, D. P. Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7-36) analog Bioorg. Med. Chem. Lett. 2004, 14, 4395-4398
29. Blonde, L. Clinical trial results of GLP-1-related agents: the early evidence Adv. Stud. Med. 2005, 5, S1074-S1078
30. Ahrén, B.; Burke, B. Using albumin to improve the therapeutic properties of diabetes treatments Diabetes, Obes. Metab. 2012, 14, 121-129
31. Knudsen, L. B. Liraglutide: the therapeutic promise from animal models Int. J. Clin. Pract. 2010, 64, 4-11
32. Kerr, B. D.; Flatt, P. R.; Gault, V. A. Effects of gamma-glutamyl linker on DPP-IV resistance, duration of action and biological efficacy of acylated glucagon-like peptide-1 Biochem. Pharmacol. 2010, 80, 396-401
33. Han, J.; Huang, X.; Sun, L.; Li, Z.; Qian, H.; Huang, W. Novel fatty chain-modified glucagon-like peptide-1 conjugates with enhanced stability and prolonged in vivo activity Biochem. Pharmacol. 2013, 86, 297-308
34. Joseph, K.; Moser, A. C.; Basiaga, S. B. G.; Schiel, J. E.; Hage, D. S. Evaluation of alternatives to dicoumarin as probes for Sudlow site I of human serum albumin: characterization by high-performance affinity chromatography J. Chromatogr., A 2009, 1216, 3492-3500
35. Hess, K.; Grant, P. J. Inflammation and thrombosis in diabetes Thromb. Haemostasis 2011, 105 (Suppl. 1) S43-S54
36. Ni, S. J.; Zhang, H. B.; Huang, W. L.; Zhou, J. P.; Qian, H. Solid phase synthesis of fatty acid modified glucagon-like peptide-1 (7-36) amide under thermal and controlled microwave irradiation Chin. Chem. Lett. 2010, 21, 27-30
37. Baggio, L. L.; Drucker, D. J. Biology of incretins: GLP-1 and GIP Gastroenterology 2007, 132, 2131-2157
38. Sloop, K. W.; Willard, F. S.; Brenner, M. B.; Ficorilli, J.; Valasek, K.; Showalter, A. D.; Farb, T. B.; Cao, J. X. C.; Cox, A. L.; Michael, M. D. Novel small molecule glucagon-like peptide-1 receptor agonist stimulates insulin secretion in rodents and from human islets Diabetes 2010, 59, 3099-3107
39. Al-Sabah, S.; Donnelly, D. 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. 2009, 140, 339-346
40. Miranda, L. P.; Winters, K. A.; Gegg, C. V.; Patel, A.; Aral, J.; Long, J.; Zhang, J.; Diamond, S.; Guido, M.; Stanislaus, S. Design and synthesis of conformationally constrained glucagon-like peptide-1 derivatives with increased plasma stability and prolonged in vivo activity J. Med. Chem. 2008, 51, 2758-2765
41. Li, Y.; Zheng, X.; Tang, L.; Xu, W.; Gong, M. GLP-1 analogs containing disulfide bond exhibited prolonged half-life in vivo than GLP-1 Peptides 2011, 32, 1303-1312
42. Kim, T. H.; Jiang, H. H.; Lee, S.; Youn, Y. S.; Park, C. W.; Byun, Y.; Chen, X.; Lee, K. C. Mono-PEGylated dimeric exendin-4 as high receptor binding and long-acting conjugates for type 2 anti-diabetes therapeutics Bioconjugate Chem. 2011, 22, 625-632
43. Young, A. A.; Gedulin, B. R.; Bhavsar, S.; Bodkin, N.; Jodka, C.; Hansen, B.; Denaro, M. Glucose-lowering and insulin-sensitizing actions of exendin-4: studies in obese diabetic (ob/ob, db/db) mice, diabetic fatty Zucker rats, and diabetic rhesus monkeys (Macaca mulatta) Diabetes 1999, 48, 1026-1034
44. Buse, J. B.; Rosenstock, J.; Sesti, G.; Schmidt, W. E.; Montanya, E.; Brett, J. H.; Zychma, M.; Blonde, L. Liraglutide once a day versus exenatide twice a day for type 2 diabetes: a 26-week randomised, parallel-group, multinational, open-label trial (LEAD-6) Lancet 2009, 374, 39-47
45. Nielsen, L. L.; Young, A. A.; Parkes, D. G. Pharmacology of exenatide (synthetic exendin-4): a potential therapeutic for improved glycemic control of type 2 diabetes Regul. Pept. 2004, 117, 77-88
46. Rolin, B.; Larsen, M. O.; Gotfredsen, C. F.; Deacon, C. F.; Carr, R. D.; Wilken, M.; Knudsen, L. B. The long-acting GLP-1 derivative NN2211 ameliorates glycemia and increases β-cell mass in diabetic mice Am. J. Physiol.: Endocrinol. Metab. 2002, 283, E745-E752
47. Son, S.; Chae, S. Y.; Kim, C. W.; Choi, Y. G.; Jung, S. Y.; Lee, S.; Lee, K. C. Preparation and structural, biochemical, and pharmaceutical characterizations of bile acid-modified long-acting exendin-4 derivatives J. Med. Chem. 2009, 52, 6889-6896
48. Chen, W.; Zhou, Y.; Zhang, H.; Qian, H.; Huang, W.; Yang, B.; Han, J.; Zhou, J.; Chi, Y.; Ni, S. Stability and bioactivity studies on dipeptidyl peptidase IV resistant glucogan-like peptide-1 analogues Protein Pept. Lett. 2012, 19, 203-211
49. Kim, I.; Kim, T. H.; Ma, K.; Lee, E. S.; Kim, D.; Oh, K. T.; Lee, D. H.; Lee, K. C.; Youn, Y. S. Synthesis and evaluation of human serum albumin-modified exendin-4 conjugate via heterobifunctional polyethylene glycol linkage with protracted hypoglycemic efficacy Bioconjugate Chem. 2010, 21, 1513-1519