A new GLP-1 analogue with prolonged glucose-lowering activity in vivo via backbone-based modification at the N-terminus

Bioorganic and Medicinal Chemistry

Volumn 24, Issue 6, 2016, Pages 1163-1170

  Bai, Xiaohui ^a   Niu, Youhong ^a   Zhu, Jingjing ^a   Yang, An Qi ^a   Wu, Yan Fen ^a   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Amide N methylation; b Peptide; Drug design; GLP 1 analogues; N terminus modifications of GLP 1

Indexed keywords

3 (9 FLUORENYLMETHOXYCARBONYL AMINO)BUTYRIC ACID; 9 FLUORENYLMETHOXYCARBONYL ALANINE; 9 FLUORENYLMETHOXYCARBONYL GLYCINE; 9 FLUORENYLMETHOXYCARBONYL PHENYLALANINE; DIPEPTIDYL PEPTIDASE IV INHIBITOR; GLUCAGON LIKE PEPTIDE 1 DERIVATIVE; GLUCAGON LIKE PEPTIDE 1 RECEPTOR; UNCLASSIFIED DRUG; ANTIDIABETIC AGENT; GLUCAGON LIKE PEPTIDE 1; GLUCOSE BLOOD LEVEL;

AMINO TERMINAL SEQUENCE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; GLUCOSE LOWERING ACTIVITY; HYDROGEN BOND; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PROTEIN DEPLETION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DIABETES MELLITUS, TYPE 2; DRUG EFFECTS; GLUCOSE BLOOD LEVEL; HUMAN; METABOLISM; SYNTHESIS;

BLOOD GLUCOSE; DIABETES MELLITUS, TYPE 2; GLUCAGON-LIKE PEPTIDE 1; HUMANS; HYPOGLYCEMIC AGENTS; MOLECULAR STRUCTURE;

EID: 84959036712     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2016.01.036     Document Type: Article

References (64)

1. C. Orskov, M. Bersani, A.H. Johnsen, P. Hojrup, and J.J. Holst J. Biol. Chem. 264 1989 12826
2. C. Orskov, J.J. Holst, S. Knuhtsen, F.G. Baldissera, S.S. Poulsen, and O.V. Nielsen Endocrinology 119 1986 1467
3. L.L. Baggio, and D.J. Drucker Gastroenterology 132 2007 2131
4. B. Thorens Diabete MeTable 21 1995 311
5. C. Orskov Diabetologia 35 1992 701
6. R. Burcelin, W. Dolci, and B. Thorens Metabolism 48 1999 252
7. G.C. Weir, S. Mojsov, G.K. Hendrick, and J.F. Habener Diabetes 38 1989 338
8. S. Mojsov, G.C. Weir, and J.F. Habener J. Clin. Invest. 79 1987 616
9. J.J. Holst, C. Orskov, O.V. Nielsen, and T.W. Schwartz Febs. Lett. 211 1987 169
10. C.F. Deacon, A.H. Johnsen, and J.J. Holst J. Clin. Endocrinol. MeTable 80 1995 952
11. T.J. Kieffer, C.H. McIntosh, and R.A. Pederson Endocrinology 136 1995 3585
12. R. Mentlein, B. Gallwitz, and W.E. Schmidt Eur. J. Biochem. 214 1993 829
13. K. Hupe-Sodmann, G.P. McGregor, R. Bridenbaugh, R. Goke, B. Goke, H. Thole, B. Zimmermann, and K. Voigt Regul. Peptides 58 1995 149
14. D. Kim, L. Wang, M. Beconi, G.J. Eiermann, M.H. Fisher, H. He, G.J. Hickey, J.E. Kowalchick, B. Leiting, K. Lyons, F. Marsilio, M.E. McCann, R.A. Patel, A. Petrov, G. Scapin, S.B. Patel, R.S. Roy, J.K. Wu, M.J. Wyvratt, B.B. Zhang, L. Zhu, N.A. Thornberry, and A.E. Weber J. Med. Chem. 48 2005 141
15. W.H. Ramadan, and W.K. Kabbara Vasc. Health Risk Manag. 11 2015 125
16. D.J. Augeri, J.A. Robl, D.A. Betebenner, D.R. Magnin, A. Khanna, J.G. Robertson, A. Wang, L.M. Simpkins, P. Taunk, Q. Huang, S.P. Han, B. Abboa-Offei, M. Cap, L. Xin, L. Tao, E. Tozzo, G.E. Welzel, D.M. Egan, J. Marcinkeviciene, S.Y. Chang, S.A. Biller, M.S. Kirby, R.A. Parker, and L.G. Hamann J. Med. Chem. 48 2005 5025
17. P.P. Toth Vasc. Health Risk Manag. 11 2015 9
18. M. Eckhardt, E. Langkopf, M. Mark, M. Tadayyon, L. Thomas, H. Nar, W. Pfrengle, B. Guth, R. Lotz, P. Sieger, H. Fuchs, and F. Himmelsbach J. Med. Chem. 50 2007 6450
19. A.H. Barnett Expert Opin. Drug Saf. 14 2015 149
20. E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell, and T.E. Hughes J. Med. Chem. 46 2003 2774
21. G. Ayvaz, L. Keskin, F. Akin, H.S. Dokmetas, E. Tasan, I.B. Ar, and E. Uren Curr. Med. Res. Opin. 2015 1
22. L.J. Scott Drugs 74 2014 2161
23. L.B. Knudsen, P.F. Nielsen, P.O. Huusfeldt, N.L. Johansen, K. Madsen, F.Z. Pedersen, H. Thogersen, M. Wilken, and H. Agerso J. Med. Chem. 43 2000 1664
24. A.M. Thompson, and J.M. Trujillo Ann. Pharmacother. 49 2015 351
25. W. Glaesner, A.M. Vick, R. Millican, B. Ellis, S.H. Tschang, Y. Tian, K. Bokvist, M. Brenner, A. Koester, N. Porksen, G. Etgen, and T. Bumol Diabetes Metab. Res. Rev. 26 2010 287
26. A. Chaudhuri, N. Kuhadiya, H. Ghanim, and P. Dandona Diabetes Care 37 2014 e218
27. J. Eng Mt Sinai J. Med. 59 1992 147
28. A. Wettergren, L. Pridal, M. Wojdemann, and J.J. Holst Regul. Peptides 77 1998 83
29. F.P. O'Harte, A.M. Gray, Y.H. Abdel-Wahab, and P.R. Flatt Peptides 18 1997 1327
30. M.H. Holtmann, S. Ganguli, E.M. Hadac, V. Dolu, and L.J. Miller J. Biol. Chem. 271 1996 14944
31. M. Dong, Z. Li, M. Zang, D.I. Pinon, T.P. Lybrand, and L.J. Miller J. Biol. Chem. 278 2003 48300
32. D.M.R. Lopez, A. Willshaw, A. Kuntzsch, R. Rudolph, and D. Donnelly J. Biol. Chem. 278 2003 10195
33. M. Dong, Z. Li, D.I. Pinon, T.P. Lybrand, and L.J. Miller J. Biol. Chem. 279 2004 2894
34. S. Runge, C. Gram, H. Brauner-Osborne, K. Madsen, L.B. Knudsen, and B.S. Wulff J. Biol. Chem. 278 2003 28005
35. R.M. Solano, I. Langer, J. Perret, P. Vertongen, M.G. Juarranz, P. Robberecht, and M. Waelbroeck J. Biol. Chem. 276 2001 1084
36. S. Runge, H. Thogersen, K. Madsen, J. Lau, and R. Rudolph J. Biol. Chem. 283 2008 11340
37. K.R. Heard, W. Wu, Y. Li, P. Zhao, I. Woznica, J.H. Lai, M. Beinborn, D.G. Sanford, M.T. Dimare, A.K. Chiluwal, D.E. Peters, D. Whicher, J.L. Sudmeier, and W.W. Bachovchin J. Med. Chem. 56 2013 8339
38. Z. Gao, Y. Tang, J. Chen, R. Bai, Q. Zhang, Y. Hou, Y. Lu, and G. Bai Peptides 30 2009 1874
39. Q. Xiao, J. Giguere, M. Parisien, W. Jeng, S.A. St-Pierre, P.L. Brubaker, and M.B. Wheeler Biochemistry-Us 40 2001 2860
40. E.G. Siegel, B. Gallwitz, G. Scharf, R. Mentlein, C. Morys-Wortmann, U.R. Folsch, J. Schrezenmeir, K. Drescher, and W.E. Schmidt Regul. Peptides 79 1999 93
41. B.D. Green, V.A. Gault, M.H. Mooney, N. Irwin, P. Harriott, B. Greer, C.J. Bailey, F.P. O'Harte, and P.R. Flatt Biol. Chem. 385 2004 169
42. C.F. Deacon, L.B. Knudsen, K. Madsen, F.C. Wiberg, O. Jacobsen, and J.J. Holst Diabetologia 41 1998 271
43. B. Gallwitz, T. Ropeter, C. Morys-Wortmann, R. Mentlein, E.G. Siegel, and W.E. Schmidt Regul. Peptides 86 2000 103
44. B.D. Green, M.H. Mooney, V.A. Gault, N. Irwin, C.J. Bailey, P. Harriott, B. Greer, P.R. Flatt, and F.P.M. O Harte Metabolism 53 2004 252
45. Y. Chi, H. Zhang, W. Huang, J. Zhou, Y. Zhou, H. Qian, and S. Ni Bioorg. Med. Chem. 16 2008 7607
46. B.D. Green, V.A. Gault, M.H. Mooney, N. Irwin, C.J. Bailey, P. Harriott, B. Greer, P.R. Flatt, and F.P. O'Harte J. Mol. Endocrinol. 31 2003 529
47. B. Gallwitz, M. Witt, G. Paetzold, C. Morys-Wortmann, B. Zimmermann, K. Eckart, U.R. Folsch, and W.E. Schmidt Eur. J. Biochem. 225 1994 1151
48. K. Madsen, L.B. Knudsen, H. Agersoe, P.F. Nielsen, H. Thøgersen, M. Wilken, and N.L. Johansen J. Med. Chem. 50 2007 6126
49. K. Adelhorst, B.B. Hedegaard, L.B. Knudsen, and O. Kirk J. Biol. Chem. 269 1994 6275
50. M.E. Doyle, N.H. Greig, H.W. Holloway, J.A. Betkey, M. Bernier, and J.M. Egan Endocrinology 142 2001 4462
51. Q. Cai, L. Fu, Z. Wang, N. Gan, X. Dai, and Y. Wang J. Biol. Chem. 289 2014 16046
52. L. Doedens, F. Opperer, M. Cai, J.G. Beck, M. Dedek, E. Palmer, V.J. Hruby, and H. Kessler J. Am. Chem. Soc. 132 2010 8115
53. J. Chatterjee, F. Rechenmacher, and H. Kessler Angew. Chem., Int. Ed. 52 2013 254
54. C.K. Wang, S.E. Northfield, B. Colless, S. Chaousis, I. Hamernig, R.J. Lohman, D.S. Nielsen, C.I. Schroeder, S. Liras, D.A. Price, D.P. Fairlie, and D.J. Craik Proc. Natl. Acad. Sci. U.S.A. 111 2014 17504
55. J. Chatterjee, B. Laufer, and H. Kessler Nat. Protoc. 7 2012 432
56. R.W. Cheloha, A. Maeda, T. Dean, T.J. Gardella, and S.H. Gellman Nat. Biotechnol. 32 2014 653
57. L.M. Johnson, D.E. Mortenson, H.G. Yun, W.S. Horne, T.J. Ketas, M. Lu, J.P. Moore, and S.H. Gellman J. Am. Chem. Soc. 134 2012 7317
58. M.D. Boersma, H.S. Haase, K.J. Peterson-Kaufman, E.F. Lee, O.B. Clarke, P.M. Colman, B.J. Smith, W.S. Horne, W.D. Fairlie, and S.H. Gellman J. Am. Chem. Soc. 134 2012 315
59. V. Azzarito, K. Long, N.S. Murphy, and A.J. Wilson Nat. Chem. 5 2013 161
60. W.S. Horne, M.D. Boersma, M.A. Windsor, and S.H. Gellman Angew. Chem., Int. Ed. 47 2008 2853
61. H. Ishiyama, K. Yoshizawa, and J. Kobayashi Tetrahedron 68 2012 6186
62. J. Han, X. Huang, L. Sun, Z. Li, H. Qian, and W. Huang Biochem. Pharmacol. 86 2013 297
63. J. Zhou, S. Ni, H. Zhang, H. Qian, Y. Chi, W. Huang, L. Yu, X. Hu, and W. Chen Protein Pept. Lett. 17 2010 1290
64. M. Stoffel, R.R. Espinosa, M.M. Le Beau, and G.I. Bell Diabetes 42 1993 1215