Synthesis and bioactivity evaluation of dipeptidyl peptidase IV resistant glucagon-like peptide-1 analogues

Protein and Peptide Letters

Volumn 17, Issue 10, 2010, Pages 1290-1295

  Zhou, Jinpei ^a   Ni, Shuaijian ^a   Zhang, Huibin ^a   Qian, Hai ^a   Chi, Yushi ^a   Huang, Wenlong ^a   Yu, Lu ^a   Hu, Xiaowen ^b   Chen, Wei ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b NANJING MEDICAL UNIVERSITY   (China)

Author keywords

Glucagon like peptide 1; Hypoglycemic; Microwave assisted synthesis; Solid phase peptide synthesis

Indexed keywords

ANTIDIABETIC AGENT; DIPEPTIDYL PEPTIDASE IV INHIBITOR; DRUG DERIVATIVE; GLUCAGON LIKE PEPTIDE 1;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG RESISTANCE; DRUG STABILITY; ENERGY METABOLISM; MALE; MASS SPECTROMETRY; METABOLISM; MOLECULAR GENETICS; MOUSE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; DIPEPTIDYL-PEPTIDASE IV INHIBITORS; DRUG RESISTANCE; DRUG STABILITY; ENERGY METABOLISM; GLUCAGON-LIKE PEPTIDE 1; HYPOGLYCEMIC AGENTS; MALE; MASS SPECTROMETRY; MICE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP;

MUS;

EID: 77958460870     PISSN: 09298665     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986610792231546     Document Type: Article

References (19)

1. Abraham, E.J.; Leech, C.A.; Lin, J.C.; Zulewski, H.; Habener, J.F. Insulinotropic hormone glucagon-like peptide-1 differentiation of human pancreatic islet-derived progenitor cells into insulinproducing cells. Endocrinology, 2002, 143(8), 3152-3161.
2. Nauck, M.A.; Weber, I.; Bach, I.; Richter, S.; Orskov, C.; Holst, J.J.; Schmiegel, W. Normalization of fasting glycaemia by intravenous GLP-1 ([7-36 amide]or [7-37]) in type 2 diabetic patients. Diabet. Med., 1998, 15(11), 937-945.
3. Orskov, C. Glucagon-like peptide-1, a new hormone of the enteroinsular axis. Diabetologia, 1992, 35(8), 701-711.
4. Hui, H.; Zhao, X.; Perfetti, R. Structure and function studies of glucagon-like peptide-1 (GLP-1): the designing of a novel pharmacological agent for the treatment of diabetes. Diabetes. Metab. Res. Rev., 2005, 21(4), 313-331.
5. Qualmann, C.; Nauck, M.A.; Holst, J.J.; Orskov, C.; Creutzfeldt, W. Insulinotropic actions of intravenous glucagon-like peptide-1 (GLP-1) [7-36 amide] in the fasting state in healthy subjects. Acta Diabetol., 1995, 32(1), 13-16.
6. Hvidberg, A.; Nielsen, M.T.; Hilsted, J.; Orskov, C.; Holst, J.J. Effect of glucagon-like peptide-1 (proglucagon 78-107amide) on hepatic glucose production in healthy man. Metabolism, 1994, 43(1), 104-108.
7. Turton, M.D.; O'Shea, D.; Gunn, I.; Beak, S.A.; Edwards, C.M.; Meeran, K.; Choi, S.J.; Taylor, G.M.; Heath, M.M.; Lambert, P.D.; Wilding, J.P.; Smith, D.M.; Ghatei, M.A.; Herbert, J.; Bloom, S.R. A role for glucagon-like peptide-1 in the central regulation of feeding. Nature, 1996, 379(6560), 69-72.
8. Hartmann, B.; Harr, M.B.; Jeppesen, P.B.; Wojdemann, M.; Deacon, C.F.; Mortensen, P.B.; Holst, J.J. In vivo and in vitro degradation of glucagon-like peptide-2 in humans. J. Clin. Endocrinol. Metab., 2000, 85(8), 2884-2888.
9. 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., 1993, 214(3), 829-835.
10. Green, B.D.; Mooney, M.H.; Gault, V.A.; Irwin, N.; Bailey, C.J.; Harriott, P.; Greer, B.; Flatt, P.R.; O'Harte, F.P. Lys9 for Glu9 substitution in glucagon-like peptide-1(7-36)amide confers dipeptidylpeptidase IV resistance with cellular and metabolic actions similar to those of established antagonists glucagon-like peptide-1(9-36)amide and exendin (9-39). Metabolism, 2004, 53(2), 252-259.
11. O'Harte, F.P.; Mooney, M.H.; Lawlor, A.; Flatt, P.R. N-terminally modified glucagon-like peptide-1(7-36) amide exhibits resistance to enzymatic degradation while maintaining its antihyperglycaemic activity in vivo. Biochim. Biophys. Acta, 2000, 1474(1), 13-22.
12. Gallwitz, B.; Ropeter, T.; Morys-Wortmann, C.; Mentlein, R.; Siegel, E.G.; Schmidt, W.E. GLP-1-analogues resistant to degradation by dipeptidyl-peptidase IV in vitro. Regul. Pept., 2000, 86(1-3), 103-111.
13. Gault, V.A.; Flatt, P.R.; Harriott, P.; Mooney, M.H.; Bailey, C.J.; O'Harte, F.P. Improved biological activity of Gly2- and Ser2-substituted analogues of glucose-dependent insulinotrophic polypeptide. J. Endocrinol., 2003, 176(1), 133-141.
14. Merrifield, R.B. Solid Phase Synthesis (Nobel Lecture). Angew. Chem. Int. Ed. Engl., 1985, 24(10), 799-810.
15. Albericio, F. Developments in peptide and amide synthesis. Curr. Opin. Chem. Biol., 2004, 8(3), 211-221.
16. 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(16), 7607-7614.
17. Bacsa, B.; Horvati, K.; Bosze, S.; Andreae, F.; Kappe, C.O. Solidphase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies. J. Org. Chem., 2008, 73(19), 7532-7542.
18. Bacsa, B.; Desai, B.; Dibo, G.; Kappe, C.O. Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation. J. Pept. Sci., 2006, 12(10), 633-638.
19. Gallwitz, B.; Witt, M.; Paetzold, G.; Morys-Wortmann, C.; Zimmermann, B.; Eckart, K.; Folsch, U.R.; Schmidt, W.E. Structure/activity characterization of glucagon-like peptide-1. Eur. J. Biochem., 1994, 225(3), 1151-1156.