Inhibition of dipeptidyl-peptidase IV catalyzed peptide truncation by Vildagliptin ((2S)-{[(3-hydroxyadamantan-1-yl)amino]acetyl}-pyrrolidine-2- carbonitrile)

Biochemical Pharmacology

Volumn 70, Issue 1, 2005, Pages 134-143

  Brandt, Inger ^a   Joossens, Jurgen ^a   Chen, Xin ^b   Maes, Marie Berthe ^a   Scharpé, Simon ^a   De Meester, Ingrid ^a   Lambeir, Anne Marie ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

Dipeptidyl peptidase IV; GIP; GLP 1; LAF237; Protease inhibitor; Substance P

Indexed keywords

AMINOPEPTIDASE P; DIPEPTIDYL PEPTIDASE 2; DIPEPTIDYL PEPTIDASE 8; DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; GASTRIC INHIBITORY POLYPEPTIDE; GLUCAGON LIKE PEPTIDE 1; MICROSOMAL AMINOPEPTIDASE; PEPTIDASE; PEPTIDE; PROLYL ENDOPEPTIDASE; SUBSTANCE P; UNCLASSIFIED DRUG; VILDAGLIPTIN;

ARTICLE; BINDING AFFINITY; CATALYST; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; DRUG POTENCY; DRUG TARGETING; ENZYME INHIBITION; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITION KINETICS; MOLECULAR INTERACTION; PHARMACODYNAMICS; PRIORITY JOURNAL; PROTEIN DEGRADATION;

ADAMANTANE; ANTIGENS, CD26; BINDING SITES; CACO-2 CELLS; HUMANS; KINETICS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 20444406121     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.04.009     Document Type: Article

References (37)

1. A.M. Lambeir, C. Durinx, S. Scharpé, and I. De Meester Dipeptidyl-peptidase 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 2003 209 294
2. S.N. Davis, and D.K. Granner Insulin, oral hypoglycemic agents and the pharmacology of the endocrine pancreas J.G. Hardman L.E. Limbird The pharmacological basis of therapeutics 10th ed. 2001 Mcgraw-Hill 1679 1714
3. J.D. Drucker Therapeutic potential of dipeptidyl peptidase IV inhibitors for the treatment of type 2 diabetes Expert Opin Invest Drugs 12 2003 87 100
4. A. Weber Dipeptidyl peptidase IV inhibitors for the treatment of diabetes J Med Chem 47 2004 4135 4141
5. R. Mentlein Dipeptidyl peptidase IV (CD26)-role in the inactivation of regulatory peptides Regul Pept 85 1999 9 24
6. B. Ahrén, M. Landin-Olsson, P.A. Jansson, M. Svensson, D. Holmes, and A. Schweizer Inhibition of dipeptidyl peptidase-4 reduces glycemia, sustains insulin levels, and reduces glucagon levels in type 2 diabetes J Clin Endocrinol Metab 89 2004 2078 2084
7. C.F. Deacon, B. Ahrén, and J.J. Holst Inhibitors of dipeptidyl peptidase IV: a novel approach for the prevention and treatment of Type 2 diabetes? Expert Opin Invest Drugs 13 2004 1091 1102
8. International nonproprietary names for pharmaceutical substances (INN), recommended international nonproprietary names: list 52 WHO Drug information 2004;18:263.
9. E.B. Villhauer, J.A. Brinkman, G. Naderi, B.F. Burkey, B.E. Dunning, and K. Prasad 1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties J Med Chem 46 2003 2774 2789
10. D. Barlocco LAF-237 Curr Opin Invest Drugs 5 2004 1094 1100
11. C.A. Abbott, D.M. Yu, E. Woollatt, G.R. Sutherland, G.W. McCaughan, and M.D. Gorrel Cloning, expression and chromosomal localization of a novel human dipeptidyl peptidase (DPP) IV homolog, DPP8 Eur J Biochem 267 2000 6140 6150
12. C. Olsen, and N. Wagtmann Identification and characterization of human DPP9, a novel homologue of dipeptidyl peptidase IV Gene 299 2002 185 193
13. G. Lankas, B. Leiting, R.S. Roy, G. Eiermann, T. Biftu, and D. Kim Inhibition of DPP8/9 results in toxicity in preclinical species: potential importance of selective dipeptidyl peptidase IV inhibition for the treatment of Type 2 DM Diabetes 53 Suppl. 2 2004 A2 7-OR
14. I. De Meester, G. Vanhoof, A.M. Lambeir, and S. Scharpé Use of immobilized adenosine deaminase (EC 3.5.4.4) for the rapid purification of native human CD26/dipeptidyl peptidase IV (EC 3.4.14.5) J Immunol Methods 189 1996 99 105
15. Z. Szeltner, V. Renner, and L. Polgar Substrate- and pH-dependent contribution of oxyanion binding site to the catalysis of prolyl oligopeptidase, a paradigm of the serine oligopeptidase family Protein Sci 9 2000 353 360
16. Y.S. Chen, C.H. Chien, C.M. Goparaju, J.T.A. Hsu, P.H. Liang, and X. Chen Purification and characterization of human prolyl dipeptidase DPP8 in Sf9 insect cells Protein Expr Purif 35 2004 142 146
17. M.B. Maes, A.M. Lambeir, K. Gilany, K. Senten, P. Van der Veken, and B. Leiting Kinetic investigation of human dipeptidyl peptidase II (DPPII)-mediated hydrolysis of dipeptide derivatives and its identification as quiescent cell proline dipeptidase (QPP)/dipeptidyl peptidase 7 (DPP7) Biochem J 386 2005 315 324
18. A. Stockel-Maschek, B. Stiebitz, R. Koelsch, and K. Neubert A continuous fluorimetric assay for aminopeptidase P detailed analysis of product inhibition Anal Biochem 322 2003 60 6717
19. Leatherbarrow RJ. GraFit Version 5. Horley, UK: Erithacus Software Ltd; 2001.
20. J.I. Venäläinen, R.O. Juvonen, J.A. Garcia-Horsman, E.A.A. Wallén, J.A.M. Christiaans, and E.M. Jarho Slow-binding inhibitors of prolyl oligopeptidase with different functional groups at the P1 site Biochem J 382 2004 1003 1008
21. A.M. Lambeir, C. Durinx, P. Proost, J. Van Damme, S. Scharpé, and I. De Meester Kinetic study of the processing by dipeptidyl-peptidase IV/CD26 of neuropeptides involved in pancreatic insulin secretion FEBS Lett 507 2001 327 330
22. W.T. Jiaang, Y.S. Chen, T. Hsu, S.H. Wu, C.H. Chien, and C.N. Chang Novel isoindoline compounds for potent and selective inhibition of prolyl dipeptidase DPP8 Bioorg Med Chem Lett 15 2005 687 691
23. R. Mentlein, B. Gallwitz, and W.E. Schmidt 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 1993 829 835
24. R.P. Pauly, F. Rosche, M. Wemann, C.H. McIntosh, R.A. Pederson, and H.U. Demuth Investigation of glucose-dependent insulinotropic polypeptide-(1-42) 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 J Biol Chem 271 1996 23222 23229
25. M. Kikuchi, K. Fukuyama, and W.L. Epstein Soluble dipeptidyl peptidase IV from terminal differentiated rat epidermal cells: purification and its activity on synthetic and natural peptides Arch Biochem Biophys 266 1998 369 376
26. I. Naush, and E. Heymann Substance P in human plasma is degraded by dipeptidyl peptidase IV, not by cholinesterase J Neurochem 44 1985 1354 1357
27. T.E. Hughes, M.D. Mone, M.E. Russell, S.C. Weldon, and E.B. Villhauer NVP-DPP728 (1-[[[2-[5-Cyanopyridin-2-yl)amino]ethyl]amino]acetyl]-2-cyano-(S)- pyrrolidine), a slow-binding inhibitor of dipeptidyl peptidase IV Biochemistry 38 1999 11597 11603
28. K. Augustyns, P. Van der Veken, K. Senten, and A. Haemers Dipeptidyl peptidase IV inhibitors as new therapeutic agents for the treatment of Type 2 diabetes Expert Opin Ther Patents 13 2003 1 12
29. H. Hiramatsu, A. Yamamoto, K. Kyono, Y. Higashiyama, C. Fukushima, and H. Shima The crystal structure of human dipeptidyl peptidase IV (DPP IV) complex with diprotin A Biol Chem 385 2004 561 564
30. C. Oefner, A. D'Arcy, A. Mac Sweeney, S. Pierau, R. Gardiner, and G.E. Dale High-resolution structure of human apo dipeptidyl peptidase IV/CD26 and its complex with 1-[([2-[(5-iodopyridin-2-yl)amino]-ethyl]amino)-acetyl]-2-cyano- (S)-pyrrolidine Acta Crystallogr D Biol Crystallogr 59 2003 1206 1212
31. K. Aertgeerts, S. Ye, M.G. Tennant, M.L. Kraus, J. Rogers, and B.C. Sang Crystal structure of human dipeptidyl peptidase IV in complex with a decapeptide reveals details on substrate specificity and tetrahedral intermediate formation Protein Sci 13 2004 412 421
32. H.B. Rasmussen, S. Branner, F.C. Wiberg, and N. Wagtmann Crystal structure of human dipeptidyl peptidase IV/CD 26 in complex with a substrate analog Nat Struct Biol 10 2003 19 25
33. M. Engel, T. Hoffmann, L. Wagner, M. Wermann, U. Heiser, and R. Kiefersauer The crystal structure of dipepidyl peptidase IV (CD26) reveals its functional regulation and enzymatic mechanism Proc Natl Acad Sci USA 100 2003 5063 5068
34. A.M. Lambeir, P. Proost, C. Durinx, G. Bal, K. Senten, and K. Augustyns Kinetic investigation of chemokine truncation by CD26/dipeptidyl peptidase IV reveals a striking selectivity within the chemokine family J Biol Chem 276 2001 29839 29845
35. L. Zhu, C. Tamvakopoulos, D. Xie, J. Dragovic, X. Shen, and J.E. Fenyk-Melody The role of dipeptidyl peptidase IV in the cleavage of glucagon family peptides: in vivo metabolism of pituitary adenylate cyclase activating polypeptide-(1-38) J Biol Chem 278 2003 22418 22423
36. S. Lorey, A. Stockel-Maschek, J. Faust, W. Brandt, Stiebitz, and M.D. Gorrell Different modes of dipeptidyl peptidase IV (CD26) inhibition by oligopeptides derived from the N-terminus of HIV-1 Tat indicate at least two inhibitor binding sites Eur J Biochem 270 2003 2147 2156
37. S.A. Hinke, K. Kuhn-Wache, T. Hoffmann, R.A. Pederson, C.H. McIntosh, and H.U. Demuth Metformin effects on dipeptidylpeptidase IV degradation of glucagon-like peptide-1 Biochem Biophys Res Commun 291 2002 1302 1308