Fluoro-olefins as peptidomimetic inhibitors of dipeptidyl peptidases

Journal of Medicinal Chemistry

Volumn 48, Issue 6, 2005, Pages 1768-1780

  Van Der Veken, Pieter ^a   Senten, Kristel ^a   Kertèsz, István ^a   De Meester, Ingrid ^a   Lambeir, Anne Marie ^a   Maes, Marie Berthe ^a   Scharpé, Simon ^a   Haemers, Achiel ^a   Augustyns, Koen ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMIDE; DIPEPTIDYL PEPTIDASE II; DIPEPTIDYL PEPTIDASE IV; FLUORO OLEFINS; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; FEASIBILITY STUDY; HYDROLYSIS; MOLECULAR DYNAMICS; MOLECULAR STABILITY; NONHUMAN; OLEFINATION; OXIDATION; RAT; SYNTHESIS;

ALKENES; ANTIGENS, CD26; DIPEPTIDYL PEPTIDASES; DRUG STABILITY; MODELS, MOLECULAR; NITRILES; PEPTIDES; PIPERIDINES; PROTEASE INHIBITORS; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15444376078     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0495982     Document Type: Article

References (40)

1. Tourwé, D. The Synthesis of Peptide Analogues with a Modified Peptide Bond. Janssen Chim. Acta 1985, 3, 3-18.
2. For a review focusing on retroinversopeptides but also covering a broad spectrum of isosteric peptide bond surrogates, see the following. Fletcher, D. M.; Campbell, M. M. Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior. Chem. Rev. 1998, 98, 763-795.
3. Abraham, W. R.; Ellison, S. L. R.; Schonholzer, P., Thomas, W. A. A Theoretical and Crystallographic Study of the Geometries and Conformations of Fluoroolefins as Peptide Analogs. Tetrahedron 1988, 42, 2101-2110.
4. Dugave, C.; Demange, L. Cis-Trans Isomerization of Organic Molecules and Biomolecules: Implications and Applications. Chem. Rev. 2003, 103, 2475-2532.
5. Cieplak, P.; Kollman, A.; Radomski, J. P. Molecular Design of Fluorine-Containing Peptide Mimetics. ACS Symp. Ser. 1996, 639, 143-156.
6. Allmendinger, T.; Furet, P.; Hungerbühler, E. Fluoroolefin Dipeptide Isosteres-I. The Synthesis of GlyΨ(CF=CH)Gly and Racemic PheΨ(CF=CH)Gly. Tetrahedron Lett. 1990, 31, 7297-7300.
7. Allmendinger, T.; Felder, E.; Hungerbühler, E. Fluoroolefin Dipeptide Isosteres-II. Enantioselective Synthesis of Both Antipodes of the Phe-Gly Dipeptide Mimic. Tetrahedron Lett. 1990, 31, 7301-7304.
8. Andres, C. J.; MacDonald, T. L.; Ocain, T. D.; Longhi, D. Conformationally Defined Analogs of Prolylamides-Trans-Prolyl Peptidomimetics. J. Org. Chem. 1993, 58, 6609-6613.
9. Amide isosteric replacements are commonly indicated using the symbol Ψ[ ], where the Ψ indicates the absence of an amide bond and the structure that is replacing the amide is indicated between brackets. Fok, Y. F.; Yankeelow, J. A. Biochem. Biophys. Res. Commun. 1977, 74, 273.
10. Bartlett, P. A.; Otake, A. Fluoroalkenes as Peptide Isosteres: Ground State Inhibitors of Thermolysin. J. Org. Chem. 1995, 60, 3107-3111.
11. Rosenblum, J. S.; Kozarich, J. W. Prolyl Peptidases: A Serine Protease Subfamily with High Potential for Drug Discovery. Curr. Opin. Chem. Biol. 2003, 7, 1-9.
12. Augustyns, K.; Van der Veken, P.; Senten, K.; Haemers, A. Dipeptidyl Peptidase IV Inhibitors as New Therapeutic Agents for the Treatment of Type 2 Diabetes. Expert Opin. Ther. Pat. 2003, 13 (4), 499-510.
13. Drucker D. J. Therapeutic Potential of Dipeptidyl Peptidase IV Inhibitors for the Treatment of Type 2 Diabetes. Expert Opin. Invest. Drugs 2003, 12, 87-100.
14. Ashworth, D. M.; Atrash, B.; Baker, G. R.; Baxter, A. J.; Jenkins, P. D.; Jones, D. M.; Szelke, M. 2-Cyanopyrrolidines as Potent, Stable Inhibtors of Dipeptidyl Peptidase IV. Bioorg. Med. Chem. Lett. 1996, 6 (10), 1163-1166.
15. Engel, M.; Hoffmann, T.; Wagner, L.; Wermann, M.; Heiser, U.; Kiefersauer, R.; Huber, R.; Bode, W.; Demuth, H. U.; Brandstetter, H. The Crystal Structure of Dipeptidyl Peptidase IV (CD26) Reveals Its Functional Regulation and Enzymatic Mechanism. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5063-5068.
16. Parmee, E. R.; He, J.; Mastracchio, A.; Edmondson, S. D.; Colwell, L.; Eiermann, G.; Feeney, W. P.; Habulihaz, B.; He, H.; Kilburn, R.; Leiting, B.; Lyons, K.; Marsilio, F.; Patel, R. A.; Petrov, A.; Di Salvo, J.; Wu, J. K.; Thornberry, N. A.; Weber, A. E. 4-Aminocyclohexylglycine Analogues of Potent Dipeptidyl Peptidase IV Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 43-46.
17. Ashton, W. T.; Dong, H.; Sisco, R. M.; Doss, G. A.; Leiting, B.; Patel, R. A.; Wu, J. K.; Marsilio, F.; Thornberry, N. A.; Weber, A. E. Diastereoselective Synthesis and Configuration-Dependent Activity of (3-Substituted-cycloalkyl)glycine Pyrrolidides and Thiazolidides as Dipeptidyl Peptidase IV Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 859-863.
18. Caldwell, C. G.; Chen, P.; He, J.; Parmee, E. R.; Leiting, B.; Marsilio, F.; Patel, R. A.; Wu, J. K.; Eiermann, G. J.; Petrov, A.; He, H.; Lyons, K. A.; Thornberry, N. A.; Weber, A. E. Fluoropyrrolidine Amides as Dipeptidyl Peptidase IV Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 1265-1268.
19. Hughes, T. E.; Mone, M. D.; Russel, M. E.; Weldon, S. C.; Villhauer, E. B. 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 1999, 38, 11597-11603.
20. Patent by NOVARTIS AG: US6124305, 2000.
21. Villhauer, E. B.; Brinkman, J. A.; Naderi, G. B.; Burkey, B. F.; Dunning, B. E.; Prasas, K.; Mangold, B. L.; Russell, M. E.; Hughes, T. E. 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., 2003, 46 (13), 2774-2789.
22. Magnin, D. R.; Robl, J. A.; Sulsky, R. B.; Augeri, D. J.; Huang, Y.; Simpkins, L. M.; Taunk, P. C.; Betebenner, D. A.; Robertson, J. G.; Abboa-Offei, B. E.; Wang, A.; Cap, M.; Xin, L.; Tao, L.; Sitkoff, D. F.; Malley, M. F.; Gougoutas, J. Z.; Khanna, A.; Huang, Q.; Han, S. P.; Parker, R. A.; Hamann, L. G. Synthesis of Novel Potent Dipeptidyl Peptidase IV Inhibitors with Enhanced Chemical Stability: Interplay between the N-Terminal Amino Acid Alkyl Side Chain and the Cyclopropyl Group of α-Aminoacyl-L-cis-4,5-methanoprolinenitrile- Based Inhibitors. J. Med. Chem. 2004, 47, 2587-2598.
23. Senten, K.; Van der Veken, P.; Bal, G.; De Meester, I.; Lambeir, A. M.; Sharpé, S.; Bauvois, B.; Haemers, A.; Augutyns, K. Development of Potent and Selective Dipeptidyl Peptidase II Inhibitors. Bioorg. Med. Chem. Lett. 2002, 12, 2825-2828.
24. Senten, K.; Van der Veken, P.; De Meester, I.; Lambeir, I.; Scharpé, S.; Haemers, A.; Augustyns, K. Design, Synthesis and SAR of Potent and Selective Dipeptide-Derived Inhibitors for Dipeptidyl Peptidases. J. Med. Chem. 2003, 46, 5005-5014.
25. Senten, K.; Van der Veken, P.; De Meester, I.; Lambeir, A. M.; Scharpé, S.; Haemers, A.; Augustyns, K. γ-Amino-Substituted Analogues of 1-[(S)-2,4-Diaminobutanoyl]piperidine as Highly Potent and Selective Dipeptidyl Peptidase II Inhibitors. J. Med. Chem. 2004, 47, 2906-2916.
26. Lin, J.; Toscano, P. J.; Welch, J. T. Inhibition of Dipeptidyl Peptidase IV (DPP IV) by Fluoroolefin-Containing N-Peptidyl-O-Hydroxylamine Peptidomimetics. Proc. Nat. Acad. Sci. U.S.A. 1998, 95, 14020-14024.
27. Zhao, K.; Lim, D. S.; Funaki, T.; Welch, J. T. Inhibition of Dipeptidyl Peptidase IV (DPP IV) by 2-(2-Amino-1-fluoro-propylidene)- cyclopentanecarbonitrile, a Fluoroolefin Containing Peptidomimetic. Bioorg. Med. Chem. 2003, 11, 207-215.
28. Welch, J. T.; Lin, J.; Boros, L. G.; DeCorte, B.; Bergmann, K.; Gimi, R. ACS Symp. Ser. 1996, 639, 129-142.
29. 2-Positions Is Important for Catalytic Activity of Some Proline-Specific Proteases. Biochim. Biophys. Acta 1983, 743, 452-456.
30. Welch, J. T.; Lin, J. Fluoroolefin Containing Dipeptide Isosteres as Inhibitors of Dipeptidyl Peptidase IV (CD 26). Tetrahedron 1996, 52, 291-304.
31. Otaka, A.; Watanabe, H.; Yukimasa, A.; Oishi, S.; Tamamura, H.; Fujii, N. New Access to Alpha-Substituted (Z)-Fluoroalkene Dipeptide Isosteres Utilizing Organocopper Reagents under "Reduction-Oxidative Alkylation (R-OA)" Conditions. Tetrahedron Lett. 2001, 42, 5443-5446.
32. Otaka, A.; Watanabe, H.; Mitsuyama, E.; Yukimasa, A.; Tamamura, H.; Fujii, N. Synthesis of (Z)-Fluoroalkene Dipeptide Isosteres Utilizing Organocopper-Mediated Reduction of Gamma,Gamma-Difluoro-Alpha,Beta-Enoates. Tetrahedron Lett. 2001, 42, 285-287.
33. Van der Veken, P.; Kertesz, I.; Senten, K.; Haemers, A.; Augustyns, K. Synthesis of (E)- and (Z)-Fluoro-Olefin Analogues of Potent Dipeptidyl Peptidase IV Inhibitors. Tetrahedron Let. 2003, 44, 6231-6234.
34. Rasmussen, H. B.; Branner, S.; Wiberg, F. C.; Wagtmann, N. Crystal Structure of Human Dipeptidyl Peptidase IV/CD26 in Complex with a Substrate Analog. Nat. Struct. Biol. 2003, 10, 19-25.
35. Thoma, R.; Löffler, B.; Stihle, M.; Huber, W.; Ruf, A.; Hennig, M. Structural Basis of Proline-Specific Exopeptidase Activity As Observed in Human Dipeptidyl Peptidase IV. Structure 2003, 11, 947-959.
36. Aertgeerts, K.; Ye, S.; Tennant, M. G.; Kraus, M. L.; Roger, J.; Sang, B. C.; Skene, R. J.; Webb, D. R.; Prasad, G. R. Crystal Structure of Human Dipeptidyl Peptidase IV in Complex with a Decapeptide Reveals Details on Substrate Specificity and Tetrahedral Intermediate Formation. Protein Sci. 2004, 13 (2), 412-421.
37. Stöckel-Maschek, A.; Mrestani-Klaus, C.; Stiebitz, B.; Demuth, H.-U.; Neubert, K. Thioxo Amino Acid Pyrrolidides and Thiazolidides: New Inhibitors of Proline Specific Peptidases. Biochim. Biophys. Acta 2000, 1479, 15-31.
38. De Meester, I.; Vanhoof, G.; Lambeir, A.-M.; Scharpé, S. Use of Immobilized Adenosine Deaminase for the Rapid Purification of Native Human CD26 Dipeptidyl Peptidase IV. J. Immunol. Methods 1996, 189 (1), 99-105.
39. Fukasawa, K. M.; Fukasawa, K.; Higaki, K.; Shiina, N.; Ohno, M.; Ito, S.; Otogoto J.; Ota, N. Cloning and Functional Expression of Rat Kidney Dipeptidyl Peptidase II. Biochem. J. 2001, 353, 283-290.
40. Leatherbarrow, R. J. GraFit, version 5; Erithacus Software Ltd.: Horley, U.K., 2001.