Phosphinic pseudo-tripeptides as potent inhibitors of matrix metalloproteinases: A structure-activity study

Journal of Medicinal Chemistry

Volumn 42, Issue 14, 1999, Pages 2610-2620

  Vassiliou, Stamatia ^b   Mucha, Artur ^e   Cuniasse, Philippe ^a   Georgiadis, Dimitris ^b   Lucet Levannier, Karine ^a   Beau, Fabrice ^a   Kannan, Rama ^d   Murphy, Gillian ^c   Knäuper, Vera ^c   Rio, Marie Christine ^d   Basset, Paul ^d   Yiotakis, Athanasios ^b   Dive, Vincent ^a  

^a DIF   (France)

^b UNIVERSITY OF ATHENS   (Greece)

^c UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^d INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^e WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGENASE; GELATINASE A; GELATINASE B; MATRILYSIN; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; PHOSPHINIC ACID DERIVATIVE; PHOSPHINIC PSEUDOTRIPEPTIDE; STROMELYSIN; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METALLOENDOPEPTIDASES; OLIGOPEPTIDES; PHOSPHINES; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033566137     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9900164     Document Type: Article

References (48)

1. Birkedal-Hansen, H. Matrix Metalloproteinases. Adv. Dent. Res. 1995, 9, 16.
2. Coussens, L. M.; Werb, Z. Matrix Metalloproteinases and the Development of Cancer. Chem. Biol. 1996, 3, 895-904.
3. Yu, A. E.; Hewitt, R. E.; Connor, E. W.; Stetler-Stevenson, W. G. Matrix Metalloproteinases. Novel Targets for Directed Cancer Therapy. Drugs Aging 1997, 11, 229-244.
4. Cawston, T. E. Metalloproteinase Inhibitors and the Prevention of Connective Tissue Breakdown. Pharmacol. Ther. 1996, 70, 163-182.
5. Chandler, S.; Miller, K. M.; Clements, J. M.; Lury, J.; Corkill, D.; Anthony, D. C.; Adams, S. E.; Gearing, A. J. Matrix Metalloproteinases, Tumor Necrosis Factor and Multiple Sclerosis: an Overview. J. Neuroimmunol. 1997, 72, 155-161.
6. Cleutjens, J. P. The Role of Matrix Metalloproteinases in Heart Disease. Cardiovasc. Res. 1996, 30, 816-821.
7. Celentano, D. C.; Frishman, W. H. Matrix Metalloproteinases and Coronary Artery Disease: a Novel Therapeutic Target. J. Clin. Pharmacol. 1997, 37, 991-1000.
8. Yong, V. W.; Krekoski, C. A.; Forsyth, P. A.; Bell, R.; Edwards, D. R. Matrix Metalloproteinases and Diseases of the CNS. Trends Neurosci. 1998, 21, 75-80.
9. Brown, P. D. Matrix Metalloproteinase Inhibitors in the Treatment of Cancer. Med. Oncol. 1997, 14, 1-10.
10. Johnson, L. L.; Dyer, R.; Hupe, D. J. Matrix Metalloproteinases. Curr. Opin. Chem. Biol. 1998, 2, 466-471.
11. Massova, I.; Kotra, L. P.; Fridman, R.; Mobashery, S. Matrix Metalloproteinases: Structures, Evolution, and Diversification. Faseb J. 1998, 12, 1075-1095.
12. Basset, P.; Bellocq, J. P.; Wolf, C.; Stoll, I.; Hutin, P.; Limacher, J. M.; Podhajcer, O. L.; Chenard, M. P.; Rio, M. C.; Chambon, P. A Novel Metalloproteinase Gene Specifically Expressed in Stromal Cells of Breast Carcinomas. Nature 1990, 348, 699-704.
13. Murphy, G.; Segain, J. P.; O'Shea, M.; Cockett, M.; Ioannou, C.; Lefebvre, O.; Chambon, P.; Basset, P. The 28-kDa N-Terminal Domain of Mouse Stromelysin-3 has the General Properties of a Weak Metalloproteinase. J. Biol. Chem. 1993, 268, 15435-15441.
14. Noel, A.; Santavicca, M.; Stoll, I.; L'Hoir, C.; Staub, A.; Murphy, G.; Rio, M. C.; Basset, P. Identification of Structural Determinants Controlling Human and Mouse Stromelysin-3 Proteolytic Activities. J. Biol. Chem. 1995, 270, 22866-22872.
15. Pei, D.; Weiss, S. J. Furin-Dependent Intracellular Activation of the Human Stromelysin-3 Zymogen. Nature 1995, 375, 244-247.
16. Santavicca, M.; Noel, A.; Angliker, H.; Stoll, I.; Segain, J. P.; Anglard, P.; Chretien, M.; Seidah, N.; Basset, P. Characterization of Structural Determinants and Molecular Mechanisms Involved in Pro-Stromelysin-3 Activation by 4-Aminophenylmercuric Acetate and Furin-Type Convertases. Biochem. J. 1996, 315, 953-958.
17. Noel, A. C.; Lefebvre, O.; Maquoi, E.; VanHoorde, L.; Chenard, M. P.; Mareel, M.; Foidart, J. M.; Basset, P.; Rio, M. C. Stromelysin-3 Expression Promotes Tumor Take in Nude Mice. J. Clin. Invest. 1996, 97, 1924-1930.
18. Masson, R.; Lefebvre, O.; Noel, A.; Fahime, M. E.; Chenard, M. P.; Wendling, C.; Kebers, F.; LeMeur, M.; Dierich, A.; Foidart, J. M.; Basset, P.; Rio, M. C. In Vivo Evidence that the Stromelysin-3 Metalloproteinase Contributes in a Paracrine Manner to Epithelial Cell Malignancy. J. Cell. Biol. 1998, 140, 1535-1541.
19. Mucha, A.; Cuniasse, P.; Kannan, R.; Beau, F.; Yiotakis, A.; Basset, P.; Dive, V. Membrane Type-1 Matrix Metalloprotease and Stromelysin-3 Cleave more Efficiently Synthetic Substrates Containing Unusual Amino Acids in their P1′ Positions. J. Biol. Chem. 1998, 273, 2763-2768.
20. Beckett, R. P.; Whittaker, M. Matrix Metalloproteinase Inhibitors 1998. Exp. Opin. Ther. Patents 1998, 8, 259-282.
21. Yiotakis, A.; Vassiliou, S.; Jiracek, J.; Dive, V. Protection of the Hydroxyphosphinyl Function of Phosphinic Dipeptides By Adamantyl. Application to the Solid-Phase Synthesis of Phosphinic Peptides. J. Org. Chem. 1996, 61, 6601-6605.
22. Jiracek, J.; Yiotakis, A.; Vincent, B.; Lecoq, A.; Nicolaou, A.; Checler, F.; Dive, V. Development of Highly Potent and Selective Phosphinic Peptide Inhibitors of Zinc Endopeptidase 24-15 using Combinatorial Chemistry. J. Biol. Chem. 1995, 270, 21701-21706.
23. Jiracek, J.; Yiotakis, A.; Vincent, B.; Checler, F.; Dive, V. Development of the First potent and Selective Inhibitor of the Zinc Endopeptidase Neurolysin using a Systematic Approach Based on Combinatorial Chemistry of Phosphinic Peptides. J. Biol. Chem. 1996, 271, 19606-19611.
24. Grams, F.; Dive, V.; Yiotakis, A.; Yiallouros, I.; Vassiliou, S.; Zwilling, R.; Bode, W.; Stocker, W. Structure of astacin with a transition-state analogue inhibitor [letter]. Nat. Struct. Biol. 1996, 3, 671-675.
25. Eistetter, K.; Wolf, H. P. Synthesis and Hypoglycemic Activity of Phenylalkyloxiranecarboxylic Acid Derivatives. J. Med. Chem. 1982, 25, 109-113.
26. Amri, H.; Rambaud, M.; Villieras, J. Esters α-Méthyléniques par Substitution d'Ether et d'Acétates Dérivés de l'α-(Hydroxyméthyl) Acrylate d'éthyle. J. Organomet. Chem. 1990, 384, 1-11.
27. Baldwin, J.; Arlington, R.; Birch, D.; Crawford, J.; Sweeney, J. Radical Reactions in Synthesis: Carbon-Carbon Bond Formation from 2-Substituted Allyl Teralkyl Stannanes. J. Chem. Soc., Chem. Commun. 1986, 1339-1340.
28. Boyd, E. A.; Boyd, M. E. K.; Loh, V. M., Jr. Facile Synthesis of Functionalised Phenylphosphinic Acid Derivatives. Tetrahedron Lett. 1996, 37, 1651-1654.
29. Lovejoy, B.; Cleasby, A.; Hassell, A. M.; Longley, K.; Luther, M. A.; Weigl, D.; McGeehan, G.; McElroy, A. B.; Drewry, D.; Lambert, M. H.; et al. Structure of the Catalytic Domain of Fibroblast Collagenase Complexed with an Inhibitor. Science 1994, 263, 375-377.
30. Bode, W.; Reinemer, P.; Huber, R.; Kleine, T.; Schnierer, S.; Tschesche, H. The X-ray Crystal Structure of the Catalytic Domain of Human Neutrophil Collagenase Inhibited by a Substrate Analogue Reveals the Essentials for Catalysis and Specificity. Embo J. 1994, 13, 1263-1269.
31. Lovejoy, B.; Hassell, A. M.; Luther, M. A.; Weigl, D.; Jordan, S. R. Crystal Structures of Recombinant 19-kDa Human Fibroblast Collagenase Complexed to Itself. Biochemistry 1994, 33, 8207-8217.
32. Borkakoti, N.; Winkler, F. K.; Williams, D. H.; D'Arcy, A.; Broadhurst, M. J.; Brown, P. A.; Johnson, W. H.; Murray, E. J. Structure of the Catalytic Domain of Human Fibroblast Collagenase Complexed with an Inhibitor. Nat. Struct. Biol. 1994, 1, 106-110.
33. Stams, T.; Spurlino, J. C.; Smith, D. L.; Wahl, R. C.; Ho, T. F.; Qoronfleh, M. W.; Banks, T. M.; Rubin, B. Structure of Human Neutrophil Collagenase Reveals Large S1′ Specificity Pocket. Nat. Struct. Biol. 1994, 1, 119-123.
34. Spurlino, J. C.; Smallwood, A. M.; Carlton, D. D.; Banks, T. M.; Vavra, K. J.; Johnson, J. S.; Cook, E. R.; Falvo, J.; Wahl, R. C.; Pulvino, T. A.; Wendoloski, J. J.; Smith, D. L. 1.56 A Structure of Mature Truncated Human Fibroblast Collagenase. Proteins 1994, 19, 98-109.
35. Browner, M. F.; Smith, W. W.; Castelhano, A. L. Matrilysin-Inhibitor Complexes: Common Themes Among Metalloproteases. Biochemistry 1995, 34, 6602-6610.
36. Babine, R. E.; Bender, S. L. Molecular Recognition of Protein-Ligand Complexes: Applications to Drug Design. Chem. Rev. 1997, 97, 1359-1472.
37. Levy, D. E.; Lapierre, F.; Liang, W.; Ye, W.; Lange, C. W.; Li, X.; Grobelny, D.; Casabonne, M.; Tyrrell, D.; Holme, K.; Nadzan, A.; Galardy, R. E. Matrix Metalloproteinase Inhibitors: a Structure-Activity Study. J. Med. Chem. 1998, 41, 199-223.
38. Tamura, Y.; Watanabe, F.; Nakatani, T.; Yasui, K.; Fuji, M.; Komurasaki, T.; Tsuzuki, H.; Maekawa, R.; Yoshioka, T.; Kawada, K.; Sugita, K.; Ohtani, M. Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2): N-Sulfonylamino Acid Derivatives. J. Med. Chem. 1998, 41, 640-649.
39. Pikul, S.; McDow Dunham, K. L.; Almstead, N. G.; De, B.; Natchus, M. G.; Anastasio, M. V.; McPhail, S. J.; Snider, C. E.; Taiwo, Y. O.; Eydel, T.; Dunaway, C. M.; Gu, F.; Mieling, G. E. Discovery of Potent, Achiral Matrix Metalloproteinase Inhibitors. J. Med. Chem. 1998, 41, 3568-3571.
40. Vilieras, J.; Rambaud, M. Wittig-Horner Reaction in Heterogeneous Media; 1. An Easy Synthesis of Ethylα-Hydroxymethylacrylate and Ethyl α-Halomethylacrylates using Formaldehyde in Water. Synthesis 1982, 924-926.
41. Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. 1-Aminoalkyl-phosphonous Acids. Part 1. Isosters of the Protein Amino Acids. J. Chem. Soc., Perkin Trans. 1 1984, 2845-2853.
42. Murphy, G.; Cockett, M. I.; Stephens, P. E.; Smith, B. J.; Docherty, A. J. Stromelysin is an Activator of Procollagenase. A Study with Natural and Recombinant Enzymes. Biochem. J. 1987, 248, 265-268.
43. Murphy, G.; Cockett, M. I.; Ward, R. V.; Docherty, A. J. Matrix Metalloproteinase Degradation of Elastin, Type IV Collagen and Proteoglycan. A Quantitative Comparison of the Activities of 95 kDa and 72 kDa Gelatinases, Stromelysins-1 and -2 and Punctuated Metalloproteinase (PUMP). Biochem. J. 1991, 277, 277-279.
44. Murphy, G.; Crabbe, T. Gelatinases A and B. Methods Enzymol. 1995, 248, 470-484.
45. Kannan, R.; Ruff, M.; Kochins, J. G.; Manly, S. P.; Stoll, I.; El Fahime, M.; Noël, A.; Foidart, J.-M.; Rio, M.-C.; Dive, V.; Basset, P. Purification of Active Metalloproteinase Catalytic Domain and Its Use for Screening of Specific Stromelysin-3 Inhibitors. Protein Expression Purif. 1999, 16, 76-83.
46. Knight, C. G.; Willenbrock, F.; Murphy, G. A Novel Coumarin-Labeled Peptide for Sensitive Continuous Assays of the Matrix Metalloproteinases. FEBS Lett. 1992, 296, 263-266.
47. Cornish-Bowden, A.; Eisenthal, R. Estimation of Michaelis Constant and Maximum Velocity from the Direct Linear Plot. Biochim. Biophys. Acta 1978, 523, 268-272.
48. Horovitz, A.; Levitzki, A. An Accurate Method for Determination of Receptor-Ligand and Enzyme-Inhibitor Dissociation Constants from Displacement Curves. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 6654-6658.