Design and synthesis of malonic acid-based inhibitors of human neutrophil collagenase (MMP8)

Journal of Medicinal Chemistry

Volumn 41, Issue 3, 1998, Pages 339-345

  Von Reedern, Erich Graf ^a,c   Grams, Frank ^b   Brandstetter, Hans ^a,d   Moroder, Luis ^a  

^a MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c SANOFI   (France)

^d MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGENASE INHIBITOR; DIPEPTIDE DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; MALONIC ACID DERIVATIVE; MALONIC ACID HYDROXAMATE; NEUTROPHIL COLLAGENASE; NEUTROPHIL COLLAGENASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER INVASION; DRUG CONFORMATION; DRUG DESIGN; DRUG FORMULATION; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; JOINT DESTRUCTION; MOLECULAR WEIGHT; NEUTROPHIL; X RAY CRYSTALLOGRAPHY;

COLLAGENASES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALONATES; MATRIX METALLOPROTEINASE 8; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0032576767     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9706426     Document Type: Article

References (34)

1. Schwartz, M. A.; Van Wart, H. E. Synthetic Inhibitors of Bacterial and Mammalian Interstitial Collagenases. Prog. Med. Chem. 1992, 29, 271-334.
2. Beckett, R. P.; Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Recent Advances in Matrix Metalloproteinase Inhibitor Research. Drug Discuss. Today 1996, 1, 16-26.
3. Hagmann, W. K.; Lark, M. W.; Becker, J. W. Inhibition of Matrix Metalloproteinases. Annu. Rep. Med. Chem. 1996, 31, 231-240.
4. Murphy, G. Matrix Metalloproteinases and their Inhibitors. Acta Orthop. Scand., (Suppl. 266), 1995, 66, 55-60.
5. Beckett, R. P. Recent Advances in the Field of Matrix Metalloproteinase Inhibitors. Exp. Opin. Ther. Pat. 1996, 6, 1305-1315.
6. Lovejoy, B.; Cleasby, A.; Hassell, A. M.; Longley, K.; Luther, M. A.; Weigl, D.; McGeehan, G.; McElroy, A. B.; Drewry, D.; Lambert, M. H.; Jordan, S. R. Structure of the Catalytic Domain of Fibroblast Collagenase Complexed with an Inhibitor. Science 1994, 263, 375-377.
7. 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. Nature Struct. Biol. 1994, 1, 106-110.
8. 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. Nature Struct. Biol. 1994, 1, 119-123.
9. 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.
10. 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 Å Structure of Mature Truncated Human Fibroblast Collagenase. Proteins Struct. Funct. Genet. 1994, 19, 98-109.
11. Grams, F.; Reinemer, P.; Powers, F. C.; Kleine, T.; Pieper, M.; Tschesche, H.; Huber, R.; Bode, W. X-ray Structures of Human Neutrophil Collagenase Complexed with Peptide Hydroxamate and Peptide Thiol Inhibitors. Eur. J. Biochem. 1995, 228, 830- 841.
12. Reinemer, P.; Grams, F.; Huber, R.; Kleine, T.; Schnierer, S.; Pieper, M.; Tschesche, H.; Bode, W. Structural Implications for the Role of the N-Terminus in the "Superactivation" of Collagenases. FEBS Lett. 1994, 338, 227-233.
13. Gooley, P. R.; O'Connell, J. F.; Marcy, A. I.; Cuca, G. C.; Salowe, S. P.; Bush, B. L.; Hermes, J. D.; Esser, C. K.; Hagmann, W. K.; Springer, J. P.; Johnson, B. A. The NMR Stucture of the Inhibited Catalytic Domain of Human Stromelysin-1. Nature Struct. Biol. 1994, 1, 111-118.
14. Lovejoy, B.; Hassell, A. M.; Luther, A. M.; Weigl, D.; Jordan, S. R. Crystal-Structures of Recombinant 19-kDa Human Fibroblast Collagenase Complexed to Itself. Biochemistry 1994, 33, 8207- 8217.
15. Grams, F.; Crimmin, M.; Hinnes, P.; Huxley, P.; Pieper, M.; Tschesche, H.; Bode, W. Structure Determination and Analysis of Human Neutrophil Collagenase Complexed with a Hydroxamate Inhibitor. Biochemistry 1995, 34, 14012-14020.
16. Van Doren, S. R.; Kurochkin, A. V.; Hu, W. D.; Ye, Q. Z.; Johnson, L. L.; Hupe, D. J.; Zuiderweg, E. R. P. Solution Structure of the Catalytic Domain of Human Stromelysin Complexed with a Hydrophobic Inhibitor. Protein Sci. 1995, 4, 2487-2498.
17. Browner, M. F.; Smith, W. W.; Castelhano, A. L. Matrilysin- Inhibitor Complexes: Common Themes among Metalloproteases. Biochemistry 1995, 34, 6602-6610.
18. Dhanaraj, V.; Ye, Q.-Z.; Johnson, L. L.; Hupe, D. J.; Ortwine, D. F.; Dunbar, J. B.; Rubin, J. R.; Pavlovsky, A.; Humblet, C.; Blundell, T. L. X-Ray Structure of a Hydroxamate Inhibitor Complex of Stromelysin Catalytic Domain and its Comparison with Members of the Zinc Metalloproteinase Superfamily. Nature Struct. Biol. 1990, 4, 375-386.
19. Becker, J. W.; Marcy, A. I.; Rokosz, L. L.; Axel, M. G.; Burbaum, J. J.; Fitzgerald, P. M. D.; Cameron, P. M.; Esser, C. K.; Hagmann, W. K.; Hermes, J. D.; Springer, J. P. Stromelysin- 1-3-Dimensional Structure of the Inhibited Catalytic Domain and of the C-Truncated Proenzyme. Protein Sci. 1995, 4, 1966- 1976.
20. Nishino, N.; Powers, J. C. Peptide Hydroxamic Acids as Inhibitors of Thermolysin. Biochemistry 1978, 17, 2846-2850.
21. Johnson, W. H.; Roberts, N. A.; Borkakoti, N. Collagenase Inhibitors: Their Design and Potential Therapeutic Use. J. Enzymol. Inhib. 1987, 2, 1-22.
22. Betz, M.; Huxley, P.; Davies, S. J.; Mushtaq, Y.; Pieper, M.; Tschesche, H.; Bode, W.; Gomis-Rüth, F. X. 1.8-Å Crystal Structure of the Catalytic Domain of Human Neutrophil Collagenase (Matrix-Metalloproteinase-8) Complexed with a Peptidomimetic Hydroxamate Primed-Side Inhibitor with a Distinct Selectivity Profile. Eur. J. Biochem. 1997, 247, 356-363.
23. Bihovsky, R.; Levinson, B. L.; Loewi, R. C.; Erhardt, P. W.; Polokoff, M. A. Hydroxamic Acids as Potent Inhibitors of Endothelin-Converting Enzyme from Human Bronchiolar Smooth Muscle. J. Med. Chem. 1995, 38, 2119-2129.
24. Fournie-Zaluski, M.-C.; Coulaud, A.; Bouboutou, R.; Chaillet, P.; Devin, J.; Waksman, G.; Costentin, J.; Roques, B. P. New Bidantates as Full Inhibitors of Enkephalin-Degrading Enzymes: Synthesis and Analgesic Properties. J. Med. Chem. 1985, 28, 1158-1168.
25. Nishino, N.; Powers, J. C. Design of Potent Reversible Inhibitors for Thermolysin. Peptides Containing Zinc Coordinating Ligands and their Use in Affinity Chromatography. Biochemistry 1979, 18, 4340-4347.
26. Brandstetter, H.; Engh, R. A.; Graf von Roedern, E.; Moroder, L.; Huber, R.; Bode, W.; Grams, F. Structure of Malonic-Acid- Based Inhibitors Bound to Human Neutrophil Collagenase. Protein Sci., submitted.
27. Wünsch, E. Houben-Weyl, Methoden der Organischen Chemie, Synthese von Peptiden; Springer-Verlag: Stuttgart, 1974; Vols. 15/I and 15/II.
28. Stack, M. S.; Gray, R. D. Comparison of Vertebrate Collagenase and Gelatinase Using a New Fluorogenic Substrate Peptide. J. Biol. Chem. 1989, 264, 4277-4281.
29. i Values for Tight Binding Inhibitors from Dose Response Plots. Bioorg. Med. Chem. Lett. 1995, 5, 1947-1952.
30. Böhm, H. J. LUDI: Rule-Based Automatic Design of New Substituents for Enzyme Inhibitor Leads. J. Comput.-Aided Mol. Des. 1992, 6, 593-606.
31. Boettcher, M.; Henklein, P.; Hoffmann, K.; Heder, G.; Siems, W. E.; Niedrich, H. Synthese von N-substituierten Aminosäure- p-nitrobenzylestern als potentielle ACE-Inhibitoren. (Synthesis of N-substituted amino acid p-nitrobenzyl esters as potential ACE-inhibitors.) Pharmazie 1986, 41, 140.
32. Hammond, K. M.; Fisher, N.; Morgan, E. N.; Tanner, E. M.; Franklin, C. S. 3: 5-Dioxo-1: 2-diphenylpyrazolidines. The 4-Hydroxy- and Certain 4-Alkoxy- and 4-Alkylamino-Analogues. J. Chem. Soc. 1957, 1062-1067.
33. Cignarella, G. Synthesis and Configuration of trans-1-Amino- 4-benzyl-2,6-dimethylpiperazine as an Intermediate of Semisynthetic Rifamycins. J. Heterocycl. Chem. 1974, 11, 985-988.
34. Corey, E. J. The Mechanism of the Decarboxylation of αβ- and βγ-Unsaturated Malonic Acid Derivatives. J. Am. Chem. Soc. 1952, 74, 5897-5905.