Carbamoylphosphonates, a new class of in vivo active matrix metalloproteinase inhibitors. 1. Alkyl- and cycloalkylcarbamoylphosphonic acids

Journal of Medicinal Chemistry

Volumn 47, Issue 11, 2004, Pages 2826-2832

  Breuer, Eli ^a   Salomon, Claudio J ^a   Katz, Yiffat ^a   Chen, Weibin ^a   Lu, Shuiming ^a   Röschenthaler, Gerd Volker ^b   Hadar, Rivka ^a   Reich, Reuven ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMOYLPHOSPHONIC ACID; CYCLOOCTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; GELATINASE A; GELATINASE B; INTERSTITIAL COLLAGENASE; MATRIX METALLOPROTEINASE INHIBITOR; N CYCLOOCTYLCARBAMOYLPHOSPHONIC ACID; N CYCLOPENTYLCARBAMOYLPHOSPHONIC ACID; N CYCLOPROPYLCARBAMOYLPHOSPHONIC ACID; NEUTROPHIL COLLAGENASE; PHOSPHONIC ACID DERIVATIVE; STROMELYSIN; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BASEMENT MEMBRANE; CONTROLLED STUDY; DRUG POTENCY; DRUG RESEARCH; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; IC 50; IN VITRO STUDY; IN VIVO STUDY; MELANOMA; MOUSE; NONHUMAN; PH;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTINEOPLASTIC AGENTS; BASEMENT MEMBRANE; CAPILLARIES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HYDROGEN-ION CONCENTRATION; MATRIX METALLOPROTEINASES; MICE; NEOPLASM INVASIVENESS; PHOSPHONIC ACIDS; PROTEIN BINDING; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; ZINC;

EID: 2442713986     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030386z     Document Type: Article

References (42)

1. Partial preliminary accounts of this work were presented at the XVIth International Symposium of Medicinal Chemistry, Bologna, Italy, Sept 18-22, 2000, Abstract no. PC35, at the International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec 14-19, 2000, Abstract no. MEDI0214, and at the XVth International Conference on Phosphorus Chemistry, Jul 29-Aug. 3, 2001, Sendai, Japan, Abstract no. C24.
2. Partial preliminary accounts of this work were presented at the XVIth International Symposium of Medicinal Chemistry, Bologna, Italy, Sept 18-22, 2000, Abstract no. PC35, at the International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec 14-19, 2000, Abstract no. MEDI0214, and at the XVth International Conference on Phosphorus Chemistry, Jul 29-Aug. 3, 2001, Sendai, Japan, Abstract no. C24.
3. Partial preliminary accounts of this work were presented at the XVIth International Symposium of Medicinal Chemistry, Bologna, Italy, Sept 18-22, 2000, Abstract no. PC35, at the International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec 14-19, 2000, Abstract no. MEDI0214, and at the XVth International Conference on Phosphorus Chemistry, Jul 29-Aug. 3, 2001, Sendai, Japan, Abstract no. C24.
4. For recent reviews, see Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Design and therapeutic application of matrix metalloproteinase inhibitors. Chem. Rev. 1999, 99, 2735-2776.
5. Wojtowicz-Praga, S.; Clinical potential of matrix metalloprotease inhibitors. Drugs R&D 1999, 1, 117-129.
6. De, B.; Natchus, M. G.; Cheng, M.; Pikul, S.; Almstead, N. G.; Taiwo, Y. O.; Snider, C. E.; Chen, L.; Barnett, B.; Gu, F.; Dowty, M. The next generation of MMP inhibitors: design and synthesis. Ann. N. Y. Acad. Sci. 1999, 878, 40-60.
7. Johnson, L. L.; Dyer, R.; Hupe, D. J. Matrix metalloproteases. Curr. Opin. Chem. Biol. 1998, 2, 466.
8. Hidalgo, M.; Eckhardt, S. G.; Development of Matrix Metalloproteinase Inhibitors in Cancer Therapy. J. Natl. Cancer Inst. 2001, 93, 178-193.
9. Kleiner, D. E.; Stetler-Stevenson, W. G. Matrix metalloproteinases and metastasis. Cancer Chemother. Pharmacol. 1999; 43 Suppl., S42-51.
10. Billinghurst, R. C.; Dahlberg, L.; Ionescu, M.; Reiner, A.; Tanzer, M.; Zukor, D.; Chen, J.; Van Wart, H.; Poole, A. R. Selective enhancement of collagenase-mediated cleavage of resident type II collagen in cultured osteoarthritic cartilage and arrest with a synthetic inhibitor that spares collagenase 1 (matrix metalloproteinase 1). Arthritis Rheum. 2000, 43, 673.
11. Ikeda, U.; Shimada, K. Matrix metalloproteinases and coronary artery diseases. Clin. Cardiol. 2003, 26, 55-59.
12. Pilcher, B. K.; Wang, M.; Qin, X.-J.; Parks, W. C.; Senior, R. M.; Welgus, H. G. Role of matrix metalloproteinases and their inhibition in cutaneous wound healing and allergic contact hypersensitivity. Ann. N. Y. Acad. Sci. 1999, 878, 12-24.
13. Morphy, J. R.; Beeley, N. R. A.; Boyce, B. A.; Leonard, J.; Mason, B.; Millican, A.; Millar, K.; O'Connel, J. P.; Porter, J. Potent and Selective Inhibitors of Gelatinase-A 2. Carboxylic and Phosphonic Acid Derivatives. Bioorg. Med. Chem. Lett. 1994, 4, 2747.
14. Buchardt, J.; Schiødt. C. B.; Krog-Jensen, C.; Delaissé, J.-M.; Foged, N. T.; Meldal, M. Solid-Phase Combinatorial Library of Phosphinic Peptides for Discovery of Matrix Metalloproteinase Inhibitors. J. Comb. Chem. 2000, 2, 624-638 and refs 4-10 cited therein.
15. (a) Caldwell, C. G.; Sahoo, S. P.; Polo, S. A.; Eversole, R. R.; Lanza, T. J.; Mills, S. G.; Niedzwiecki, L. M.; Izquierdo-Martin, M.; Chang, B. C. Phosphinic acid inhibitors of matrix metalloproteinases. Bioorg. Med. Chem. Lett. 1996, 6, 323-8.
16. (b) Goulet, J. L.; Kinneary, J. F.; Durrette, P. L.; Stein, R. L.; Harrison, R. K.; Izquierdo-Martin, M.; Kuo, D. W.; Lin, T.-Y.; Hagmann, W. K. Inhibition of Stromelysin-1 (MMP-3) by peptidyl phosphinic acids. Bioorg. Med. Chem. Lett. 1994, 4, 1221-1224.
17. (a) Breuer, E. Acylphosphonates and their derivatives. In The chemistry of organophosphorus compounds; Hartley, F. R., Ed.; John Wiley & Sons, Ltd.: New York, 1996; Vol 4, pp 653-729.
18. (b) McKenna, C. E.; Kashemirov, B. A. Recent Progress in Carbonylphosphonate Chemistry. Topics Curr. Chem. 2002, 220, 201-238.
19. Mathew, M.; Fowler, B. O.; Breuer, E.; Golomb, G.; Alferiev, I. S.; Eidelman, N. Synthesis, Characterization, and Crystal Structure of Dicalcium Glutarylbisphosphonate Dihydrate: A Covalently Pillared Layer Structure with the Potential for Epitaxial Growth on Hydroxyapatite. Inorg. Chem. 1998, 37, 6485-6494.
20. (a) Rowsell, S.; Hawtin, P.; Minshull, C. A.; Jepson, H.; Brockbank, S. M. V.; Barratt, D. G.; Slater, A. M.; McPheat, W. L.; Waterson, D.; Henney, A. M.; Pauptit, R. A.; Crystal Structure of Human MMP9 in Complex with a Reverse Hydroxamate Inhibitor. J. Mol. Biol. 2002, 319, 173-181.
21. (b) 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.
22. (c) 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.
23. (d) Dhanaraj, V.; Williams, M. G.; Ye, Q.-Z.; Molina, F.; Johnson, L. L. ; Ortwine, D. F.; Pavlovsky, A.; Rubin, J. R.; Skeean, R. W.; White, A. D.; Humblet, C.; Hupe, D. J.; Blundell, T. L. X-ray structure of gelatinase a catalytic domain complexed with a hydroxamate Inhibitor. Croat. Chem. Acta 1999, 72, 575-591.
24. (e) Grams, F.; Crimmin, M.; Hinnes, L.; 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.
25. Farkas, E.; Katz, Y.; Bhusare, S.; Reich, R.; Röschenthaler, G.-V.; Königsmann, M.; Breuer, E. Carbamoylphosphonate based matrix metalloproteinase (MMP) inhibitor metal complexes - solution studies and stability constants. Towards a zinc selective binding group. J. Biol. Inorg. Chem. 2004, 9, in press.
26. (a) Nylen, P. Beitrag zur Kenntnis der Organischen Phosphorverbindungen. (Contribution to the knowledge of organic phosphorus compounds.) Chem. Berichte 1924, 57, 1023-1038.
27. (b) Arbusov, B. A.; Rizpolozhenskii, N. I. Diethylamides of esters of phosphonoformic acid. lzvest. Akad. Nauk. S. S. S. R., Otdel Khim. Nauk. 1952, 847-853. Chem. Abstr. 1953, 47, 10457.
28. (b) Arbusov, B. A.; Rizpolozhenskii, N. I. Diethylamides of esters of phosphonoformic acid. lzvest. Akad. Nauk. S. S. S. R., Otdel Khim. Nauk. 1952, 847-853. Chem. Abstr. 1953, 47, 10457.
29. (c) Reetz, T.; Chadwick, D. H.; Hardy, E. E.; Kaufman, S. Carbamoylphosphonates, J. Am. Chem. Soc. 1955, 77, 3813-3816.
30. (d) Fox. R. B.; Venezky, D. L. The Base-catalyzed reaction of dialkyl phosphonates with isocyanates. J. Am. Chem. Soc. 1956, 78, 1661-1663.
31. Salomon, C. J.; Breuer, E. Facile "One-Pot" Preparation of Phosphonothiolformates - A Convenient Approach to Carbamoylphosphonates. Synlett 2000, 815-816.
32. Grisley, D. W., Jr. The reaction of sodium dialkyl phosphonates with carbonyl sulfide and with carbon disulfide. J. Org. Chem. 1961, 26, 2544.
33. Reich R.; Blumenthal M.; Liscovitch M. Role of phospholipase D in laminin-induced production of gelatinase A (MMP-2) in metastatic cells. Clin. Exp. Metastasis 1995, 13 134-140.
34. Baragi, V. M.; Shaw, B. J.; Renkiewicz, R. R.; Kuipers, P. J.; Welgus, H. G.; Mathrubutham, M.; Cohen, J. R.; Rao, A. versatile assay for gelatinases using succinylated gelatin. Matrix Biol. 2000, 3, 267-273.
35. Grant, D. S.; Tashiro, K.; Segui-Real, B.; Yamada, Y.; Martin, G. R.; Kleinman, H. K. Two different laminin domains mediate the differentiation of human endothelial cells into capillary-like structures in vitro. Cell 1989, 58, 933-943.
36. Poste, G.; Doll, J.; Hart, I. R.; Fidler. I. J. In Vitro Selection of Murine B16 Melanoma Variants With Enhanced Tissue-Invasive Properties. Cancer Res. 1980, 40, 1636-1644.
37. (a) Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Matrix metalloproteinase inhibitors and cancer: trials and tribulations. Science 2002, 295, 2387-2392.
38. (b) Egeblad, M.; Werb, Z. New functions for the matrix metalloproteinases in cancer progression. Nat. Rev. Cancer 2002, 2, 161-174.
39. Overall, C.; Lopez-Otin C. Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat. Rev. Cancer 2002, 9, 657-672.
40. Augé, F.; Hornebeck, W.; Decarme, M.; Laronze, J.-Y. Improved gelatinase A selectivity by novel zinc binding groups containing Galardin derivatives. Bioorg. Med. Chem, Lett. 2003, 13, 1783-1786.
41. The increased activity of amides as compared to esters in phospholipase A2 inhibitors was attributed previously to stronger binding of calcium by the amides: (a) Davidson, F. F.; Hajdu, J.; Dennis, E. A. 1-Stearyl 2-stearoylaminodeoxy phosphatidylcholine, a potent reversible inhibitor of phospholipase A2. Biochem. Biophys. Res. Commun. 1986, 137, 587-592.
42. (b) Thunnissen, M. M.; Ab, E.; Kalk, K. H.; Drenth. J.; Dijkstra.; B. W. ; Kuipers, O. P.; Dijkman. R.; de Haas. G. H.; Verheij, H. M. X-ray structure of phospholipase A2 complexed with a substrate-derived inhibitor. Nature 1990, 347, 689-691.