Review of hydroxamic matrix metalloproteinase inhibitors and their therapeutic potential
Authors:
J. Šille; V. Garaj; M. Šramko; M. Remko
Authors‘ workplace:
Univerzita Komenského Bratislava, Farmaceutická fakulta, Katedra farmaceutickej chémie, SR
Published in:
Čes. slov. Farm., 2009; 58, 95-102
Category:
Review Articles
Overview
The hydroxamic acid moiety is the key structural element for the potency of the inhibitors against metalloprotease enzymes. However, the selectivity of the inhibitors towards various metalloproteases depends on the structures of the templates or scaffolds as well as the variations of the substituents. A combination of the traditional substrate- and mechanism-based approaches and the new technologies, such as the structural-based drug design as well as combinatorial chemistry, will be essential for the future development of specific protease inhibitors. Success in a clinical trial of new hydroxamic acid-based inhibitors is expected soon.
Key words:
hydroxamates – MMP – TACE – metalloenzymes – metalloproteinases
Sources
1. Bode, W., Gomis-Rüth, F.X., Stöckler, W.: FEBS Lett., 1993; 331, 134–140.
2. Hooper, N. L.: FEBS Lett., 1994; 354, 1–6.
3. Georgiadis, D., Yiotakis, A.: Bioorg. Med. Chem., 2008; 16, 8781–8794.
4. Whitakker, M., Floyd, C. D., Brown, P., Gearing, A. J. H.: Chem. Rev., 1999; 99, 2735–2776.
5. Rao, B. G.: Curr. Pharm. Des., 2005; 11, 295–322.
6. Turk, B.: Nat. Rev. Drug. Disc., 2006; 5, 785–799.
7. Flannery, C. R.: Front. Biosci., 2006; 11, 544–569.
8. Baran, I., Varekova, R. S., Parthasarathi, L., Suchomel, S., Casey, F., Shields, D. C.: J. Chem. Inf. Model., 2007; 47, 464–474.
9. Skiles, J.W., Monovich, L.G., Jeng, A.Y.: Annual Reports in Medicinal Chemistry, 2000; 35, 167–176.
10. Hagmann, W.K., Lark, W.K., Becker, J.W.: Annual Reports in Medicinal Chemisry, 1996; 31, 231–240.
11. Nicolotti, O., Miscioscia, T. F., Lonetti, F., Muncipinto, G., Carotti, A.: J. Chem. Inf. Model., 2007; 47, 2439–2448.
12. Hu, J., Van den Steen, P. E., Sang, Q. X., Opdenakker, G.: Nat. Rev. Drug Disc., 2007; 6, 480–498.
13. Hutchinson, J. W., Tierney, G. M., Parsons, S. L., Davis, T. R. J.: J. Bone Joint Surg. (Br), 1998; 80–B: 907–908.
14. Abbenante, G., Fairlie, D. P.: Med. Chem., 2005; 1, 71–104.
15. Peterson, J. T.: Heart Fail. Rev., 2004; 9, 63–79.
16. Zucker, S., Cao, J., Chen, W. T.: Oncogene, 2000; 19, 6642–6650.
17. Martin, F. M., Beckett, R. P., Bellamy, C. L., Courtney, P. F., Davies, S. J., Drummond, A. H., Dodd, R., Pratt, L. M., Patel, S. R., Ricketts, M. L., Todd, R. S., Tuffnell, A. R., Ward, J. W. S., Whittaker, M.: Bioorg. Med. Chem. Lett., 1999; 9, 2887–2892.
18. Hanessian, S., Moitessier, N., Therrien, E.: J. Computer-Aided Mol. Design, 2001; 15, 873–881.
19. Hanessian, S., Moitessier, N., Gauchet, C., Viau, M.: J. Med. Chem., 2001; 44, 3066–3074.
20. O’Brien, P. M., Ortwine, D. F., Pavlovsky, A. G., Picard, J. A., Sliskovic, D. R., Roth, B. D., Dyer, R. D., Johnson, L. L., Man, C. F., Hallak, H.: J. Med. Chem., 2000; 43, 156–166.
21. Parker M. H., Ortwine D. F., O’Brien P. M., Lunney E. A., Banotai C. A., Mueller W. T., McConnell P., Brouillette C. G.: Bioorg. Med. Chem. Lett., 2000; 10, 2427–2430.
22. Robinson, R. P., Laird, E. R., Blake, J. F., Bordner, J., Donahue, K. M., Lopresti–Morrow, L. L., Mitchell, P. G., Reese, M. R., Reeves, L. M., Stam, E., Yocum, S. A.: J. Med. Chem., 2000; 43, 2293–2296.
23. Barta, T. E., Becker, D. P., Bedell, L. J., De Crescenzo, G. A., McDonald, J. J., Munie, G. E., Rao, S., Shieh, H.–S., Stegeman, R., Stevens, A. M., Villamil, C. I.: Bioorg. Med. Chem. Lett., 2000; 10, 2815–2817.
24. Fray, M. J., Burslem, M. F., Dickinson, R. P.: Bioorg. Med. Chem. Lett., 2001; 11, 567–570.
25. Fray M. J., Dickinson R. P.: Bioorg. Med. Chem. Lett., 2001; 11, 571–574.
26. Baxter, A. D., Bhogal, R., Bird, J., Keily, J. F., Manallack, D. T., Montana, J. G., Owen, D. A., Pitt, W. R., Watson, R. J., Wills, R. E.: Bioorg. Med. Chem. Lett., 2001; 11, 1465–1468.
27. Wada, C. K., Holms, J. H., Curtin, M. L., Dai, Y., Florjancic, A. S., Garland, R. B., Guo, Y., Heyman, H. R., Stacey, J. R., Steinman, D. H., Albert, D. H., Bouska, J. J., Elmore, I. N., Goodfellow, C. L., Marcotte, P. A., Tapang, P., Morgan, D. W., Michaelides, M. R., Davidsen, S. K.: J. Med. Chem., 2002; 45, 219–232.
28. Seals, D. F., Courtneidge S. A.: Genes Dev., 2003; 17, 7–30.
29. Huovila A. P., Turner A. J., Pelto–Huikko M., Kärkkäinen I., Ortiz R. M.: Trends Biochem. Sci., 2005; 30, 413–422.
30. Black, R. A.: Int. J. Biochem. Cell Biol., 2002; 34, 1–5.
31. Moss M. L., Bartsch J. W.: Biochemistry, 2004; 43, 7227–7235.
32. Moss M. L., Sklair-Tavron L., Nudelman R.: Nat. Clin. Pract. Rheumatol., 2008; 4, 300–309.
33. Grootveld M., McDermott M. F.: Curr. Opin. Investig. Drugs, 2003; 4, 598–602.
34. Thabet, M. M., Huizinga, T. W.: Curr. Opin. Investig. Drugs, 2006; 7, 1014–1019.
35. Xue, C. B., He, X., Corbett, R. L., Roderick, J., Wasserman, Z. R., Liu, R. Q., Jaffee B. D., Covington, M. B., Qian, M., Trzaskos, J. M., Newton, R. C., Magolda, R. L., Wexler, R. R., Decicco, C. P.: J. Med. Chem., 2001; 44, 3351–3354.
36. Holms, J., Mast, K., Marcotte, P., Elmore, I., Li, J., Pease, L., Glaser, K., Morgan, D., Michaelides, M., Davidsen, S.: Bioorg. Med. Chem. Lett., 2001; 11, 2907–2910.
37. Duan, J. J., Chen, L., Wasserman, Z. R., Lu, Z., Liu, R. Q., Covington, M. B., Qian, M., Hardman, K. D., Magolda, R. L., Newton, R. C., Christ, D. D., Wexler, R. R., Decicco, C. P.: J. Med. Chem., 2002; 45, 4954–4957.
38. Wasserman, Z. R., Duan, J. J., Voss, M. E., Xue, C. B., Cherney, R. J., Nelson, D. J., Hardman, K. D., Decicco, C. P.: Chem. Biol., 2003; 10, 215–223.
39. Niu, X., Umland, S., Ingram, R., Beyer, B. M., Liu, Y. H., Sun, J., Lundell, D., Orth, P.: Arch. Biochem. Biophys., 2006; 451, 43–50.
40. Cherney, R. J., Duan, J. J., Voss, M. E., Chen, L., Wang, L., Meyer, D. T., Wasserman, Z. R., Hardman, K. D., Liu, R. Q., Covington, M. B., Qian M., Mandlekar, S., Christ, D. D., Trzaskos, J. M., Newton, R. C., Magolda, R. L.,Wexler, R. R., Decicco, C. P.: J. Med. Chem., 2003; 46, 1811–1823.
41. Xue, C. B., He, X., Roderick, J., Corbett, R. L., Duan, J. J., Liu, R. Q., Covington, M. B., Qian, M., Ribadeneira, M. D., Vaddi, K., Christ, D. D., Newton, R. C., Trzaskos, J. M., Magolda, R. L., Wexler, R. R., Decicco, C. P.: Bioorg. Med. Chem. Lett., 2003; 13, 4299–4304.
42. Gilmore, J. L., King, B. W., Harris, C., Maduskuie, T., Mercer, S. E., Liu, R. Q., Covington, M. B., Qian, M., Ribadeneria, M. D., Vaddi, K., Trzaskos, J. M., Newton, R. C., Decicco, C. P., Duan, J. J.: Bioorg. Med. Chem. Lett., 2006; 16, 2699–2704.
43. Wang, X., Feuerstein, G. Z., Xu, L., Wang, H., Schumacher, W. A., Ogletree, M. L., Taub, R., Duan, J. J., Decicco, C. P., Liu, R. Q.: Mol. Pharmacol., 2004; 65, 890–896.
44. Chen, X. T., Ghavimi, B., Corbett, R. L., Xue, C. B., Liu, R. Q., Covington, M. B., Qian, M., Vaddi, K. G., Christ, D. D., Hartman, K. D., Ribadeneira, M. D., Trzaskos, J. M., Newton, R. C., Decicco, C. P., Duan, J. J.: Bioorg. Med. Chem. Lett., 2007; 17, 1865–1870.
45. Lu, Z., Ott, G. R., Anand, R., Liu, R. Q., Covington, M. B., Vaddi, K., Qian, M., Newton, R. C., Christ, D. D., Trzaskos, J., Duan, J. J.: Bioorg. Med. Chem. Lett., 2008, 18, 1958–1962.
46. Levin, J. I., Chen, J. M., Du, M. T., Nelson, F. C., Killar, L. M., Skala, S., Sung, A., Jin, G., Cowling, R., Barone, D., March, C. J., Mohler, K. M., Black, R. A., Skotnicki, J. S.: Bioorg. Med. Chem. Lett., 2002; 12, 1199–1202.
47. Levin, J. I., Chen, J. M. Cheung, K., Cole, D., Crago, C., Santos, E. D., Du, X., Khafizova, G., MacEwan, G., Niu, C., Salaski, E. J., Zask, A., Cummons, T., Sung, A., Xu, J., Zhang, Y., Xu, W., Ayral–Kaloustian, S., Jin, G., Cowling, R., Barone, D., Mohler, K. M., Black, R. A., Skotnicki, J. S.: Bioorg. Med. Chem. Lett., 2003; 13, 2799–2803 .
48. Zhang, Y., Hegen, M., Xu, J., Keith, J. C. Jr., Jin, G., Du X., Cummons, T., Sheppard, B. J., Sun, L., Zhu, Y., Rao, V. R., Wang, Q., Xu, W., Cowling, R., Nickerson–Nutter, C. L., Gibbons, J., Skotnicki, J., Lin, L. L., Levin, J.: Int. Immunopharmacol., 2004; 4, 1845–1847.
49. Zhu, Z., Mazzola, R., Sinning, L., McKittrick, B., Niu, X., Lundell, D., Sun, J., Orth, P., Guo, Z., Madison, V., Ingram, R., Beyer, B. M.: J. Med. Chem., 2008; 51, 725–736.
50. Lukacova, V., Zhang, Y., Kroll, D. M., Raha, S., Comez, D., Balaz, S.: J. Med. Chem., 2005; 48, 2361–2370.
51. Gomis-Rüth, F. X.: Molecular, Mol. Biotechnol., 2003; 24, 157–202.
52. Boliang L., Kexin Y.: Mini Rev. Med. Chem., 2003; 3, 609–620.
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Pharmacy Clinical pharmacologyArticle was published in
Czech and Slovak Pharmacy
2009 Issue 3
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