Inhibition of adamalysin II and MMPs by phosphonate analogues of snake venom peptides

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 2, 1999, Pages 389-394

  D'Alessio, Silvana ^a   Gallina, Carlo ^b   Gavuzzo, Enrico ^c   Giordano, Cesare ^d   Gorini, Barbara ^d   Mazza, Fernando ^e   Paglialunga Paradisi, Mario ^d   Panini, Gabriella ^d   Pochetti, Giorgio ^c   Sella, Antonio ^a  

^a Polifarma Research Center   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

^c CNR   (Italy)

^d SAPIENZA UNIVERSITY OF ROME   (Italy)

^e UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

Adamalysin II; Matrix metalloproteinases; Retrobinding pseudopeptide inhibitors

Indexed keywords

ADAMALYSIN II; GELATINASE A; GELATINASE B; MATRILYSIN; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; NEUTROPHIL COLLAGENASE; SNAKE VENOM; STROMELYSIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG HYDROLYSIS; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

INHIBITORY CONCENTRATION 50; METALLOENDOPEPTIDASES; MODELS, CHEMICAL; SNAKE VENOMS; SPECTROPHOTOMETRY, INFRARED; TEMPERATURE;

EID: 0032980326     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00243-0     Document Type: Article

References (28)

1. (a) Morphy, J. R.; Millican, T. A.; Porter, J. R. Curr. Med. Chem. 1995, 2, 743.
2. (b) Hagmann, W. K.; Lark, M. V.; Becker, J. W. Ann. Rep. Med. Chem. 1996, 31, 231.
3. For recent reviews, see (a) Schwartz, M. A.; Van Wart, H. E. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Eds.; Elsevier Science Publishers: The Netherlands 1991; Vol 29, pp 239-270.
4. (b) Porter, J. R.; Millican, T. A.; Morphy, J. R. Exp. Opin. Ther. Patents 1995, 5, 1287.
5. (c) Becket, R. P.; Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Drug Design Today 1996, 1, 16.
6. (d) Beckett, R. P. Exp. Opin. Ther. Patents 1996, 5, 1305.
7. (e) Beckett, R. P.; Whittaker, M. Exp. Opin. Ther. Patents 1998, 8, 259.
8. Berger, A.; Schechter, J. Phil. Trans. Roy. Soc. Lond. 1970, B257, 249.
9. Babine, E.; Bender, S. L. Chem. Rev. 1997, 97, 1359.
10. Robeva, A.; Politi, V.; Shannon, J. D.; Bjarnason, J. B.; Fox, J. W. Biomed. Biochim. Acta 1991, 50, 769.
11. Cirilli, M.; Gallina, C.; Gavuzzo, E.; Giordano, C.; Gomis-Rüth, F. X.; Gorini, B.; Kress, L. F.; Mazza, F.; Paglialunga-Paradisi, M.; Pochetti, G.; Politi V. FEBS Letters, 1997, 418, 319.
12. Gomis-Rüth, F. X.; Politi, V.; Meyer, E. F.; Kress, L. F.; Bode, W. Protein Sci. 1998, 7, 283.
13. Kortylewicz, Z. P.; Galardy, R. E. J. Med. Chem. 1990, 33, 263.
14. Galardy, R. E.; Grobelny, D.; Kortylewicz, Z. P.; Poncz, L. Metalloproteinases Inhib., Proc. Matrix Metalloproteinase Conf., 1989, Matrix Suppl. n 1 1992, 259.
15. Morphy, J. R.; Beeley, N. R. A.; Boyce, B. A.; Leonard, J.; Mason, B.; Millican, A.; Millar, K.; O'Connell, J. P.; Porter, J. Bioorg. Med. Chem. Lett. 1994, 4, 2747.
16. Bird J.; De Mello, R. C.; Harper, G. P.; Hunter, D. J.; Karran, E. H.; Markwell, R. E.; Miles-Williams, A. J.; Rahman, S. S.; Ward, R. W. J. Med. Chem. 1994, 37, 158.
17. Subotkwski, W.; Kowalik, J.; Tyka, R.; Mastalerz, P. Pol. J. Chem. 1981, 55, 853.
18. Chen, F. M.; Steinhauer, R.; Benoiton, N. L. J. Org. Chem. 1983, 26, 2939.
19. Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537.
20. Stöcker, W.; Grams, F.; Baumann, U.; Reinemer, P.; Gomis-Rüth, F. X.; McKay, D. B.; Bode, W. Protein Sci. 1995, 4, 823.
21. See 7 and literature cited therein.
22. Pro-MMP-2, pro-MMP-3, pro-MMP-8 and pro-MMP-9 were supplied by G. Murphy (Strangeways Research Laboratories, Cambridge, UK). Adamalysin II was a kind gift from L. F. Kress (Roswell Park Cancer Institute, Buffalo, New York).
23. Murphy, G.; Crabbe, T. Methods in Enzymol. 1995, 248, 470.
24. Tschesche, H. Methods in Enzymol. 1995, 248, 431.
25. Nagase, H. Methods in Enzymol. 1995, 248, 449.
26. 2 for MMP-3 (G. Knight, private communication) were supplied by G. Knight (Strangeways Research Laboratories, Cambridge, UK). 2-Aminobenzoyl-Ala-Gly-Leu-Ala-p-nitrobenzylamide was purchased from Bachem (Budendorf, Switzerland).
27. Knight, C. G.; Willenbrock, F.; Murphy, G. FEBS Letters 1992, 296, 263.
28. Fox, J. W.; Campbell, R.; Beggerly, L.; Bjarnason, J. B. Eur. J. Biochem. 1986, 156, 65.