Protease inhibitors: Synthesis of potent bacterial collagenase and matrix metalloproteinase inhibitors incorporating N-4- nitrobenzylsulfonylglycine hydroxamate moieties

Journal of Medicinal Chemistry

Volumn 43, Issue 9, 2000, Pages 1858-1865

  Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGENASE; COLLAGENASE INHIBITOR; GELATINASE A; GELATINASE B; HYDROXAMIC ACID DERIVATIVE; MATRIX METALLOPROTEINASE INHIBITOR; N 4 NITROBENZYLSULFONYLGLYCINE HYDROXAMATE; NEUTROPHIL COLLAGENASE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CLOSTRIDIUM HISTOLYTICUM; DRUG DESIGN; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INACTIVATION; EXTRACELLULAR MATRIX; HUMAN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

HUMANS; METALLOENDOPEPTIDASES; MICROBIAL COLLAGENASE; MOLECULAR WEIGHT; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034075487     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990594k     Document Type: Article

References (48)

1. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Design and therapeutic application of matrix metalloproteinase inhibi-tors. Chem. Rev. 1999, 99, 2735-2776.
2. Bottomley, K. M.; Johnson, W. H.; Walter, D. S. Matrix metalloproteinase inhibitors in arthritis. J. Enzyme Inhib. 1998, 13, 79-102.
3. (a) Babine, R. E.; Bender, S. L. Molecular recognition of protein-ligand complexes: Applications to drug design. Chem. Rev. 1997, 97, 1359-1472.
4. (b) Zook, S. E.; Dagnino, R., Jr.; Deason, M. E.; Bender, S. L. PCT Int. Appl. WO 97/20824.
5. Supuran, C. T.; Scozzafava, A. Matrix metalloproteinase inhibitors. In Proteinase and Peptidase Inhibition: Recent Potential Targets for Drug Development; Smith, H. J., Simons, C., Eds.; Harwood Academic Press: London, 2000; in press.
6. (a) Nagase, H.; Woessner, J. F., Jr. Matrix metalloproteinases. J. Biol. Chem. 1999, 274, 21491-21494.
7. (b) Dioszegi, M.; Cannon, P.; Van Wart, H. E. Vertebrate collagenases. Methods Enzymol. 1995, 248, 413-431.
8. (c) Tschesche, H. Human neutrophil collagenase. Methods Enzymol. 1995, 248, 431-449.
9. (a) Johnson, L. L.; Dyer, R.; Hupe, D. J. Matrix metalloproteinases. Curr. Opin. Chem. Biol. 1998, 2, 466-471.
10. (b) Williams, S.; Barnes, J.; Wakisaka, A.; Ogasa, H.; Liang, C. T. Treatment of osteoporosis with MMP inhibitors. Ann. N. Y. Acad. Sci. 1999, 878, 191-200.
11. Kahari, V. M.; Saarialho-Kere, U. Matrix metalloproteinases and their inhibitors in tumour growth and invasion. Ann. Med. 1999, 31, 34-45.
12. (a) Graff von Roedern, E.; Grams, F.; Brandstetter, H.; Moroder, L. Design and synthesis of malonic acid-based inhibitors of human neutrophil collagenase (MMP-8) J. Med. Chem. 1998, 41, 339-345.
13. (b) 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.
14. (c) Grams, F.; Reinemer, P.; Powers, J. C.; Kleine, T.; Pieper, M.; Tschesche, H.; Huber, R.; Bode, W. X-ray structures of human neutrophil collagenase complexed with hydroxamate and peptide thiols inhibitors. Implications for substrate binding and rational drug design. Eur. J. Biochem. 1995, 228, 830-841.
15. (d) Bode, W.; Fernandez-Catalan, C.; Grams, F.; Gomis-Ruth, F. X.; Nagase, H.; Tschesche, H.; Maskos, K. Insights into MMP-TIMPS interactions. Ann. N. Y. Acad. Sci. 1999, 878, 73-91.
16. (a) MacPherson, L. J.; Bayburt, E. K.; Capparelli, M. P.; Carroll, B. J.; Goldstein, R.; Justice, M. R.; Zhu, L.; Hu, S.; Melton, R. A.; Fryer, L.; Goldberg, R. L.; Doughty, J. R.; Spirito, S.; Blancuzzi, V.; Wilson, D.; O'Byrne, E. M.; Ganu, V.; Parker, D. T. Discovery of CGS 27023A, a nonpeptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. J. Med. Chem. 1997, 40, 2525-2532.
17. (b) Jeng, A. Y.; Chou, M.; Parker, D. T. Sulfonamide-based hydroxamic acids as potent inhibitors of mouse macrophage metalloelastase. Bioorg. Med. Chem. Lett. 1998, 8, 897-902.
18. 2′ pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 1691-1696.
19. (d) Almstead, N. G.; Bradley, R. S.; Pikul, S.; De, B.; Natchus, M. G.; Taiwo, Y. O.; Gu, F.; Williams, L. E.; Hynd, B. A.; Janusz, M. J.; Dunaway, C. M.; Mieling, G. E. Design, synthesis and biological evaluation of potent thiazine and thiazepine-based matrix metalloproteinase inhibitors. J. Med. Chem. 1999, 42, 4547-4562.
20. (e) Cheng, M.; De, B.; Almstead, N. G.; Pikul, S.; Dowty, M. E.; Dietsch, C. R.; Dunaway, C. M.; Gu, F.; Hsieh, L. C.; Janusz, M. J.; Taiwo, Y. O.; Natchus, M. G. Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold. J. Med. Chem. 1999, 42, 5426-5436.
21. (a) Kiyama, R.; Tamura, Y.; Watanabe, F.; Tsuzuki, H.; Ohtani, M.; Yodo, M. Homology modeling of gelatinase catalytic domains and docking simulations of novel sulfonamide inhibitors. J. Med. Chem. 1999, 42, 1723-1738.
22. (b) Krumme, D.; Wenzel, H.; Tschesche, H. Hydroxamate derivatives of substrate analogous peptides containing aminomalonic acid are potent inhibitors of matrix metalloproteinases. FEBS Lett. 1998, 436, 209-212.
23. (c) Supuran, C. T.; Briganti, F.; Mincione, G.; Scozzafava, A. Protease inhibitors: Synthesis of L-alanine hydroxamate sulfonylated derivatives as inhibitors of Clostridium histolyticum collagenase. J. Enzyme Inhib. 2000, 75, in press.
24. (a) Bond, M. D.; Van Wart, H. E. Purification and separation of individual collagenases of Clostridium histolyticum using red dye ligand chromatography. Biochemistry 1984, 23, 3077-3085.
25. (b) Bond, M. D.; Van Wart, H. E. Characterization of the individual collagenases from Clostridium histolyticum. Biochemistry 1984, 23, 3085-3091.
26. (c) Van Wart, H. E. Clostridium collagenases. In Handbook of Proteolytic Enzymes - CD ROM; Rawlings, N. D., Barrett, A. J., Woessner, J. F., Eds.; Academic Press: London, 1998; Chapter 368.
27. Rawlings, N. D.; Barrett, A. J. Evolutionary families of metallopeptidases. Methods Enzymol. 1995, 248, 183-228.
28. Rood, J. I. Virulence genes of Clostridium perfringens. Annu. Rev. Microbiol. 1998, 52, 333-360.
29. (a)Matsushita, O.; Jung, C. M.; Minami, J.; Katayama, S.;Nishi, N.; Okabe, A. A study of the collagen-binding domain of a 116-kDa Clostridium histolyticum collagenase. J. Biol. Chem. 1998, 273, 3643-3648.
30. (b) Matsushita, O.; Jung, C. M.; Minami, J.; Katayama, S.; Minami, J.; Takashi, Y.; Okabe, A. Gene duplication and multiplicity of collagenase in Clostridium histolyticum. J. Bacteriol. 1999, 181, 923-933.
31. Jung, C. M.; Matsushita, O.; Katayama, S.; Minami, J.; Sakurai, J.; Okabe, A. Identification of metal ligands in the Clostridium histolyticum ColH collagenase. J. Bacteriol. 1999, 181, 2816-2822.
32. (a) Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J. Med. Chem. 1999, 42, 2641-2650.
33. (b) Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 1999, 42, 3690-3700.
34. Borras, J.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: is the tail more important than the ring? Bioorg. Med. Chem. 1999, 7, 2397-2406.
35. (a) Supuran, C. T.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G. Carbonic anhydrase inhibitors. Part 71. Synthesis and ocular pharmacology of a new class of watersoluble, topically effective intraocular pressure lowering sulfonamides incorporating picolinoyl moieties. Eur. J. Pharm. Sci. 1999, 8, 317-328.
36. (b) Scozzafava, A.; Briganti, F.; Ilies, M. A.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus the cytosolic isozymes. J. Med. Chem. 2000, 43, 292-300.
37. (a) Pavlovsky, A. G.; Williams, M. G.; Ye, Q.; Ortwine, D. F.; Purchase, C. F., II; White, A. D.; Dhanaraj, V.; Roth, B. D.; Johnson, L. L.; Hupe, D.; Humblet, C.; Blundell, T. L. X-ray structure of human stromelysin catalytic domain complexed with nonpeptide inhibitors: Implications for inhibitor selectivity. Protein Sci. 1999, 8, 1455-1462.
38. (b) 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. Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Arylsulfonylureido and arylureido-substituted aromatic and heterocyclic sulfonamides: towards selective inhibitors of car-bonic anhydrase isozyme I. J. Enzymol. Inhib. 1999, 14, 343-363.
40. Moy, F. J.; Chanda, P. K.; Chen, J. M.; Cosmi, S.; Edris, W.; Skotnicki, J. S.; Wilhelm, J.; Powers, R. NMR solution structure of the catalytic fragment of human fibroblast collagenase complexed with a sulfonamide derivative of a hydroxamic acid compound. Biochemistry 1999, 38, 7085-7096.
41. (a) Scozzafava, A.; Supuran, C. T. Protease inhibitors. Part 8. Synthesis of potent Clostridium histolyticum collagenase inhibitors incorporating sulfonylated L-alanine hydroxamate moieties. Bioorg. Med. Chem. 2000, 8, 637-645.
42. (b) Scozzafava, A.; Supuran, C. T. Protease inhibitors: Synthesis of Clostridium histolyticum collagenase inhibitors incorporating sulfonyl-L-alanine hydroxamate moieties. Bioorg. Med. Chem. Lett. 2000, 10, 499-502.
43. Bieth, J. G. Theoretical and practical aspects of proteinase inhibition kinetics. Methods Enzymol. 1995, 248, 59-84.
44. (a) Powers, J. C.; Kam, C. M. Peptide thioester substrates for serine peptidases and metalloendopeptidases. Methods Enzymol. 1995, 248, 3-18.
45. (b) Johnson, L. L.; Bornemeier, D. A.; Janowicz, J. A.; Chen, J.; Pavlovsky, A. G.; Ortwine, D. F. Effect of species differences on stromelysin-1 (MMP-3) inhibitor potency. J. Biol. Chem. 1999, 274, 24881-24887.
46. Van Wart, H. E.; Steinbrink, D. R. A continuous spectrophotometric assay for Clostridium histolyticum collagenase. Anal. Biochem. 1981, 113, 156-165.
47. Nagase, H. Activation mechanisms of matrix metalloproteinases. Biol. Chem. 1997, 378, 151-160.
48. Jacobsen, E. J.; Mitchell, M. A.; Hendges, S. K.; Belonga, K. L.; Skaletzky, L. L.; Stelzer, L. S.; Lindberg, T. J.; Fritzen, E. L.; Schostarez, H. J.; O'Sullivan, T. J.; et al. Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors. J. Med. Chem. 1999, 42, 1525-1536.