Development of a water-soluble matrix metalloproteinase inhibitor as an intra-arterial infusion drug for prevention of restenosis after angioplasty

Journal of Medicinal Chemistry

Volumn 46, Issue 16, 2003, Pages 3497-3501

  Masuda, Takeshi ^a   Nakayama, Yasuhide ^a  

^a NATIONAL CEREBRAL AND CARDIOVASCULAR CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GELATINASE A; GELATINASE B; MACROPHAGE ELASTASE; MATRIX METALLOPROTEINASE INHIBITOR; N HYDROXY 5 CARBOXYLETHYLCARBONYLOXY 2 METHYL 4 (4 PHENOXYBENZOYL)AMINOPENTANAMIDE; N HYDROXY 5 HYDROXY 2 METHYL 4 (4 PHENOXYBENZOYL)AMINOPENTANAMIDE; N,N DIMETHYLACRYLAMIDE; ONO M 11 335; POLY[N,N DIMETHYLACRYLAMIDE CO N HYDROXY 5 [2 [N [2 (ISOPROPENYLCARBONYLOXY)ETHYL]CARBAMOYL]ETHYLCARBONYLOXY] 2 METHYL 4 (4 PHENOXYBENZOYL)AMINOPENTANAMIDE]; UNCLASSIFIED DRUG;

ANGIOPLASTY; ARTICLE; CHEMICAL REACTION; DRUG DESIGN; DRUG SYNTHESIS; DRUG UPTAKE; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; RESTENOSIS; ULTRAVIOLET SPECTROSCOPY;

ACRYLAMIDES; ANGIOPLASTY, TRANSLUMINAL, PERCUTANEOUS CORONARY; BENZAMIDES; CORONARY RESTENOSIS; HUMANS; HYDROXAMIC ACIDS; INFUSIONS, INTRA-ARTERIAL; MAGNETIC RESONANCE SPECTROSCOPY; MATRIX METALLOPROTEINASES; POLYMERS; POSTOPERATIVE COMPLICATIONS; PROTEASE INHIBITORS; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET; STENTS; STEREOISOMERISM; VINYL COMPOUNDS; WATER;

EID: 0041342060     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020356g     Document Type: Article

References (31)

1. Massova, I.; Kotra, L. P.; Fridman, R.; Mobashery, S. Matrix metaloproteinases: structures, evolution, and diversification. FASEB J. 1998, 12, 1075-1095. Hidalgo, M.; Eckhardt, S. G. Development of matrix metalloproteinase inhibitors in cancer therapy. J. Natl. Cancer Inst. 2001, 93, 178-193.
2. Massova, I.; Kotra, L. P.; Fridman, R.; Mobashery, S. Matrix metaloproteinases: structures, evolution, and diversification. FASEB J. 1998, 12, 1075-1095. Hidalgo, M.; Eckhardt, S. G. Development of matrix metalloproteinase inhibitors in cancer therapy. J. Natl. Cancer Inst. 2001, 93, 178-193.
3. Dollery, C. M.; McEwan, J. R.; Henney, A. M. Matrix metalloproteinases and cardiovasucular disease. Circ. Res. 1995, 77, 863-868.
4. Galis, Z. S.; Muszynski, M.; Sukhova, G. K.; Simon-Morrissey, E.; Unemori, E. N.; Lark, M. W.; Amento, E.; Libby, P. Cytokine-stimulated human vascular smooth muscle cells synthesized a complement of enzymes required for extracellular matrix digestion. Circ. Res. 1994, 75, 181-189.
5. Nagase, H. Activation mechanisms of matrix metalloproteinases. Biol. Chem. 1997, 378, 151-160.
6. Sato, H.; Takino, T.; Okada, Y.; Cao, J.; Shinagawa, A.; Yamamoto, E.; Seiki M. A matrix metalloproteinase expressed on the surface of invasive tumour cells. Nature 1994, 370, 61-65.
7. Baker, A. H.; Zaltsman, A. B.; George, S. J.; Newby, A. C. Divergent effects of tissue inhibitor of metalloproteinase-1, -2 or -3 overexpression on rat vascular smooth muscle cell invasion, proliferation, and death in vivo. J. Clin. Invest. 1998, 101, 1478-1487.
8. Supuran, C. T.; Scozzafava, A. In Matrix metalloproteinases (MMPs) in proteinase and peptidase inhibition: Recent potential targets for drug development; Smith, H. J., Simons, C., Eds.; Taylor & Francis: London & New York, 2002; pp 35-61. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. Design and therapeutic application of matrix metalloproteinase inhibitors. Chem. Rev. 1999, 99, 2735-2776.
9. Supuran, C. T.; Scozzafava, A. In Matrix metalloproteinases (MMPs) in proteinase and peptidase inhibition: Recent potential targets for drug development; Smith, H. J., Simons, C., Eds.; Taylor & Francis: London & New York, 2002; pp 35-61. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. Design and therapeutic application of matrix metalloproteinase inhibitors. Chem. Rev. 1999, 99, 2735-2776.
10. Matter, H.; Schwab, W.; Barbier, D.; Billen, G.; Hasse, B.; Neises, B.; Schudok, M.; Thorwart, W.; Schreuder, H.; Brachvogel, V.; Lonze, P.; Weithmann, KU. Quantitative structure-activity relationship of human neutrophil collagenase (MMP-8) inhibitors using comparative molecular field analysis and X-ray structure analysis. J. Med. Chem. 1999, 42, 1908-1920.
11. Gavuzzo, E.; Pochetti, G.; Mazza, F.; Gallina, C.; Gorini, B.; D'Alessio, S.; Pieper, M.; Tschesche, H.; Tucker, P. A. Two crystal structures of human neutrophil collagenase, one complexed with a prime- and the other with an unprimed-side inhibitor: implications for drug design. J. Med. Chem. 2000, 43, 3377-3385.
12. Jia, MC.; Schwartz, M. A.; Sang, Q. A. Suppression of human microvascular endothelial cell invasion and morphogenesis with synthetic matrixin inhibitors. Targeting angiogenesis with MMP inhibitors. Adv. Exp. Med. Biol. 2000, 476, 181-94. Graf von Roedern, E.; Grams, F.; Brandstetter, H.; Moroder, L. Design and synthesis of malonic acid-based inhibitors of human neutrophil collagenase (MMP8). J. Med. Chem. 1998, 41, 339-345.
13. Jia, MC.; Schwartz, M. A.; Sang, Q. A. Suppression of human microvascular endothelial cell invasion and morphogenesis with synthetic matrixin inhibitors. Targeting angiogenesis with MMP inhibitors. Adv. Exp. Med. Biol. 2000, 476, 181-94. Graf von Roedern, E.; Grams, F.; Brandstetter, H.; Moroder, L. Design and synthesis of malonic acid-based inhibitors of human neutrophil collagenase (MMP8). J. Med. Chem. 1998, 41, 339-345.
14. Kip1 in vascular muscle cell migration. Circulation 2001, 103, 2967-2972.
15. Kip1 in vascular muscle cell migration. Circulation 2001, 103, 2967-2972.
16. Marx, S. O.; Marks, A. R. The development of Rapamycin and its application to stent restenosis. Circulation 2001, 104, 852-855.
17. 3 receptor blockade. Atheroscleosis 2002, 163, 269-277.
18. 3 receptor blockade. Atheroscleosis 2002, 163, 269-277.
19. Li, C.; Cantor, W. J.; Nili, N.; Robinson, R.; Fenkell, L.; Tran, Y. L.; Whittingham, H. A.; Tsui, W.; Cheema, A. N.; Sparkes, J. D.; Pritzker, K.; Levy, D. E.; Strauss, B. H. Arterial repair after stenting and the effects of GM6001, a matrix metalloproteinase inhibitor. J. Am. Col. Card. 2002, 39, 1852-1858.
20. Yamada, A.; Uegaki, A.; Nakamura, T.; Ogawa, K. ONO-4817, an orally active matrix metalloproteinase inhibitor, prevents lipopolysaccharide-induced proteoglycan release from the joint cartilage in guinea pigs. Inflamm. Res. 2000, 49, 144-146. Mori, T.; Yamasaki, S.; Masui, F.; Matsuda, M.; Sasabe, H.; Zhou, Y. F. Suppression of the development of experimentally induced uterine adenomyosis by a novel matrix metalloproteinase inhibitor, ONO-4817, in mice. Exp. Biol. Med. 2001, 226, 429-433. Muraishi, Y.; Mitani, N.; Fuse, H.; Saiki, I. Effect of a matrix metalloproteinase inhibitor (ONO-4817) on lung metastasis of murine renal cell carcinoma. Anticancer Res. 2001, 21, 3845-52. Sawada, S.; Murakami, K.; Yamaura, T.; Mitani, N.; Tsukada, K.; Saiki, I. Therapeutic and analysis model ofintrahepatic metastasis reflects clinical behavior of hepatocellular carcinoma. Jpn. J. Cancer Res. 2002, 93, 190-197.
21. Yamada, A.; Uegaki, A.; Nakamura, T.; Ogawa, K. ONO-4817, an orally active matrix metalloproteinase inhibitor, prevents lipopolysaccharide-induced proteoglycan release from the joint cartilage in guinea pigs. Inflamm. Res. 2000, 49, 144-146. Mori, T.; Yamasaki, S.; Masui, F.; Matsuda, M.; Sasabe, H.; Zhou, Y. F. Suppression of the development of experimentally induced uterine adenomyosis by a novel matrix metalloproteinase inhibitor, ONO-4817, in mice. Exp. Biol. Med. 2001, 226, 429-433. Muraishi, Y.; Mitani, N.; Fuse, H.; Saiki, I. Effect of a matrix metalloproteinase inhibitor (ONO-4817) on lung metastasis of murine renal cell carcinoma. Anticancer Res. 2001, 21, 3845-52. Sawada, S.; Murakami, K.; Yamaura, T.; Mitani, N.; Tsukada, K.; Saiki, I. Therapeutic and analysis model ofintrahepatic metastasis reflects clinical behavior of hepatocellular carcinoma. Jpn. J. Cancer Res. 2002, 93, 190-197.
22. Yamada, A.; Uegaki, A.; Nakamura, T.; Ogawa, K. ONO-4817, an orally active matrix metalloproteinase inhibitor, prevents lipopolysaccharide-induced proteoglycan release from the joint cartilage in guinea pigs. Inflamm. Res. 2000, 49, 144-146. Mori, T.; Yamasaki, S.; Masui, F.; Matsuda, M.; Sasabe, H.; Zhou, Y. F. Suppression of the development of experimentally induced uterine adenomyosis by a novel matrix metalloproteinase inhibitor, ONO-4817, in mice. Exp. Biol. Med. 2001, 226, 429-433. Muraishi, Y.; Mitani, N.; Fuse, H.; Saiki, I. Effect of a matrix metalloproteinase inhibitor (ONO-4817) on lung metastasis of murine renal cell carcinoma. Anticancer Res. 2001, 21, 3845-52. Sawada, S.; Murakami, K.; Yamaura, T.; Mitani, N.; Tsukada, K.; Saiki, I. Therapeutic and analysis model ofintrahepatic metastasis reflects clinical behavior of hepatocellular carcinoma. Jpn. J. Cancer Res. 2002, 93, 190-197.
23. Yamada, A.; Uegaki, A.; Nakamura, T.; Ogawa, K. ONO-4817, an orally active matrix metalloproteinase inhibitor, prevents lipopolysaccharide-induced proteoglycan release from the joint cartilage in guinea pigs. Inflamm. Res. 2000, 49, 144-146. Mori, T.; Yamasaki, S.; Masui, F.; Matsuda, M.; Sasabe, H.; Zhou, Y. F. Suppression of the development of experimentally induced uterine adenomyosis by a novel matrix metalloproteinase inhibitor, ONO-4817, in mice. Exp. Biol. Med. 2001, 226, 429-433. Muraishi, Y.; Mitani, N.; Fuse, H.; Saiki, I. Effect of a matrix metalloproteinase inhibitor (ONO-4817) on lung metastasis of murine renal cell carcinoma. Anticancer Res. 2001, 21, 3845-52. Sawada, S.; Murakami, K.; Yamaura, T.; Mitani, N.; Tsukada, K.; Saiki, I. Therapeutic and analysis model ofintrahepatic metastasis reflects clinical behavior of hepatocellular carcinoma. Jpn. J. Cancer Res. 2002, 93, 190-197.
24. Noguchi, T.; Yasuda, S.; Itoh, T.; Arai, T.; Kanda, K.; Tsutsui, N.; Nakayama, Y.; Nonogi, H.; Matsuda, T. New multifunctional percutaneous transluminal coronary angioplasty catheter device capable of balloon infusion, local drug delivery and coronary perfusion. J. Cardiol. 2000, 35, 41-45.
25. Yasuda, S.; Noguchi, T.; Gohda, M.; Arai, T.; Tsutsui, N.; Nakayama, Y.; Matsuda, T.; Nonogi, H. Local delivery of low-dose docetaxel, a novel microtubule polymerizing agent, reduces neointimal hyperplasia in a balloon-injured rabbit iliac artery model. Cardiovasc. Res. 2002, 53, 481-486.
26. Yasuda, S.; Kanna, M.; Sakuragi, S.; Kojima, S.; Nakayama, Y.; Miyazaki, S.; Matsuda, T.; Kangawa, K.; Nonogi, H. Local delivery of single low-dose of C-type natriuretic peptide, an endogenous vascular modulator, inhibits neointimal hyperplasia in a balloon-injured rabbit iliac artery model. J. Cardiovasc. Pharmacol. 2002, 39, 784-788.
27. Gottsauner-Wolf, M.; Jang, Y.; Penn, M. S.; Kaplan, A.; Ellis, S. G.; Chisolm G. M.; Topol, E. J.; Lincoff, A. M. Quantitative evaluation of local drug delivery using the infusa sleeve catheter. Cathet. Cardiovasc. Diagn. 1997, 42, 102-108. Suzuki, T.; Kopia, G.; Hayashi, S.; Baily, L. R.; Llanos, G.; Wilensky, R.; Klugherz, B. D.; Papandreou, G.; Nayaran, P.; Leon, M. B.; Yeung, A. C.; Tio, F.; Tsao, P. S.; Falotico, R.; Carter A. J. Stent-based delivery of sirolimus reduces neointimal formation in a porcine coronary model. Circulation 2001, 104, 1188-1193.
28. Gottsauner-Wolf, M.; Jang, Y.; Penn, M. S.; Kaplan, A.; Ellis, S. G.; Chisolm G. M.; Topol, E. J.; Lincoff, A. M. Quantitative evaluation of local drug delivery using the infusa sleeve catheter. Cathet. Cardiovasc. Diagn. 1997, 42, 102-108. Suzuki, T.; Kopia, G.; Hayashi, S.; Baily, L. R.; Llanos, G.; Wilensky, R.; Klugherz, B. D.; Papandreou, G.; Nayaran, P.; Leon, M. B.; Yeung, A. C.; Tio, F.; Tsao, P. S.; Falotico, R.; Carter A. J. Stent-based delivery of sirolimus reduces neointimal formation in a porcine coronary model. Circulation 2001, 104, 1188-1193.
29. 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. Pouticello, G. S.; Freedman, M. B.; Habecker, C. N.; Lyle, P. A.; Schwam, H.; Varga, S. L.; Christy, M. E.; Randall, W. C.; Baldwin, J. J. Thienothiopyran-2-sulfonamides: A novel class of water-soluble carbonic anhydrase inhibitors. J. Med. Chem. 1987, 30, 591-597.
30. 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. Pouticello, G. S.; Freedman, M. B.; Habecker, C. N.; Lyle, P. A.; Schwam, H.; Varga, S. L.; Christy, M. E.; Randall, W. C.; Baldwin, J. J. Thienothiopyran-2-sulfonamides: A novel class of water-soluble carbonic anhydrase inhibitors. J. Med. Chem. 1987, 30, 591-597.
31. Knight, C. G.; Willenbrock, F.; Murphy, G. A novel coumarin-labeled peptide for sensitive continuous assay of the matrix metaloproteinases. FEBS Lett. 1992, 296, 263-266.