Matrix metalloproteinase inhibitors based on the 3-mercaptopyrrolidine core

Journal of Medicinal Chemistry

Volumn 56, Issue 11, 2013, Pages 4357-4373

  Jin, Yonghao ^a   Roycik, Mark D ^a   Bosco, Dale B ^a   Cao, Qiang ^a   Constantino, Manuel H ^a   Schwartz, Martin A ^a   Sang, Qing Xiang Amy ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGENASE 3; CYCLOPENTANE DERIVATIVE; GELATINASE A; INTERSTITIAL COLLAGENASE; MATRILYSIN; MATRIX METALLOPROTEINASE 14; MATRIX METALLOPROTEINASE INHIBITOR; PYRROLIDINE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG OXIDATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME KINETICS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYDROGEN BOND; MITSUNOBU REACTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

CELLS, CULTURED; CYCLOPENTANES; DRUG STABILITY; HUMANS; KINETICS; MATRIX METALLOPROTEINASE INHIBITORS; MATRIX METALLOPROTEINASES; MESENCHYMAL STROMAL CELLS; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; SULFONAMIDES;

EID: 84879063553     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400529f     Document Type: Article

References (66)

1. Decock, J.; Thirkettle, S.; Wagstaff, L.; Edwards, D. R. Matrix metalloproteinases: protective roles in cancer J. Cell. Mol. Med. 2011, 15, 1254-1265
2. Iyer, R. P.; Patterson, N. L.; Fields, G. B.; Lindsey, M. L. The history of matrix metalloproteinases: milestones, myths, and misperceptions Am. J. Physiol.: Heart Circ. Physiol. 2012, 303, H919-930
3. Martins, V. L.; Caley, M.; O'Toole, E. A. Matrix metalloproteinases and epidermal wound repair Cell Tissue Res. 2013, 351, 255-268
4. Candelario-Jalil, E.; Yang, Y.; Rosenberg, G. A. Diverse roles of matrix metalloproteinases and tissue inhibitors of metalloproteinases in neuroinflammation and cerebral ischemia Neuroscience 2009, 158, 983-994
5. Rosell, A.; Lo, E. H. Multiphasic roles for matrix metalloproteinases after stroke Curr. Opin. Pharmacol. 2008, 8, 82-89
6. Lehrke, M.; Greif, M.; Broedl, U. C.; Lebherz, C.; Laubender, R. P.; Becker, A.; von Ziegler, F.; Tittus, J.; Reiser, M.; Becker, C.; Goke, B.; Steinbeck, G.; Leber, A. W.; Parhofer, K. G. MMP-1 serum levels predict coronary atherosclerosis in humans Cardiovasc. Diabetol. 2009, 8, 50
7. Tuomainen, A. M.; Nyyssonen, K.; Laukkanen, J. A.; Tervahartiala, T.; Tuomainen, T. P.; Salonen, J. T.; Sorsa, T.; Pussinen, P. J. Serum matrix metalloproteinase-8 concentrations are associated with cardiovascular outcome in men Arterioscler., Thromb., Vasc. Biol. 2007, 27, 2722-2728 (Pubitemid 350158928)
8. Johnson, J. L.; George, S. J.; Newby, A. C.; Jackson, C. L. Divergent effects of matrix metalloproteinases 3, 7, 9, and 12 on atherosclerotic plaque stability in mouse brachiocephalic arteries Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15575-15580 (Pubitemid 41528098)
9. Baker, A. H.; Edwards, D. R.; Murphy, G. Metalloproteinase inhibitors: biological actions and therapeutic opportunities J. Cell Sci. 2002, 115, 3719-3727 (Pubitemid 35203598)
10. Ahonen, M.; Poukkula, M.; Baker, A. H.; Kashiwagi, M.; Nagase, H.; Eriksson, J. E.; Kahari, V. M. Tissue inhibitor of metalloproteinases-3 induces apoptosis in melanoma cells by stabilization of death receptors Oncogene 2003, 22, 2121-2134 (Pubitemid 36539562)
11. Bond, M.; Murphy, G.; Bennett, M. R.; Newby, A. C.; Baker, A. H. Tissue inhibitor of metalloproteinase-3 induces a Fas-associated death domain-dependent type II apoptotic pathway J. Biol. Chem. 2002, 277, 13787-13795 (Pubitemid 34967982)
12. Guedez, L.; Courtemanch, L.; Stetler-Stevenson, M. Tissue inhibitor of metalloproteinase (TIMP)-1 induces differentiation and an antiapoptotic phenotype in germinal center B cells Blood 1998, 92, 1342-1349 (Pubitemid 28369048)
13. Valente, P.; Fassina, G.; Melchiori, A.; Masiello, L.; Cilli, M.; Vacca, A.; Onisto, M.; Santi, L.; Stetler-Stevenson, W. G.; Albini, A. TIMP-2 over-expression reduces invasion and angiogenesis and protects B16F10 melanoma cells from apoptosis Int. J. Cancer 1998, 75, 246-253 (Pubitemid 28100066)
14. Visse, R.; Nagase, H. Matrix metalloproteinases and tissue inhibitors of metalloproteinases: structure, function, and biochemistry Circ. Res. 2003, 92, 827-839 (Pubitemid 36542523)
15. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. Design and therapeutic application of matrix metalloproteinase inhibitors Chem. Rev. 1999, 99, 2735-2776
16. Bode, W.; Fernandez-Catalan, C.; Tschesche, H.; Grams, F.; Nagase, H.; Maskos, K. Structural properties of matrix metalloproteinases Cell. Mol. Life Sci. 1999, 55, 639-652 (Pubitemid 29221596)
17. Park, H. I.; Jin, Y.; Hurst, D. R.; Monroe, C. A.; Lee, S.; Schwartz, M. A.; Sang, Q. X. The intermediate S1′ pocket of the endometase/matrilysin-2 active site revealed by enzyme inhibition kinetic studies, protein sequence analyses, and homology modeling J. Biol. Chem. 2003, 278, 51646-51653 (Pubitemid 38020410)
18. Babine, R. E.; Bender, S. L. Molecular recognition of protein-ligand complexes: applications to drug design Chem. Rev. 1997, 97, 1359-1472 (Pubitemid 127659602)
19. Sang, Q. X.; Jin, Y.; Newcomer, R. G.; Monroe, S. C.; Fang, X.; Hurst, D. R.; Lee, S.; Cao, Q.; Schwartz, M. A. Matrix metalloproteinase inhibitors as prospective agents for the prevention and treatment of cardiovascular and neoplastic diseases Curr. Top. Med. Chem. 2006, 6, 289-316
20. Kontogiorgis, C. A.; Papaioannou, P.; Hadjipavlou-Litina, D. J. Matrix metalloproteinase inhibitors: a review on pharmacophore mapping and (Q)SARs results Curr. Med. Chem. 2005, 12, 339-355 (Pubitemid 40305624)
21. Peterson, J. T. Matrix metalloproteinase inhibitor development and the remodeling of drug discovery Heart Failure Rev. 2004, 9, 63-79 (Pubitemid 38202142)
22. White, C. M. Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors Pharmacotherapy 1998, 18, 588-599 (Pubitemid 28228341)
23. Duchin, K. L.; McKinstry, D. N.; Cohen, A. I.; Migdalof, B. H. Pharmacokinetics of captopril in healthy subjects and in patients with cardiovascular diseases Clin. Pharmacokinet. 1988, 14, 241-259
24. Sang, Q. A.; Schwartz, M. A.; Li, H.; Chung, L. W.; Zhau, H. E. Targeting matrix metalloproteinases in human prostate cancer Ann. N.Y. Acad. Sci. 1999, 878, 538-540 (Pubitemid 29353606)
25. Sang, Q. X.; Jia, M. C.; Schwartz, M. A.; Jaye, M. C.; Kleinman, H. K.; Ghaffari, M. A.; Luo, Y. L. New thiol and sulfodiimine metalloproteinase inhibitors and their effect on human microvascular endothelial cell growth Biochem. Biophys. Res. Commun. 2000, 274, 780-786 (Pubitemid 30663697)
26. Schwartz, M. A.; Van Wart, H. Mercaptosulfide Metalloproteinase Inhibitors. 5,455,262, Oct 3, 1995.
27. 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.; Hudlicky, T.; Mandel, M. Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold J. Med. Chem. 1999, 42, 5426-5436 (Pubitemid 30036776)
28. Cheng, X. C.; Wang, Q.; Fang, H.; Xu, W. F. Advances in matrix metalloproteinase inhibitors based on pyrrolidine scaffold Curr. Med. Chem. 2008, 15, 374-385 (Pubitemid 351266943)
29. Natchus, M. G.; Bookland, R. G.; De, B.; Almstead, N. G.; Pikul, S.; Janusz, M. J.; Heitmeyer, S. A.; Hookfin, E. B.; Hsieh, L. C.; Dowty, M. E.; Dietsch, C. R.; Patel, V. S.; Garver, S. M.; Gu, F.; Pokross, M. E.; Mieling, G. E.; Baker, T. R.; Foltz, D. J.; Peng, S. X.; Bornes, D. M.; Strojnowski, M. J.; Taiwo, Y. O. Development of new hydroxamate matrix metalloproteinase inhibitors derived from functionalized 4-aminoprolines J. Med. Chem. 2000, 43, 4948-4963 (Pubitemid 32039016)
30. Li, X.; Li, J. Recent advances in the development of MMPIs and APNIs based on the pyrrolidine platforms Mini-Rev. Med. Chem. 2010, 10, 794-805
31. Hurst, D. R.; Schwartz, M. A.; Ghaffari, M. A.; Jin, Y.; Tschesche, H.; Fields, G. B.; Sang, Q. X. Catalytic- and ecto-domains of membrane type 1-matrix metalloproteinase have similar inhibition profiles but distinct endopeptidase activities Biochem. J. 2004, 377, 775-779 (Pubitemid 38221851)
32. Hurst, D. R.; Schwartz, M. A.; Jin, Y.; Ghaffari, M. A.; Kozarekar, P.; Cao, J.; Sang, Q. X. Inhibition of enzyme activity of and cell-mediated substrate cleavage by membrane type 1 matrix metalloproteinase by newly developed mercaptosulphide inhibitors Biochem. J. 2005, 392, 527-536 (Pubitemid 43022732)
33. Jin, Y. H.; Ghaffari, M. A.; Schwartz, M. A. A practical synthesis of differentially-protected cis -1,2-cyclopentanedithiols and cis -3,4-pyrrolidinedithiol Tetrahedron Lett. 2002, 43, 7319-7321 (Pubitemid 35287104)
34. Mitsunobu, O.; Yamada, M. Preparation of esters of carboxylic and phosphoric acid via quaternary phosphonium salts Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382
35. DeCrescenzo, G.; Abbas, Z. S.; Freskos, J. N.; Getman, D. P.; Heintz, R. M.; Mischke, B. V.; McDonald, J. J. Thiol Sulfonamide Metalloprotease Inhibitors. 6,747,027, Jun 8, 2004.
36. Rao, B. G.; Bandarage, U. K.; Wang, T.; Come, J. H.; Perola, E.; Wei, Y.; Tian, S. K.; Saunders, J. O. Novel thiol-based TACE inhibitors: rational design, synthesis, and SAR of thiol-containing aryl sulfonamides Bioorg. Med. Chem. Lett. 2007, 17, 2250-2253 (Pubitemid 46484304)
37. Cheng, X. C.; Wang, Q.; Fang, H.; Xu, W. F. Role of sulfonamide group in matrix metalloproteinase inhibitors Curr. Med. Chem. 2008, 15, 368-373 (Pubitemid 351266942)
38. Ami, E.; Ohrui, H. Lipase-catalyzed kinetic resolution of (±)-trans- and cis-2-azidocycloalkanols Biosci., Biotechnol., Biochem. 1999, 63, 2150-2156 (Pubitemid 129549038)
39. Hugenberg, V.; Breyholz, H. J.; Riemann, B.; Hermann, S.; Schober, O.; Schafers, M.; Gangadharmath, U.; Mocharla, V.; Kolb, H.; Walsh, J.; Zhang, W.; Kopka, K.; Wagner, S. A new class of highly potent matrix metalloproteinase inhibitors based on triazole-substituted hydroxamates: (radio)synthesis and in vitro and first in vivo evaluation J. Med. Chem. 2012, 55, 4714-4727
40. Kolodziej, S. A.; Hockerman, S. L.; DeCrescenzo, G. A.; McDonald, J. J.; Mischke, D. A.; Munie, G. E.; Fletcher, T. R.; Stehle, N.; Swearingen, C.; Becker, D. P. MMP-13 selective isonipecotamide alpha-sulfone hydroxamates Bioorg. Med. Chem. Lett. 2010, 20, 3561-3564
41. Tommasi, R. A.; Weiler, S.; McQuire, L. W.; Rogel, O.; Chambers, M.; Clark, K.; Doughty, J.; Fang, J.; Ganu, V.; Grob, J.; Goldberg, R.; Goldstein, R.; Lavoie, S.; Kulathila, R.; Macchia, W.; Melton, R.; Springer, C.; Walker, M.; Zhang, J.; Zhu, L.; Shultz, M. Potent and selective 2-naphthylsulfonamide substituted hydroxamic acid inhibitors of matrix metalloproteinase-13 Bioorg. Med. Chem. Lett. 2011, 21, 6440-6445
42. Lu, C.; Li, X. Y.; Hu, Y.; Rowe, R. G.; Weiss, S. J. MT1-MMP controls human mesenchymal stem cell trafficking and differentiation Blood 2010, 115, 221-229
43. Mannello, F. Multipotent mesenchymal stromal cell recruitment, migration, and differentiation: What have matrix metalloproteinases got to do with it? Stem Cells 2006, 24, 1904-1907 (Pubitemid 44474165)
44. Ries, C.; Egea, V.; Karow, M.; Kolb, H.; Jochum, M.; Neth, P. MMP-2, MT1-MMP, and TIMP-2 are essential for the invasive capacity of human mesenchymal stem cells: differential regulation by inflammatory cytokines Blood 2007, 109, 4055-4063 (Pubitemid 46641761)
45. Janusz, M. J.; Hookfin, E. B.; Brown, K. K.; Hsieh, L. C.; Heitmeyer, S. A.; Taiwo, Y. O.; Natchus, M. G.; Pikul, S.; Almstead, N. G.; De, B.; Peng, S. X.; Baker, T. R.; Patel, V. Comparison of the pharmacology of hydroxamate- and carboxylate-based matrix metalloproteinase inhibitors (MMPIs) for the treatment of osteoarthritis Inflammation Res. 2006, 55, 60-65
46. Abdul-Hay, S. O.; Lane, A. L.; Caulfield, T. R.; Claussin, C.; Bertrand, J.; Masson, A.; Choudhry, S.; Fauq, A. H.; Maharvi, G. M.; Leissring, M. A. Optimization of peptide hydroxamate inhibitors of insulin-degrading enzyme reveals marked substrate-selectivity J. Med. Chem. 2013, 56, 2246-2255
47. Marek, L.; Hamacher, A.; Hansen, F. K.; Kuna, K.; Gohlke, H.; Kassack, M. U.; Kurz, T. Histone deacetylase (HDAC) inhibitors with a novel connecting unit linker region reveal a selectivity profile for HDAC4 and HDAC5 with improved activity against chemoresistant cancer cells J. Med. Chem. 2013, 56, 427-436
48. Choi, E.; Lee, C.; Cho, M.; Seo, J. J.; Yang, J. S.; Oh, S. J.; Lee, K.; Park, S. K.; Kim, H. M.; Kwon, H. J.; Han, G. Property-based optimization of hydroxamate-based gamma-lactam HDAC inhibitors to improve their metabolic stability and pharmacokinetic profiles J. Med. Chem. 2012, 55, 10766-10770
49. Tandon, A.; Sinha, S. Structural insights into the binding of MMP9 inhibitors Bioinformation 2011, 5, 310-314
50. Heim-Riether, A.; Taylor, S. J.; Liang, S.; Gao, D. A.; Xiong, Z.; Michael August, E.; Collins, B. K.; Farmer, B. T., 2nd; Haverty, K.; Hill-Drzewi, M.; Junker, H. D.; Mariana Margarit, S.; Moss, N.; Neumann, T.; Proudfoot, J. R.; Keenan, L. S.; Sekul, R.; Zhang, Q.; Li, J.; Farrow, N. A. Improving potency and selectivity of a new class of non-Zn-chelating MMP-13 inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 5321-5324
51. Tu, G.; Xu, W.; Huang, H.; Li, S. Progress in the development of matrix metalloproteinase inhibitors Curr. Med. Chem. 2008, 15, 1388-1395 (Pubitemid 351997789)
52. Gupta, S. P.; Patil, V. M. Specificity of binding with matrix metalloproteinases Experientia, Suppl. 2012, 103, 35-56
53. 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.; Maggiora, L. L.; Stuchly, C. W.; Laborde, A. L.; Kubicek, M. F.; Poorman, R. A.; Beck, J. M.; Miller, H. R.; Petzold, G. L.; Scott, P. S.; Truesdell, S. E.; Wallace, T. L.; Wilks, J. W.; Fisher, C.; Goodman, L. V.; Kaytes, P. S. Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors J. Med. Chem. 1999, 42, 1525-1536 (Pubitemid 29226724)
54. Terp, G. E.; Cruciani, G.; Christensen, I. T.; Jorgensen, F. S. Structural differences of matrix metalloproteinases with potential implications for inhibitor selectivity examined by the GRID/CPCA approach J. Med. Chem. 2002, 45, 2675-2684 (Pubitemid 34627640)
55. Bruttomesso, A. C.; Doller, D.; Gros, E. G. Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16- cis -γ-carbolactones Bioorg. Med. Chem. 1999, 7, 943-947 (Pubitemid 29238089)
56. Puerta, D. T.; Griffin, M. O.; Lewis, J. A.; Romero-Perez, D.; Garcia, R.; Villarreal, F. J.; Cohen, S. M. Heterocyclic zinc-binding groups for use in next-generation matrix metalloproteinase inhibitors: potency, toxicity, and reactivity J. Biol. Inorg. Chem. 2006, 11, 131-138 (Pubitemid 43228206)
57. Sun, J.; Song, F.; Zhang, W.; Sexton, B. E.; Windsor, L. J. Effects of alendronate on human osteoblast-like MG63 cells and matrix metalloproteinases Arch. Oral Biol. 2012, 57, 728-736
58. Flipo, M.; Charton, J.; Hocine, A.; Dassonneville, S.; Deprez, B.; Deprez-Poulain, R. Hydroxamates: relationships between structure and plasma stability J. Med. Chem. 2009, 52, 6790-6802
59. Oger, F.; Lecorgne, A.; Sala, E.; Nardese, V.; Demay, F.; Chevance, S.; Desravines, D. C.; Aleksandrova, N.; Le Guevel, R.; Lorenzi, S.; Beccari, A. R.; Barath, P.; Hart, D. J.; Bondon, A.; Carettoni, D.; Simonneaux, G.; Salbert, G. Biological and biophysical properties of the histone deacetylase inhibitor suberoylanilide hydroxamic acid are affected by the presence of short alkyl groups on the phenyl ring J. Med. Chem. 2010, 53, 1937-1950
60. Salmi-Smail, C.; Fabre, A.; Dequiedt, F.; Restouin, A.; Castellano, R.; Garbit, S.; Roche, P.; Morelli, X.; Brunel, J. M.; Collette, Y. Modified cap group suberoylanilide hydroxamic acid histone deacetylase inhibitor derivatives reveal improved selective antileukemic activity J. Med. Chem. 2010, 53, 3038-3047
61. 18F-SAHA) J. Med. Chem. 2011, 54, 5576-5582
62. Guerrant, W.; Patil, V.; Canzoneri, J. C.; Oyelere, A. K. Dual targeting of histone deacetylase and topoisomerase II with novel bifunctional inhibitors J. Med. Chem. 2012, 55, 1465-1477
63. Govindaraju, T.; Kumar, V. A.; Ganesh, K. N. (1 S,2 R /1 R,2 S)- cis -Cyclopentyl PNAs (cpPNAs) as constrained PNA analogues: synthesis and evaluation of aeg-cpPNA chimera and stereopreferences in hybridization with DNA/RNA J. Org. Chem. 2004, 69, 5725-5734 (Pubitemid 39079629)
64. Kamal, A.; Sandbhor, M.; Ali Shaik, A. Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol Bioorg. Med. Chem. Lett. 2004, 14, 4581-4583 (Pubitemid 39043989)
65. Park, H. I.; Turk, B. E.; Gerkema, F. E.; Cantley, L. C.; Sang, Q. X. Peptide substrate specificities and protein cleavage sites of human endometase/matrilysin-2/matrix metalloproteinase-26 J. Biol. Chem. 2002, 277, 35168-35175
66. Knight, C. G.; Willenbrock, F.; Murphy, G. A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases FEBS Lett. 1992, 296, 263-266