Design and synthesis of potent, selective inhibitors of matriptase

ACS Medicinal Chemistry Letters

Volumn 3, Issue 7, 2012, Pages 530-534

  Colombo, Éloïc ^a   Désilets, Antoine ^a   Duchêne, Dominic ^a   Chagnon, Félix ^a   Najmanovich, Rafael ^a   Leduc, Richard ^a   Marsault, Eric ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

matriptase; slow tight binding inhibitor; type II transmembrane serine protease

Indexed keywords

BENZOTHIAZOLE; ENZYME INHIBITOR; MATRIPTASE; PEPTIDOMIMETIC AGENT; SERINE PROTEINASE;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 84863846098     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3000534     Document Type: Article

References (33)

1. Antalis, T. M.; Bugge, T. H.; Wu, Q. Membrane-anchored serine proteases in health and disease Prog. Mol. Transl. Sci. 2011, 99, 1-50
2. List, K.; Haudenschild, C. C.; Sbazo, R.; Chen, W.; Wahl, S. M.; Swaim, W.; Engelholm, L. H.; Behrendt, N.; Bugge, T. H. Matriptase/MT-SP1 is required for postnatal survival, epidermal barrier function, hair follicle development, and thymic homeostasis Oncogene 2002, 21, 3765-3779
3. Lee, S. L.; Dickson, R. B.; Lin, C. Y. Activation of hepatocyte growth factor and urokinase/plasminogen activator by matriptase, an epithelial membrane serine protease J. Biol. Chem. 2000, 275, 36720-36725
4. Netzel-Arnett, S.; Currie, B. M.; Sbzabo, R.; Lin, C. Y.; Chen, L. M.; Chai, K. X.; Antalis, T. M.; Bugge, T. H.; List, K. Evidence for a matriptase-prostasin proteolytic cascade regulating terminal epidermal differentiation J. Biol. Chem. 2006, 281, 32941-32945
5. Takeuchi, T.; Harris, J. L.; Huang, W.; Yan, K. W.; Coughlin, S. R.; Craik, C. S. Cellular localization of membrane-type serine protease1 and identification of protease-activated receptor-2 and single-chain urokinase-type plasminogen activator as substrates J. Biol. Chem. 2000, 275, 26333-263342
6. He, Y.; Wortmann, A.; Burke, L. J.; Reid, J. C; Adams, M. N.; Abdul-Jabbar, I.; Quigley, J. P.; Leduc, R.; Kirchhofer, D.; Hooper, J. D. Proteolysis-induced N-terminal ectodomain shedding of the integral membrane glycoprotein CUB domain-containing protein 1 (CDCP1) is accompagnied by tyrosine phosphorylation of its C-terminal domain and recruitment of Src and PKCdelta J. Biol. Chem. 2010, 285, 26162-26173
7. Ustach, C. V.; Huang, W.; Conley-LaComb, M. K.; Lin, C. Y.; Che, M.; Abrams, J.; Kim, H. R. A novel signalling axis of matriptase/PDGF-D/B-PDGFR in human prostate cancer Cancer Res. 2010, 70, 9631-9640
8. Oberst, M. D.; Chen, L. Y.; Kiyomiya, K.; Williams, C. A.; Lee, M. S.; Johnson, M. D.; Dickson, R. B.; Lin, C. Y. HAI-1 regulates activation and expression of matriptase, a membrane-bound serine protease Am. J. Physiol. Cell. Physiol. 2005, 289, 462-470
9. Basel-Vanagaite, L.; Attia, R.; Ishida-Yamamoto, A.; Rainshtein, L.; Ben Amitai, D.; Lurie, R.; Pasmanik-Chor, M.; Indelman, M.; Zvulunov, A.; Saban, S.; Magal, N.; Sprecher, E.; Shohat, M. Autosomal recessive ichthyosis with hypotrichosis caused by mutation in ST14, encoding type II transemembrane serine protease matriptase Am. J. Hum. Genet. 2007, 80, 467-477
10. Désilets, A.; Béliveau, F.; Vandal, G.; McDufflo, F. O.; Lavigne, P.; Leduc, R. Mutation G827R in matriptase causing autosomal recessive ichthyosis with hypotrichosis yields an inactive protease J. Biol. Chem. 2008, 283, 10535-10542
11. Milner, J. M.; Patel, A.; Davidson, R. K.; Swingler, T. E.; Désilets, A.; Young, D. A.; Kelso, E. B.; Donell, S. T.; Cawston, T. E.; Clark, I. M.; Ferrell, W. R.; Plevin, R.; Lockhart, J. C.; Leduc, R.; Rowan, A. D. Matriptase is a novel intiator of cartilage matrix degradation in osteoarthritis Arthritis Rheum. 2010, 61, 1955-1966
12. Netzel-Arnett, S.; Buzza, M. S.; Shea-Donohue, T.; Désilets, A.; Leduc, R.; Fasano, A.; Bugge, T. H.; Antalis, T. M. Matriptase protects against experimental colitis and promotes intestinal barrier recovery Inflamm. Bowel Dis. 2011, 10.1002/ibd.21930
13. List, K. Matriptase: A culprit in cancer? Future Oncol. 2009, 5, 97-104
14. List, K.; Szabo, R.; Molinolo, A.; Sriuranpong, V.; Redeye, V.; Murdock, T.; Burke, B.; Nielsen, B. S.; Gutkind, J. S.; Bugge, T. H. Deregulated matriptase causes ras-independent multistage carcinogenesis and promotes ras-mediated malignant transformation Genes Dev. 2005, 19, 1934-1950
15. Galkin, A. V.; Mullen, L.; Fox, W. D.; Brown, J.; Duncan, D.; Moreno, O.; Madison, E. L.; Agus, D. B. CVS-3983, a selective matriptase inhibitor, suppresses the growth of androgen independent prostate tumor xenografts Prostate 2004, 3, 228-235
16. Stoop, A. A.; Craik, C. S. Engineering of macromolecular scaffold to develop specific protease inhibitors Nat. Biotechnol. 2003, 21, 1063-1068
17. Désilets, A.; Longpré, J. M.; Beaulieu, M. E.; Leduc, R. Inhbition of Human matriptase by eglin c variants FEBS Lett. 2006, 580, 2227-2232
18. Li, P.; Jiang, S.; Lee, S. L.; Lin, C. Y.; Johnson, M. D.; Dickson, R. B.; Michejda, C. J.; Roller, P. Design and Synthesis of novel and potent inhibitors of the type II transmenbrane protease, matriptase, based upon the dunflower Trypsin inhbitor-1 J. Med. Chem. 2007, 50, 5976-5983
19. Long, Y. Q.; Lee, S. L.; Lin, C. Y.; Enyedy, I. J.; Wang, S.; Li, P.; Dickson, R. B.; Peter, P. R. Synthesis and Evaluation of the sunflower derived trypsin inhibitor as a potent inhibitor of the type II transmenbrane serine protease, matriptase Bioorg. Med. Chem. Lett. 2001, 11, 2515-2519
20. J. Enyedy, I.; Sheau-Ling, L.; Kuo, A. H.; Dickson, R. B.; Lin, C. Y.; Wang, S. Structure based approch for discovery of bis-benzamidines as novel inhibitors of matriptase J. Med. Chem. 2001, 44, 1349-1355
21. Jiang, S.; Li, P.; Lee, S. L.; Lin, C. Y.; Long, Y. Q.; Johnson, M. D.; Dickson, R. B.; Roller, P. P. Design and synthesis of redox stable analogues of sunflower trypsin inhibitors (SFTI-1) on solid support, potent inhibitors of matriptase Org. Lett. 2007, 9, 9-12
22. Steinmetzer, T.; Dönnecke, D.; Korsonewski, C.; Steinmetzer, P.; Schuzle, A.; Martin Saupe, S.; Scheweinitz, A. Modification of the N-terminal sulfonyl residue in 3-amidinophenylalanine-based on matriptase inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 67-73
23. Steinmetzer, T.; Schuzle, A.; Stürrzebecher, A.; Dönnecke, D.; Uhland, K.; Schuster, O.; Steinmetzer, P.; Müller, F.; Friedrich, R.; Than, M. E.; Bode, W.; Stürzebecher, J. Secondary Amides of sulfonated 3-amidinophenylalanine. New potent and selective inhibitors of matriptase J. Med. Chem. 2006, 49, 4116-4126
24. Tekeste Sisay, M.; Steinmetzer, T.; Stirnberg, M.; Hammami, M.; Bajorath, J.; Gütschow, M. Identification of the first low-molecular-weight of matriptase-2 J. Med. Chem. 2010, 53, 5523-5535
25. Costanzo, M. J.; Almond, H. R., Jr.; Hecker, L. R.; Schott, M. R.; Yabut, S. C.; Zhang, H. C.; Andrade-Gordon, P.; Corcoran, T. W.; Giardino, E. C.; Kauffman, J. A.; Lewis, J. M.; de Garavilla, L.; Haertlein, B. J.; Maryanoff, B. E. In-depth study of tripeptide based alpha-Ketoheterocycles as inhibitors of thrombin. Effective utilization of the S1′ subsite and its implications to structure-based drug design J. Med. Chem. 2005, 48, 1984-2008
26. Venkatraman, S.; Bogen, S. L.; Arasappan, A.; Bennett, F.; Chen, K.; Jao, E.; Liu, Y. T.; Lovey, R.; Hendrata, S.; Huang, Y.; Pan, W.; Parekh, T.; Pinto, P.; Popov, V.; Pike, R.; Ruan, S.; Santhanam, B.; Vibulban, B.; Wu, W.; Yang, W.; Kong, J.; Liang, X.; Wong, J.; Liu, R.; Butkiewciz, N.; Chase, R.; Hart, A.; Agrawal, S.; Ingravallo, P.; Pichardo, J.; Kong, R.; Baroudy, B.; Malcom, B.; Guo, Z.; Prongay, A.; Madison, V.; Broske, L.; Cui, X.; Cheng, K. C.; Hsieh, Y.; Brisson, J. M.; Prelusky, D.; Korfmacher, W.; White, R.; Bogdanowich-Knipp, S.; Pavlosky, A.; Bradley, P.; Saksena, A. K.; Ganguly, A.; Piwinski, J.; Girijavallabhan, V.; Njoroge, F. G. Discovery of (1R,5S)-N-[3-amino-1- (cyclobutylmethyl)-2,3-dioxopropyl]-3-[[[(1,1-dimethylethyl)amino]carbonyl] amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimetyl-3-azabicyclo[3.1.0]hexan-2(S) -carboxamide (SCH503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: a potential therapeutic agent for the treatment of hepatitis C infection J. Med. Chem. 2006, 49, 6074-6086
27. Kwong, A. D.; Kauffman, R. S.; Hurter, P.; Mueller, P. Discovery and development of telaprevir: an NS3-4A protease inhibitor for treating genotype 1 chronic hepatitis C virus Nat. Biotechnol. 2001, 29, 993-1003
28. Béliveau, F.; Désilets, A.; Leduc, R. Probing the substrate specifities of matriptase, matriptase-2, hepsin and DESC1 with internally quenched fluorescent peptides FEBS J. 2009, 276, 2213-2226
29. Frigerio, M.; Santagostimo, M.; Sputore, S.; Palmisano, G. Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX) in DMSO: A New Insight into an Old Hypervalent Iodine Reagent J. Org. Chem. 1995, 60, 7272-7276
30. Copeland, R. A Practical Introduction to Structure, Mechanism and Data Analysis; Wiley-VCH: New-York, 2000; Chapter 10, pp 1-397.
31. Bieth, J. G. Theoretical and pratical aspects of proteinase inhibition kinetics Methods Enzymol. 1995, 248, 59-84
32. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank Nucleic Acids Res. 2000, 28, 235-242
33. The PyMOL Molecular Graphics System, Version 1.2r1pre; Schrödinger, LLC, 26.