A selective reversible azapeptide inhibitor of human neutrophil proteinase 3 derived from a high affinity FRET substrate

Biochemical Pharmacology

Volumn 83, Issue 6, 2012, Pages 788-796

  Epinette, Christophe ^a   Croix, Cécile ^a   Jaquillard, Lucie ^b   Marchand Adam, Sylvain ^a,c   Kellenberger, Christine ^d   Lalmanach, Gilles ^a   Cadene, Martine ^b   Viaud Massuard, Marie Claude ^a   Gauthier, Francis ^a   Korkmaz, Brice ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^c UNIVERSITY HOSPITAL OF TOURS   (France)

^d Centre National de la Recherche Scientifique   (France)

Author keywords

Azapeptide; Drug development; Inhibitor; Lung diseases; Proteinase 3 (myeloblastin)

Indexed keywords

AZAPRO 3; CATHEPSIN G; IONOPHORE; LEUKOCYTE ELASTASE; MYELOBLASTIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; CHEMICAL BOND; CONCENTRATION (PARAMETERS); ENZYME ACTIVE SITE; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMAN; HUMAN CELL; NEUTROPHIL; OXIDATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DEGRADATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SOLUBILITY;

AMINO ACID SEQUENCE; CATHEPSIN G; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DESIGN; FLOW CYTOMETRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMANS; KINETICS; LEUKOCYTE ELASTASE; MOLECULAR SEQUENCE DATA; MYELOBLASTIN; NEUTROPHILS; OLIGOPEPTIDES; PEPTIDES; PNEUMONIA; PROTEIN BINDING; PROTEINASE INHIBITORY PROTEINS, SECRETORY; PROTEOLYSIS; SPUTUM; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 84857038221     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.12.023     Document Type: Article

References (31)

1. B. Korkmaz, M. Horwitz, D.E. Jenne, and A. Gauthier Neutrophil elastase, proteinase 3 and cathepsin G as therapeutic targets in human diseases Pharmacol Rev 62 2010
2. B. Korkmaz, T. Moreau, and F. Gauthier Neutrophil elastase, proteinase 3 and cathepsin G: physicochemical properties, activity and physiopathological functions Biochimie 90 2008 227 242 (Pubitemid 351187763)
3. C.G. Kallenberg Pathogenesis of PR3-ANCA associated vasculitis J Autoimmun 30 2008 29 36
4. C.G. Kallenberg, P. Heeringa, and C.A. Stegeman Mechanisms of disease: pathogenesis and treatment of ANCA-associated vasculitides Nat Clin Pract Rheumatol 2 2006 661 670 (Pubitemid 44830855)
5. L. Halbwachs-Mecarelli, G. Bessou, P. Lesavre, S. Lopez, and V. Witko-Sarsat Bimodal distribution of proteinase 3 (PR3) surface expression reflects a constitutive heterogeneity in the polymorphonuclear neutrophil pool FEBS Lett 374 1995 29 33
6. C.A. Owen, and E.J. Campbell The cell biology of leukocyte-mediated proteolysis J Leukoc Biol 65 1999 137 150 (Pubitemid 29077006)
7. B. Korkmaz, S. Attucci, M.L. Jourdan, L. Juliano, and F. Gauthier Inhibition of neutrophil elastase by alpha1-protease inhibitor at the surface of human polymorphonuclear neutrophils J Immunol 175 2005 3329 3338 (Pubitemid 41170554)
8. N. Hu, J. Westra, and C.G. Kallenberg Membrane-bound proteinase 3 and its receptors: relevance for the pathogenesis of Wegener's Granulomatosis Autoimmun Rev 8 2009 510 514
9. V. Witko-Sarsat, N. Reuter, and L. Mouthon Interaction of proteinase 3 with its associated partners: implications in the pathogenesis of Wegener's granulomatosis Curr Opin Rheumatol 22 2010 1 7
10. U. Jerke, S. Rolle, G. Dittmar, B. Bayat, S. Santoso, and A. Sporbert Complement receptor Mac-1 is an adaptor for NB1 (CD177)-mediated PR3-ANCA neutrophil activation J Biol Chem 286 2011 7070 7081
11. B. Korkmaz, E. Hajjar, T. Kalupov, N. Reuter, M. Brillard-Bourdet, and T. Moreau Influence of charge distribution at the active site surface on the substrate specificity of human neutrophil protease 3 and elastase. A kinetic and molecular modeling analysis J Biol Chem 282 2007 1989 1997 (Pubitemid 47076700)
12. B. Korkmaz, S. Attucci, M.A. Juliano, T. Kalupov, M.L. Jourdan, and L. Juliano Measuring elastase, proteinase 3 and cathepsin G activities at the surface of human neutrophils with fluorescence resonance energy transfer substrates Nat Protoc 3 2008 991 1000 (Pubitemid 351818687)
13. T. Moreau, K. Baranger, S. Dade, S. Dallet-Choisy, N. Guyot, and M.L. Zani Multifaceted roles of human elafin and secretory leukocyte proteinase inhibitor (SLPI), two serine protease inhibitors of the chelonianin family Biochimie 90 2008 284 295 (Pubitemid 351172573)
14. B. Walker, and J.F. Lynas Strategies for the inhibition of serine proteases Cell Mol Life Sci 58 2001 596 624 (Pubitemid 32382260)
15. P.D. Edwards, and P.R. Bernstein Synthetic inhibitors of elastase Med Res Rev 14 1994 127 194 (Pubitemid 24087947)
16. J. Zhong, and W.C. Groutas Recent developments in the design of mechanism-based and alternate substrate inhibitors of serine proteases Curr Top Med Chem 4 2004 1203 1216 (Pubitemid 39172332)
17. W.C. Groutas, D. Dou, and K.R. Alliston Neutrophil elastase inhibitors Expert Opin Ther Pat 21 2011 339 354
18. C. Adessi, and C. Soto Converting a peptide into a drug: strategies to improve stability and bioavailability Curr Med Chem 9 2002 963 978 (Pubitemid 34498572)
19. A. Zega Azapeptides as pharmacological agents Curr Med Chem 12 2005 589 597 (Pubitemid 40331053)
20. J.C. Powers, R. Boone, D.L. Carroll, B.F. Gupton, C.M. Kam, and N. Nishino Reaction of azapeptides with human leukocyte elastase and porcine pancreatic elastase. New inhibitors and active site titrants J Biol Chem 259 1984 4288 4294 (Pubitemid 14127789)
21. R. Zhang, J.P. Durkin, and W.T. Windsor Azapeptides as inhibitors of the hepatitis C virus NS3 serine protease Bioorg Med Chem Lett 12 2002 1005 1008 (Pubitemid 34242789)
22. G. Jegot, C. Derache, S. Castella, H. Lahouassa, E. Pitois, and M.L. Jourdan A substrate-based approach to convert SerpinB1 into a specific inhibitor of proteinase 3, the Wegener's granulomatosis autoantigen FASEB J 25 2011 3019 3031
23. A. Bhowmik, T.A. Seemungal, R.J. Sapsford, J.L. Devalia, and J.A. Wedzicha Comparison of spontaneous and induced sputum for investigation of airway inflammation in chronic obstructive pulmonary disease Thorax 53 1998 953 956 (Pubitemid 28494335)
24. M.W. Ziegenhagen, P. Zabel, G. Zissel, M. Schlaak, and J. Muller-Quernheim Serum level of interleukin 8 is elevated in idiopathic pulmonary fibrosis and indicates disease activity Am J Respir Crit Care Med 157 1998 762 768
25. S. Venkatraman, J. Kong, S. Nimkar, Q.M. Wang, J. Aube, and R.P. Hanzlik Design, synthesis, and evaluation of azapeptides as substrates and inhibitors for human rhinovirus 3C protease Bioorg Med Chem Lett 9 1999 577 580 (Pubitemid 29090656)
26. B. Korkmaz, J. Jaillet, M.L. Jourdan, A. Gauthier, F. Gauthier, and S. Attucci Catalytic activity and inhibition of wegener antigen proteinase 3 on the cell surface of human polymorphonuclear neutrophils J Biol Chem 284 2009 19896 19902
27. C.P. Rooney, C. Taggart, R. Coakley, N.G. McElvaney, and S.J. O'Neill Anti-proteinase 3 antibody activation of neutrophils can be inhibited by alpha1-antitrypsin Am J Respir Cell Mol Biol 24 2001 747 754 (Pubitemid 32550598)
28. M.D. Bailey, T. Halmos, N. Goudreau, E. Lescop, and M. Llinas-Brunet Novel azapeptide inhibitors of hepatitis C virus serine protease J Med Chem 47 2004 3788 3799 (Pubitemid 38900344)
29. B.F. Gupton, D.L. Carroll, P.M. Tuhy, C.M. Kam, and J.C. Powers Reaction of azapeptides with chymotrypsin-like enzymes. New inhibitors and active site titrants for chymotrypsin A alpha, subtilisin BPN′, subtilisin Carlsberg, and human leukocyte cathepsin G J Biol Chem 259 1984 4279 4287 (Pubitemid 14127788)
30. C.P. Dorn, M. Zimmerman, S.S. Yang, E.C. Yurewicz, B.M. Ashe, and R. Frankshun Proteinase inhibitors. I. Inhibitors of elastase J Med Chem 20 1977 1464 1468
31. M. Drag, and G.S. Salvesen Emerging principles in protease-based drug discovery Nat Rev Drug Discov 9 2010 690 701