Synthesis, stability, biochemical and pharmacokinetic properties of a new potent and selective 4-oxo-β-lactam inhibitor of human leukocyte elastase

References

• Bode W, Meyer E, Powers JC. Human-leukocyte and porcine pancreatic elastase - X-ray crystal-structures, mechanism, substrate-specificity, and mechanism-based inhibitors. Biochemistry 1989;28:1951–1963.
   PubMed Web of Science ®Google Scholar
• Barnes PJ. Chronic obstructive pulmonary disease: A growing but neglected global epidemic. PLos Med 2007;4:779–780.
   Google Scholar
• Chua F, Laurent GJ. Neutrophil elastase: mediator of extracellular matrix destruction and accumulation. Proc Am Thorac Soc 2006;3:424–427.
   PubMedGoogle Scholar
• Lee WL, P. Downey G. Leukocyte elastase physiological functions and role in acute lung injury. Am J Respir Crit Care Med 2001;164:896–904.
   PubMed Web of Science ®Google Scholar
• Moraes TJ, Chow CW, Downey GP. Proteases and lung injury. Crit Care Med 2002;13:S189–S194.
   Google Scholar
• World Health Report 2000 statistical annex. World Health Organization. 2000 [cited January 2009]; Available from: http://www.who.int/whr/2000/en/statistics.htm.
   Google Scholar
• Roughley PJ, Barrett AJ. The degradation of cartilage proteoglycans by tissue proteinases proteoglycan structure and its susceptibility to proteolysis. Biochem J 1977;167:629–637.
   PubMed Web of Science ®Google Scholar
• Pham CTN. Neutrophil serine proteases: specific regulators of inflammation. Nature Rev Immunol 2006;6:541–550.
   PubMed Web of Science ®Google Scholar
• Barnes PJ, Hansel TT. Prospects for new drugs for chronic obstructive pulmonary disease. The Lancet 2004;364:985–996.
   PubMed Web of Science ®Google Scholar
• Abbenante G, Fairlie DP. Protease inhibitors in the clinic. Med Chem 2005;1:71–104.
   PubMed Web of Science ®Google Scholar
• Malhotra S, Man SFP, Sin DD. Emerging drugs for the treatment of chronic obstructive pulmonary disease. Exp Opinion Emerging Drugs 2006;11:275–291.
   PubMedGoogle Scholar
• Ohbayashi H. Current synthetic inhibitors of human neutrophil elastase. Exp Opin Ther Pat 2002;12:65–84.
   Web of Science ®Google Scholar
• Mulchande J, Guedes RC, Tsang WY, Page MI, Moreira R, Iley J. Azetidine-2,4-diones (4-Oxo-b-lactams) as scaffolds for designing elastase inhibitors. J Med Chem 2008;51:1783–1790.
   PubMed Web of Science ®Google Scholar
• Mulchande J, Oliveira R, Carrasco M, Gouveia L, Guedes RC, Iley J, Moreira R. Azetidine-2,4-diones (4-oxo-b-lactams) are potent and selective inhibitors of human leukocyte elastase J Med Chem 2010;53:241–253.
   PubMed Web of Science ®Google Scholar
• Log P value calculated using molinspiration. [cited November 2009]; Available from: http://www.molinspiration.com
   Google Scholar
• Groutas WC, Epp JB, Venkataraman R, Kuang RZ, Truong TM, McClenahan JJ, Prakash O. Design, synthesis, and in vitro inhibitory activity toward human leukocyte elastase, cathepsin G, and proteinase 3 of saccharin-derived sulfones and congeners. Bioorg Med Chem 1996;4:1393–1400.
   PubMed Web of Science ®Google Scholar
• Groutas WC, Kuang R, Venkataraman R, Epp JB, Ruan S, Prakash O. Structure-based design of a general class of mechanism-based inhibitors of the serine proteinases employing a novel amino acid-derived heterocyclic scaffold. Biochemistry 1997;36:4739–4750.
   PubMed Web of Science ®Google Scholar
• Groutas WC, Kuang RZ, Ruan SM, Epp JB, Venkataraman R, Truong TM. Potent and specific inhibition of human leukocyte elastase, cathepsin g and proteinase 3 by sulfone derivatives employing the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold. Bioorg Med Chem 1998;6:661–671.
   PubMed Web of Science ®Google Scholar
• He S, Kuang RZ, Venkataraman R, Tu J, Truong TM, Chan HK, Groutas WC. Potent inhibition of serine proteases by heterocyclic sulfide derivatives of 1,2,5-thiadiazolidin-3-one 1,1 dioxide. Bioorg Med Chem 2000;8:1713–1717.
   PubMed Web of Science ®Google Scholar
• Li Y, Yang Q, Dou D, Alliston KR, Groutas WC. Inactivation of human neutrophil elastase by 1,2,5-thiadiazolidin-3-one 1,1 dioxide-based sulfonamides. Bioorg Med Chem 2008;16:692–698.
   PubMed Web of Science ®Google Scholar
• Li Y, Dou DF, He GJ, Lushington GH, Groutas WC. Mechanism-based inhibitors of serine proteases with high selectivity through optimization of S ‘ subsite binding. Bioorg Med Chem 2009;17:3536–3542.
   PubMed Web of Science ®Google Scholar
• Mulchande J, Martins L, Moreira R, Archer M, Oliveira TF, Iley J. The efficiency of C-4 substituents in activating the b-lactam scaffold towards serine proteases and hydroxide ion. Org Biomol Chem 2007;5:2617–2626.
   PubMedGoogle Scholar
• Copeland RA. Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists New Jersey: John Wiley and Son, 2005. pp. 141–177.
   Google Scholar
• Gaspar MM, Cruz A, Penha AE, Reymao J, Sousa AC, Eleuterio CV, Domingues SA, Fraga AG, Filho AL. Rifabutin encapsulated in liposomes exhibits increased therapeutic activity in a model of disseminated tuberculosis. Int J Antimicrob Agents 2008;31:37–45.
   PubMed Web of Science ®Google Scholar
• Morrison JF, Walsh CT. The behavior and significance of slow-binding enzyme inhibitors. Adv Enzymol 1988;61:201–301.
   PubMedGoogle Scholar
• Gutschow M, Neumann U. Novel thieno[2,3-d][1,3]oxazin-4-ones as inhibitors of human leukocyte elastase. J Med Chem 1998;41:1729–1740.
   PubMed Web of Science ®Google Scholar
• Doherty JB, Ashe BM, Argenbright LW, Barker PL, Bonney RJ, Chandler GO, Dahlgren ME, Dorn CP, Finke PE. Cephalosporin antibiotics can be modified to inhibit human-leukocyte elastase. Nature 1986;322:192–194.
   PubMed Web of Science ®Google Scholar
• Finke PE, Dorn CP, Kissinger AL, Shah SK, Ball RG, Chabin R, Davie P, Dellea PS, Doherty JB. Orally-Active, Intracellular Inhibitors of Human-Leukocyte Elastase (Hle). 22nd National Meeting of the American Chemical Society; 1995 Aug; Chicago; 1995: 83–MEDI.
   Google Scholar
• Ilies MA, Scozzafava A, Supuran CT. Therapeutic applications of serine protease inhibitors. Expert Opin Ther Pat 2002;12:1181–1214.
   Web of Science ®Google Scholar
• Korkmaz B, Moreau T, Gauthier F. Neutrophil elastase, proteinase 3 and cathepsin G: physicochemical properties, activity and physiopathological functions. Biochimie 2008;90:227–242.
   PubMed Web of Science ®Google Scholar
• Alpegiani M, Bissolino P, Corigli R, Delnero S, Perrone E, Rizzo V, Sacchi N, Cassinelli G, Franceschi G, Baici A.Cephem sulfones as inactivators of human-leukocyte elastase .5. 7-Alpha-methoxy-1,1-dioxocephem-4-ketone and 7-alpha-chloro-1,1-dioxocephem-4-ketone. J Med Chem 1994;37:4003–4019.
   PubMedGoogle Scholar
• Vincent SH, Painter SK, LufferAtlas D, Karanam BV, McGowan E, Cioffe C, Doss G, Chiu SHL.Orally active inhibitors of human leukocyte elastase .2. Disposition of L-694,458 in rats and rhesus monkeys. Drug Metab Dispos 1997;25:932–939.
   PubMedGoogle Scholar