Inhibition of leukocyte elastase, polymorphonuclear chemoinvasion, and inflammation-triggered pulmonary fibrosis by a 4-alkyliden-β-lactam with a galloyl moiety

Journal of Pharmacology and Experimental Therapeutics

Volumn 316, Issue 2, 2006, Pages 539-546

  Dell'Aica, Isabella ^a   Sartor, Luigi ^a   Galletti, Paola ^b   Giacomini, Daria ^b   Quintavalla, Arianna ^b   Calabrese, Fiorella ^c   Giacometti, Cinzia ^c   Brunetta, Enrico ^c   Piazza, Francesco ^c   Agostini, Carlo ^c   Garbisa, Spiridione ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF PADUA MEDICAL SCHOOL   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 ALKYLIDENE BETA LACTAM; BETA LACTAM ANTIBIOTIC; CATHEPSIN G; FLAVONOID; GELATINASE A; GELATINASE B; LEUKOCYTE ELASTASE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME RELEASE; HUMAN; HUMAN CELL; INFLAMMATORY CELL; LUNG FIBROSIS; POLYMORPHONUCLEAR CELL; PRIORITY JOURNAL;

ANIMALS; BETA-LACTAMS; BLEOMYCIN; CELL SURVIVAL; CELLS, CULTURED; CHEMOTAXIS, LEUKOCYTE; ENZYME INHIBITORS; GALLIC ACID; HUMANS; LEUKOCYTE ELASTASE; MATRIX METALLOPROTEINASE 9; MICE; MICE, INBRED C57BL; NEUTROPHILS; PULMONARY FIBROSIS;

EID: 31144450693     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.105.096248     Document Type: Article

References (37)

1. Balckwill F and Mantovani A (2001) Inflammation and cancer: back to Virchow? Lancet 357:539-545.
2. Benelli R, Barbero A, Ferrini S, Scapini P, Cassatella M, Bussolino F, Tacchetti C, Noonan DM, and Albini A (2000) Human immunodeficiency virus transactivator protein (Tat) stimulates chemotaxis, calcium mobilization and activation of human polymorphonuclear leukocytes: implications for Tat-mediated pathogenesis. J Infect Dis 182:1643-1651.
3. Cainelli G, Galletti P, Garbisa S, Giacomini D, Sartor L, and Quintavalla A (2003a) 4-Alkylidene-azetidin-2-ones: novel inhibitors of leukocyte elastase and gelatinase. Bioorg Med Chem 11:5391-5399.
4. Cainelli G, Galletti P, Garbisa S, Giacomini D, Sartor L, and Quintavalla A (2005) 4-Alkyliden-beta-lactams conjugated to polyphenols: synthesis and inhibitory activity on matrix proteinases. Bioorg Med Chem 13:6120-6132.
5. Cainelli G, Giacomini D, Galletti P, and Quintavalla A (2003b) Synthesis of novel 4-(2-oxoethylidene)azetidin-2-ones by a Lewis acid mediated reaction of acyldiazo compounds. Eur J Org Chem 9:1765-1774.
6. Campbell EJ, Campbell MA, and Boukedes SS (2000) Quantum proteolysis by neutrophils. Implications for pulmonary emphysema in α1-antitrypsin deficiency. Chest (Suppl 1):303S.
7. Christensen PJ, Goodman RE, Pastoriza L, Moore B, and Toews B (1999) Induction of lung fibrosis in the mouse by intratracheal instillation of fluorescein isothiocyanate is not T-cell dependent. Am J Pathol 155:1773-1779.
8. Clemente A, Domingos A, Grancho AP, Iley J, Moreira R, Neres J, Palma N, Santana AB, and Valente E (2001) Design, synthesis and stability of N-acyloxymethyl- and N-aminocarbonyloxymethyl-2-azetidinones as human leukocyte elastase inhibitors. Bioorg Med Chem Lett 11:1065-1068.
9. Corbel M, Belleguic C, Boichot E, and Lagente V (2002) Involvement of gelatinases (MMP-2 and MMP-9) in the development of airway inflammation and pulmonary fibrosis. Cell Biol Toxicol 18:51-61.
10. Delclaux C, Delacourt C, D'Ortho MP, Boyer V, Lafuma C, and Harf A (1996) Role of gelatinase B and elastase in human polymorphonuclear neutrophil migration across basement membrane. Am J Respir Cell Mol Biol 14:288-295.
11. Donà M, Dell'Aica I, Calabrese F, Benelli R, Morini M, Albini A, and Garbisa S (2003) Neutrophil restraint by green tea: inhibition of inflammation, associated angiogenesis and pulmonary fibrosis. J Immunol 170:4335-4341.
12. Dri P, Haas E, Cramer R, Menegazzi R, Gasparini C, Martinelli R, Scheurich P, and Patriarca P (1999) Role of the 75-kDa TNF receptor in TNF-induced activation of neutrophil respiratory burst. J Immunol 162:460-466.
13. Egeblad M and Werb Z (2002) New functions for the matrix metalloproteinases in cancer progression. Nat Rev Cancer 2:161-174.
14. Esparza J, Kruse M, Lee J, Michaud M, and Madri JA (2004) MMP-2 null mice exhibit an early onset and severe experimental autoimmune encephalomyelitis due to an increase in MMP-9 expression and activity. FASEB J 18:1682-1691.
15. Garbisa S, Biggin S, Cavallarin N, Sartor L, Benelli R, and Albini A (1999) Tumor invasion: molecular shears blunted by green tea. Nat Med 5:1216.
16. Garbisa S, Sartor L, Biggin S, Salvato B, Benelli R, and Albini A (2000) Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechi-3-gallate. Cancer 91:822-832.
17. Gerard S, Galleni M, Dive G, and Marchand-Brynaert J (2004) Synthesis and evaluation of N1/C4-substituted beta-lactmas as PPE and HLE inhibitors. Bioorg Med Chem 12:129-138.
18. Greengrass CW and Hoople DWT (1981) Reaction of 4-acetoxy-2-azetidinone with tertiary carbanions: preparation of 4-alkyl- and 4-alkylidene-2- azetidinones. Tetrahedron Lett 22:1161-1164.
19. Keane MP, Belperio JA, Moore TA, Moore BB, Arenberg DA, Smith RE, Burdick MD, Kunkel SL, and Strieter RM (1999) Neutralization of the CXC chemokine, macrophage inflammatory protein-2, attenuates bleomycin-induced pulmonary fibrosis. J Immunol 162:5511-5518.
20. Knight WB, Chabin R, and Green B (1992) Inhibition of human serine proteases by substituted 2-azetidinones. Arch Biochem Biophys 296:704-708.
21. Knight WB, Maycock AL, Green BG, Ashe BM, Gale P, Weston H, Finke PE, Hagmann WK, Shah SK, and Doherty JB (1992) Mechanism of inhibition of human leukocyte elastase by two cephalosporin derivatives. Biochemistry 31: 4980-4986.
22. Konaklieva MI (2002) β-Lactams as inhibitors of serine enzymes: an update. Med Chem Rev 1:133-140.
23. Kuhn D, Coates C, Daniel K, Chen D, Bhuiyan M, Kazi A, Turos E, and Dou QP (2004) β-Lactams and their potential use as novel anticancer chemotherapeutics drugs. Front Biosci 9:2605-2617.
24. Lazo JS and Hoyt DG (1990) The molecular basis of interstitial pulmonary fibrosis caused by antineoplastic agents. Cancer Treat Rev 17:165-167.
25. LeeWand Downey GP (2001) Leukocyte elastase. Physiological functions and role in acute lung injury. Am J Respir Crit Care Med 164:896-904.
26. Miller NJ, Rice-Evans CA, Davies MJ, Gopinathan V, and Milner A (1993) A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin Sci 84:407-412.
27. Moore BB, Paine R 3rd, Christensen PJ, Moore TA, Sitterding S, Ngan R, Wilke CA, Kuziel WA, and Toews GB (2001) Protection from pulmonary fibrosis in the absence of CCR2 signaling. J Immunol 167:4368-4377.
28. Pezzato E, Donà M, Sartor L, Dell'Aica I, Benelli R, Albini A, and Garbisa S (2003) Proteinase-3 directly activates MMP-2 and degrades gelatin and Matrigel; differential inhibition by (-)epigallocatechin-3-gallate. J Leukoc Biol 74:88-94.
29. Prasad K, Kneussel P, Schulz G, and Stuetz P (1982) A new method of carbon extension at C-4 of azetidinones. Tetrahedron Lett 23:1247-1250.
30. Rice WG and Weiss SJ (1990) Regulation of proteolysis at the neutrophil-substrate interface by secretory leukoprotease inhibitor. Science (Wash DC) 249:178-181.
31. Sartor L, Pezzato E, Dell'Aica I, Caniato R, Biggin S, and Garbisa S (2002a) Inhibition of matrix-proteases by polyphenols: chemical insights for anti-inflammatory and anti-invasion drug design. Biochem Pharmacol 64:229-237.
32. Sartor L, Pezzato E, and Garbisa S (2002b) (-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema and invasion. J Leukoc Biol 71:73-79.
33. Selman M, King TE, and Pardo A (2001) Idiopathic pulmonary fibrosis: prevailing and evolving hypotheses about its pathogenesis and implications for therapy. Ann Intern Med 134:136-151.
34. Sternlicht MD and Werb Z (1999) Neutrophil elastase and Cathepsin G, in Extracellular Matrix, Anchor and Adhesion Proteins (Kreis T and Vale R eds) pp 543-545, Oxford University Press, Oxford, UK.
35. Taylor P, Anderson V, Dowden J, Flitsch SL, Turner NJ, Loughran K, and Walkinshaw MD (1999) Novel mechanism of inhibition of elastase by β-lactams is defined by two inhibitor crystal complexes. J Biol Chem 274:24901-24905.
36. Teshima T, Griffin JC, and Powers JC (1982) A new class of heterocyclic serine protease inhibitors. Inhibition of human leukocyte elastase, porcine pancreatic elastase, cathepsin G, and bovine chymotrypsin A alpha with substituted benzoxazinones, quinazolines and anthranilates. J Biol Chem 257:5085-5091.
37. van Acker SABE, Tromp MNJL, Haenen GRMM, van der Vijgh WJF, and Bast A (1995) Flavonoids as scavengers of nitric oxide radical. Biochem Biophys Res Commun 214:755-759.