Inhibition of secreted phospholipase A2. 4-Glycerol derivatives of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one with broad activities

Journal of Medicinal Chemistry

Volumn 50, Issue 7, 2007, Pages 1618-1626

  Touaibia, Mohamed ^a   Djimdé, Atimé ^a   Cao, Fei ^a   Boilard, Eric ^b   Bezzine, Sofiane ^b   Lambeau, Gérard ^b   Redeuilh, Catherine ^a   Lamouri, Aazdine ^a   Massicot, France ^a,c   Chau, François ^a   Dong, Chang Zhi ^a   Heymans, Françoise ^a  

^a Laboratoire de Pharmacochimie   (France)

^b INSTITUT DE PHARMACOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^c FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DIHYDRO 3 (4 TETRADECYLOXYBENZYL) 1,2,4 4H OXADIAZOL 5 ONE DERIVATIVE; GLYCEROL DERIVATIVE; INDOLE DERIVATIVE; ME INDOXAM; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; LIPOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

GLYCEROL; HUMANS; HYDROPHOBICITY; OXADIAZOLES; PHOSPHOLIPASES A; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34147191563     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060082n     Document Type: Article

References (46)

1. Six, D. A.; Dennis, E. A. The expanding superfamily of phospholipase A(2) enzymes: classification and characterization. Biochim. Biophys. Acta 2000, 1488, 1-19.
2. Kudo, I.; Murakami, M. Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat. 2002, 68-69, 3-58.
3. Nevalainen, T. J.; Haapamaki, M. M.; Gronroos, J. M. Roles of secretory phospholipases A(2) in inflammatory diseases and trauma. Biochim. Biophys. Acta 2000, 1488, 83-90.
4. Green, J. A.; Smith, G. M.; Buchta, R.; Lee, R.; Ho, K. Y.; Rajkovic, I. A.; Scott, K. F. Circulating phospholipase A2 activity associated with sepsis and septic shock is indistinguishable from that associated with rheumatoid arthritis. Inflammation 1991, 15, 355-367.
5. Seilhamer, J. J.; Pruzanski, W.; Vadas, P.; Plant, S.; Miller, J. A.; Kloss, J.; Johnson, L. K. Cloning and recombinant expression of phospholipase A2 present in rheumatoid arthritic synovial fluid. J. Biol. Chem. 1989, 264, 5335-5338.
6. Kramer, R. M.; Hession, C.; Johansen, B.; Hayes, G.; McGray, P.; Chow, E. P.; Tizard, R.; Pepinsky, R. B. Structure and properties of a human non-pancreatic phospholipase A2. J. Biol. Chem. 1989, 264, 5768-5775.
7. Minami, T.; Tojo, H.; Shinomura, Y.; Matsuzawa, Y.; Okamoto, M. Increased group II phospholipase A2 in colonic mucosa of patients with Crohn's disease and ulcerative colitis. Gut 1994, 35, 1593-1598.
8. Nevalainen, T. J.; Gronroos, J, M.; Kortesuo, P. T. Pancreatic and synovial type phospholipases A2 in serum samples from patients with severe acute pancreatitis. Gut 1993, 34, 1133-1136.
9. Andersen, S.; Sjursen, W.; Laegreid, A.; Volden, G.; Johansen, B. Elevated expression of human nonpancreatic phospholipase A2 in psoriatic tissue. Inflammation 1994, 18, 1-12.
10. Kim, D. K.; Fukuda, T.; Thompson, B. T.; Cockrill, B.; Hales, C.; Bonventre, J. V. Bronchoalveolar lavage fluid phospholipase A2 activities are increased in human adult respiratory distress syndrome. Am. J. Physiol. 1995, 269, 109-118.
11. Balboa, M. A.; Balsinde, J.; Winstead, M. V.; Tischfield, J. A.; Dennis. E. A. Novel group V phospholipase A2 involved in arachidonic acid mobilization in murine P388D1 macrophages. J. Biol. Chem. 1996, 271, 32381-32384.
12. Reddy, S. T.; Winstead, M. V.; Tischfield, J. A.; Herschman, H. R. Analysis of the secretory phospholipase A2 that mediates prostaglandin production in mast cells. J. Biol. Chem. 1997, 272, 13591-13596.
13. Cho, W. Structure, function, and regulation of group V phospholipase A(2). Biochim. Biophys. Acta 2000, 1488, 48-58.
14. Haas, U.; Podda, M.; Behne, M.; Gurrieri, S.; Alonso, A.; Furstenberger, G.; Pfeilschifter, J.; Lambeau, G.; Gelb, M. H.; Kaszkin, M. Characterization and differentiation-dependent regulation of secreted phospholipases A in human keratinocytes and in healthy and psoriatic human skin. J. Invest. Dermatol. 2005, 124, 204-211.
15. Murakami, M.; Yoshihara, K.; Shimbara, S.; Sawada, M.; Inagaki, N.; Nagai, H.; Naito, M.; Tsuruo, T.; Moon, T. C.; Chang, H. W.; Kudo, I. Group IID heparin-binding secretory phospholipase A(2) is expressed in human colon carcinoma cells and human mast cells and up-regulated in mouse inflammatory tissues. Eur. J. Biochem. 2002, 269, 2698-2707.
16. Seeds, M. C.; Jones, K. A.; Duncan Hite, R.; Willingham, M. C.; Borgerink, H. M.; Woodruff, R. D.; Bowton, D. L.; Bass, D. A. Cell-specific expression of group X and group V secretory phospholipases A(2) in human lung airway epithelial cells. Am. J. Respir. Cell Mol. Biol. 2000, 23, 37-44.
17. Masuda, S.; Murakami, M.; Matsumoto, S.; Eguchi, N.; Urade, Y.; Lambeau, G.; Gelb, M. H.; Ishikawa, Y.; Ishii, T.; Kudo, I. Localization of various secretory phospholipase A2 enzymes in male reproductive organs. Biochim. Biophys. Acta 2004, 1686, 61-76.
18. Leistad, L.; Feuerherm, A. J.; Ostensen, M.; Faxvaag, A.; Johansen, B. Presence of secretory group IIa and V phospholipase A2 and cytosolic group IValpha phospholipase A2 in chondrocytes from patients with rheumatoid arthritis. Clin. Chem. Lab. Med. 2004, 602-610.
19. Ishimoto, Y.; Yamada, K.; Yamamoto, S.; Ono, T.; Notoya, M.; Hanasaki, K. Group V and X secretory phospholipase A(2)s-induced modification of high-density lipoprotein linked to the reduction of its antiatherogenic functions. Biochim. Biophys. Acta 2003, 1642, 129-138.
20. Munoz, N. M.; Kim, Y. J.; Meliton, A. Y.; Kim, K. P.; Han, S. K.; Boetticher, E.; O'Leary, E.; Myou, S.; Zhu, X.; Bonventre, J. V.; Leff, A. R.; Cho, W. Human group V phospholipase A2 induces group IVA phospholipase A2-independent cysteinyl leukotriene synthesis in human eosinophils. J. Biol. Chem. 2003, 278, 38813-38820.
21. Han, S. K.; Kim, K. P.; Koduri, R.; Bittova, L.; Munoz, N. M.; Leff, A. R.; Wilton, D. C.; Gelb, M. H.; Cho, W. Roles of Trp31 in high membrane binding and proinflammatory activity of human group V phospholipase A2. J. Biol. Chem. 1999, 274, 11881-11888.
22. Bezzine, S.; Koduri, R. S.; Valentin, E.; Murakami, M.; Kudo, I.; Ghomashchi, F.; Sadilek, M.; Lambeau, G.; Gelb, M. H. Exogenously added human group X secreted phospholipase A(2) but not the group IB, IIA, and V enzymes efficiently release arachidonic acid from adherent mammalian cells. J. Biol. Chem. 2000, 275, 3179-3191.
23. Mounier, C. M.; Ghomashchi, F.; Lindsay, M. R.; James, S.; Singer, A. G.; Parton, R. G.; Gelb, M. H. Arachidonic acid release from mammalian cells transfected with human groups IIA and X secreted phospholipase A(2) occurs predominantly during the secretory process and with the involvement of cytosolic phospholipase A(2)-alpha. J. Biol. Chem. 2004, 279, 25024-25038.
24. Satake, Y.; Diaz, B. L.; Balestrieri, B.; Lam, B. K.; Kanaoka, Y.; Grusby, M. J.; Arm, J. P. Role of group V phospholipase A2 in zymosan-induced eicosanoid generation and vascular permeability revealed by targeted gene disruption. J. Biol. Chem. 2004, 279, 16488-16494.
25. 2 hydrolysis of low-density lipoprotein results in spontaneous particle aggregation and promotes macrophage foam cell formation. Arterioscler. Thromb. Vasc. Biol. 2004, 24, 762-767.
26. Hanasaki, K.; Yamada, K.; Yamamoto, S.; Ishimoto, Y.; Saiga, A.; Ono, T.; Ikeda, M.; Notoya, M.; Kamitani, S.; Arita, H. Potent modification of low density lipoprotein by group X secretory phospholipase A2 is linked to macrophage foam cell formation. J. Biol. Chem. 2002, 227, 29116-29124.
27. Saiga, A.; Uozumi, N.; Ono, T.; Seno, K.; Ishimoto, Y.; Arita, H.; Shimizu, T.; Hanasaki, K. Group X secretory phospholipase A2 can induce arachidonic acid release and eicosanoid production without activation of cytosolic phospholipase A2 alpha. Prostaglandins Other Lipid Mediat. 2005, 75, 79-89.
28. Valentin, E.; Ghomashchi, F.; Gelb, M. H.; Lazdunski, M.; Lambeau, G. On the diversity of secreted phospholipases A(2). Cloning, tissue distribution, and functional expression of two novel mouse group II enzymes. J. Biol. Chem. 1999, 274, 31195-31202.
29. Dillard, R. D.; Bach, N. J.; Draheim, S. E.; Berry, D. R.; Carlson, D. G.; Chirgadze, N. Y.; Clawson, D. K.; Hartley, L. W.; Johnson, L. M.; Jones, N. D.; McKinney, E. M.; Mihelich, E. D.; Olkowski, J. L.; Schevitz, R. W.; Smith, A. C.; Snyder, D. W.; Sommers, C. D.; Wery, J. P. Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides. J. Med. Chem. 1996, 39, 5119-5136.
30. Dillard, R. D.; Bach, N. J.; Draheim, S. E.; Berry, D. R.; Carlson, D. G.; Chirgadze, N. Y.; Clawson, D. K.; Hartley, L. W.; Johnson, L. M.; Jones, N. D.; McKinney, E. M.; Mihelich, E. D.; Olkowski, J. L.; Schevitz, R. W.; Smith, A. C.; Snyder, D. W.; Sommers, C. D.; Wery, J. P. Indole inhibitors of human nonpancreatic secretory phospholipase A2. 2. Indole-3-acetamides with additional functionality. J. Med. Chem. 1996, 39, 5137-5158.
31. Draheim, S. E.; Bach, N. J.; Dillard, R. D.; Berry, D. R.; Carlson, D. G.; Chirgadze, N. Y.; Clawson, D. K.; Hartley, L. W.; Johnson, L. M.; Jones, N. D.; McKinney, E. M.; Mihelich, E. D.; Olkowski, J. L.; Schevitz, R. W.; Smith, A. C.; Snyder, D. W.; Sommers, C. D.; Wery, J. P. Indole inhibitors of human nonpancreatic secretory phospholipase A2. 3. Indole-3-glyoxamides. J. Med. Chem. 1996, 39, 5159-5175.
32. Hagishita, S.; Yamada, M.; Shirahase, K.; Okada, T.; Murakami, Y.; Ito, Y.; Matsuura, T.; Wada, M.; Kato, T.; Ueno, M.; Chikazawa, Y.; Yamada, K.; Ono, T.; Teshirogi, I.; Ohtani, M. Potent inhibitors of secretory phospholipase A2: synthesis and inhibitory activities of indolizine and indene derivatives. J. Med. Chem. 1996, 39, 3636-3658.
33. Aitdafoun, M.; Mounier, C.; Heymans, F.; Binisti, C.; Bon, C.; Godfroid, J.-J. 4-Alkoxybenzamidines as new potent phospholipase A2 inhibitors. Biochem. Pharmacol. 1996, 51, 737-742.
34. Binisti, C.; Touboul, E.; Mounier, C. M.; Heymans, F.; Bon, C.; Godfroid, J.-J. Structure-activity relationships in platelet activating factor. 9. From PAF-antagonism to PLA2 inhibition. J. Lipid Mediat. Cell Signal. 1997, 15, 125-144.
35. Assogba, L.; Ahamada-Himidi, A.; Meddad-Bel Habich, N.; Aoun, D.; Boukli, L.; Massicot, F.; Mounier, C. M.; Huet, J.; Lamouri, A.; Ombetta, J.-E.; Godfroid, J.-J.; Dong, C. Z.; Heymans, F. Inhibition of secretory phospholipase A2. I-Design, synthesis and structure-activity relationship studies starting from 4-tetradecyloxybenzamidine to obtain specific inhibitors of group II sPLA2s. Eur. J. Med. Chem. 2005, 40, 850-861.
36. Plocki, S.; Aoun, D.; Ahamada-Himidi, A.; Tavarès-Camarinha, F.; Dong, C. Z.; Massicot, F.; Huet, J.; Adolphe-Pierre, S.; Chau, F.; Godfroid, J.-J.; Gresh, N.; Ombetta, J.-E.; Heymans, F. Molecular modeling, design and synthesis of less lipophilic derivatives of 3-(4-tetradecyloxybenzyl)-4H- 1,2,4-oxadiazol-5-one (PMS 1062) specific for group II enzyme. Eur. J. Org. Chem. 2005, 2747-2757.
37. Dong, C. Z.; Ahamada-Himidi, A.; Plocki, S.; Aoun, D.; Touaibia, M.; Meddad-Bel Habich, N.; Huet, J.; Redeuilh, C.; Ombetta, J.-E.; Godfroid, J.-J.; Massicot, F.; Heymans, F. Inhibition of secretory phospholipase A2. 2-Synthesis and structure-activity relationship studies of 4,5-dihydro-3-(4- tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS 1062) derivatives specific for group II enzyme. Bioorg. Med. Chem. 2005, 13, 1989-2007.
38. Wheeler, T. S.; Willson, F. G. In Organic synthesis; John Wiley: New York, 1941; Collective Vol. I, p 296.
39. Serafin, B.; Milkowska, G. Arylboronic compounds. XII. Some new boradioxacyclopentane derivatives. Rocz. Chem. 1964, 38, 897-898.
40. 2. J. Biol. Chem. 2002, 277, 48535-48549.
41. 2. Biochem. J. 2002, 365, 505-511.
42. Cupillard, L.; Koumanov, K.; Mattéi, M.-G.; Lazdunski, M.; Lambeau, G. Cloning, chromosomal mapping, and expression of a novel human secretory phospholipase A2. J. Biol. Chem. 1997, 272, 15745-15752.
43. Wagner, G.; Horn, H. Synthesis of aromatic amidino compounds with ether structure. Pharmazie 1975, 30, 353-357.
44. Boruwa, J.; Bhuyan, R.; Gogoi, N.; Barua, N. C. Chemoselective tetrahydropyranylation of primary alcohols under freezing water pressure. Indian J. Chem. B 2005, 44, 331-334.
45. Radvanyi, F.; Jordan, L.; Russo-Marie, F.; Bon, C. A sensitive and continuous fluorometric assay for phospholipase A2 using pyrene-labeled phospholipids in the presence of serum albumin. Anal. Biochem. 1989, 117, 103-109.
46. Mounier, C.; Faili, H.; Vargaftig, B. B.; Bon, C.; Hatmi, M. Secretory phospholipase A2 is not required for arachidonic acid liberation during platelet activation. Eur. J. Biochem. 1993, 216, 169-175.