New potent and selective polyfluoroalkyl ketone inhibitors of GVIA calcium-independent phospholipase A2

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 18, 2013, Pages 5823-5829

  Magrioti, Victoria ^a   Nikolaou, Aikaterini ^a   Smyrniotou, Annetta ^b   Shah, Ishita ^c   Constantinou Kokotou, Violetta ^b   Dennis, Edward A ^c   Kokotos, George ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

GVIA iPLA2; Inhibitor; Pentafluoroethyl ketones; Phospholipase A2; Polyfluoroalkyl ketone

Indexed keywords

1,1 DIFLUORO 5 PHENYLPENTAN 2 ONE; 1,1 DIFLUORO 6 PHENYLHEXAN 2 ONE; 1,1,1 TRIFLUORO 6 (2 METHOXYPHENYL)HEXAN 2 ONE; 1,1,1 TRIFLUORO 6 (4 FLUOROPHENYL)HEXAN 2 ONE; 1,1,1 TRIFLUORO 6 (4 METHOXYPHENYL)HEXAN 2 ONE; 1,1,1 TRIFLUORO 6 (6 METHOXYNAPHTHALEN 1 YL)HEXAN 2 ONE; 1,1,1 TRIFLUORO 6 (NAPHTHALEN 1 YL)HEXAN 2 ONE; 1,1,1 TRIFLUORO 6 [4 (TRIFLUOROMETHYL)PHENYL]HEXAN 2 ONE; 1,1,1,2,2 PENTAFLUORO 7 (2 METHOXYPHENYL)HEPTAN 3 ONE; 1,1,1,2,2 PENTAFLUORO 7 (4 FLUROPHENYL)HEPTAN 3 ONE; 1,1,1,2,2 PENTAFLUORO 7 (4 METHOXYPHENYL)HEPTAN 3 ONE; 1,1,1,2,2 PENTAFLUORO 7 (NAPHTHALEN 1 YL)HEPTAN 3 ONE; 1,1,1,2,2 PENTAFLUORO 7 [4 (TRIFLUOROMETHYL)PHENYL]HEPTAN 3 ONE; 1,1,1,2,2 PENTAFLUOROHEPTAN 7 (6 METHOXYNAPHTHALEN 2 YL)HEPTAN 3 ONE; 1,1,1,2,2,3,3 HEPTAFLUORO 8 (NAPHTHALEN 1 YL)OCTAN 4 ONE; 4 (BIPHENYL 2 YL) 1,1,1 TRIFLUOROBUTAN 2 ONE; 5 (BIPHENYL 2 YL) 1,1,1,2,2 PENTAFLUOROPENTAN 3 ONE; 6 (2,4 DIMETHOXYPHENYL) 1,1,1 TRIFLUOROHEXAN 2 ONE; 6 (3,4 DIMETHOXYPHENYL) 1,1,1 TRIFLUOROHEXAN 2 ONE; 6 (BENZO[D][1,3]DIOXO 5 YL) 1,1,1 TRIFLUOROHEXAN 2 ONE; 6 (BIPHENYL 4 YL) 1,1,1 TRIFLUOROHEXAN 2 ONE; 7 (2,4 DIMETHOXYPHENYL) 1,1,1,2,2 PENTAFLUOROHEPTAN 3 ONE; 7 (3,4 DIMETHOXYPHENYL) 1,1,1,2,2 PENTAFLUOROHEPTAN 3 ONE; 7 (BENZO[D][1,3]DIOXOL 5 YL) 1,1,1,2,2 PENTAFLUOROHEPTAN 3 ONE; 7 (BIPHENYL 4 YL) 1,1,1,2,2 PENTAFLUOROHEPTAN 3 ONE; CALCIUM INDEPENDENT PHOSPHOLIPASE A2; CALCIUM INDEPENDENT PHOSPHOLIPASE A2 INHIBITOR; ESTERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; ENZYME INHIBITION; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

GVIA IPLA(2); INHIBITOR; PENTAFLUOROETHYL KETONES; PHOSPHOLIPASE A(2); POLYFLUOROALKYL KETONE;

FLUORINE; GROUP VI PHOSPHOLIPASES A2; KETONES; PHOSPHOLIPASE A2 INHIBITORS; PROTEIN BINDING; PROTEIN ISOFORMS;

EID: 84882898599     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.07.010     Document Type: Article

References (45)

1. J.E. Burke, and E.A. Dennis Cardiovasc. Drugs Ther. 23 2009 45
2. E.A. Dennis, J. Cao, Y.-H. Hsu, V. Magrioti, and G. Kokotos Chem. Rev. 111 2011 6130
3. M. Ghosh, D.E. Tucker, S.A. Burchett, and C.C. Leslie Prog. Lipid Res. 45 2006 487
4. J.D. Clark, L.L. Lin, R.W. Kriz, C.S. Ramesha, L.A. Sultzman, A.Y. Lin, N. Milona, and J.L. Knopf Cell 65 1991 1043
5. R.M. Kramer, E.F. Roberts, J. Manetta, and J.E. Putnam J. Biol. Chem. 266 1991 5268
6. C.M. Mounier, F. Ghomashchi, M.R. Lindsay, S. James, A.G. Singer, R.G. Parton, and M.H. Gelb J. Biol. Chem. 279 2004 25024
7. Y. Satake, B.L. Diaz, B. Balestrieri, B.K. Lam, Y. Kanaoka, M.J. Grusby, and J.P. Arm J. Biol. Chem. 279 2004 16488
8. Y. Shirai, J. Balsinde, and E.A. Dennis Biochim. Biophys. Acta 1735 2005 119
9. E.J. Ackermann, E.S. Kempner, and E.A. Dennis J. Biol. Chem. 269 1994 9227
10. J. Tang, R.W. Kriz, N. Wolfman, M. Shaffer, J. Seehra, and S.S. Jones J. Biol. Chem. 272 1997 8567
11. M.A. Balboa, J. Balsinde, S.S. Jones, and E.A. Dennis J. Biol. Chem. 272 1997 8576
12. S.G. Sedgwick, and S.J. Smerdon Trends Biochem. Sci. 24 1999 311
13. J. Balsinde, I.D. Bianco, E.J. Ackermann, K. Conde-Frieboes, and E.A. Dennis Proc. Natl. Acad. Sci. U.S.A. 92 1995 8527
14. J. Balsinde, M.A. Balboa, and E.A. Dennis J. Biol. Chem. 272 1997 29317
15. J. Balsinde, and E.A. Dennis J. Biol. Chem. 272 1997 16069
16. S. Ramanadham, F.F. Hsu, A. Bohrer, Z. Ma, and J. Turk J. Biol. Chem. 274 1999 13915
17. H. Birbes, S. Drevet, J.F. Pageaux, M. Lagarde, and C. Laugier Eur. J. Biochem. 267 2000 7118
18. Z. Ma, A. Bohrer, M. Wohltmann, S. Ramanadham, F.F. Hsu, and J. Turk Lipids 36 2001 689
19. Z. Ma, S. Ramanadham, M. Wohltmann, A. Bohrer, F.F. Hsu, and J. Turk J. Biol. Chem. 276 2001 13198
20. J. Balsinde, and M.A. Balboa Cell. Signalling 17 2005 1052
21. J. Balsinde, R. Perez, and M.A. Balboa Biochim. Biophys. Acta 1761 2006 1344
22. D.K. Zachman, A.J. Chicco, S.A. McCune, R.C. Murphy, R.L. Moore, and G.C. Sparagna J. Lipid Res. 51 2010 525
23. X. Lei, S.E. Barbour, and S. Ramanadham Biochimie 92 2010 627
24. S.B. Hooks, and B.S. Cummings Biochem. Pharmacol. 76 2008 1059
25. W.P. Wilkins, and S.E. Barbour Curr. Drug Targets 9 2008 683
26. C.M. Jenkins, A. Cedars, and R.W. Gross Cardiovasc. Res. 82 2009 240
27. J. Cao, J.E. Burke, and E.A. Dennis J. Biol. Chem. 288 2013 1806
28. V. Magrioti, and G. Kokotos Anti-Inflammatory Anti-Allergy Agents Med. Chem. 5 2006 189
29. V. Magrioti, and G. Kokotos Expert Opin. Ther. Pat. 20 2010 1
30. V. Magrioti, and G. Kokotos Expert Opin. Ther. Pat. 23 2013 333
31. E.J. Ackermann, K. Conde-Frieboes, and E.A. Dennis J. Biol. Chem. 270 1995 445
32. K. Conde-Frieboes, L.J. Reynolds, Y. Lio, M. Hale, H.H. Wasserman, and E.A. Dennis J. Am. Chem. Soc. 118 1996 5519
33. Y.C. Lio, L.J. Reynolds, J. Balsinde, and E.A. Dennis Biochim. Biophys. Acta 1302 1996 55
34. Y.-H. Hsu, D.S. Dumlao, J. Cao, and E.A. Dennis PLoS One 8 2013 e59267
35. H. Song, S. Ramanadham, S. Bao, F.-F. Hsu, and J. Turk Biochemistry 45 2006 1061
36. C. Baskakis, V. Magrioti, N. Cotton, D. Stephens, V. Constantinou- Kokotou, E.A. Dennis, and G. Kokotos J. Med. Chem. 51 2008 8027
37. G. Kokotos, Y.H. Hsu, J.E. Burke, C. Baskakis, C.G. Kokotos, V. Magrioti, and E.A. Dennis J. Med. Chem. 53 2010 3602
38. A. Kalyvas, C. Baskakis, V. Magrioti, V. Constantinou-Kokotou, D. Stephens, R. Lpez-Vales, J.Q. Lu, V.W. Yong, E.A. Dennis, G. Kokotos, and S. David Brain 132 2009 1221
39. Y.-H. Hsu, D. Bucher, J. Cao, S. Li, S.-W. Yang, G. Kokotos, V.L. Woods, J.A. McCammon, and E.A. Dennis J. Am. Chem. Soc. 135 2013 1330
40. D. Stephens, E. Barbayianni, V. Constantinou-Kokotou, A. Peristeraki, D.A. Six, J. Cooper, R. Harkewicz, R.A. Deems, E.A. Dennis, and G. Kokotos J. Med. Chem. 49 2006 2821
41. D.A. Six, E. Barbayianni, V. Loukas, V. Constantinou-Kokotou, D. Hadjipavlou-Litina, D. Stephens, A.C. Wong, V. Magrioti, P. Moutevelis- Minakakis, S. Baker, E.A. Dennis, and G. Kokotos J. Med. Chem. 50 2007 4222
42. G. Kokotos, D.A. Six, V. Loukas, T. Smith, V. Constantinou-Kokotou, D. Hadjipavlou-Litina, S. Kotsovolou, A. Chiou, C.C. Beltzner, and E.A. Dennis J. Med. Chem. 47 2004 3615
43. Makriyannis, A.; Nikas, S. P.; Alapafuja, S. O.; Shukla, V. G. WO Patent 2008/013963 A2.
44. Makriyannis, A.; Nikas, S. P.; Alapafuja, S. O.; Shukla, V. G. WO Patent 2009/052319 A1.
45. J. Ichikawa, T. Sonoda, and H. Kobayashi Tetrahedron Lett. 30 1989 5437