Structure-activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 24, 2008, Pages 10257-10269

  Antonopoulou, Georgia ^a   Barbayianni, Efrosini ^a   Magrioti, Victoria ^a   Cotton, Naomi ^b   Stephens, Daren ^b   Constantinou Kokotou, Violetta ^c   Dennis, Edward A ^b   Kokotos, George ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

2 Oxoamides; Amides; Amino acids; Inhibitors; Phospholipase A2

Indexed keywords

AMINO ACID DERIVATIVE; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

AMIDES; AMINO ACIDS; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; PHOSPHOLIPASES A2; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 56349108542     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.046     Document Type: Article

References (54)

1. Schaloske R.H., and Dennis E.A. Biochim. Biophys. Acta 1761 (2006) 1246
2. Balsinde J., Winstead M.V., and Dennis E.A. FEBS Lett. 531 (2002) 2
3. Six D.A., and Dennis E.A. Biochim. Biophys. Acta 1488 (2000) 1
4. Kudo I., and Murakami M. Prostaglandins Other Lipid Mediat. 68-69 (2002) 3
5. Leslie C.C. Prostaglandins Leukot. Essent. Fatty Acids 70 (2004) 373
6. Bonventre J.V., Huang Z., Taheri M.R., O'Leary E., Li E., Moskowitz M.A., and Sapirstein A. Nature 390 (1997) 622
7. Uozumi N., Kume K., Nagase T., Nakatani N., Ishii S., Tashiro F., Komagata Y., Maki K., Ikuta K., Ouchi Y., Miyazaki J., and Shimizu T. Nature 390 (1997) 618
8. Kalyvas A., and David S. Neuron 41 (2004) 323
9. Marusic S., Leach M.W., Pelker J.W., Azoitei M.L., Uozumi N., Cui J.Q., Shen M.W.H., DeClercq C.M., Miyashiro J.S., Carito B.A., Thakker P., Simmons D.L., Leonard J.P., Shimizu T., and Clark J.D. J. Exp. Med. 202 (2005) 841
10. For reviews, see. Winstead M.V., Balsinde J., and Dennis E.A. Biochim. Biophys. Acta 1488 (2000) 28
11. Balsinde J., and Balboa M.A. Cell. Signalling 17 (2005) 1052
12. Satake Y., Diaz B.L., Balestrieri B., Lam B.K., Kanaoka Y., Grusby M.J., and Arm J.P. J. Biol. Chem. 279 (2004) 16488
13. Mounier C.M., Ghomashchi F., Lindsay M.R., James S., Singer A.G., Parton R.G., and Gelb M.H. J. Biol. Chem. 279 (2004) 25024
14. Kuwata H., Nonaka T., Murakami M., and Kudo I. J. Biol. Chem. 280 (2005) 25830
15. Shirai Y., Balsinde J., and Dennis E.A. Biochim. Biophys. Acta 1735 (2005) 119
16. Ni Z., Okeley N.M., Smart B.P., and Gelb M.H. J. Biol. Chem. 281 (2006) 16245
17. Chen J., Engle S.J., Seilhamer J.J., and Tischfield J.A. J. Biol. Chem. 269 (1994) 2365
18. Chen Y., and Dennis E.A. Biochim. Biophys. Acta 1394 (1998) 57
19. Murakami M., Shimbara S., Kambe T., Kuwata H., Winstead M.V., Tischfield J.A., and Kudo I. J. Biol. Chem. 273 (1998) 14411
20. For recent reviews see. Balestrieri B., and Arm J.P. Biochim. Biophys. Acta 1761 (2006) 1280
21. Rosengren B., Jonsson-Rylander A.-C., Peilot H., Camejo G., and Hurt-Camejo E. Biochim. Biophys. Acta 1761 (2006) 1301
22. Magrioti V., and Kokotos G. Anti-Inflamm. Anti-Allergy Agents Med. Chem. 5 (2006) 189
23. McKew J.C., Foley M.A., Thakker P., Behnke M.L., Lovering F.E., Sum F.-W., Tam S., Wu K., Shem M.W.H., Zhang W., Gonzalez M., Liu S., Mahadevan A., and Sard H. J. Med. Chem. 49 (2006) 135
24. Lee K.L., Foley M.A., Chen L.R., Behnke M.L., Lovering F.E., Kirincich S.J., Wang W.H., Shim J., Tam S., Shen M.W.H., Khor S.P., Xu X., Goodwin D.G., Ramarao M.K., Nickerson-Nutter C., Donahue F., Ku M.S., Clark J.D., and Mckew J.C. J. Med. Chem. 50 (2007) 1380
25. Lee K.L., Behnke M.L., Foley M.A., Chen L., Wang W., Vargas R., Nunez J., Tam S., Mollova N., Xu X., Shen M.W.H., Ramarao M.K., Goodwin D.G., Nickerson-Nutter C.L., Abraham W.M., Williams C., Clark J.D., and McKew J.C. Bioorg. Med. Chem. 16 (2008) 1345
26. Ludwig J., Bovens S., Brauch C., Elfringhoff A.S., and Lehr M. J. Med. Chem. 49 (2006) 2611
27. Kokotos G., Kotsovolou S., Six D.A., Constantinou-Kokotou V., Beltzner C.C., and Dennis E.A. J. Med. Chem. 45 (2002) 2891
28. Kokotos G., Six D.A., Loukas V., Smith T., Constantinou-Kokotou V., Hadjipavlou-Litina D., Kotsovolou S., Chiou A., Beltzner C.C., and Dennis E.A. J. Med. Chem. 47 (2004) 3615
29. Constantinou-Kokotou V., Peristeraki A., Kokotos C.G., Six D.A., and Dennis E.A. J. Pept. Sci. 11 (2005) 431
30. Yaksh T.L., Kokotos G., Svensson C.I., Stephens D., Kokotos C.G., Fitzsimmons B., Hadjipavlou-Litina D., Hua X.-Y., and Dennis E.A. J. Pharmacol. Exp. Ther. 316 (2006) 466
31. Stephens D., Barbayianni E., Constantinou-Kokotou V., Peristeraki A., Six D.A., Cooper J., Harkewicz R., Deems R.A., Dennis E.A., and Kokotos G. J. Med. Chem. 49 (2006) 2821
32. Six D.A., Barbayianni E., Loukas V., Constantinou-Kokotou V., Hadjipavlou-Litina D., Stephens D., Wong A.C., Magrioti V., Moutevelis-Minakakis P., Baker S., Dennis E.A., and Kokotos G. J. Med. Chem. 50 (2007) 4222
33. Moutevelis-Minakakis P., Neokosmidi A., Filippakou M., Stephens D., Dennis E.A., and Kokotos G. J. Pept. Sci. 13 (2007) 634
34. Antonopoulou G., Magrioti V., Stephens D., Constantinou-Kokotou V., Dennis E.A., and Kokotos G. J. Pept. Sci. 14 (2008) 1111
35. Reid R.C. Curr. Med. Chem. 12 (2005) 3011
36. Beaton H.G., Bennion C., Connolly S., Cook A.R., Gensmantel N.P., Hallam C., Hardy K., Hitchin B., Jackson C.G., and Robinson D.H. J. Med. Chem. 37 (1994) 557
37. Hansford K.A., Reid R.C., Clark C.I., Tyndall J.D.A., Whitehouse M.W., Guthrie T., McGeary R.P., Schafer K., Martin J.L., and Fairlie D.P. ChemBioChem 4 (2003) 181
38. Arumugam T.V., Arnold N., Proctor L.M., Newman M., Reid R.C., Hansford K.A., Fairlie D.P., Shiels I.A., and Taylor S.M. Br. J. Pharmacol. 140 (2003) 71
39. Woodruff T.M., Arumugam T.V., Shiels I.A., Newman M.L., Ross P.A., Reid R.C., Fairlie D.P., and Taylor S.M. Int. Immunopharm. 5 (2005) 883
40. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
41. Ma Z., and Bobbitt J.M. J. Org. Chem. 56 (1991) 6110
42. Leanna M.R., Sowin T.J., and Morton H.E. Tetrahedron Lett. 33 (1992) 5029
43. Takacs J.M., Jaber M.R., Clement F., and Walters C. J. Org. Chem. 63 (1998) 6757
44. Kokotos G. Synthesis (1990) 299
45. Kokotos G., and Noula C. J. Org. Chem. 61 (1996) 6994
46. Chiou A., Markidis T., Constantinou-Kokotou V., Verger R., and Kokotos G. Org. Lett. 2 (2000) 347
47. Kokotos G., Verger R., and Chiou A. Chem. Eur. J. 6 (2000) 4211
48. Chiou A., Verger R., and Kokotos G. Lipids 36 (2001) 535
49. Kotsovolou S., Chiou A., Verger R., and Kokotos G. J. Org. Chem. 66 (2001) 962
50. Kokotos G. J. Mol. Catal. B-Enzym. 22 (2003) 255
51. Fawzi M.M., and Gutsche C.D. J. Org. Chem. 31 (1966) 1390
52. Hadei N., Assen B.E., Kantchen B., O' Brien C.J., and Organ M.G. J. Org. Chem. 70 (2005) 8503
53. Spencer T.A., Onofrey T.J., Cann R.O., Russel J.S., Lee L.E., Blanchard D.E., Castro A., Gu P., Jiang G., and Shechter J. J. Org. Chem. 64 (1999) 807
54. Kokotos G., Constantinou-Kokotou V., Noula C., Nicolaou A., and Gibbons W.A. Int. J. Pept. Protein Res. 48 (1996) 160