Inhibitors of cytosolic phospholipase A2α as potential anti-inflammatory drugs

Anti-Inflammatory and Anti-Allergy Agents in Medicinal Chemistry

Volumn 5, Issue 2, 2006, Pages 149-161

  Lehr, Matthias ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Inflammation; Inhibitors; Phospholipase A2

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; AMIDE; ANILIDE; ANTIINFLAMMATORY AGENT; ARACHIDONIC ACID DERIVATIVE; ARACHIDONYL TRIFLUOROMETHYL KETONE; AZALOMYCIN; BMS 229724; CALCIUM; DEXAMETHASONE; DICLOFENAC; ECOPLADIB; ENZYME INHIBITOR; IBUPROFEN; KETONE DERIVATIVE; LEUKOTRIENE; LINOLEIC ACID; LINOLENIC ACID; LIPID; LIPOPROTEIN; MEMBRANE PHOSPHOLIPID; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; PROSTAGLANDIN; SCALARADIAL; SERINE PROTEINASE INHIBITOR; THIELOCIN B3; THROMBOCYTE ACTIVATING FACTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; WY 48489;

ALZHEIMER DISEASE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CALCIUM TRANSPORT; CREUTZFELDT JAKOB DISEASE; DEGENERATIVE DISEASE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DETERMINATION; DRUG METABOLISM; DRUG RESEARCH; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME PHOSPHORYLATION; ENZYME REGULATION; GUINEA PIG; HUMAN; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; KNOCKOUT MOUSE; MOUSE; NONHUMAN; OTITIS; PARKINSON DISEASE; PATHOPHYSIOLOGY; PAW EDEMA; PROSTAGLANDIN SYNTHESIS; PROTEIN SYNTHESIS; RABBIT; RAT; SKIN INFLAMMATION; STIMULUS RESPONSE; STROKE;

EID: 33744477349     PISSN: 18715230     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152306776872488     Document Type: Article

References (93)

1. Serhan, C.N.; Haeggström, J.Z.; Leslie, C.C. FASEB J. 1996, 10, 1147.
2. Ryborg, A.K.; Deleuran, B.; Sogaard, H.R.; Kragballe, K. Acta Derm. Venereol. 2000, 80, 242.
3. Connolly, S.; Robinson, D.H. Expert Opin. Ther. Patents 1993, 3, 1141.
4. Connolly, S.; Robinson, D.H. Expert Opin. Ther. Patents 1995, 5, 673.
5. Tibes, U.; Friebe, W.G. Expert Opin. Invest. Drugs 1997, 6, 279.
6. Lehr, M. Expert Opin. Ther. Patents 2001, 11, 1123.
7. Clark, J.D.; Tam, S. Expert Opin. Ther. Patents 2004, 14, 937.
8. Six, D.A.; Dennis, E.A. Biochim. Biophys. Acta. 2000, 1488, 1.
9. Kudo, I.; Murakami, M. Prostaglandins Other Lipid Mediat. 2002, 68-69, 3.
10. Rouault, M.: Bollinger, J.G.; Lazdunski, M.; Gelb, M.H.; Lambeau, G. Biochemistry 2003, 42, 11494.
11. Laine, V.J.; Grass, D.S.; Nevalainen, T.J. Infect. Immun. 2000, 68, 87.
12. Gronroos, J.O.; Laine, V.J.; Janssen, M.J.; Egmond, M.R.; Nevalainen, T.J. J. Immunol. 2001, 166, 4029.
13. Macphee, C.H. Curr. Opin. Pharmacol. 2001, 1, 121.
14. Akiba, S.; Sato, T. Biol. Pharm. Bull. 2004, 27, 1174.
15. Hirabayashi, T.; Murayama, T.; Shimizu, T. Biol. Pharm. Bull. 2004, 27, 1168
16. Mayer, R. J.; Marshall, L.A. FASEB J. 1993, 7, 339.
17. Lin, L.L.; Lin, A.Y.; Knopf, J.L. Proc. Nat. Acad. Sci. USA 1992, 89, 6147.
18. Uozumi, N.; Shimizu, T. Prostaglandins Other Lipid Mediat. 2002, 68-69, 59.
19. Miyaura, C.; Inada, M.; Matsumoto, C.; Ohshiba, T.; Uozumi, N.; Shimizu, T.; Ito, A. J. Exp. Med. 2003, 197, 1303.
20. Hegen, M.; Sun, L.; Uozumi, N.; Kume, K.; Goad, M.E.; Nickerson-Nutter, C.L.; Shimizu, T.; Clark, J.D. J. Exp. Med. 2003, 197, 1297.
21. Bonventre, J.V. Trends Immunol. 2004, 25, 116.
22. Amandi-Burgermeister, E.; Tibes, U.; Kaiser, B.M.; Friebe, W.G.; Scheuer, W.V. Eur. J. Pharmacol. 1997, 326, 237.
23. Marshall, L.A.; Winkler, J.D.; Griswold, D.E.; Bolognese, B.; Roshak, A.; Sung, C.M.; Webb, E.F.; Jacobs, R. J. J. Pharmacol. Exp. Ther. 1994, 268, 709.
24. Seno, K.; Okuno, T.; Nishi, K.; Murakami, Y.; Watanabe, F.; Matsuura, T.; Wada, M.; Fujii, Y.; Yamada, M.; Ogawa, T.; Okada, T.; Hashizume, H.; Kii, M.; Hara, S.; Hagishita, S.; Nakamoto, S.; Yamada, K.; Chikazawa, Y.; Ueno, M.; Teshirogi, I.; Ono, T.; Ohtani, M. J. Med. Chem. 2000, 43, 1041.
25. Varghese, J.; Rydel, R.E.; Thorsett, E.G. (Athena Neurosciences, Inc.) WO9825893, 2000.
26. Varghese, J.; Rydel, R.E.; Dappen, M.S.; Thorsett, E.G. (Elan Pharm. Inc.) WO0027824, 2000.
27. Street, I.P.; Lin, H.K.; Laliberte, F.; Ghomashchi, F.; Wang, Z.; Perrier, H.; Tremblay, N.M.; Huang, Z.; Weech, P.K.; Gelb, M.H. Biochemistry 1993, 32, 5935.
28. Connolly, S.; Bennion, C.; Botterell, S.; Croshaw, P.J.; Hallam, C.; Hardy, K.; Hartopp, P.; Jackson, C.G.; King, S.J.; Lawrence, L.; Mete, A.; Murray, D.; Robinson, D.H.; Smith, G.M.; Stein, L.; Walters, I.; Wells, E.; Withnall, W.J. J. Med. Chem. 2002, 45, 1348.
29. Märki, F.; Breitenstein, W.; Beriger, E.; Bernasconi, R.; Caravatti, G.; Francis, J.E.; Paioni, R.; Wehrli, H.U.; Wiederkehr, R. Agents Actions 1993, 38, 202.
30. Burke, J.R.; Davern, L.B.; Stanley, P.L.; Gregor, K.R.; Banville, J.; Remillard, R.; Russell, J.W.; Brassil, P.J.; Witmer, M.R.; Johnson, G.; Tredup, J.A.; Tramposch, K.M. J. Pharmacol. Exp. Ther. 2001, 298, 376.
31. Lucas, R.; Ubeda, A.; Paya, M.; Alves, M.; del Olmo, E.; Lopez, J.L.; San Feliciano, A. Bioorg. Med. Chem. Lett. 2000, 10, 285.
32. Ghomashchi, F.; Loo, R.; Balsinde, J.; Bartoli, F.; Apitz-Castro, R.; Clark, J.D.; Dennis, E.A.; Gelb, M.H. Biochim. Biophys. Acta 1999, 1420, 45.
33. Kokotos, G.; Kotsovolou, S.; Six, D.A.; Constantinou-Kokotou, V.; Beltzner, C.C.; Dennis, E.A. J. Med. Chem. 2002, 45, 2891.
34. Conde-Frieboes, K.; Reynolds, L.J.; Lio, Y.C.; Hale, M.R.; Wasserman, H.H.; Dennis, E.A. J. Am. Chem. Soc. 1996, 118, 5519.
35. Banville, J.; Plamondon, S.; Gai, Y.; Balasubramanian, N. (Bristol-Myers Squibb Comp.) US6492550, 2002.
36. Bayburt, T.; Yu, B.Z.; Street, I.; Ghomashchi, F.; Laliberte, F.; Perrier, H.; Wang, Z.; Homan, R.; Jain, M.K.; Gelb, M.H. Anal. Biochem. 1995, 232, 7.
37. Huang, Z.; Laliberte, F.; Tremblay, N.M.; Weech, P.K.; Street, I.P. Anal. Biochem. 1994, 222, 110.
38. Seehra, J.S.; Xiang, Y.; Bemis, J.; McKew, J.; Kaila, N.; Chen, L. (Genetics Institute, Inc.) WO9943672, 1999.
39. Reynolds, L.J.; Hughes, L.L.; Yu, L.; Dennis, E.A. Anal. Biochem. 1994, 217, 25.
40. Ono, T.; Yamada, K.; Chikazawa, Y.; Ueno, M.; Nakamoto, S.; Okuno, T.; Seno, K. Biochem. J. 2002, 363, 727.
41. Schmitt, M.; Lehr, M. J. Pharm. Biomed. Anal. 2004, 35, 135.
42. Mosior, M.; Six, D.A.; Dennis, E.A. J. Biol. Chem. 1998, 273, 2184.
43. Burke, J.R.; Witmer, M.R.; Tredup, J.; Micanovic, R.; Gregor, K.R.; Lahiri, J.; Tramposch, K.M.; Villafranca, J.J. Biochemistry 1995, 34, 15165.
44. Burke, J.R.; Witmer, M.R.; Zusi, F.C.; Gregor, K.R.; Davern, L.B.; Padmanabha, R.; Swann, R.T.; Smith, D.; Tredup, J.A.; Micanovic, R.; Manly, S.P.; Villafranca, J.J.; Tramposch, K.M. J. Biol. Chem. 1999, 274, 18864.
45. 2. Wong and Dennis, Eds., Plenum Press: New York, 1990, P.169.
46. Kokotos, G.; Six, D.A.; Loukas, V.; Smith, T.; Constantinou-Kokotou, V.; Hadjipavlou-Litina, D.; Kotsovolou, S.; Chiou, A.; Beltzner, C.C.; Dennis, E.A. J. Med. Chem. 2004, 47, 3615.
47. Ghomashchi, F.; Stewart, A.; Hefner, Y.; Ramanadham, S.; Turk, J.; Leslie, C.C.; Gelb, M.H. Biochim. Biophys. Acta 2001, 1513, 160.
48. Seno, K.; Ohtani, M.; Watanabe, F. (Shionogi & Co., Ltd.) EP0976748, 2000.
49. Kato, T.; Watanabe, F.; Seno, K. (Shionogi & Co., Ltd.) EP0848004, 1998.
50. Kennedy, B.; Payette, P.; Riendeau, D.; Weech, P.; Gresser, M. Mediat. Inflamm. 1994, 3, 307.
51. Seehra, J.S.; Kaila, N.; McKew, J.C.; Lovering, F.; Bemis, J.E.; Xiang, Y. (Genetics Institute, Inc.) WO9943651, 1999.
52. Lehr, M. Pharm. Pharmacol. Lett. 1992, 2, 176.
53. Lehr, M.; Schulze Elfringhoff, A. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 312.
54. Riendeau, D.; Guay, J.; Weech, P.K.; Laliberte, F.; Yergey, J.; Li, C.; Desmarais, S.; Perrier, H.; Liu, S.; Nicoll-Griffith, D.; Street, I.P. J. Biol. Chem. 1994, 269, 15619.
55. Seno, K.; Okuno, T.; Nishi, K.; Murakami, Y.; Yamada, K.; Nakamoto, S.; Ono, T. Bioorg. Med. Chem. Lett. 2001, 11, 587.
56. Takagi, M; Ishimitsu, K.; Nishibe, T. (Nippon Soda Co., Ltd.) EP1277743, 2003.
57. Tibes, U.; Vondran, A.; Rodewald, E.; Friebe, W.-G.; Schäfer, W.; Scheuer, W. Int. Arch. Allergy Immunol. 1995, 107, 432.
58. Laufer, S.; Lehr, M.; Tries, S. Prostaglandins Leukotrienes Essential Fatty Acids 1996, 55 (Suppl.1), 91.
59. Tries, S.; Neher, K.; Laufer, S.; Abraham, W.M.; Lehr, M. Mediat. Inflamm. 1999, 8(Suppl.1), S123.
60. Friebe, W.-G.; Tibes, U.; Scheuer, W. (Roche Diagnostics GmbH) WO9915493, 1999.
61. Xiang, Y.; Bemis, J.; McKew, J.; Kaila, N. (Genetics Institute, Inc.) WO9808818, 1998.
62. Seehra, J.S.; McKew, J.C.; Lovering, F.; Bemis, J.E.; Xiang, Y.; Chen, L.; Knopf, J.L. (Genetics Institute, Inc.) WO9943654, 1999.
63. Drug Data Report 2004, 26, 226.
64. Teshirogi, I.; Matsutani, S.; Shirahase, K.; Fujii, Y.; Yoshida, T.; Tanaka, K.; Ohtani, M. J. Med. Chem. 1996, 39, 5183.
65. Ohtani, M.; Kato, T.; Hori, Y. (Shionogi & Co., Ltd.) EP0646569, 1995.
66. Yazawa, K.; Shinohara, Y.; Shinohara, T.; Kamimura, D.; Suenaga, K.; Yamada, K. (Sagami Chem. Res. Center) JP2000119292, 2000.
67. Edwards, P.D.; Bernstein, P.R. Med. Res. Rev. 1994, 14, 127.
68. Sanderson, P.E.J. Med. Res.Rev. 1999, 19, 179.
69. Trimble, L.A.; Street, I.P.; Perrier, H.; Tremblay, N.M.; Weech, P.K.; Bernstein, M.A. Biochemistry 1993, 32, 12560.
70. Risse, D.; Schulze Elfringhoff, A.; Lehr, M. J. Chromatogr. B, 2002, 769, 185.
71. Lehr, M. Arch. Pharm. Pharm. Med. Chem. 1996, 329, 386.
72. Griessbach, K.; Lehr, M. Pharm. Pharmacol. Commun. 1999, 5, 389.
73. Ackermann, E.; Conde-Frieboes, K.; Dennis, E.A. J. Biol. Chem. 1995, 270, 445.
74. Burke, J.R. Current Opinion Invest. Drugs 2001, 2, 1549.
75. Banville, J.; Johnson, G.; Zusi, F.; Burke, J. (Bristol-Myers Squibb Comp.) WO9915129, 1999.
76. Banville, J.; Marinier, A.; Gai, Y.; Plamondon, S.; Roy, S.; Balasubramanian, N. (Bristol-Myers Squibb Comp.) US6414179, 2002.
77. Lio, Y.-C.; Reynolds, L.J.; Balsinde, J.; Dennis, E.A. Biochim. Biophys. Acta 1996, 1302, 55.
78. Banner, B.L.; Weber, G.F. (Hoffmann-La Roche, Inc.) US5451600, 1995.
79. Lehr, M. J. Med. Chem. 1997, 40, 2694.
80. Lehr, M. J. Med. Chem. 1997, 40, 3381.
81. Lehr, M. (Merckle GmbH) WO9513266, 1995.
82. Lehr, M. (Merckle GmbH) WO98/05637, 1998
83. Lehr, M.; Klimt, M.; Schulze Elfringhoff, A. Bioorg. Med. Chem. Lett. 2001, 11, 2569.
84. McKew, J.C.; Lovering, F.; Clark, J.D.; Bemis, J.; Xiang, Y.; Shen, M.; Zhang, W.; Alvarez, J.C.; Joseph-McCarthy, D. Bioorg. Med. Chem. Lett. 2003, 13, 4501.
85. McKew, J.C.; Tam, S.Y.; Clark, J.D.; Lee, K.L.; Chen, L.; Thakker, P.; Sum, F.-W.; Behnke, M.L.; Hu, B. (Wyeth) WO03048122, 2003.
86. Walters, I.; Bennion, C.; Connolly, S.; Croshaw, P.J.; Hardy, K.; Hartopp, P.; Jackson, C.G.; King, S.J.; Lawrence, L.; Mete, A.; Murray, D; Robinson, D.H.; Stein, L.; Wells, E.; Withnall W. J. Bioorg. Med. Chem. Lett. 2004, 14, 3645.
87. Connolly, S.; Mete, A. (AstraZeneca) WO0034254, 2000.
88. Banville, J.; Remillard, R.; Balasubramanian, N.; Bouthillier, G.; Martel, A. (Bristol-Myers Squibb Comp.) US2002037875, 2002.
89. Lehr, M.; Ludwig, J. (Merckle, GmbH) WO2004069797, 2004.
90. Clemens, J.A.; Sofia, M.J.; Stephenson, D.T. (Eli Lilly & Co.) WO9517183, 1995.
91. Perrier, H.; Prasit, P.; Street, I.; Wang, Z. (Merck Frosst Canada, Inc.) US5453443, 1995.
92. Makita, A.; Isobe, Y.; Tomizawa, H.; Chiba, S.; Sasaki, M. (Japan Energy Corp.) JP2000038380, 2000.
93. Ohtani, M.; Kato, T. (Shionogi & Co., Ltd.) EP0675114, 1995.