Inhibition of 5-oxo-6,8,11,14-eicosatetraenoic acid-induced activation of neutrophils and eosinophils by novel indole oxe receptor antagonists

Journal of Medicinal Chemistry

Volumn 57, Issue 2, 2014, Pages 364-377

  Gore, Vivek ^b,c   Gravel, Sylvie ^a   Cossette, Chantal ^a   Patel, Pranav ^b,c   Chourey, Shishir ^b   Ye, Qiuji ^b   Rokach, Joshua ^b   Powell, William S ^a  

^a MCGILL UNIVERSITY   (Canada)

^b Florida Institute of Technology ^*  (United States)

^c Navinta LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 BIS(IODOMETHYL)CYCLOPROPANE; 2 [1[2 (2 HEXYL 1H INDOL 1 YL) 2 OXOETHYL]CYCLOPROPYL]ACETIC ACID; 2,2' (CYCLOPROPANE 1,1 DIYL)DIACETIC ACID; 2,2' (CYCLOPROPANE 1,1 DIYL)DIACETONITRILE; 4 (2 HEXYL INDOL 1 YL) 4 OXO BUTYRIC ACID; 5 (2 HEX 1 ENYL INDOL 1 YL) 5 OXO PENTANOIC ACID; 5 (2 HEXYL 1 INDOL 1 YL) 3 METHYL 5 OXOPENTANOIC ACID; 5 (2 HEXYL 1 INDOL 1 YL) 3,3 DIMETHYL 5 OXOPENTANOIC ACID; 5 (2 HEXYL 1 METHYL 1H INDOL 3 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (2 HEXYL 1 METHYL 1H INDOL 3 YL) 5 OXO PENTANOIC ACID; 5 (2 HEXYL 3 METHYL 1H INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (2 HEXYL 6 METHOXY 1H INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (5 BROMO 2 HEXYL 1 METHYL 1H INDOL 3 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (5 BROMO 2 HEXYL 1H INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (5 CHLORO 2 HEXYL 1 METHYL 1H INDOL 3 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (5 CHLORO 2 HEXYL 1 METHYL 1H NDOL 3 YL) 5 OXO PENTANOIC ACID; 5 (5 CHLORO 2 HEXYL 1H INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (6 BROMO 2 HEXYL 1H INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (6 CHLORO 2 HEXYL 1 METHYL 1H INDOL 3 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 (6 CHLORO 2 HEXYL INDOL 1 YL) 3 METHYL 5 OXO PENTANOIC ACID; 5 CHLORO 2 HEXYL 1 METHYL 1H INDOLE; 5 OXO 5 [2 (UNDEC 1 EN 1 YL) 1 INDOL 1 YL]PENTANOIC ACID; 5 OXO 6,8,11,14 ICOSATETRAENOIC ACID; 6 CHLORO 2 HEX 1 ENYL 1H INDOLE; 6 CHLORO 2 HEXYL 1H INDOLE; 6 OXASPIRO[2.5]OCTANE 5,7 DIONE; ARACHIDONIC ACID; DIMETHYL 2,2' (CYCLOPROPANE 1,1 DIYL)DIACETATE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACTIN POLYMERIZATION; ALLERGIC RHINITIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; ASTHMA; CALCIUM CELL LEVEL; CALCIUM MOBILIZATION; CHEMOTAXIS; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG METABOLISM; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; EOSINOPHIL; EOSINOPHIL ACTIVATION; GRANULOCYTE FUNCTION; LEUKOCYTE ACTIVATION; LIVER HOMOGENATE; MALE; MEDIATOR; NONHUMAN; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION;

ACTINS; ANIMALS; ARACHIDONIC ACIDS; CHEMOTAXIS, LEUKOCYTE; EOSINOPHILS; INDOLES; LIVER; MOLECULAR MIMICRY; NEUTROPHILS; POLYMERIZATION; RATS; RECEPTORS, EICOSANOID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84893029056     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401292m     Document Type: Article

References (36)

1. Haeggstrom, J. Z.; Funk, C. D. Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease Chem. Rev. 2011, 111, 5866-5898
2. Grant, G. E.; Rokach, J.; Powell, W. S. 5-Oxo-ETE and the OXE receptor Prostaglandins Other Lipid Mediators 2009, 89, 98-104
3. Powell, W. S.; Gravelle, F.; Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes J. Biol. Chem. 1992, 267, 19233-19241
4. Powell, W. S.; Gravelle, F.; Gravel, S. Phorbol myristate acetate stimulates the formation of 5-oxo-6,8,11,14-eicosatetraenoic acid by human neutrophils by activating NADPH oxidase J. Biol. Chem. 1994, 269, 25373-25380
5. Erlemann, K. R.; Rokach, J.; Powell, W. S. Oxidative stress stimulates the synthesis of the eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid by inflammatory cells J. Biol. Chem. 2004, 279, 40376-40384 (Pubitemid 39287625)
6. Graham, F. D.; Erlemann, K. R.; Gravel, S.; Rokach, J.; Powell, W. S. Oxidative stress-induced changes in pyridine nucleotides and chemoattractant 5-lipoxygenase products in aging neutrophils Free Radical Biol. Med. 2009, 47, 62-71
7. Nakamura, M.; Shimizu, T. Leukotriene receptors Chem. Rev. 2011, 111, 6231-6298
8. 2+ transients, actin reorganization, superoxide-anion production and receptor up-regulation Eur. J. Biochem. 1996, 236, 1003-1009
9. O'Flaherty, J. T.; Taylor, J. S.; Kuroki, M. The coupling of 5-oxo-eicosanoid receptors to heterotrimeric G proteins J. Immunol. 2000, 164, 3345-3352 (Pubitemid 30149000)
10. Powell, W. S.; MacLeod, R. J.; Gravel, S.; Gravelle, F.; Bhakar, A. Metabolism and biologic effects of 5-oxoeicosanoids on human neutrophils J. Immunol. 1996, 156, 336-342 (Pubitemid 26006981)
11. Powell, W. S.; Chung, D.; Gravel, S. 5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration J. Immunol. 1995, 154, 4123-4132
12. Muro, S.; Hamid, Q.; Olivenstein, R.; Taha, R.; Rokach, J.; Powell, W. S. 5-Oxo-6,8,11,14-eicosatetraenoic acid induces the infiltration of granulocytes into human skin J. Allergy Clin. Immunol. 2003, 112, 768-774 (Pubitemid 37260395)
13. Brink, C.; Dahlen, S. E.; Drazen, J.; Evans, J. F.; Hay, D. W.; Rovati, G. E.; Serhan, C. N.; Shimizu, T.; Yokomizo, T. International Union of Pharmacology XLIV. Nomenclature for the oxoeicosanoid receptor Pharmacol. Rev. 2004, 56, 149-157 (Pubitemid 38314582)
14. i/o J. Biol. Chem. 2002, 277, 31459-31465 (Pubitemid 34968946)
15. Jones, C. E.; Holden, S.; Tenaillon, L.; Bhatia, U.; Seuwen, K.; Tranter, P.; Turner, J.; Kettle, R.; Bouhelal, R.; Charlton, S.; Nirmala, N. R.; Jarai, G.; Finan, P. Expression and characterization of a 5-oxo-6 E,8 Z,11 Z,14 Z -eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils Mol. Pharmacol. 2003, 63, 471-477 (Pubitemid 36297316)
16. Takeda, S.; Yamamoto, A.; Haga, T. Identification of a G protein-coupled receptor for 5-oxo-eicosatetraenoic acid Biomed. Res. Tokyo 2002, 23, 101-108 (Pubitemid 41708460)
17. Iikura, M.; Suzukawa, M.; Yamaguchi, M.; Sekiya, T.; Komiya, A.; Yoshimura-Uchiyama, C.; Nagase, H.; Matsushima, K.; Yamamoto, K.; Hirai, K. 5-Lipoxygenase products regulate basophil functions: 5-oxo-ETE elicits migration, and leukotriene B(4) induces degranulation J. Allergy Clin. Immunol. 2005, 116, 578-585 (Pubitemid 41267131)
18. Sturm, G. J.; Schuligoi, R.; Sturm, E. M.; Royer, J. F.; Lang-Loidolt, D.; Stammberger, H.; Amann, R.; Peskar, B. A.; Heinemann, A. 5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent chemoattractant for human basophils J. Allergy Clin. Immunol. 2005, 116, 1014-1019 (Pubitemid 41571781)
19. Sarveswaran, S.; Ghosh, J. OXER1, a G protein-coupled oxoeicosatetraenoid receptor, mediates the survival-promoting effects of arachidonate 5-lipoxygenase in prostate cancer cells Cancer Lett. 2013, 336, 185-195
20. Grant, G. E.; Rubino, S.; Gravel, S.; Wang, X.; Patel, P.; Rokach, J.; Powell, W. S. Enhanced formation of 5-oxo-6,8,11,14-eicosatetraenoic acid by cancer cells in response to oxidative stress, docosahexaenoic acid and neutrophil-derived 5-hydroxy-6,8,11,14-eicosatetraenoic acid Carcinogenesis 2011, 32, 822-828
21. Powell, W. S.; Rokach, J. Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE Prog. Lipid Res. 2005, 44, 154-183 (Pubitemid 40733083)
22. O'Flaherty, J. T.; Cordes, J. F.; Lee, S. L.; Samuel, M.; Thomas, M. J. Chemical and biological characterization of oxo-eicosatetraenoic acids Biochim. Biophys. Acta 1994, 1201, 505-515
23. Patel, P.; Cossette, C.; Anumolu, J. R.; Gravel, S.; Lesimple, A.; Mamer, O. A.; Rokach, J.; Powell, W. S. Structural requirements for activation of the 5-oxo-6 E,8 Z,11 Z,14 Z -eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity J. Pharmacol. Exp. Ther. 2008, 325, 698-707 (Pubitemid 351574804)
24. Powell, W. S.; Gravel, S.; Khanapure, S. P.; Rokach, J. Biological inactivation of 5-oxo-6,8,11,14-eicosatetraenoic acid by human platelets Blood 1999, 93, 1086-1096 (Pubitemid 29067875)
25. Blättermann, S.; Peters, L.; Ottersbach, P. A.; Bock, A.; Konya, V.; Weaver, C. D.; Gonzalez, A.; Schroder, R.; Tyagi, R.; Luschnig, P.; Gab, J.; Hennen, S.; Ulven, T.; Pardo, L.; Mohr, K.; Gutschow, M.; Heinemann, A.; Kostenis, E. A biased ligand for OXE-R uncouples Ga and Gbg signaling within a heterotrimer Nature Chem. Biol. 2012, 8, 631-638
26. Gore, V.; Patel, P.; Chang, C. T.; Sivendran, S.; Kang, N.; Ouedraogo, Y. P.; Gravel, S.; Powell, W. S.; Rokach, J. 5-Oxo-ETE Receptor Antagonists J. Med. Chem. 2013, 56, 3725-3732
27. 3a-VI in human urine J. Lipid Res. 2006, 47, 2515-2524 (Pubitemid 44936113)
28. Huang, Z. H.; Hii, C. S.; Rathjen, D. A.; Poulos, A.; Murray, A. W.; Ferrante, A. N-6 and N-3 polyunsaturated fatty acids stimulate translocation of protein kinase Calpha, -betaI, -betaII and -epsilon and enhance agonist-induced NADPH oxidase in macrophages Biochem. J. 1997, 325 (Pt 2) 553-557
29. Serhan, C. N.; Petasis, N. A. Resolvins and protectins in inflammation resolution Chem. Rev. 2011, 111, 5922-5943
30. Blattermann, S.; Peters, L.; Ottersbach, P. A.; Bock, A.; Konya, V.; Weaver, C. D.; Gonzalez, A.; Schroder, R.; Tyagi, R.; Luschnig, P.; Gab, J.; Hennen, S.; Ulven, T.; Pardo, L.; Mohr, K.; Gutschow, M.; Heinemann, A.; Kostenis, E. A biased ligand for OXE-R uncouples Ga and Gbg signaling within a heterotrimer Nature Chem. Biol. 2012, 8, 631-638
31. Stamatiou, P. B.; Chan, C. C.; Monneret, G.; Ethier, D.; Rokach, J.; Powell, W. S. 5-Oxo-6,8,11,14-eicosatetraenoic acid stimulates the release of the eosinophil survival factor granulocyte-macrophage colony stimulating factor from monocytes J. Biol. Chem. 2004, 279, 28159-28164 (Pubitemid 38900090)
32. Böyum, A. Isolation of mononuclear cells and granulocytes from human blood. Isolation of mononuclear cells by one centrifugation, and of granulocytes by combining centrifugation and sedimentation at 1 g Scand. J. Clin. Lab. Invest. 1968, 21 (Suppl. 97) 77-89
33. Howard, T. H.; Oresajo, C. O. The kinetics of chemotactic peptide-induced change in F-actin content, F-actin distribution, and the shape of neutrophils J. Cell Biol. 1985, 101, 1078-1085 (Pubitemid 16258234)
34. Powell, W. S. Precolumn extraction and reversed-phase high-pressure liquid chromatography of prostaglandins and leukotrienes Anal. Biochem. 1987, 164, 117-131
35. Khanapure, S. P.; Shi, X. X.; Powell, W. S.; Rokach, J. Total synthesis of a potent proinflammatory 5-oxo-ETE and its 6,7-dihydro biotransformation product J. Org. Chem. 1998, 63, 337-342 (Pubitemid 128494078)
36. 4 Tetrahedron Lett. 1982, 23, 2631-2634