Discovery of a novel activator of 5-lipoxygenase from an anacardic acid derived compound collection

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 24, 2013, Pages 7763-7778

  Wisastra, Rosalina ^a   Kok, Petra A M ^a   Eleftheriadis, Nikolaos ^a   Baumgartner, Matthew P ^b   Camacho, Carlos J ^b   Haisma, Hidde J ^a   Dekker, Frank J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

Author keywords

Allosteric binding; Anacardic acid; Cyclooxygenase 2; Enzyme kinetics; Human 5 lipoxygenase

Indexed keywords

1 (4 BROMOPHENYL)DECAN 1 ONE; 1 (BROMOMETHYL) 3 (HEPTYLOXY)BENZENE; 1 (BROMOMETHYL) 4 (HEPTYLOXY)BENZENE; 1 (BROMOMETHYL) 4 (NONYLOXY)BENZENE; 1 (BROMOMETHYL) 4 [(3,7 DIMETHYLOCTYL)OXY]BENZENE; 1 BROMO 4 DECYLBENZENE; 1(BROMOMETHYL) 4 (PENTYLOXY)BENZENE; 2 [[3 (HEPTYLOXY)BENZYL]OXY] 6 HYDROXYBENZOIC ACID; 2,2 DIMETHYL 5 [[4 (NONYLOXY)BENZYL]OXY] 4H BENZO[D][1,3]DIOXIN 4 ONE; 2,2 DIMETHYL 5 [[4 (PENTYLOXY)BENZYL]OXY]; 5 [[3 (HEPTYLOXY)BENZYL]OXY] 2,2 DIMETHYL 4H BENZO[D][1,3]DIOXIN 4 ONE; 5 [[4 (HEPTYLOXY)BENZYL]OXY] 2,2 DIMETHYL 4H BENZO[D][1,3]DIOXIN 4 ONE; 5 [[4 [(3,7 DIMETHYLOCTYL)OXY]BENZYL]OXY] 2,2 DIMETHYL 4H BENZO[D][1,3]DIOXIN 4 ONE; [(4 DECYLPHENYL)ETHYNYL]TRIMETHYLSILANE; [3 (HEPTYLOXY)PHENYL]METHANOL; [3 (ONYLOXY)PHENYL]METHANOL; [4 (HEPTYLOXY)PHENYL]METHANOL; [4 (NONYLOXY)PHENYL]METHANOL; [4 (PENTYLOXY)PHENYL]METHANOL; [4 [(3,7 DIMETHYLOCTYL)OXY]PHENYL]METHANOL; ANACARDIC ACID; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONIC ACID; BENZYL 2,4 BIS(BENZYLOXY) 6 [(4 DECYLPHENYL)ETHYNYL]BENZOATE; LINOLEIC ACID; POTASSIUM 2 [[4 (HEPTYLOXY)BENZYL]OXY] 6 HYDROXYBENZOATE; POTASSIUM 2 [[4 [(3,7 DIMETHYLOCTYL)OXY]BENZYL]OXY] 6 HYDROXYBENZOATE; POTASSIUM 2 HYDROXY 6 [[4 (NONLOXY)BENZYL]OXY]BENZOATE; POTASSIUM 2 HYDROXY 6 [[4 (PENTYLOXY)BENZYL]OXY]BENZOATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALLOSTERISM; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME REGULATION; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

ALLOSTERIC BINDING; ANACARDIC ACID; CYCLOOXYGENASE-2; ENZYME KINETICS; HUMAN 5-LIPOXYGENASE;

ANACARDIC ACIDS; ARACHIDONATE 5-LIPOXYGENASE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84888437158     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.10.015     Document Type: Article

References (55)

1. J. Martel-Pelletier, D. Lajeunesse, P. Reboul, and J. Pelletier Ann. Rheum. Dis. 62 2003 501
2. S.A. Gillmor, A. Villasenor, R. Fletterick, E. Sigal, and M.F. Browner Nat. Struct. Biol. 4 1997 1003
3. E. Sigal Am. J. Physiol. 260 1991 L13
4. N. Epp, G. Fürstenberger, K. Müller, S. de Juanes, M. Leitges, I. Hausser, F. Thieme, G. Liebisch, G. Schmitz, and P. Krieg J. Cell Biol. 177 2007 173
5. K.N. Ikei, J. Yeung, P.L. Apopa, J. Ceja, J. Vesci, T.R. Holman, and M. Holinstat J. Lipid Res. 53 2012 2546
6. J.A. Hunter, W.E. Finkbeiner, J.A. Nadel, E.J. Goetzl, and M.J. Holtzman Proc. Natl. Acad. Sci. 82 1985 4633
7. J.A. Nadel, D.J. Conrad, I.F. Ueki, A. Schuster, and E. Sigal J. Clin. Invest. 87 1991 1139
8. A.R. Brash, W.E. Boeglin, and M.S. Chang Proc. Natl. Acad. Sci. 94 1997 6148
9. C.D. Brown, I. Kilty, M. Yeadon, and S. Jenkinson Inflamm. Res. 50 2001 321
10. P. Chanez, C. Bonnans, C. Chavis, and I. Vachier Am. J. Respir. Cell Mol. Biol. 27 2002 655
11. H.W. Chu, S. Balzar, J.Y. Westcott, J.B. Trudeau, Y. Sun, D.J. Conrad, and S.E. Wenzel Clin. Exp. Allergy 32 2002 1558
12. V.R. Shannon, P. Chanez, J. Bousquet, and M.J. Holtzman Am. Rev. Respir. Dis. 147 1993 1024
13. Y. Piao, Y. Du, H. Oshima, J. Jin, M. Nomura, T. Yoshimoto, and M. Oshima Carcinogenesis 29 2008 440
14. E. Rásó, B. Döme, B. Somlai, A. Zacharek, W. Hagmann, K.V. Honn, and J. Tímár Melanoma Res. 14 2004 245
15. S. Gupta, M. Srivastava, N. Ahmad, K. Sakamoto, D.G. Bostwick, and H. Mukhtar Cancer 91 2001 737
16. L.G. Melstrom, D.J. Bentrem, M.R. Salabat, T.J. Kennedy, X. Ding, M. Strouch, S.M. Rao, R.C. Witt, C.A. Ternent, M.S. Talamonti, R.H. Bell, and T.A. Adrian Clin. Cancer Res. 14 2008 6525
17. N. Nathoo, R.A. Prayson, J. Bondar, L. Vargo, S. Arrigain, E.J. Mascha, J.H. Suh, G.H. Barnett, and M. Golubic Neurosurgery 58 2006 347
18. J. Wilborn, M. Bailie, M. Coffey, M. Burdick, R. Strieter, and M. Peters-Golden J. Clin. Invest. 97 1996 1827
19. L.Y. Zou J. Cancer Mol. 2 2006 227
20. C.N. Serhan, N. Chiang, and T.E. Van Dyke Nat. Rev. Immunol. 8 2008 349
21. C. Edenius, J. Haeggström, and J.Å. Lindgren Biochem. Biophys. Res. Commun. 157 1988 801
22. A. Hashimoto, I. Hayashi, Y. Murakami, Y. Sato, H. Kitasato, R. Matsushita, N. Iizuka, K. Urabe, M. Itoman, S. Hirohata, and H. Endo J. Rheumatol. 34 2007 2144
23. M. Sobrado, M.P. Pereira, I. Ballesteros, O. Hurtado, D. Fernández-López, J.M. Pradillo, J.R. Caso, J. Vivancos, F. Nombela, J. Serena, I. Lizasoain, and M.A. Moro J. Neurosci. 29 2009 3875
24. F.M. Matschinsky Nat. Rev. Drug Disc. 8 2009 399
25. W.L. Smith, D.L. DeWitt, and R.M. Garavito Annu. Rev. Biochem. 69 2000 145
26. G.D. Anderson, S.D. Hauser, K.L. McGarity, M.E. Bremer, P.C. Isakson, and S. Gregory J. Clin. Invest. 97 1996 2672
27. B.K. Reuter, S. Asfaha, A. Buret, K.A. Sharkey, and J.L. Wallace J. Clin. Invest. 98 1996 2076
28. J. Hendel, and O.H. Nielsen Am. J. Gastroenterol. 92 1997 1170
29. S.L. Kargman, G.P. O'Neill, P.J. Vickers, J.F. Evans, J.A. Mancini, and S. Jothy Cancer Res. 55 1995 2556
30. F. Cianchi, C. Cortesini, P. Bechi, O. Fantappiè, L. Messerini, A. Vannacci, I. Sardi, G. Baroni, V. Boddi, R. Mazzanti, and E. Masini Gastroenterology 121 2001 1339
31. R. Wisastra, M. Ghizzoni, A. Boltjes, H.J. Haisma, and F.J. Dekker Bioorg. Med. Chem. 20 2012 5027
32. A.R. Brash J. Biol. Chem. 274 1999 23679
33. M. Ghizzoni, A. Boltjes, C.d. Graaf, H.J. Haisma, and F.J. Dekker Bioorg. Med. Chem. 18 2010 5826
34. M. Ghizzoni, J. Wu, T. Gao, H.J. Haisma, F.J. Dekker, and Y. George Zheng Eur. J. Med. Chem. 47 2012 337
35. M. Uchiyama, H. Ozawa, K. Takuma, Y. Matsumoto, M. Yonehara, K. Hiroya, and T. Sakamoto Org. Lett. 8 2006 5517
36. D.C. Harrowven, T. Woodcock, and P.D. Howes Angew. Chem., Int. Ed. 44 2005 3899
37. P. Sista, H. Nguyen, J.W. Murphy, J. Hao, D.K. Dei, K. Palaniappan, J. Servello, R.S. Kularatne, B.E. Gnade, B. Xue, P.C. Dastoor, M.C. Biewer, and M.C. Stefan Macromolecules 43 2010 8063
38. S. Tranchimand, T. Tron, C. Gaudin, and G. Iacazio Synth. Commun. 36 2006 587
39. D.F. Back, G. Manzoni de Oliveira, M.A. Ballin, and V.A. Corbellini Inorg. Chim. Acta 363 2010 807
40. M.J. Gibian, and R.A. Galaway Biochemistry 15 1976 4209
41. T.J. Ha, and I. Kubo J. Agric. Food Chem. 53 2005 4350
42. R.A. Copeland, J.M. Williams, J. Giannaras, S. Nurnberg, M. Covington, D. Pinto, S. Pick, and J.M. Trzaskos Proc. Natl. Acad. Sci. 91 1994 11202
43. J. Verhagen, J.F. Vliegenthart, and J. Boldingh Chem. Phys. Lipids 22 1978 255
44. V. Leskovac Compr. Enzyme Kinet. 2004 111
45. N.C. Gilbert, S.G. Bartlett, M.T. Waight, D.B. Neau, W.E. Boeglin, A.R. Brash, and M.E. Newcomer Science 331 2011 217
46. N.C. Gilbert, Z. Rui, D.B. Neau, M.T. Waight, S.G. Bartlett, W.E. Boeglin, A.R. Brash, and M.E. Newcomer FASEB J. 26 2012 3222
47. The pymol Molecular Graphics System, Version 1.5.0.4. Schödinger LLC.
48. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605
49. K.S. Lee, S.R. Kim, H.S. Park, S.J. Park, K.H. Min, K.Y. Lee, S.M. Jin, and Y.C. Lee J. Allergy Clin. Immunol. 119 2007 141
50. F. Okamoto, K. Saeki, H. Sumimoto, S. Yamasaki, and T. Yokomizo J. Biol. Chem. 285 2010 41113
51. C. Thompson, A. Cloutier, Y. Bossé, C. Poisson, P. Larivée, P.P. McDonald, J. Stankova, and M. Rola-Pleszczynski J. Biol. Chem. 283 2008 1974
52. A. Deb, S.J. Haque, T. Mogensen, R.H. Silverman, and B.R.G. Williams J. Immunol. 166 2001 6170
53. J. Boström, J.R. Greenwood, and J. Gottfries J. Mol. Graph. Model. 21 2003 449
54. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson J. Comput. Chem. 30 2009 2785
55. D.R. Koes, M.P. Baumgartner, and C.J. Camacho J. Chem. Inf. Model. 53 2013 1893