Development of a fluorescent intensity assay amenable for high-throughput screening for determining 15-Lipoxygenase activity

Journal of Biomolecular Screening

Volumn 15, Issue 6, 2010, Pages 671-679

  Dahlström, Märta ^a   Forsström, Daniel ^a   Johannesson, Malin ^a   Huque Andersson, Yasmin ^a   Björk, Marie ^a,c   Silfverplatz, Erik ^a   Sanin, Andrei ^b   Schaal, Wesley ^b   Pelcman, Benjamin ^b   Forsell, Pontus K A ^a,d  

^a Vitro Pharmacology   (Sweden)

^b Pharmacia and Upjohn AB   (Sweden)

^c Devyser AB   (Sweden)

^d ASTRAZENECA R AND D   (Sweden)

Author keywords

15 lipoxygenase; arachidonic acid; cell based assay; cell based assays; lipid hydroperoxides; screening

Indexed keywords

ARACHIDONATE 15 LIPOXYGENASE; ANTIOXIDANT; DIPHENYL-1-PYRENYLPHOSPHINE; LIPID PEROXIDE; MOLECULAR LIBRARY; ORGANOPHOSPHORUS COMPOUND; PYRENE DERIVATIVE;

ANIMAL CELL; ARTICLE; CELL ASSAY; CONTROLLED STUDY; CYTOTOXICITY; ENZYME ACTIVATION; ENZYME ASSAY; FLUORESCENCE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IC 50; MOLECULAR CLONING; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN PURIFICATION; ANALYSIS; BIOASSAY; CHEMISTRY; DRUG EFFECTS; IC50; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; METABOLISM; MOLECULAR LIBRARY; OXIDATION REDUCTION REACTION; PHARMACOLOGY; PROCEDURES; REPRODUCIBILITY; TUMOR CELL LINE;

ANTIOXIDANTS; ARACHIDONATE 15-LIPOXYGENASE; BIOLOGICAL ASSAY; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; CLONING, MOLECULAR; ENZYME ASSAYS; FLUORESCENCE; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; INHIBITORY CONCENTRATION 50; LIPID PEROXIDES; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; PYRENES; REPRODUCIBILITY OF RESULTS; SMALL MOLECULE LIBRARIES;

EID: 77955809811     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057110373383     Document Type: Article

References (40)

1. Schneider C., Pratt D., Porter N., Brash A.: Control of oxygenation in lipoxygenase and cyclooxygenase catalysis. Chem Biol 2007 ; 14: 473-488.
2. Edgemond WS, Hillard CJ, Falck JR, Kearn CS, Campbell WB: Human platelets and polymorphonuclear leukocytes synthesize oxygenated derivatives of arachidonylethanolamide (anandamide): their affinities for cannabinoid receptors and pathways of inactivation. Mol Pharmacol 1998 ; 54: 180-188.
3. Moody J., Kozak K., Ji C., Marnett L.: Selective oxygenation of the endocannabinoid 2-arachidonylglycerol by leukocyte-type 12-lipoxygenase. Biochemistry. 2001 ; 40: 861-866. (Pubitemid 32108577)
4. Kozak KR, Gupta RA, Moody JS, Ji C., Boeglin WE, DuBois RN, et al. 15-Lipoxygenase metabolism of 2-arachidonylglycerol. J Biol Chem 2002 ; 277: 23278-23286.
5. Hampson A., Hill W., Zan-Phillips M., Makriyannis A., Leung E., Eglen R., et al. Anandamide hydroxylation by brain lipoxygenase:metabolite structures and potencies at the cannabinoid receptor. Biochim Biophys Acta 1995 ; 1259: 173-179.
6. Feltenmark S., Gautam N., Brunnstrom A., Griffiths W., Backman L., Edenius C., et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. PNAS 2008 ; 105: 680-685.
7. Claesson H., Griffiths W., Brunnstrom A., Schain F., Andersson E., Feltenmark S., et al. Hodgkin Reed-Sternberg cells express 15-lipoxygenase-1 and are putative producers of eoxins in vivo: novel insight into the inflammatory features of classical Hodgkin lymphoma. FEBS J 2008 ; 275: 4222-4234.
8. Claesson H-E.: On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma. Prostaglandins Other Lipid Mediat 2009 ; 89: 120-125.
9. Kuhn H., Walther M., Kuban R.: Mammalian arachidonate 15-lipoxygenases structure, function, and biological implications. Prostaglandins Other Lipid Mediat 2002 ;68- 69: 263-290.
10. Van Dyke TE, Serhan CN: Resolution of inflammation: a new paradigm for the pathogenesis of periodontal diseases. J Dent Res 2003 ; 82: 82-90.
11. Andersson CK, Claesson H-E., Rydell-Tormanen K., Swedmark S., Hallgren A., Erjefalt JS: Mice lacking 12/15-lipoxygenase have attenuated airway allergic inflammation and remodeling. Am J Respir Cell Mol Biol 2008 ; 39: 648-656.
12. Hajek A., Lindley A., Favoreto S., Carter R., Schleimer R., Kuperman D.: 12/15-Lipoxygenase deficiency protects mice from allergic airways inflammation and increases secretory IgA levels. J Allergy Clin Immunol 2008 ; 122: 633-639.
13. Liu C., Xu D., Liu L., Schain F., Brunnstrom A., Bjorkholm M., Claesson HE, Sjoberg J.: 15-Lipoxygenase-1 induces expression and release of chemokines in cultured human lung epithelial cells. Am J Physiol Lung Cell Mol Physiol 2009 ; 297: L196 - L203.
14. Kayama Y., Minamino T., Toko H., Sakamoto M., Shimizu I., Takahashi H., et al. Cardiac 12/15 lipoxygenase-induced inflammation is involved in heart failure. J Exp Med 2009 ; 206: 1565-1574.
15. Cornicelli J., Trivedi B.: 15-Lipoxygenase and its inhibition: a novel therapeutic target for vascular disease. Curr Pharm Des 1999 ; 5: 11-20.
16. Bocan T., Rosebury W., Mueller S., Kuchera S., Welch K., Daugherty A., et al. A specific 15-lipoxygenase inhibitor limits the progression and monocyte-macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit. Atherosclerosis 1998 ; 136: 203-216.
17. Zhao L., Pratico D., Rader D., Funk C.: 12/15-Lipoxygenase gene disruption and vitamin E administration diminish atherosclerosis and oxidative stress in apolipoprotein E deficient mice through a final common pathway. Prostaglandins Other Lipid Mediat 2005 ; 78 (1-4). 185-193.
18. Pratico D., Zhukareva V., Yao Y., Uryu K., Funk CD, Lawson JA, et al. 12/15-Lipoxygenase is increased in Alzheimers disease: possible involvement in brain oxidative stress. Am J Pathol 2004 ; 164: 1655-1662.
19. Vahsen S., Rakowski K., Ledwig D., Dietze-Schroeder D., Swifka J., Sasson S., et al. Altered GLUT4 translocation in skeletal muscle of 12/15-lipoxygenase knockout mice. Horm Metab Res 2006 ; 38: 391-396.
20. Xu Z., Li S., Lanting L., Kim Y., Shanmugam N., Reddy M., et al. Relationship between 12/15-lipoxygenase and COX-2 in mesangial cells: potential role in diabetic nephropathy. Kidney Int 2006 ; 69: 512-519.
21. van Leyen K., Arai K., Jin G., Kenyon V., Gerstner B., Rosenberg P., et al. Novel lipoxygenase inhibitors as neuroprotective reagents. J Neurosci Res 2008 ; 86: 904-909.
22. Kenyon V., Chorny I., Carvajal W., Holman T., Jacobson M.: Novel human lipoxygenase inhibitors discovered using virtual screening with homology models. J Med Chem 2006 ; 49: 1356-1363.
23. Brathe A., Gundersen L., Malterud K., Rise F.: 6-substituted purines as inhibitors of 15-lipoxygenase: a structure-activity study. Arch Pharm (Weinheim) 2005 ; 338: 159-166.
24. Gundersen L., Malterud K., Negussie A., Rise F., Teklu S., Ostby O.: Indolizines as novel potent inhibitors of 15-lipoxygenase. Bioorg Med Chem 2003 ; 11: 5409-5415.
25. Carroll J., Jonsson E., Ebel R., Hartman M., Holman T., Crews P.: Probing sponge-derived terpenoids for human 15-lipoxygenase inhibitors. J Org Chem 2001 ; 66: 6847-6851.
26. Sadeghian H., Seyedi S., Saberi M., Arghiani Z., Riazi M.: Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors. Bioorg Med Chem 2008 ; 16: 890-901.
27. Weinstein D., Liu W., Ngu K., Langevine C., Combs D., Zhuang S., et al. Discovery of selective imidazole-based inhibitors of mammalian 15-lipoxygenase: highly potent against human enzyme within a cellular environment. Bioorg Med Chem Lett 2007 ; 17: 5115-5120.
28. Sadeghian H., Attaran N., Jafari Z., Saberi M., Pordel M., Riazi M.: Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them. Bioorg Med Chem 2009 ; 17: 2327-2335.
29. Weinstein D., Liu W., Gu Z., Langevine C., Ngu K., Fadnis L., et al. Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase. Bioorg Med Chem Lett 2005 ; 15: 1435-1440.
30. Bakavoli M., Nikpour M., Rahimizadeh M., Saberi M., Sadeghian H.: Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives, as potent 15-lipoxygenase inhibitors. Bioorg Med Chem 2007 ; 15: 2120-2126.
31. Bakavoli M., Sadeghian H., Tabatabaei Z., Rezaei E., Rahimizadeh M., Nikpour M.: SAR comparative studies on pyrimido[4,5-b][1,4] benzothiazine derivatives as 15-lipoxygenase inhibitors, using ab initio calculations. J Mol Model 2008 ; 14: 471-478.
32. Schewe T., Sadik C., Klotz L., Yoshimoto T., Kuhn H., Sies H.: Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase. Biol Chem 2001 ; 382: 1687-1696.
33. Johannesson M., Backman L., Claesson H-E., Forsell PKA: Cloning, purification and characterization of non-human primate 12/15-lipoxygenases. Prostaglandins Leukot Essent Fatty Acids 2010 ; 82: 121-129.
34. Akasaka K., Ijichi S., Watanabe K., Ohrui H., Meguro H.: High-performance liquid chromatography and post-column derivatization with diphenyl-1- pyrenylphosphine for fluorimetric determination of triacylglycerol hydroperoxides. J Chromatogr 1992 ; 596: 197-202.
35. Ohshima T., Hopia A., German J., Frankel E.: Determination of hydroperoxides and structures by high-performance liquid chromatography with post-column detection with diphenyl-1-pyrenylphosphine. Lipids 1996 ; 31: 1091-1096.
36. Okimotoa Y., Watanabea A., Nikia E., Yamashitab T., Noguchia N.: A novel fluorescent probe diphenyl-1-pyrenylphosphine to follow lipid peroxidation in cell membranes. FEBS Lett 2000 ; 474: 137-140.
37. Takahashi M., Shibata M., Niki E.: Estimation of lipid peroxidation of live cells using a fluorescent probe, diphenyl-1-pyrenylphosphine. Free Radic Biol Med 2001 ; 31: 164-174.
38. Gavino VC, Miller JS, Ikharebha SO, Milo GE, Cornwell DG: Effect of polyunsaturated fatty acids and antioxidants on lipid peroxidation in tissue cultures. J Lipid Res 1981 ; 22: 763-769.
39. Zhang J-H., Chung TDY, Oldenburg KR: A simple statistical parameter for use in evaluation and validation of high throughput screening assays. J Biomol Screen 1999 ; 4: 67-73.
40. Kratky D., Lass A., Abuja P., Esterbauer H., Kuhn H.: A sensitive chemiluminescence method to measure the lipoxygenase catalyzed oxygenation of complex substrates. Biochim Biophys Acta 1999 ; 1437: 13-22.