Pitfalls in the use of arachidonic acid oxidation products to assign lipoxygenase activity in cancer cells

Free Radical Research

Volumn 43, Issue 10, 2009, Pages 951-956

  Niknami, Marzieh ^a   Dong, Qihan ^a   Witting, Paul K ^b,c  

^a UNIVERSITY OF SYDNEY   (Australia)

^b ANZAC Research Institute   (Australia)

^c University of Sydney   (Australia)

Author keywords

Arachidonic acid; Eicosanoid; Lipid oxidation; Regiochemistry; Stereochemistry

Indexed keywords

ARACHIDONIC ACID; ICOSANOID; LIPOXYGENASE;

ARTICLE; CANCER CELL; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; ISOMER; ISOMERISM; LIPID OXIDATION; PROSTATE CANCER; STEREOCHEMISTRY;

ARACHIDONIC ACID; CELL GROWTH PROCESSES; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; EICOSANOIDS; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; LIPOXYGENASE; MALE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PROSTATIC NEOPLASMS; STEREOISOMERISM;

EID: 70450250187     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760903145013     Document Type: Article

References (37)

1. Stocker R, Keaney Jr JF. Role of oxidative modifications in atherosclerosis. Physiol Rev 2004;84:1381-1478.
2. Marnett LJ, Honn KV. Overview of articles on eicosanoids and cancer. Cancer Metas Rev 1994;13:237-239.
3. Pidgeon GP, Lysaght J, Krishnamoorthy S, Reynolds JV, O'Byrne K, Nie D, Honn KV. Lipoxygenase metabolism: roles in tumor progression and survival. Cancer Metas Rev 2007;26:503-524.
4. Patel MI, Kurek C, Dong Q. The arachidonic acid pathway and its role in prostate cancer development and progression. J Urol 2008;179:1668-1675.
5. Pidgeon GP, Kandouz M, Meram A, Honn KV. Mechanisms controlling cell cycle arrest and induction of apoptosis after 12-lipoxygenase inhibition in prostate cancer cells. Cancer Res 2002;62:2717-2721.
6. Tong WG, Ding XZ, Adrian TE. The mechanisms of lipoxygenase inhibitor-induced apoptosis in human breast cancer cells. Biochem Biophys Res Commun 2002;296:942-948.
7. Faas FH, Dang AQ, Pollard M, Hong XM, Fan K, Luckert PH, Schutz M. Increased phospholipid fatty acid remodeling in human and rat prostatic adenocarcinoma tissues. J Urol 1996;156:243-248.
8. Hong J, Bose M, Ju J, Ryu JH, Chen X, Sang S, Lee MJ, Yang CS. Modulation of arachidonic acid metabolism by curcumin and related beta-diketone derivatives: effects on cytosolic phospholipase A(2), cyclooxygenases and 5-lipoxygenase. Carcinogenesis 2004;25:1671-1679.
9. Nony PA, Kennett SB, Glasgow WC, Olden K, Roberts JD. 15S-Lipoxygenase-2 mediates arachidonic acid-stimulated adhesion of human breast carcinoma cells through the activation of TAK1, MKK6, and p38 MAPK. J Biol Chem 2005;280:31413-31419.
10. Shappell SB, Boeglin WE, Olson SJ, Kasper S, Brash AR. 15-Lipoxygenase-2 (15-LOX-2) is expressed in benign prostatic epithelium and reduced in prostate adenocarcinoma. Am J Pathol 1999;155:235-245.
11. Shappell SB, Gupta RA, Manning S, Whitehead R, Boeglin WE, Schneider C, Case T, Price J, Jack GS, Wheeler TM, Matusik RJ, Brash AR, Dubois RN. 15 s-Hydroxyeicosate-traenoic acid activates peroxisome proliferator-activated receptor gamma and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res 2001;61:497-503.
12. Kaduce TL, Fang X, Harmon SD, Oltman CL, Dellsperger KC, Teesch LM, Gopal VR, Falck JR, Campbell WB, Weintraub NL, Spector AA. 20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells. J Biol Chem 2004;279:2648-2656.
13. Pommery J, Pommery N, Henichart JP. Modification of eicosanoid profile in human blood treated by dual COX/ LOX inhibitors. Prost Leuko Essent Fatty Acids 2005;73:411-417.
14. Upston JM, Witting PK, Brown AJ, Stocker R, Keaney JF Jr. Effect of vitamin E on aortic lipid oxidation and intimal proliferation after arterial injury in cholesterol-fed rabbits. Free Radic Biol Med 2001;31:1245-1253.
15. Rayner BS, Stocker R, Lay PA, Witting PK. Regio-and stereo-chemical oxidation of linoleic acid by human myoglobin and hydrogen peroxide: Tyr(103) affects rate and product distribution. Biochem J 2004;381:365-372.
16. Upston JM, Neuzil J, Witting PK, Alleva R, Stocker R. Oxidation of free fatty acids in low density lipoprotein by 15-lipoxygenase stimulates nonenzymic, alpha-tocopherol-mediated peroxidation of cholesteryl esters. J Biol Chem 1997;272:30067-30074.
17. Chamulitrat W, Mason RP. Lipid peroxyl radical intermediates in the peroxidation of polyunsaturated fatty acids by lipoxygenase. Direct electron spin resonance investigations. J Biol Chem 1989;264:20968-20973.
18. Sved P, Scott KF, McLeod D, King N, Singh J, Tsatralis T, Nikolov B, Boulas J, Nallan L, Gelb MH, Sajinovic M, Russell P, Dong Q. Oncogenic action of secreted phospholipase A2 in prostate cancer. Cancer Res 2004;64:6934-6940.
19. Yue H, Jansen SA, Strauss KI, Borenstein MR, Barbe MF, Rossi LJ, Murphy E. A liquid chromatography/mass spectro-metric method for simultaneous analysis of arachidonic acid and its endogenous eicosanoid metabolites prostaglandins, dihydroxyeicosatrienoic acids, hydroxyeicosatetraenoic acids, and epoxyeicosatrienoic acids in rat brain tissue. J Pharm Biomed Anal 2007;43:1122-1134.
20. Berg C, Hammarstrom S, Herbertsson H, Lindstrom E, Svensson AC, Soderstrom M, Tengvall P, Bengtsson T. Platelet-induced growth of human fibroblasts is associated with an increased expression of 5-lipoxygenase. Thromb Haemost 2006;96:652-659.
21. Espada CE, Berra MA, Martinez MJ, Eynard AR, Pasqualini ME. Effect of Chia oil (Salvia Hispanica) rich in ra-3 fatty acids on the eicosanoid release, apoptosis and T-lymphocyte tumor infiltration in a murine mammary gland adenocarcinoma. Prost Leuko Essent Fatty Acids 2007;77:21-28.
22. Ma KF, Yang HY, Chen Z, Qi LY, Zhu DY, Lou YJ. Enhanced expressions and activations of leukotriene C4 synthesis enzymes in D-galactosamine/ lipopolysacchar-ide-induced rat fulminant hepatic failure model. World J Gastroenterol 2008;14:2748-2756.
23. Shappell SB, Boeglin WE, Olson SJ, Kasper S, Brash AR. 15-lipoxygenase-2 (15-LOX-2) is expressed in benign prostatic epithelium and reduced in prostate adenocarcinoma. Am J Pathol 1999;155:235-245.
24. Gugliucci A, Ranzato L, Scorrano L, Colonna R, Petronilli V, Cusan C, Prato M, Mancini M, Pagano F, Bernardi P. Mitochondria are direct targets of the lipoxygenase inhibitor MK886. A strategy for cell killing by combined treatment with MK886 and cyclooxygenase inhibitors. J Biol Chem 2002l;277:31789-31795.
25. Anderson KM, Seed T, Alrefai W, Ou D, Harris JE. NTBN, a free radical spin trap induces programmed cell death in human pancreatic cancer (PANC-1) cells. Anticancer Res 1998;18:3213-3222.
26. Ou D, Bonomi P, Jao W, Jadko S, Harris JE, Anderson KM. The mode of cell death in H-358 lung cancer cells cultured with inhibitors of 5-lipoxygenase or the free radical spin trap, NTBN. Cancer Let 2001;166:223-231.
27. Heydeck D, Upston JM, Viita H, Yla-Herttuala S, Stocker R. Oxidation of LDL by rabbit and human 15-lipoxygenase: prevalence of nonenzymatic reactions. J Lipid Res 2001;42:1082-1088.
28. Kuhn H, Chaitidis P, Roffeis J, Walther M. Arachidonic acid metabolites in the cardiovascular system: the role of lipoxygenase isoforms in atherogenesis with particular emphasis on vascular remodeling. J Cardiovasc Pharm 2007;50:609-620.
29. Kuhn H, Heydeck D, Hugou I, Gniwotta C. In vivo action of 15-lipoxygenase in early stages of human atherogenesis. J Clin Invest 1997;99:888-893.
30. Deems R, Buczynski MW, Bowers-Gentry R, Harkewicz R, Dennis EA. Detection and quantitation of eicosanoids via high performance liquid chromatography-electrospray ioniza-tion-mass spectrometry. Methods Enzymol 2007;432:59-82.
31. Blewett AJ, Varma D, Gilles T, Libonati JR, Jansen SA. Development and validation of a high-performance liquid chromatography-electrospray mass spectrometry method for the simultaneous determination of 23 eicosanoids. J Pharm Biomed Anal 2008;46:653-662.
32. Chiaro CR, Patel RD, Perdew GH. 12(R)-Hydroxy-5(Z),8(Z),10(E),14(Z)- eicosatetraenoic acid
33. [12(R)-HETE], an arachidonic acid derivative, is an activator of the aryl hydrocarbon receptor. Mol Pharmacol 2008;74:1649-1656.
34. Ciccoli R, Sahi S, Singh S, Prakash H, Zafiriou MP, Ishdorj G, Kock JL, Nigam S. Oxygenation by COX-2 (cyclo-oxygenase-2) of 3-HETE (3-hydroxy- eicosatetraenoic acid), a fungal mimetic of arachidonic acid, produces a cascade of novel bioactive 3-hydroxyeicosanoids. Biochem J 2005; 390:737-747.
35. Schneider C, Brash AR. Lipoxygenase-catalyzed formation of R-configuration hydroperoxides. Prostaglandins Other Lipid Mediat 2002;68-69:291-301.
36. Frohberg P, Drutkowski G, Wobst I. Monitoring eicosanoid biosynthesis via lipoxygenase and cyclooxygenase pathways in human whole blood by single HPLC run. J Pharm Biomed Anal 2006;41:1317-1324.
37. Somvanshi RK, Singh AK, Saxena M, Mishra B, Dey S. Development of novel peptide inhibitor of Lipoxygenase based on biochemical and BIAcore evidences. Biochim Biophys Acta 2008;1784:1812-1817.