Omega-3 N-acylethanolamines are endogenously synthesised from omega-3 fatty acids in different human prostate and breast cancer cell lines

Prostaglandins Leukotrienes and Essential Fatty Acids

Volumn 85, Issue 6, 2011, Pages 305-310

  Brown, I ^a   Wahle, K W J ^a,b   Cascio, M G ^a   Smoum Jaouni, R ^c   Mechoulam, R ^c   Pertwee, R G ^a   Heys, S D ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Breast cancer; Endocannabinoid; N 3 PUFA; N acylethanolamine; Prostate cancer

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; DOCOSAHEXAENOYL ETHANOLAMIDE; EICOSAPENTAENOYL ETHANOLAMIDE; ENDOCANNABINOID; OMEGA 3 FATTY ACID; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MALE; PRIORITY JOURNAL; PROSTATE CANCER; TANDEM MASS SPECTROMETRY;

AMIDOHYDROLASES; BREAST NEOPLASMS; CELL LINE, TUMOR; ENDOCANNABINOIDS; ETHANOLAMINES; FATTY ACIDS, OMEGA-3; FEMALE; HUMANS; MALE; PROSTATIC NEOPLASMS; TANDEM MASS SPECTROMETRY;

EID: 80055068558     PISSN: 09523278     EISSN: 15322823     Source Type: Journal    
DOI: 10.1016/j.plefa.2011.09.007     Document Type: Article

References (23)

1. Gomez del Pulgar T., Velasco G., Guzman M. The CB1 cannabinoid receptor is coupled to the activation of protein kinase B/Akt. Biochem. J. 2000, 347:369-373.
2. Sarfaraz S., Afaq F., Adhami V.M., Malik A., Mukhtar H. Cannabinoid receptor agonist-induced apoptosis of human prostate cancer cells LNCaP proceeds through sustained activation of ERK1/2 leading to G1 cell cycle arrest. J. Biol. Chem. 2006, 281:39480-39491.
3. De Petrocellis L., Melck D., Palmisano A., Bisogno T., Laezza C., Bifulco M., Di Marzo V. The endogenous cannabinoid anandamide inhibits human breast cancer cell proliferation. Proc. Natl. Acad. Sci. U.S.A 1998, 95:8375-8380.
4. Mimeault M., Pommery N., Wattez N., Bailly C., Henichart J.P. Anti-proliferative and apoptotic effects of anandamide in human prostatic cancer cell lines: implication of epidermal growth factor receptor down-regulation and ceramide production. Prostate 2003, 56:1-12.
5. Sarfaraz S., Afaq F., Adhami V.M., Mukhtar H. Cannabinoid receptor as a novel target for the treatment of prostate cancer. Cancer Res. 2005, 65:1635-1641.
6. Xu X., Liu Y., Huang S., Liu G., Xie C., Zhou J., Fan W., Li Q., Wang Q., Zhong D., Miao X. Overexpression of cannabinoid receptors CB1 and CB2 correlates with improved prognosis of patients with hepatocellular carcinoma. Cancer Genet. Cytogenet. 2006, 171:31-38.
7. Qamri Z., Preet A., Nasser M.W., Bass C.E., Leone G., Barsky S.H., Ganju R.K. Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer. Mol. Cancer. Ther. 2009, 8:3117-3129.
8. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992, 258:1946-1949.
9. Hussey H.J., Tisdale M.J. Effect of polyunsaturated fatty acids on the growth of murine colon adenocarcinomas in vitro and in vivo. Br. J. Cancer 1994, 70:6-10.
10. Kato T., Kolenic N., Pardini R.S. Docosahexaenoic acid (DHA), a primary tumor suppressive omega-3 fatty acid, inhibits growth of colorectal cancer independent of p53 mutational status. Nutr. Cancer 2007, 58:178-187.
11. Clarke R.G., Lund E.K., Latham P., Pinder A.C., Johnson I.T. Effect of eicosapentaenoic acid on the proliferation and incidence of apoptosis in the colorectal cell line HT29. Lipids 1999, 34:1287-1295.
12. Menendez J.A., Lupu R., Colomer R. Exogenous supplementation with omega-3 polyunsaturated fatty acid docosahexaenoic acid (DHA; 22:6n-3) synergistically enhances taxane cytotoxicity and downregulates Her-2/neu (c-erbB-2) oncogene expression in human breast cancer cells. Eur. J. Cancer Prev. 2005, 14:263-270.
13. Shaikh I.A., Brown I., Schofield A.C., Wahle K.W., Heys S.D. Docosahexaenoic acid enhances the efficacy of docetaxel in prostate cancer cells by modulation of apoptosis: the role of genes associated with the NF-kappaB pathway. Prostate 2008, 68:1635-1646.
14. Artmann A., Petersen G., Hellgren L.I., Boberg J., Skonberg C., Nellemann C., Hansen S.H., Hansen H.S. Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine. Biochim. Biophys. Acta 1781, 2008:200-212.
15. Berger A., Crozier G., Bisogno T., Cavaliere P., Innis S., Di Marzo V. Anandamide and diet: inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets. Proc. Natl. Acad. Sci. U.S.A 2001, 98:6402-6406.
16. Wood J.T., Williams J.S., Pandarinathan L., Janero D.R., Lammi-Keefe C.J., Makriyannis A. Dietary docosahexaenoic acid supplementation alters select physiological endocannabinoid-system metabolites in brain and plasma. J. Lipid Res. 2010, 51:1416-1423.
17. Schmid P.C., Wold L.E., Krebsbach R.J., Berdyshev E.V., Schmid H.H. Anandamide and other N-acylethanolamines in human tumors. Lipids 2002, 37:907-912.
18. Balvers M.G., Verhoeckx K.C., Plastina P., Wortelboer H.M., Meijerink J., Witkamp R.F. Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. Biochim. Biophys. Acta 1801, 2010:1107-1114.
19. Brown I., Cascio M.G., Wahle K.W., Smoum R., Mechoulam R., Ross R.A., Pertwee R.G., Heys S.D. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 2010, 31:1584-1591.
20. Kozak K.R., Crews B.C., Morrow J.D., Wang L.H., Ma Y.H., Weinander R., Jakobsson P.J., Marnett L.J. Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J. Biol. Chem. 2002, 277:44877-44885.
21. Joosten M.M., Balvers M.G., Verhoeckx K.C., Hendriks H.F., Witkamp R.F. Plasma anandamide and other N-acylethanolamines are correlated with their corresponding free fatty acid levels under both fasting and non-fasting conditions in women. Nutr. Metab. (London) 2010, 7:49.
22. Burns T., Maciejewski S.R., Hamilton W.R., Zheng M., Mooss A.N., Hilleman D.E. Effect of omega-3 fatty acid supplementation on the arachidonic acid:eicosapentaenoic acid ratio. Pharmacotherapy 2007, 27:633-638.
23. Shaikh I.A., Brown I., Wahle K.W., Heys S.D. Enhancing cytotoxic therapies for breast and prostate cancers with polyunsaturated fatty acids. Nutr. Cancer 2010, 62:284-296.