Formation and antiproliferative effect of prostaglandin E3 from eicosapentaenoic acid in human lung cancer cells

Journal of Lipid Research

Volumn 45, Issue 6, 2004, Pages 1030-1039

  Yang, Peiying ^a   Chan, Diana ^a   Felix, Edward ^a   Cartwright, Carrie ^a   Menter, David G ^a   Madden, Timothy ^a   Klein, Russell D ^b   Fischer, Susan M ^b   Newman, Robert A ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

3 fatty acids; Cell proliferation; Cyclooxygenase enzymes; Eicosanoid metabolism; Malignant cells

Indexed keywords

CELECOXIB; CYCLOOXYGENASE 2; FISH OIL; ICOSAPENTAENOIC ACID; PROSTAGLANDIN E3;

ARTICLE; CANCER CELL; CELL GROWTH; CELL PROLIFERATION; CELL STRAIN; CELL STRAIN A549; CONTROLLED STUDY; CYTOKINE PRODUCTION; HUMAN; HUMAN CELL; LUNG CANCER; PRIORITY JOURNAL; TUMOR CELL;

ALPROSTADIL; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLOOXYGENASE 2; DNA; EICOSAPENTAENOIC ACID; HUMANS; LUNG NEOPLASMS; MEMBRANE PROTEINS; MICROSCOPY, FLUORESCENCE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRAZOLES; SULFONAMIDES;

EID: 2542488133     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M300455-JLR200     Document Type: Article

References (35)

1. Dubois, R. N., S. B. Abramson, L. Crofford, R. A. Gupta, L. S. Simon, L. B. A. Van De Putte, and P. E. Lipsky. 1998. Cyclooxygenase in biology and disease. FASEB J. 12: 1063-1073.
2. Bartsch, H., J. Nair, and R. W. Owen. 1999. Dietary polyunsaturated fatty acids and cancers of the breast and colorectum: emerging evidence for their role as risk modifiers. Carcinogenesis. 20: 2209-2218.
3. Terry, P., P. Lichtenstein, M. Feychting, A. Ahlbom, and A. Wolk. 2001. Fatty fish consumption and risk of prostate cancer. Lancet. 357: 1764-1766.
4. Takezaki, T., K. Hirose, M. Inoue, N. Hamajima, Y. Yatabe, T. Mitsudomi, T. Sugiura, T. Kuroishi, and K. Tajima. 2001. Dietary factors and lung cancer risk in Japanese: with special reference to fish consumption and adenocarcinomas. Br. J. Cancer. 84: 1199-1206.
5. Zhang, J., E. H. Temme, and H. Kesteloot. 2000. Fish consumption is inversely associated with male lung cancer mortality in countries with high levels of cigarette smoking or animal fat consumption. Int. J. Epidemiol. 29: 615-621.
6. Rose, D. P., and J. M. Connolly. 1999. Omega-3 fatty acids as cancer chemopreventive agents. Pharmacol. Ther. 83: 218-238.
7. Needleman, P., A. Raz, M. S. Minkes, J. A. Ferrendelli, and H. Specher. 1979. Triene prostaglandins: prostacyclin and thromboxane biosynthesis and unique biological properties. Proc. Natl. Acad. Sci. USA. 23: 1005-1014.
8. Spector, A. A., T. L. Kaduce, P. H. Figard, K. C. Norton, J. C. Hoak, and R. L. Czervionke. 1983. Eicosapentaenoic acid and prostacyclin production by cultured human endothelial cells. J. Lipid Res. 24: 1595-1604.
9. Kulkarni, P. S., and B. D. Srinivasan. 1986. Eicosapentaenoic acid metabolism in human and rabbit anterior uvea. Prostaglandins. 31: 1158-1164.
10. 3 is formed in vivo in man after dietary eicosapentaenoic acid. Nature. 4: 743-755.
11. 3α are excreted in human urine after ingestion of n-3 polyunsaturated fatty acids. Biochim. Biophys. Acta. 963: 501-508.
12. 2 stimulate the growth of normal but not tumor mouse mammary epithelial cells: evidence for alterations in the signaling pathways in tumor cells. Prostaglandins Leukot. Essent. Fatty Acids. 51: 437-443.
13. Bagga, D., L. Wang, R. Farias-Eisner, J. A. Glaspy, and S. T. Reddy. 2003. Differential effects of prostaglandin derived from ω-6 and ω-3 polyunsaturated fatty acids on COX-2 expression and IL-6 secretion. Proc. Natl. Acad. Sci. USA. 100: 1751-1756.
14. Hasturk, S., B. Kemp, S. K. Kalapurakal, J. M. Kurie, W. K. Honh, and J. S. Lee. 2002. Expression of cyclooxygenase-1 and cyclooxygenase-2 in bronchial epithelium and nonsmall cell lung carcinoma. Cancer. 94: 1023-1031.
15. Yang, P., E. Felix, T. Madden, S. M. Fischer, and R. A. Newman. 2002. Quantitative high-performance liquid chromatography/electrospray ionization tandem mass spectrometric analysis of 2- and 3-series prostaglandins in cultured tumor cells. Anal. Biochem. 308: 168-177.
16. 2 transactivates EGF receptors: a novel mechanism for promoting colon cancer growth and gastrointestinal hypertrophy. Nat. Med. 8: 289-293.
17. Culp, B. R., B. G. Titus, and W. E. M. Lands. 1979. Inhibition of prostaglandin biosynthesis by eicosapentaenoic acid. Prostaglandins Med. 3: 269-278.
18. de Bravo, M. G., R. J. de Antuneo, J. Toledo, M. E. De Tomas, O. F. Mercuri, and C. Quintans. 1991. Effects of an eicosapentaenoic and docosahexaenoic acid concentrate on a human lung carcinoma grown in nude mice. Lipids. 26: 866-870.
19. Aronson, W. J., J. A. Glaspy, S. T. Reddy, D. Reese, D. Heber, and D. Bagga. 2001. Modulation of omega-3/omega-6 polyunsaturated ratios with dietary fish oils in men with prostate cancer. Urology. 58: 283-288.
20. Dohadwala, M., J. Luo, L. Zhu, Y. Lin, G. J. Dougherty, S. Sharma, M. Huang, M. Pold, R. K. Batra, and S. M. Dubinett. 2001. Non-small cell lung cancer cyclooxygenase-2-dependent invasion is mediated by CD44. J. Biol. Chem. 276: 20809-20812.
21. Laneuville, O., D. K. Brener, N. Xu, Z. H. Huang, D. A. Gage, L. T. Waston, M. Lagarde, D. L. DeWitt, and W. L. Smith. 1995. Fatty acid substrate specificities of human prostaglandin-endoperoxide H synthase-1 and -2. J. Biol. Chem. 270: 19330-19336.
22. Meade, E. A., W. L. Smith, and D. L. DeWitt. 1993. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J. Biol. Chem. 268: 6610-6614.
23. Smith, C. J., Y. Zhang, C. M. Koboldt, J. Muhannad, B. S. Zweifel, A. Shaffer, J. J. Talley, J. L. Masferrer, K. Seibert, and P. C. Isakson. 1998. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc. Natl. Acad. Sci. USA. 95: 13313-13318.
24. Tapiero, H., G. Nguyen Ba, P. Couvreur, and K. D. Tew. 2002. Polyunsaturated fatty acids (PUFA) and eicosanoids in human health and pathologies. Biomed. Pharmacother. 56: 215-222.
25. Prescott, S. M., and F. A. Fitzpatrick. 2000. Cyclooxygenase and carcinogenesis. Biochim. Biophys. Acta. 1470: M69-M78.
26. Belury, M. A., K. E. Patrick, M. Locniskar, and S. M. Fischer. 1989. Eicosapentaenoic and arachidonic acid: comparison of metabolism and activity in murine epidermal cells. Lipids. 24: 423-429.
27. 3. Prostaglandins. 18: 423-438.
28. 2 regulation of cyclooxygenase expression in keratinocytes is mediated via cyclic nucleotide-linked prostaglandin receptors. J. Lipid Res. 41: 873-881.
29. Lo, C., K. C. Chiu, M. Fu, R. Lo, and S. Helton. 1999. Fish oil augments macrophage cyclooxygenase II (COX-2) gene expression induced by endotoxin. J. Surg. Res. 86: 103-107.
30. Hardman, W. E. 2002. Omega-3 fatty acids to augment cancer therapy. J. Nutr. 132 (Suppl.): 3508-3512.
31. Rao, C. V., Y. Hirose, C. Indranie, and B. S. Reddy. 2001. Modulation of experimental colon tumorigenesis by type and amounts of dietary fatty acids. Cancer Res. 61: 1927-1933.
32. Kempen, E. C., P. Yang, E. Felix, T. Madden, and R. A. Newman. 2001. Simultaneous quantification of arachidonic acid metabolites in cultured tumor cells using high-performance liquid chromatogoraphy/electrospray ionization tandem mass spectrometry. Anal. Biochem. 297: 183-190.
33. Chapkin, R. S., M. Y. Hong, Y. Y. Fan, L. A. Davidson, L. M. Sanders, C. E. Herderson, R. Barhoumi, R. C. Burghardt, N. D. Turner, and J. R. Lupton. 2002. Dietary n-3 PUFA alter colonocyte mitochondrial membrane composition and function. Lipids. 37: 193-199.
34. 2 increases growth and motility of colorectal carcinoma cells. J. Biol. Chem. 276: 18075-18081.
35. Okuyama, T., S. Ishihara, H. Sato, M. A. K. Rumi, K. Kawashima, Y. Miyaoka, H. Suetsugu, H. Kazumori, C. F. Ortega Cava, Y. Kodowaki, R. Fuhuda, and Y. Kinoshita. 2002. Activation of prostaglandin E2-receptor EP2 and EP4 pathways induces growth inhibition in human gastric carcinoma cell lines. J. Lab. Clin. Med. 140: 92-102.