Roles of eicosanoids in prostate cancer

Future Lipidology

Volumn 3, Issue 4, 2008, Pages 453-467

  Nithipatikom, Kasem ^a   Campbell, William B ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

Arachidonic acid; Cyclooxygenase; Cytochrome P450; Eicosanoids; Endocannabinoids; Lipoxygenase; Prostate cancer

Indexed keywords

3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 5 HYDROXYICOSATETRAENOIC ACID; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONIC ACID; CANNABINOID 1 RECEPTOR; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; CYTOCHROME P450; DAZMEGREL; ENDOCANNABINOID; ICOSANOID; LIPOXYGENASE; LIPOXYGENASE INHIBITOR; MELOXICAM; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; PROSTAGLANDIN D2; PROSTAGLANDIN E2; PROSTANOID RECEPTOR; THROMBOXANE; THROMBOXANE A2; THROMBOXANE B2;

ANTINEOPLASTIC ACTIVITY; ARACHIDONIC ACID METABOLISM; CANCER INHIBITION; CARCINOGENESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; METASTASIS INHIBITION; PRIORITY JOURNAL; PROSTATE CANCER; REVIEW; SIGNAL TRANSDUCTION;

EID: 48649095706     PISSN: 17460875     EISSN: None     Source Type: Journal    
DOI: 10.2217/17460875.3.4.453     Document Type: Review

References (191)

1. Leitzmann MF, Stampfer MJ, Michaud DS et al.: Dietary intake of n-3 and n-6 fatty acids and the risk of prostate cancer. Am. J. Clin. Nutr. 80, 204-216 (2004).
2. Ritch CR, Wan RL, Stephens LB et al.: Dietary fatty acids correlate with prostate cancer biopsy grade and volume in Jamaican men. J. Urol. 177, 97-101 (2007).
3. Hughes-Fulford M, Chen Y, Tjandrawinata RR: Fatty acid regulates gene expression and growth of human prostate cancer PC-3 cells. Carcinogenesis 22, 701-707 (2001).
4. Hughes-Fulford M, Li CF, Boonyaratanakosnkit J, Sayyah S: Arachidonic acid activates phosphatidylinositol 3-kinase signaling and induces gene expression in prostate cancer. Cancer Res. 66, 1427-1433 (2006).
5. Chavarro JE, Stampfer MJ, Li H, Campos H, Kurth T, Ma J: A prospective study of polyunsaturated fatty acid levels in blood and prostate cancer risk, Cancer Epodemiol. Biomarkers Prev. 16, 1364-1370 (2007).
6. MacLean CH, Newberry SJ, Mojica WA et al.: Effects of omega-3 fatty acids on cancer risk: a systematic review. JAMA 295, 403-415 (2006).
7. Brouwer IA, Katan MB, Zock PL: Dietary α-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis J. Nutr. 134, 919-922 (2004).
8. Aronson WJ, Glaspy JA, Reddy ST, Reese D, Heber D, Bagga D: Modulation of omega-3/omega-6 polyunsaturated ratios with dietary fish oils in men with prostate cancer. Urology 58, 283-288 (2001).
9. Carmody J, Olendzki B, Reed G, Andersen. V, Rosenzweig P: A dietary intervention for recurrent prostate cancer after definitive primary treatment: results of a randomized pilot trial. Urology DOI: 10.1016/j.urology.2008.01.015 (2008) (Epub ahead of print).
10. Nie D, Che M, Grignon D, Tang B, Honn KV: Role of eicosanoids in prostate cancer progression. Cancer Metastasis Rev. 20, 195-206 (2001).
11. Chandrasekharan NV, Dai H, Roos KL et al: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/ antipyretic-drugs: cloning, structure, and expression. Proc. Natl Acad. Sci. USA 99, 13926-13931 (2002).
12. Wang MT, Honn KV, Nie D: Cyclooxygenases, prostanoids, and tumor progression. Cancer Metastasis Rev. 26, 525-534 (2007).
13. Gupta S, Srivastava M, Ahmad N, Bostwick DG, Mulchtar H: Over-expression of cyclooxygenase-2 in human prostate adenocarcinoma. Prostate 42, 73-78 (2000).
14. Madaan S, Abel PD, Chaudhary KS et al.: Cytoplasmic induction and over-expression of cyclooxygenase-2 in human prostate cancer: implications for prevention and treatment. BJU Int. 86, 736-741 (2000).
15. Yrishimura R, Sano H, Masuda C et al.: Expression of cyclooxygenase-2 in prostate carcinoma. Cancer 89, 589-596 (2000).
16. Kirschenbaum A, Klausner AP, Lee R et al.: Expression of cyclooxygenase-1 and cyclooxygenase-2 in the human prostate. Urology 56, 671-676 (2000).
17. Kirscheribaum A, Liu X, Yao S, Levine AC: The role ofcyclooxygenase-2 in prostate cancer. Urology 58, 127-131 (2001).
18. Uotila P, Valve E, Martikainen P, Nevalainen M, Nurmi M, Harkonen P: Increased expression of cyclooxygenase-2 and nitric oxide synthase-2 in human prostate cancer. Urol. Res. 29, 23-28 (2001).
19. Hussain T, Gupta S, Mukhtar H: Cyclooxygenase-2 and prostate carcinogenesis. Cancer Lett. 191, 125-135 (2003).
20. Edwards J, Mukherjee R, Munro AF, Wells AC, Almushatat A, Bartlett JM: HER2 and COX2 expression in human prostate cancer. Eur J Cancer 40, 50-55 (2004).
21. Wang W, Bergh A, Damber JE; Cyclooxygenase-2 expression correlates with local chronic inflammation and tumor neovascularization in human prostate cancer. Clin Cancer Res. 11, 3250-3256 (2005).
22. Lee LM, Pan CC, Cheng CJ, Chi CW, Liu TY: Expression. of cyclooxygenase-2 in prostate adencicarcinoma and benign. prostatic hyperplasia. Anticancer Res. 21, 1291-1294 (20101).
23. Fujita H, Koshida, K. Keller ET et al.: Cyclooxygenase-2 promotes prostate cancer progression. Prostate 53, 232-240, (2002).
24. Shappell SBi Manning S, Boeglin WE et al.: Alterations in lipoxygenase and cyclooxygenase-2 catalytic activity and mRNA expression in prostate carcinoma. Neoplasia 3, 287-303 (2091).
25. Zha S, Gage WR, Sauvageot J et al.: Cyclooxygenase-2 is up-regulated in proliferative inflammatory atrophy of the prostate, but not in prostate carcinoma. Cancer Res. 61, 8617-8623 (2001).
26. Wagner M, Loos J, Weksler N et al.: Resistance of prostate cancer cell lines to COX-2 inhibitor treatment. Biochem. Biophys. Res. Commun. 332, 800-807, (2005).
27. Lim JT, Piazza GA, Han EK et al.: Sulindac derivatives inhibit growth and induce apoptosis in human prostate cancer cell lines. Biochem. Pharmacol. 58, 1097-1107 (1999).
28. Hsu AL, Ching TT, Wang DS, Song X, Rangnekar VM, Chen CS: The cyclooxygenase-2 inhibitor celecoxib induces apoptosis by blocking Akt activation in human prostate cancer cells independently of Bcl-2. J. Biol. Chem. 275, 11397-11403 (2000).
29. Subbarayan V, Sabichi AL, Llansa N, Lippman SM, Menter DG: Differential expression of cyclooxygenase-2 and its regulation by tumor necrosis factor-α in normal and malignant prostate cells. Cancer Res. 61, 2720-2726 (2001).
30. Patel MI, Subbaramaiah K, Du B et al.: Celecoxib inhibits prostate cancer growth: evidence of a cyclooxygenase-2-indepenclent mechanism. Clin. Cancer Res. 11, 1999-2007 (2005).
31. Kakizoe T: Chemoprevention of cancer - focusing on clinical trials. Jpn J. Clin. Oncol. 33, 421-442 (2003).
32. Wen B, Deutsch E, Eschwege P et al.: Cyclooxygenase-2 inhibitor NS398 enhances antitumor effect of irradiation on hormone refractory human prostate carcinoma cells. J. Urol. 170, 2036-2039 (2003).
33. Sabichi AL, Lippman SM: COX-2 inhibitors and other NSAIDs in bladder and prostate cancer. Prog. Exp. Tumor Res. 37, 163-178 (2003).
34. Andrews J, Djakiew D, Krygier S, Andrews P: Superior effectiveness of ibuprofen compared with other NSAIDs for reducing the survival of human prostate cancer cells. Cancer Chemother. Pharmacol. 50, 277-284 (2002).
35. Kamijo T. Sato T, Nagatomi Y, Kitamura T: Induction of apoptosis by cyclooxygenase-2 inhibitors in prostate cancer cell lines. Int. J. Urol. 8, S35-S39 (2001).
36. Liu XH, Kirschenbaum A, Yao S, Lee R, Holland JF, Levine AC: Inhibition of cyclooxygenase-2 suppresses angiogenesis and the growth of prostate cancer in vivo. J. Urol. 164, 820-825 (2000).
37. Liu XH, Yao S, Kirschenbaum A, Levine AC: NS398, a selective cyclooxygenase-2 inhibitor, induces apoptosis and down-regulates bcl-2 expression in LNCaP cells. Cancer Res. 58, 4245-4249 (1998).
38. Norrish AE, Jackson RT, McRae CU: Non-steroidal anti-inflammatory drugs and prostate cancer progression. Int. J. Cancer 77, 511-515 (1998).
39. Langman MJ, Cheng KK, Gilman EA, Lancashire RJ: Effect of anti-inflammatory drugs on overall risk of common cancer: case-control study in general practice research database. BNJ 320, 1642-1646 (2000).
40. Fosslien E: Review: molecular pathology of cyclooxygenase-2 in cancer-induced angiogenesis. Ann. Clin. Lab. Sci. 31, 325-348 (2001).
41. Fosslien E: Biochemistry of cyclooxygenase (COX)-2 inhibitors and molecular pathology of COX-2 in neoplasia. Crit. Rev. Clin. Lab. Sci. 37, 431-502 (2000).
42. Jain S, Chakraborty G, Kundu GC: The crucial role of cyclooxygenase-2 in osteopontin-induced protein kinase C α/c-Src/IκB kinase α/β-dependent prostate tumor progression and angiogenesis. Cancer Res. 66, 6638-4448 (2006).
43. Aparicio Gallego G, Diaz Prado S, Jimenez Fonseca P, Garcia Campelo R, Cassinello Espinosa J, Anton Aparicio LM: Cyclooxygenase-2 (COX-2): a molecular target i it prostate cancer. Clin. Transl. Oncol. 9, 694-702 (2007).
44. Adachi M, Sakamoto H, Kawamura R, Wang W, Imai K, Shinomura Y Nonsteroidal anti-inflammatory drugs and oxidative stress in cancer cells. Histol. Histopathol. 22, 437-442 (2007).
45. Cai Y, Lee YF, Li G et al.: A new prostate cancer therapeutic approach: combination of androgen ablation with COX-2 inhibitor. Int. J. Cancer 123(1), 195-201 (2008).
46. Mehar A, Macanas-Pirard P, Mizokami A, Takahashi Y, Kass GE, Coley HM: The effects of cyclooxygenase-2 expression in prostate cancer cells: modulation of response,, to cytotoxic agents. J. Pharmacol. Exp. Ther. 324, 1181-1187 (2008).
47. Smith WL, Garavito RM, De Witt DL: Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2. J. Biol. Chem. 271, 33157-33160 (1996).
48. Khan O, Hensby CN, Williams G: Prostacyclin in prostatic cancer: a better market than bone scan or senim acid phosphatase? Br. J. Urol., 54, 26-31 (1982).
49. Drago JR, Al-Mondhiry H: The effect of prostaglandin modulators on prostate tumor growth and metastasis. Anticancer Res. 4, 391-394 (1984).
50. Schneider MR, Schillinger E, Schirner M, Skuballa W, Sturzebecher S, Witt W: Effects of prostacyclin analogues in in vivo tumor models. Adv. Prostaglandin Thromboxane Leukot. Res. 21B, 901-908 (1991).
51. Schirner M, Schneider MR: The prostacyclin analogue cicaprost inhibits metastasis of tumours of R 3327 MAT Lu prostate carcinoma and SMT 2A mammary carcinoma. J. Cancer Res. Clin. Oncol. 118, 497-501 (1992).
52. Ablin RJ: Prostaglandin E2 affects the tumor immune response in prostatic carcinoma J. Urol. 127, 997-998 (1982).
53. Chaudry AA, Wahle KW McClinton S, Moffat LE: Arachidonic acid metabolism in benign and malignant prostatic tissue in vitro: effects of fatty acids and cyclooxygenase inhibitors. Int. J. Cancer 57, 176-180 (1994).
54. 2. Adv. Exp. Med., Biol. 407, 163-170 (1997).
55. 2 in human prostatic carcinoma cells. Br. J. Cancer 75, 1111-1118 (1997).
56. 2 induces hypoxia-inducible factor-1α stabilization and nuclear localization in a human prostate cancer cell line. J. Biol. Chem. 277, 50081-50086 (2002).
57. 2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells. Br. J. Cancer 82, 2000--2006 (2000).
58. 2 recepror-mediated cAMP pathway. Mol. Carcinog. 46, 912-923 (2007).
59. 2 stimulates prostatic intraepithelial neoplasia cell growth through activation of the interleukin-6/GP130/STAT-3 signaling, pathway. Biocbem. Biophys. Res. Commun. 290, 249-255 (2002).
60. Attiga FA, Fernandez PM, Weeraratna AT, Manyak MJ, Patierno SR: Inhibitors of prostaglandin synthesis inhibit human prostate tumor cell invasiveness and reduce the release of matrix metalloproteinases. Cancer Res. 60, 4629-4637 (2000).
61. Nithiparikom K, Isbell MA, Lindholm PF, Kajdacsy-Balla A, Kaul S, Campell WB: Requirement of cyclooxygenase-2 expression and prostaglandins for human prostate cancer cell invasion. Clin. Exp. Metastasis 19, 593-601 (2002).
62. Kim J, Yang P, Suraokar M et al.: Suppression of prostate tumor cell growth by stromal cell prostaglandin D synthase-derived products. Cancer Res. 65, 6189-6198 (2005).
63. 2 induces death receptor 5 expression through mRNA stabilization independently of PPARγ and potentiates TRAIL-induced apoptosis. Mol. Cancer Ther. 5, 1827-1835 (2006).
64. Chaffer CL, Thomas DM, Thompson EW, Williams ED: PPARγ-independent induction ofgrowth arrest and apoptosis in prostate and bladder carcinoma. BMC Cancer 6, 53 (2006).
65. Nunez NP, Liu H, Meadows GG: PPAR-γ ligands and amino acid deprivation promote apoptosis of melanoma, prostate, and breast cancer cells. Cancer Lett. 236, 133-141 (2006).
66. Subbarayan V, Sabichi AI., Kim J et al.: Differential peroxisome proliferator-activated receptor-γ isoform expression and agonist effects in normal and malignant prostate cells. Cancer Epidemiol. Biomarkers Prev. 13, 1710-1716 (2004).
67. Sabichi AL, Subbarayan V, Llansa N, Lippman SM, Menter DG: Peroxisome proliferator-activated receptor-α suppresses cyclooxygenase-2 expression in human prostate cells. Cancer Epidemiol. Biomarkers Prev. 13, 1704-1709 (2004).
68. 2. Cell Growth Differ 11, 49-61 (2000).
69. 2 induces vascular endothelial growth factor in the hormone-independent prostate cancer cell line PC 3 and the urinary bladder carcinoma cell line 5637. Int. J. Oncol. 21, 915-920 (2002).
70. Henriksson P, Stege R, Green K: Profounds decrease of in vivo formation of thromboxane during oestrogen therapy. Eur. J. Clin. Invest. 26, 1186-1188, (1996).
71. Nie D, Che M, Zacharek A et al.: Differential expression of thromboxane synthase in prostate carcinoma: role in tumor cell motility. Am. J. Pathol. 164, 429-439 (2004).
72. 2 pathway in human prostate cancer correlates with tumor Gleason score and pathologic stage. Eur. Urol. 50, 1021-31; discussion 1031 (2006).
73. Li X, Wei J, Tai HH: Activation of extracellular signal-regulated kinase by 12-hydroxyheptadecatrienoic acid in prostate cancer PC3 cells. Arch. Biochem. Biophys. 467, 20-30 (2007).
74. Fujino H, Regan JW: Prostanoid receptors and phosphatidylinositol 3-kinase: a pathway to cancer? Trends Pharmacol. Sci. 24, 335-340 (2003).
75. 2 receptors and clinicopathologic features in human prostate cancer tissue. Urology 68, 1360-1365 (2006).
76. Moreno J, Krishnan AV, Peehl DM, Feldman D: Mechanisms of vitamin D-mediated growth inhibition in prostate cancer cells: inhibition of the prostaglandin pathway. Anticancer Res. 26, 2525-2530 (2006).
77. Moreno J, Krishnan AV, Swami S, Nonn L, Peehl DM, Feldman D: Regulation of prostaglandin metabolism by calcitriol attenuates growth stimulation in prostate cancer cells. Cancer Res. 65, 7917-7925 (2005).
78. Moreno J, Krishnan AV, Feldman D: Molecular mechanisms mediating the anti-proliferative effects of vitamin D in prostate cancer. J. Steroid Biochem. Mol. Biol. 97, 31-36 (2005).
79. Swami S, Krishnan AV, Moreno J, Bhattacharyya RB, Perhl DM, Feldman D: Calcitriol and genistein actions to inhibit the prostaglandin pathway: potential combination therapy to treat prostate cancer. J. Nutr. 137, 205S-210S (2007).
80. Krishnan AV, Moreno J, Noon L et al.: Novel pathways that-contribute to the anti-proliferative and chemopreventive activities of calcitriol in prostate cancer. J. Steroid Biochem. Mol. Biol. 103, 694-702 (2007).
81. Feldman D, Krishnan A, Moreno J, Swami S, Peehl DM, Srinivas S: Vitamin D inhibition of the prostaglandin pathway as therapy for prostate cancer. Nutr. Rev. 65, S113-S115 (2007).
82. Krishnan AV, Moreno J, Noon L, Swami S, Peehl DM, Feldman D: Calcitriol as a chemopreventive and therapeutic agent in prostate cancer: role of anti-inflammatory activity. J. Bone Miner. Res. 22(Suppl. 2), V74-V80 (2007).
83. 12 family of heterotrimeric G proteins in prostate cancer invasion. J. Biol. Chem. 281, 26483-26490 (2006).
84. 2 receptors in prostate carcinoma: expression and its role in regulating cell motility via small GTPase Rho. Cancer Res. 68, 115-121 (2008).
85. Pidgeon G P, Lysaght J, Krishnamoorthy S et al.: Lipoxygenase metabolism: roles in tumor progression and survival. Cancer Metastasis Rev. 26, 503-524 (2007).
86. Flamand N, Mancuso P, Serezani CH, Brock TG: Leukotrienes: mediators that have been typecast as villains. Cell Mol. Life Sci. 64, 2657-2670 (2007).
87. Matsuyama M, Yoshimura R, Mitsuhashi M et al.: Expression of lipoxygenase in human prostate cancer and growth reduction by its inhibitors. Int. J. Oncol. 24, 821-827 (2004).
88. Myers CE, Ghosh J: Lipoxygenase inhibition in prostate cancer. Eur. Urol. 35, 395-398 (1999).
89. Hong SH, Avis I, Vos MD, Martinez A, Treston AM, Mulshine JL: Relationship of arachidonic acid metabolizing enzyme expression in epithelial cancer cell lines to the growth effect of selective biochemical inhibitors. Cancer Res. 59, 2223-2228 (1999).
90. Matsuyama M, Yoshimma R, Tsuchida K et al.: Lipoxygenase inhibitors prevent urological cancer cell growth. Int. J. Mol. Med. 13, 665-668 (2004).
91. Ghosh J, Myers CE: Arachidonic acid stimulates prostate cancer cell growth: critical role of 5-lipoxygenase. Biochem. Biophys. Res. Commun. 235, 418-423 (1997).
92. Ghosh J, Myers CE: Inhibition of arachiclonate 5-lipoxygenase triggers massive apoptosis in human prostate cancer cells. Proc. Natl Acad. Sci. USA 95, 13182-13187 (1998).
93. O'Flaherry JT, Rogers LC, Chadwell BA et al.: 5(S)-hydroxy-6,8,11,14-E,Z,Z,Z-eicosatetraenoate stimulates PC3 cell signaling and growth by a receptor-dependent mechanism. Cancer Res. 62, 6817-6819 (2002).
94. Ghosh J: Rapid induction of apoptosis in prostate cancer cells by selenium: reversal by metabolites of arachidonate 5-lipoxygenase. Biochem. Biophys. Res. Commun. 315, 624-635 (2004).
95. i/o. J. Biol. Chem. 277, 31459-31465 (2002).
96. i/o-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis. Biochem. Biophys. Res. Commun. 334, 987-995 (2005).
97. Jones CE, Holden S, Tenaillon L et al.: Expression and characterization of a 5-oxo-6E,8Z, 11Z, 14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils. Mol. Pharmacol. 63, 471-477 (2003).
98. Sundaram S, Ghosh J: Expression of 5-oxoETE receptor in prostate cancer cells: critical role in survival. Biochem. Biophys. Res. Commun. 339, 93-98 (2006).
99. Rovati GE, Capra V: Cysteinyl-leukotriene receptors and cellular signals. Scientific World Journal 7, 1375-1392 (2007).
100. Matsuyama M, Hayama T, Funao K et al.: Overexpression ofcysteinyl LT1 receptor in prostate cancer and CysLT1R antagonist inhibits prostate cancer cell growth through apoptosis. Oncol. Rep. 18, 99-104 (2007).
101. Funk CD, Furci L, FitzGerald GA: Molecular cloning, primary structure, and expression of the human platelet/erythroleukemia cell 12-lipoxygenase. Proc. Natl Acad. Sci. USA 87, 5638-5642 (1990).
102. Yoshimoto T, Suzuki H, Yamamoto S, Takai T, Yokoyama C, Tanabe T. Cloning and sequence analysis of the cDNA for arachidonate 12-lipoxygenase of porcine leukocytes. Proc. Natl Acad. Sci. USA 87, 2142-2146 (1990).
103. Boeglin WE, Kim RB, Brash AR: A 12R-lipoxygenase in human skin: mechanistic evidence, molecular cloning, and expression. Proc. Natl Acad. Sci. USA 95, 6744-6749 (1998).
104. Gao X, Grignon DJ, Chbihi T et al.: Elevated 12-lipoxygenase mRNA expression correlates with advanced stage and poor differentiation of human prostate cancer. Urology 46, 227-237 (1995).
105. Gao X, Porter AT, Honn KV: Involvement of the multiple tumor suppressor genes and 12-lipoxygenase in human prostate cancer. Therapeutic implications. Adv. Exp. Med. Biol. 407, 41-53 (1997).
106. Nie D, Hillman GG, Geddes T et al.: Platelet-rype 12-lipoxygenase in a human prostate carcinoma stimulates angiogenesis and tumor growth. Cancer Res. 58, 4047-4051 (1998).
107. Nie D, Hillman GG, Geddes T et al.: Platelet-type 12-lipoxygenase regulates angiogenesis in human prostate carcinoma. Adv. Exp. Med. Biol. 469, 623-630 (1999).
108. 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. 62, 2721-2727 (2002).
109. Kandouz M, Nie D, Pidgeon GP, Krishnamoorthy S, Maddipati KR, Honn KV; Platelet-type 12-lipoxygenase activates NF-κB in prostate cancer cells. Prostaglandins Other Lipid Mediat. 71, 189-204 (2003).
110. 5 integrin expression. Cancer Res. 63, 4258-4267 (2003).
111. Gu JL, Natarajan R, Ben-Ezra J et al.: Evidence that a leukocyte type of 12-lipoxygenase is expressed and regulated by angiorensin II in human adrenal glomerulosa cells. Endocrinology 134, 70-77 (1994).
112. Nie D, Krishnamoorthy S, Jin R et al.: Mechanisms regulating tumor angiogenesis by 12-lipoxygenase in prostate cancer cells. J. Biol. Chem. 281, 18601-18609 (2006).
113. Jankun J, Aleem AM, Malgorzewicz S et al.: Synthetic curcuminoids modulate the arachidonic acid metabolism of human platelet 12-lipoxygenase and reduce sprout formation of human endothelial cells. Mol. Cancer Ther. 5, 1371-1382 (2006).
114. Timar J, Raso E, Dome B et al.: Expression, subcellutar localization and putative function of platelet-type 12-lipoxygenase in human prostate cancer cell lines of different metastatic potential. Int. J. Cancer 87, 37-43 (2000).
115. Nie D, Nemeth J, Qiao Y et al.: Increased metastatic potential in human prostate carcinoma cells by overexpression of arachidonate 12-lipoxygenase. Clin. Exp. Metastasis, 20, 657-663 (2003).
116. Natarajan R, Esworthy R, Bai W, Gu JL, Wilczynski S, Nadler J: Increased 12-lipoxygenase expression in breast cancer tissues and cells. Regulation by epidermal growth factor. J. Clin. Endocrinol. Metab. 82, 1790-1798 (1997).
117. Endsley MP, Aggarwal N, Isbell MA et al.: Diverse roles of 2-arachidonoylglycerol in invasion of prostate carcinoma cells: location, hydrolysis and 12-lipoxygenase metabolism. Int. J. Cancer 121, 984-991 (2007).
118. Nithipatikom K, Isbell MA, See WA, Campbell WB: Elevated 12- and 20-hydroxyeicosatetraenoic acid in urine of patients with prostatic diseases. Cancer Lett. 233, 219-225 (2006).
119. Hsi LC, Wilson LC, Eling TE: Opposing effects of 15-lipoxygenase-1 and -2 metabolites on MAPK signaling in prostate. Alteration in peroxisome proliferator activated receptor γ. J. Biol. Chem. 277, 40549-40556 (2002).
120. Kelavkar U, Lin Y, Landsittel D, Chandran U, Dhir R: The yin and yang of 15-lipoxygenase-1 and delta-desaturases: dietary omega-6 linoleic acid metabolic pathway in prostate. J. Carcinog. 5, 9 (2006).
121. Kelavkar UP, Cohen C, Kamitani H, Eling TE, Badr KF: Concordant induction of 15-tipoxygenase-1 and mutant p53 expression in human prostate adenocarcinoma: correlation with Gleason smog. Carcinogenesis 21, 1777-1787 (2000).
122. Kelavkar UP, Nixon JB, Cohen C, Dillehay D, Eling TE, Badr KF: Overexpression of 15-hpoxygenase-1 in PC-3 human prostate cancer cells increases tumorigenesis. Carcinogenesis 22, 1765-1773 (2001).
123. Kelavkar UP, Cohen C; 15-lipoxygenase-1 expression upregulates and activates insulin-like growth factor-1 receptor in prostate cancer cells. Neoplasia 6, 41-52 (2004).
124. Kelavkar UP, Harya NS, Hutzley J et al.: DNA methylation paradigm shift: 15-lipoxygenase-1 upregulation in prostatic intraepithelial neoplasia and prostate cancer by atypical promoter hypermethylation. Prostaglandins Other Lipid Mediat. 82, 185-197 (2007).
125. Shappell SB, Boeglin WE, Olson SJ, Kasper S, Brash AR: 15-lipoxygenase-2 (15-LOX-2) is expressed in benign prostaric epithelium and reduced in prostate adenocarcinoma. Am. J. Pathol. 155, 235-245 (1999).
126. Jack GS, Brash AR, Olson SJ et al.: Reduced 15-tipoxygenase-2 immunostaining in prostate adenocarcinoma: correlation with grade and expression in high-grade prostatic intraepithelial neoplasia. Hum. Pathol. 31, 1146-1154 (2000).
127. Tang DG, Bhatia B, Tang S, Schneider-Broussard R: 15-lipoxygenase 2 (15-LOX2) is a functional rumor suppressor that regulates human prostate epithelial cell differentiation, senescence, and growth (size). Prostaglindins Other Lipid Mediat. 82, 135-146 (2007).
128. Shappell SB, Gupta RA, Manning S et al.: 15S-hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor γ and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res. 61, 497-503 (2001).
129. Subbarayan V, Krieg P, Hsi LC et al.: 15-lipoxygenase-2 gene regulation by its product 15-(S)-hydroxyeicosatetraenoic acid through a negative feedback mechanism that involves peroxisome proliferator-activated receptor γ. Oncogene 25, 6015-6025 (2006).
130. Subbarayan V, Xu XC, Kim J et al.: Inverse relationship between 15-lipoxygenase-2 and PPAR-γ gene expression in normal epithelia compared with tumor epithelia. Neoplosia 7, 280-293 (2005).
131. Shappell SB, Olson SJ, Hannah SE et al.: Elevated expression of 12/15-lipoxygenase and cyclooxygenase-2 in a transgenic mouse model of prostate carcinoma. Cancer Res. 63, 2256-2267 (2003).
132. Kelavkar UP, Glasgow W, Olson SJ, Foster BA, Shappell SB: Overexpression of 12/15-lipoxygenase, an ortholog of human 15-hpoxygenase-1, in the prostate tumors of TRAMP mice. Neoplasia 6, 821-830 (2004).
133. Kelavkar UP, Parwani AV, Shappell SB, Martin WD: Conditional expression of human 15-lipoxygenase-1 in mouse prostate induces prostaxic intraepithelial neoplasia: the FLiMP mouse model. Neoplasia 8, 510-522 (2006).
134. Sen M, McHugh K, Hutzley J et al.: Orthotopic expression of human 15-lipoxygenase (LO)-1 in the dorsolateral prostate of normal wild-type C57BL/6 mouse causes PIN-like lesions. Prostaglandins Other Lipid Mediat. 81, 1-13 (2006).
135. Spindler SA, Sarkar FH, Sakr WA et al.: Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biocbem. Biophys. Res. Commun. 239, 775-781 (1997).
136. Wu S, Chen W, Murphy F et al.: Molecular cloning, expression, and functional significance of a cytochrome P450 highly expressed in rat heart myocytes. J. Biol. Chem. 272, 12551-12559 (1997).
137. Wang MH, Brand-Schieber E, Zand BA et al.: Cytochrome P450-derived arachidonic acid metabolism in the rat kidney: characterization of selective inhibitors. J. Pharmacol. Exp. Ther. 284, 966-973 (1998).
138. Powell PK, Wolf I, Jin R, Lasker JM: Metabolism of arachidonic acid to 20-hydroxy-5,8,11, 14-eicosatetraenoic acid by P450 enzymes in human liver: involvement of CYP4F2 and CYP4A11. J. Pharmacol. Exp. Ther. 285, 1327-1336 (1998).
139. Zeldin DC: Epoxygenase pathways of arachidonic acid metabolism. J. Biol. Chem. 276, 36059-36062 (2001).
140. Falck JR, Schueler VJ, Jacobson HR, Siddhanta AK, Pramanik B, Capdevila J: Arachidonate epoxygenase: identification of epoxyeicosatrienoic acids in rabbit kidney. J. Lipid Res. 28, 840-846 (1987).
141. Michaelis UR, Fleming I: From endothelium-derived hyperpolarizing factor (EDHF) to angiogenesis: epoxyeicosatrienoic acids (EETs) and cell signaling. Pharmacol Ther. 111, 584-595 (2006).
142. Rifkind AB, Lee C, Chang TK, Waxman DJ: Arachidonic acid metabolism by human cytochrome P450s 2C8, 2C9, 2E1, and 1A2: regioselective oxygenation and evidence fbr a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes. Arch. Biochem. Biophys. 320, 380-389 (1995).
143. Guengerich F. Human cytochrome P450 enzymes. In: Cytochrome P450: Structure, Mechanism, and Biochemistry. Ortiz de Montellano PR (Ed.). Plenum, NY, USA 473-535 (1995).
144. Yokose T, Doy M, Taniguchi T et al.: Immunohistochemical study of cytochrome P450 2C and 3A in human non-neoplastic and neoplastic tissues. Virchows Arch. 434, 401-411 (1999).
145. Chan AT, Tranah GJ, Giovannucci EL, Hunter DJ, Fuchs CS: A prospective study of genetic polymorphisms in the cytochrome P-450 2C9 enzyme and the risk for distal colorectal adenoma. Clin. Gastroenterol. Hepatol. 2, 704-712 (2004).
146. London SJ, Daly AK, Leathart JB, Navidi WC, Idle JR: Lung cancer risk in relation to the CYP2C9*1/CYP2C9*2 genetic polymorphism among African-Americans and Caucasians in Los Angeles County, California. Pharmacogenetics 6, 527-533 (1996).
147. London SJ, Sullivan-Klose T, Daly AK, Idle JR: Lung cancer risk in relation to the CYP2C9 genetic polymorphism among Caucasians in Los Angeles County. Pharmacogenetics 7, 401-404 (1997).
148. Jiang JG, Chen CL, Card JW et al.: Cytochrome P450 2J2 promotes the neoplastic phenotype of carcinoma cells and is up-regulated in human tumors. Cancer Res. 65, 4707-4715 (2005).
149. Jiang JG, Ning YG, Chen C et al.: Cytochrome p450 epoxygenase promotes human cancer metastasis. Cancer Res. 67, 6665-6674 (2007).
150. Enayetallah AE, French RA, Grant DF: Distribution ofsoluble epoxide hydrolase, cytochrome P450 2C8, 2C9 and 2J2 in human malignant neoplasms. J. Mol. Histol. 37, 133-141 (2006).
151. Murray GI, Taylor VE, McKay JA et al.: The immunohistochemical localization of drug-metabolizing enzymes in prostate cancer. J. Pathol. 177, 147-152 (1995).
152. Murata M, Watanabe M, Yamanaka M et al.: Genetic polymorphisms in cytochrome P450 (CYP) 1A1, CYP1A2, CYP2E1, glutathione S-transferase (GST) M1 and GSTT1 and susceptibility to prostate cancer in the Japanese population. Cancer Lett. 165, 171-177 (2001).
153. Sterling KM Jr, Cutroneo KR: Constitutive and inducible expression of cytochromes P4501A (CYP1A1 and CYP1A2) in normal prostate and prostate cancer cells. J. Cell Biochem. 91, 423-429 (2004).
154. Devane VA, Hanus L, Breuer A et al.: Isolation a nd structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949 (1992).
155. Mechoulam R, Ben-Shabat S, Hanus L et al.: Identification of an enclogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem. Pharmacol. 50, 83-90 (1995).
156. Sugiura T, Kondo S, Sukagawa A et al.: 2-arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 215, 89-97 (1995).
157. Laine K, Jarvinen K, Mechoulam R, Breuer A, Jarvinen T: Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid. Invest. Ophthalmol. Vis. Sci. 43, 3216-3222 (2002).
158. Suhara Y, Takayama H, Nakane S, Miyashita T, Waku K, Sugiura T: Synthesis and biological activities of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, and its metabolically stable ether-linked analogues. Chem. Pharm. Bull (Tokyo) 48, 903-907 (2000).
159. Steffens M, Zentner J, Honegger J, Feuerstein TJ: Binding affinity and agonist activity of purative endogenous cannabinoids at the human neocortical CB1 receptor. Biochem. Pharmacol. 69, 109-178 (2005).
160. Hanus L, Abu-Lafi S, Fride E et al.: 2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc. Natl. Acad. Sci. USA 98, 3662-3665 (2001).
161. Fezza F, Bisogno T, Minassi A, Appendino G, Mechoulam R, Di Matzo V: Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues. FEBS Lett. 513, 294-298 (2002).
162. Oka S, Tsuchie A, Tokumura A et al.: Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species. J. Neurochem. 85, 1374-1381 (2003).
163. Richardson D, Ortori CA, Chapman V, Kendall DA, Barrett DA: Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Anal. Biochem. 360, 216-226 (2007).
164. 2 receptor-mediated actions of anandamide in mouse brain. J. Neutrochem. 75, 2434-2444 (2000).
165. Maccarrone M, Lorenzon T, Bari M, Melino G, Finazzi-Agro A: Anandamide induces apoptosis in human cells via vanilloid receptors. Evidence for a protective role of cannabinoid receptors. J Biol. Chem. 275, 31938-31945 (2000).
166. Ueda N, Puffenbarger RA, Yamamoto S, Deutsch DG: The fatty acid amide hydrolase.(FAAH). Chem. Phys. Lipids 108, 107-121 (2000).
167. Di Marzo V, Bisogno T, De Petrocellis L et al.: Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur. J. Biochem. 264, 258-267 (1999).
168. Bari M, Battista N, Fezza F, Gasperi V, Maccarrone M: New insights into endocannabinoid degradation and its therapeutic potential. Mini Rev. Med. Chem. 6, 257-268 (2006).
169. Dinh TP, Carpenter D, Leslie FM et al.: Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc. Natl Acad. Sci. USA 99, 10819-10824 (2002).
170. Dinh TP, Freund TF, Piomelli D: A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation. Chem. Phys. Lipids 121, 149-158 (2002).
171. Dinh TP, Kathuria S, Pionielli D: RNA interference suggests a primary role for monoacylglycerol lipase in the degradation of the endocannabinoid 2-arachidonoylglycerol. Mol. Pharmacol. 66, 1260-1264 (2004).
172. Bifulco M, Laezza C, Valenti M, Ligresti A, Portella G, Di Marzo V: A new strategy to block tumor growth by inhibiting endocannabinoid inactivation. FASEB J. 18, 1606-1608 (2004).
173. Pacher P, Batkai S, Kunos G: The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol. Rev. 58, 389-462 (2006).
174. Di Marzo V, Bisogno T, De Petrocellis L: Endocannabinoids: new targets for drug development. Curr. Pharm. Des. 6, 1361-1380 (2000).
175. Ligresti A, Bisogno T, Matias I et al.: Possible endocannabinoid control of colorectal cancer growth, Gastroenterology, 125, 677-687 (2003).
176. De Petrocellis L, Melck D, Bisogno T, Di Matzo V: Endocannabinoids and fatty acid amides in cancer, inflammation and related disorders. Chem. Phys. Lipids 108, 191-209 (2000).
177. Parolaro, D, Massi P, Rubino T, Monti E: Endocannabinoids in the immune system and cancer. Prostaglandins Leukot. Essent. Fatty Acids 66, 319-332 (2002).
178. Bifulco M, Di Matzo V: Targeting the endocannabinoid system in cancer therapy: a call for further research. Nat. Med. 8, 547-550 (2002).
179. Portella G, Laezza C, Laccetti P, De Petrocellis L, Di Matzo V, Bifulco M: Inhibitory effects of cannabinoid CB1 receptor stimulation on tumor growth and metastatic spreading: actions on signals involved in angiogenesis and metastasis. FASEB J 17, 1771-1773 (2003).
180. Jones S, Howl J: Cannabinoid receptor systems: therapeutic targets for tumour intervention. Expert Opin. Ther. Targets 7, 749-758 (2003).
181. Grimaldi C, Pisanti S, Laezza C et al.: Anandamide inhibits adhesion and migration of breast cancer cells. Exp. Cell Res. 312, 363-373 (2006).
182. Bifulco M, Laezza C, Pisanti S, Gazzerro P: Cannabinoids and cancer: pros and cons of an antitumour strategy. Br. J. Pharmacol. 148, 123-135 (2006).
183. Bifulco M, Laezza C, Gazzerro P, Pentimalli F: Endocannabinoids as emerging suppressors of angiogenesis and tumor invasion (review). Oncol. Rep. 17, 813-816 (2007).
184. Flygare J, Sander B: The endocannabinoid system in cancer potential therapeutic target? Semin. Cancer Biol. 18, 176-189 (2008).
185. Izzo AA, Aviello G, Petrosino S et al.: Increased endocannabinoid levels reduce the development of precancerous lesions in the mouse colon. J. Mol. Med. 86, 89-98 (2008).
186. Mirneault M, Pommery N, Wattez N, Bailly C, Henichart JP: 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 56, 1-12 (2003).
187. Endsley MP, Thill R, Choudhry I et al.: Expression and function of fatty acid amide hydrolase in prostate cancer. Int. J. Cancer DOI: 10.1002/ijc,23674 (2008) (Epub ahead of print).
188. Melck D, De Petrocellis I., Orlando P et al.: Suppression of nerve growth factor Trk receptors and prolaccin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation. Endocrinology 141, 118-126 (2000).
189. Sanchez MG, Sanchez AM, Ruiz-Llorenre L, Diaz-Laviada I: Enhancement of androgen receptor expression induced by (R) methanandamide in prostate LNCaP cells. FEBS Lett. 555, 561-566 (2003).
190. Nithipatikom K, Endsley MP, Isbell MA et al.: 2-arachidonoylglycerol: a novel inhibitor of androgen-independent prostate cancer cell invasion. Cancer Res. 64, 8826-8830 (2004).
191. Nithipatikom K, Endsley MP, Isbell MA, Wheelock CE, Hammock BID, Campbell WB: A new class of inhibitors of 2-arachidonoylglycerol hydrolysis and invasion of prostate cancer cells. Biochem. Biophys. Res. Commun. 332, 1028-1033 (2005).