Information de reference pour ce titreAccession Number: | 00124288-201212000-00012.
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Author: | Silvente-Poirot, Sandrine; Poirot, Marc
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Institution: | Team [left pointing guillemet]Sterol Metabolism and Therapeutic Innovations in Oncology[right pointing guillemet], Cancer Research Center of Toulouse, UMR 1037 INSERM-University Toulouse III, Institut Claudius Regaud, Toulouse, France
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Title: | |
Source: | Current Opinion in Pharmacology. 12(6):696-703, December 2012.
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Abstract: | : Cholesterol epoxide hydrolase (ChEH) catalyzes the hydration of cholesterol-5,6-epoxides (5,6-EC) into cholestane-3[beta],5[alpha],6[beta]-triol. ChEH is a hetero-oligomeric complex called the anti-estrogen binding site (AEBS) comprising 3[beta]-hydroxysterol-[DELTA]8-[DELTA]7-isomerase (D8D7I) and 3[beta]-hydroxysterol-[DELTA]7-reductase (DHCR7). D8D7I and DHCR7 regulate cholesterol biosynthesis, fetal development and growth, tumor cell differentiation and death. The un-reactivity of 5,6-EC toward nucleophiles has recently been demonstrated indicating that 5,6-EC are not alkylating and carcinogenic agents as first postulated. Here we discuss recent advances in the molecular characterization of ChEH, its potential role in cancer progression and resistance as well as the interest of inhibiting ChEH and to accumulate 5,6-EC which may contribute to the anti-tumor and chemopreventive action of ChEH inhibitors used in the clinic such as tamoxifen.
(C) 2012Elsevier, Inc.
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References: | 1. Newman JW, Morisseau C, Hammock BD: Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog Lipid Res. 2005, 44:1-51.
2*. Sevanian A, McLeod LL: Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase. J Biol Chem 1986;261:54-59. This study characterizes the substrates specificity of ChEH and identifies 7-ketocholesterol, 6-ketocholestanol, and 7-ketocholestanol as specific inhibitors of this enzyme while none of the xenobiotic epoxide hydrolase inhibitors or activators affects ChEH activity, suggesting that the ChEH is distinct from the mEH.
3. Chan JT, Black HS: Skin carcinogenesis: cholesterol-5alpha, 6alpha-epoxide hydrase activity in mouse skin irradiated with ultraviolet light. Science. 1974, 186:1216-1217.
4. Poirot M, Silvente-Poirot S: Cholesterol-5,6-epoxides: chemistry, biochemistry, metabolic fate and cancer. Biochimie, in press, http://dx.doi.org/10.1016/j.bioc...- ouverture dans une nouvelle fenêtre.
5**. Paillasse MR, Saffon N, Gornitzka H, Silvente-Poirot S, Poirot M, de Medina P: Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. J Lipid Res 2012;53:718-725. This study proves that 5,6-EC are stable and un-reactive toward nucleophiles in non-catalytic conditions, ruling out that 5,6-EC are alkylating agents as initially suggested. Importantly, this study supports a biological role of ChEH distinct from that of detoxifying cells from 5,6-EC.
6**. el-Bayoumy K, Ji BY, Upadhyaya P, Chae YH, Kurtzke C, Rivenson A, Reddy BS, Amin S, Hecht SS: Lack of tumorigenicity of cholesterol epoxides and estrone-3,4-quinone in the rat mammary gland. Cancer Res 1996;56:1970-1973. High doses of 5,6[alpha]-EC and 5,6[beta]-EC injected into rat mammary glands were shown non-tumorigenic in comparison with a known carcinogen ruling out that 5,6[alpha]-ECs are involved in the etiology of breast cancer.
7. Astrom A, Eriksson M, Eriksson LC, Birberg W, Pilotti A, DePierre JW: Subcellular and organ distribution of cholesterol epoxide hydrolase in the rat. Biochim Biophys Acta. 1986, 882:359-366.
8**. de Medina P, Paillasse MR, Segala G, Poirot M, Silvente-Poirot S: Identification and pharmacological characterization of cholesterol-5,6-epoxide hydrolase as a target for tamoxifen and AEBS ligands. Proc Natl Acad Sci U S A 2010;107:13520-13525. First molecular identification of ChEH as being the AEBS complex, formed of D8D7I and DHCR7, two enzymes involved in cholesterol biosynthesis. Importantly, this study shows that several molecules with anti-cancer and chemopreventive activity used in the clinic are high affinity inhibitors of ChEH and accumulate 5,6-EC.
9. Kedjouar B, de Medina P, Oulad-Abdelghani M, Payre B, Silvente-Poirot S, Favre G, Faye JC, Poirot M: Molecular characterization of the microsomal tamoxifen binding site. J Biol Chem. 2004, 279:34048-34061.
10. Mesange F, Sebbar M, Kedjouar B, Capdevielle J, Guillemot JC, Ferrara P, Bayard F, Delarue F, Faye JC, Poirot M: Microsomal epoxide hydrolase of rat liver is a subunit of the anti-oestrogen-binding site. Biochem J. 1998;334(Pt 1):107-112.
11. Muller F, Arand M, Frank H, Seidel A, Hinz W, Winkler L, Hanel K, Blee E, Beetham JK, Hammock BD, Oesch F: Visualization of a covalent intermediate between microsomal epoxide hydrolase, but not cholesterol epoxide hydrolase, and their substrates. Eur J Biochem. 1997, 245:490-496.
12. Haeggstrom JZ: Leukotriene A4 hydrolase/aminopeptidase, the gatekeeper of chemotactic leukotriene B4 biosynthesis. J Biol Chem. 2004, 279:50639-50642.
13. Newman JW, Morisseau C, Harris TR, Hammock BD: The soluble epoxide hydrolase encoded by EPXH2 is a bifunctional enzyme with novel lipid phosphate phosphatase activity. Proc Natl Acad Sci U S A. 2003, 100:1558-1563.
14. Porter FD, Herman GE: Malformation syndromes caused by disorders of cholesterol synthesis. J Lipid Res. 2011, 52:6-34.
15. Jordan VC: SERMs: meeting the promise of multifunctional medicines. J Natl Cancer Inst. 2007, 99:350-356.
16. Bougnoux P, Hajjaji N, Couet C: The lipidome as a composite biomarker of the modifiable part of the risk of breast cancer. Prostaglandins Leukot Essent Fatty Acids. 2008, 79:93-96.
17. Payre B, de Medina P, Boubekeur N, Mhamdi L, Bertrand-Michel J, Terce F, Fourquaux I, Goudouneche D, Record M, Poirot M, Silvente-Poirot S: Microsomal antiestrogen-binding site ligands induce growth control and differentiation of human breast cancer cells through the modulation of cholesterol metabolism. Mol Cancer Ther. 2008, 7:3707-3718.
18. de Medina P, Payre B, Boubekeur N, Bertrand-Michel J, Terce F, Silvente-Poirot S, Poirot M: Ligands of the antiestrogen-binding site induce active cell death and autophagy in human breast cancer cells through the modulation of cholesterol metabolism. Cell Death Differ. 2009, 16:1372-1384.
19. de Medina P, Silvente-Poirot S, Poirot M: Tamoxifen and AEBS ligands induced apoptosis and autophagy in breast cancer cells through the stimulation of sterol accumulation. Autophagy. 2009, 5:1066-1067.
20. Reyno L, Seymour L, Tu D, Dent S, Gelmon K, Walley B, Pluzanska A, Gorbunova V, Garin A, Jassem J, Pienkowski T, et al: Phase III study of N, N-diethyl-2-[4-(phenylmethyl) phenoxy]ethanamine (BMS-217380-01) combined with doxorubicin versus doxorubicin alone in metastatic/recurrent breast cancer: National Cancer Institute of Canada Clinical Trials Group Study MA.19. J Clin Oncol. 2004, 22:269-276.
21. Deng T, Liu JC, Pritchard KI, Eisen A, Zacksenhaus E: Preferential killing of breast tumor initiating cells by N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine/tesmilifene. Clin Cancer Res. 2009, 15:119-130.
22. Ao A, Morrison BJ, Wang H, Lopez JA, Reynolds BA, Lu J: Response of estrogen receptor-positive breast cancer tumorspheres to antiestrogen treatments. PLoS One. 2011, 6:e18810.
23. Hayon T, Dvilansky A, Oriev L, Nathan I: Non-steroidal antiestrogens induce apoptosis in HL60 and MOLT3 leukemic cells; involvement of reactive oxygen radicals and protein kinase C. Anticancer Res. 1999, 19:2089-2093.
24. Yom-Tov G, Nathan I, Shpilberg O, Polliack A, Levi I: Clomiphene as a novel modality for the treatment of acute myeloid leukemia: a pilot phase II study. Leuk Res. 2012, 36:42-45.
25. Massey JB, Pownall HJ: Structures of biologically active oxysterols determine their differential effects on phospholipid membranes. Biochemistry. 2006, 45:10747-10758.
26. Ishimaru C, Yonezawa Y, Kuriyama I, Nishida M, Yoshida H, Mizushina Y: Inhibitory effects of cholesterol derivatives on DNA polymerase and topoisomerase activities, and human cancer cell growth. Lipids. 2008, 43:373-382.
27. Joseph SB, Castrillo A, Laffitte BA, Mangelsdorf DJ, Tontonoz P: Reciprocal regulation of inflammation and lipid metabolism by liver X receptors. Nat Med. 2003, 9:213-219.
28. Vedin LL, Lewandowski SA, Parini P, Gustafsson JA, Steffensen KR: The oxysterol receptor LXR inhibits proliferation of human breast cancer cells. Carcinogenesis. 2009, 30:575-579.
29. Russo V: Metabolism, LXR/LXR ligands, and tumor immune escape. J Leukoc Biol. 2011, 90:673-679.
30*. Berrodin TJ, Shen Q, Quinet EM, Yudt MR, Freedman LP, Nagpal S: Identification of 5{alpha},6{alpha}-epoxycholesterol as a novel modulator of liver x receptor activity. Mol Pharmacol 2010;78:1046-1058. This study shows that 5,6[alpha]-EC is a direct ligand of the LXR, suggesting that ChEH regulation impacts on LXR-dependent signal and biological effects.
31. Song C, Hiipakka RA, Liao S: Auto-oxidized cholesterol sulfates are antagonistic ligands of liver X receptors: implications for the development and treatment of atherosclerosis. Steroids. 2001, 66:473-479.
32. Pitroda SP, Khodarev NN, Beckett MA, Kufe DW, Weichselbaum RR: MUC1-induced alterations in a lipid metabolic gene network predict response of human breast cancers to tamoxifen treatment. Proc Natl Acad Sci U S A. 2009, 106:5837-5841.
33. Reddy BS, Wynder EL: Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer. 1977, 39:2533-2539.
34. Reddy BS, Martin CW, Wynder EL: Fecal bile acids and cholesterol metabolites of patients with ulcerative colitis, a high-risk group for development of colon cancer. Cancer Res. 1977, 37:1697-1701.
35. Cheng YW, Kang JJ, Shih YL, Lo YL, Wang CF: Cholesterol-3-beta, 5-alpha, 6-beta-triol induced genotoxicity through reactive oxygen species formation. Food Chem Toxicol. 2005, 43:617-622.
36. Aringer L, Eneroth P: Formation and metabolism in vitro of 5,6-epoxides of cholesterol and beta-sitosterol. J Lipid Res. 1974, 15:389-398.
37*. de Medina P, Silvente-Poirot S, Poirot M: Methods for determining the oncogenic condition of cell, use thereof, and methods for treating cancer. Word Patent, 2010/149941; 2010 This patent shows that an oxidative metabolite of CT is a promoter of tumors in vitro and in vivo and that its synthesis is inhibited by ChEH inhibitors.
38. Raghavan D, Brandes LJ, Klapp K, Snyder T, Styles E, Tsao-Wei D, Lieskovsky G, Quinn DI, Ramsey EW: Phase II trial of tesmilifene plus mitoxantrone and prednisone for hormone refractory prostate cancer: high subjective and objective response in patients with symptomatic metastases. J Urol. 2005;174:1808-1813, (discussion 1813).
39. Vincent M: Tesmilifene may enhance breast cancer chemotherapy by killing a clone of aggressive, multi-drug resistant cells through its action on the p-glycoprotein pump. Med Hypotheses. 2006, 66:715-731.
40. de Medina P, Paillasse MR, Payre B, Silvente-Poirot S, Poirot M: Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases. J Med Chem. 2009, 52:7765-7777.
41. Prommer E: Role of haloperidol in palliative medicine: an update. Am J Hosp Palliat Care. 2012, 29:295-301.
42. Bourrie B, Bribes E, Derocq JM, Vidal H, Casellas P: Sigma receptor ligands: applications in inflammation and oncology. Curr Opin Investig Drugs. 2004, 5:1158-1163.
43. Marques LO, Lima MS, Soares BG: Trifluoperazine for schizophrenia. Cochrane Database Syst Rev. 2004:CD003545.
44. Van Herendael H, Dorian P: Amiodarone for the treatment and prevention of ventricular fibrillation and ventricular tachycardia. Vasc Health Risk Manage. 2010, 6:465-472.
45. Wang CY, Wei Q, Han I, Sato S, Ghanbari-Azarnier R, Whetstone H, Poon R, Hu J, Zheng F, Zhang P, Wang W, et al: Hedgehog and Notch signaling regulate self-renewal of undifferentiated pleomorphic sarcomas. Cancer Res. 2012, 72:1013-1022.
46. Newland JG, Abdel-Rahman SM: Update on terbinafine with a focus on dermatophytoses. Clin Cosmet Investig Dermatol. 2009, 2:49-63.
47. Cenedella RJ: Cholesterol synthesis inhibitor U18666A and the role of sterol metabolism and trafficking in numerous pathophysiological processes. Lipids. 2009, 44:477-487.
48. Torocsik D, Szanto A, Nagy L: Oxysterol signaling links cholesterol metabolism and inflammation via the liver X receptor in macrophages. Mol Aspects Med. 2009, 30:134-152.
49. Mahfouz MM, Smith TL, Zhou Q, Kummerow FA: Cholestane-3 beta, 5 alpha, 6 beta-triol stimulates phospholipid synthesis and CTP-phosphocholine cytidyltransferase in cultured LLC-PK cells. Int J Biochem Cell Biol. 1996, 28:739-750.
50. Menendez JA, Papadimitropoulou A, Vellon L, Lupu R: A genomic explanation connecting "Mediterranean diet", olive oil and cancer: oleic acid, the main monounsaturated fatty acid of olive oil, induces formation of inhibitory "PEA3 transcription factor-PEA3 DNA binding site" complexes at the Her-2/neu (erbB-2) oncogene promoter in breast, ovarian and stomach cancer cells. Eur J Cancer. 2006, 42:2425-2432.
51. Menendez JA, Vazquez-Martin A, Ropero S, Colomer R, Lupu R: HER2 (erbB-2)-targeted effects of the omega-3 polyunsaturated fatty acid, alpha-linolenic acid (ALA; 18:3n-3), in breast cancer cells: the "fat features" of the "Mediterranean diet" as an "anti-HER2 cocktail". Clin Transl Oncol. 2006, 8:812-820.
52. Wijendran V, Hayes KC: Dietary n-6 and n-3 fatty acid balance and cardiovascular health. Annu Rev Nutr. 2004, 24:597-615.
53. Bougnoux P, Hajjaji N, Maheo K, Couet C, Chevalier S: Fatty acids and breast cancer: sensitization to treatments and prevention of metastatic re-growth. Prog Lipid Res. 2010, 49:76-86.
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Language: | English.
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Document Type: | Articles.
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Journal Subset: | Pharmacology.
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ISSN: | 1471-4892
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NLM Journal Code: | 100966133
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DOI Number: | https://dx.doi.org/10.1016/j.cop...- ouverture dans une nouvelle fenêtre
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