Importance of cholesterol and oxysterols metabolism in the pharmacology of tamoxifen and other AEBS ligands

Chemistry and Physics of Lipids

Volumn 164, Issue 6, 2011, Pages 432-437

  De Medina, Philippe ^a,c   Paillasse, Michael R ^a,c   Ségala, Gregory ^a,b   Khallouki, Farid ^a,b   Brillouet, Severine ^a,b   Dalenc, Florence ^a,b   Courbon, Frederic ^a,b   Record, Michel ^a,b   Poirot, Marc ^a,b   Silvente Poirot, Sandrine ^a,b  

^a CANCER RESEARCH CENTER OF TOULOUSE   (France)

^b INSTITUT CLAUDIUS REGAUD   (France)

^c Affichem   (France)

Author keywords

Antiestrogen; Breast cancer; Cholesterol; Cholesteryl ester; Diphenylmethane; Ring B oxysterols; Zymostenol

Indexed keywords

3BETA HYDROXYSTEROL DELTA 8 DELTA 7 ISOMERASE; ALPHA TOCOPHEROL; ANTIESTROGEN; AVASIMIBE; CHOLESTEROL; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; CHOLESTEROL EPOXIDE HYDROLASE; DESMOSTEROL; DOCOSAHEXAENOIC ACID; FULVESTRANT; ICI 164 384; OXYSTEROL; POLYUNSATURATED FATTY ACID; RALOXIFENE; SAH 58 035; SELECTIVE ESTROGEN RECEPTOR MODULATOR; TAMOXIFEN; TESMILIFENE; TRIPARANOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BREAST CANCER; CANCER HORMONE THERAPY; CELL DIFFERENTIATION; CHOLESTEROL ESTERIFICATION; DRUG PROTEIN BINDING; HUMAN; NONHUMAN; PRIORITY JOURNAL; REVIEW; STEROL METABOLISM;

ANIMALS; CHOLESTEROL; ESTROGEN RECEPTOR MODULATORS; HUMANS; LIGANDS; MICROSOMES; OXYGEN; TAMOXIFEN;

EID: 80051473510     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2011.05.005     Document Type: Review

References (38)

1. C.J. Antalis, T. Arnold, T. Rasool, B. Lee, K.K. Buhman, and R.A. Siddiqui High ACAT1 expression in estrogen receptor negative basal-like breast cancer cells is associated with LDL-induced proliferation Breast Cancer Res. Treat. 122 2010 661 670
2. S. Bemlih, M.D. Poirier, and A. El Andaloussi Acyl-coenzyme A: cholesterol acyltransferase inhibitor Avasimibe affect survival and proliferation of glioma tumor cell lines Cancer Biol. Ther. 9 2010 1025 1032
3. T.Y. Chang, B.L. Li, C.C. Chang, and Y. Urano Acyl-coenzyme A:cholesterol acyltransferases Am. J. Physiol. Endocrinol. Metab. 297 2009 E1 9
4. Y.W. Cheng, J.J. Kang, Y.L. Shih, Y.L. Lo, and C.F. Wang Cholesterol-3-beta, 5-alpha, 6-beta-triol induced genotoxicity through reactive oxygen species formation Food Chem. Toxicol. 43 2005 617 622 (Pubitemid 40255298)
5. P. de Medina, N. Boubekeur, P. Balaguer, G. Favre, S. Silvente-Poirot, and M. Poirot The prototypical inhibitor of cholesterol esterification Sah 58-035 [3-[decyldimethylsilyl]-n-[2-(4-methylphenyl)-1-phenylethyl]propanamide], is an agonist of estrogen receptors J. Pharmacol. Exp. Ther. 319 2006 139 149 (Pubitemid 44455118)
6. P. de Medina, G. Favre, and M. Poirot Multiple targeting by the antitumor drug tamoxifen: a structure-activity study Curr. Med. Chem. Anticanc. Agents 4 2004 491 508 (Pubitemid 39406262)
7. P. de Medina, M.R. Paillasse, B. Payre, S. Silvente-Poirot, and M. Poirot Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases J. Med. Chem. 52 2009 7765 7777
8. P. de Medina, M.R. Paillasse, G. Segala, M. Poirot, and S. Silvente-Poirot 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. 107 2010 13520 13525
9. P. de Medina, B. Payre, N. Boubekeur, J. Bertrand-Michel, F. Terce, S. Silvente-Poirot, and M. Poirot 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. 16 2009 1372 1384
10. P. de Medina, B.L. Payre, J. Bernad, I. Bosser, B. Pipy, S. Silvente-Poirot, G. Favre, J.C. Faye, and M. Poirot Tamoxifen is a potent inhibitor of cholesterol esterification and prevents the formation of foam cells J. Pharmacol. Exp. Ther. 308 2004 1165 1173 (Pubitemid 38263994)
11. P. de Medina, S. Silvente-Poirot, and M. Poirot Tamoxifen and AEBS ligands induced apoptosis and autophagy in breast cancer cells through the stimulation of sterol accumulation Autophagy 5 2009 1066 1067
12. K. el-Bayoumy, B.Y. Ji, P. Upadhyaya, Y.H. Chae, C. Kurtzke, A. Rivenson, B.S. Reddy, S. Amin, and S.S. Hecht Lack of tumorigenicity of cholesterol epoxides and estrone-3,4-quinone in the rat mammary gland Cancer Res. 56 1996 1970 1973 (Pubitemid 26119890)
13. H. Fuda, N.B. Javitt, K. Mitamura, S. Ikegawa, and C.A. Strott Oxysterols are substrates for cholesterol sulfotransferase J. Lipid Res. 48 2007 1343 1352 (Pubitemid 47312036)
14. M.J. Higgins, and V. Stearns Pharmacogenetics of endocrine therapy for breast cancer Annu. Rev. Med. 62 2011 281 293
15. P.L. Hwang, and A. Matin Interactions of sterols with antiestrogen-binding sites: structural requirements for high-affinity binding J. Lipid Res. 30 1989 239 245 (Pubitemid 19067229)
16. M. Jagr, J. Mraz, I. Linhart, V. Stransky, and M. Pospisil Synthesis and characterization of styrene oxide adducts with cysteine, histidine, and lysine in human globin Chem. Res. Toxicol. 20 2007 1442 1452 (Pubitemid 350057213)
17. A. Jemal, R. Siegel, E. Ward, Y. Hao, J. Xu, and M.J. Thun Cancer statistics, 2009 CA Cancer J. Clin. 59 2009 225 249
18. V.C. Jordan Chemoprevention of breast cancer with selective oestrogen-receptor modulators Nat. Rev. Cancer 7 2007 46 53 (Pubitemid 46020846)
19. B. Kedjouar, P. de Medina, M. Oulad-Abdelghani, B. Payre, S. Silvente-Poirot, G. Favre, J.C. Faye, and M. Poirot Molecular characterization of the microsomal tamoxifen binding site J. Biol. Chem. 279 2004 34048 34061 (Pubitemid 39063057)
20. T.L. Lash, E.A. Lien, H.T. Sorensen, and S. Hamilton-Dutoit Genotype-guided tamoxifen therapy: time to pause for reflection? Lancet Oncol. 10 2009 825 833
21. E. Lund, U. Diczfalusy, and I. Bjorkhem On the mechanism of oxidation of cholesterol at C-7 in a lipoxygenase system J. Biol. Chem. 267 1992 12462 12467
22. X.J. Ma, Z. Wang, P.D. Ryan, S.J. Isakoff, A. Barmettler, A. Fuller, B. Muir, G. Mohapatra, R. Salunga, J.T. Tuggle, Y. Tran, D. Tran, A. Tassin, P. Amon, W. Wang, E. Enright, K. Stecker, E. Estepa-Sabal, B. Smith, J. Younger, U. Balis, J. Michaelson, A. Bhan, K. Habin, T.M. Baer, J. Brugge, D.A. Haber, M.G. Erlander, and D.C. Sgroi A two-gene expression ratio predicts clinical outcome in breast cancer patients treated with tamoxifen Cancer Cell 5 2004 607 616 (Pubitemid 38748922)
23. A. Masala, G. Delitala, G. Lo Dico, I. Stoppelli, S. Alagna, and L. Devilla Inhibition of lactation and inhibition of prolactin release after mechanical breast stimulation in puerperal women given tamoxifen or placebo Br. J. Obstet. Gynaecol. 85 1978 134 137 (Pubitemid 8375395)
24. D.J. Meyer, and B. Ketterer 5 alpha, 6 alpha-epoxy-cholestan-3 beta-ol (cholesterol alpha-oxide): a specific substrate for rat liver glutathione transferase B FEBS Lett. 150 1982 499 502 (Pubitemid 13184096)
25. N.T. Nashed, D.P. Michaud, W. Levin, and D.M. Jerina Properties of liver microsomal cholesterol 5,6-oxide hydrolase Arch. Biochem. Biophys. 241 1985 149 162 (Pubitemid 15012023)
26. N.T. Nashed, D.P. Michaud, W. Levin, and D.M. Jerina 7-Dehydrocholesterol 5,6 beta-oxide as a mechanism-based inhibitor of microsomal cholesterol oxide hydrolase J. Biol. Chem. 261 1986 2510 2513 (Pubitemid 17218256)
27. J.W. Newman, C. Morisseau, and B.D. Hammock Epoxide hydrolases: their roles and interactions with lipid metabolism Prog. Lipid Res. 44 2005 1 51 (Pubitemid 40313218)
28. M.R. Paillasse, P. de Medina, G. Amouroux, L. Mhamdi, M. Poirot, and S. Silvente-Poirot Signaling through cholesterol esterification: a new pathway for the cholecystokinin 2 receptor involved in cell growth and invasion J. Lipid Res. 50 2009 2203 2211
29. B. Payre, P. de Medina, N. Boubekeur, L. Mhamdi, J. Bertrand-Michel, F. Terce, I. Fourquaux, D. Goudouneche, M. Record, M. Poirot, and S. Silvente-Poirot Microsomal antiestrogen-binding site ligands induce growth control and differentiation of human breast cancer cells through the modulation of cholesterol metabolism Mol. Cancer Ther. 7 2008 3707 3718
30. S.P. Pitroda, N.N. Khodarev, M.A. Beckett, D.W. Kufe, and R.R. Weichselbaum 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. 106 2009 5837 5841
31. R. Schiff, P. Reddy, M. Ahotupa, E. Coronado-Heinsohn, M. Grim, S.G. Hilsenbeck, R. Lawrence, S. Deneke, R. Herrera, G.C. Chamness, S.A. Fuqua, P.H. Brown, and C.K. Osborne Oxidative stress and AP-1 activity in tamoxifen-resistant breast tumors in vivo J. Natl. Cancer Inst. 92 2000 1926 1934 (Pubitemid 32036923)
32. G.J. Schroepfer Jr. Oxysterols: modulators of cholesterol metabolism and other processes Physiol. Rev. 80 2000 361 554 (Pubitemid 30060568)
33. A. Sevanian, and L.L. McLeod Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase J. Biol. Chem. 261 1986 54 59 (Pubitemid 16144810)
34. M.M. Shaaban Suppression of lactation by an antiestrogen, tamoxifen Eur. J. Obstet. Gynecol. Reprod. Biol. 4 1975 167 169
35. R.L. Sutherland, and M.S. Foo Differential binding of antiestrogens by rat uterine and chick oviduct cytosol Biochem. Biophys. Res. Commun. 91 1979 183 191 (Pubitemid 10183359)
36. R.L. Sutherland, L.C. Murphy, M. San Foo, M.D. Green, A.M. Whybourne, and Z.S. Krozowski High-affinity anti-oestrogen binding site distinct from the oestrogen receptor Nature 288 1980 273 275 (Pubitemid 11165875)
37. M.R. Tosi, and V. Tugnoli Cholesteryl esters in malignancy Clin. Chim. Acta 359 2005 27 45 (Pubitemid 41121953)
38. C.K. Watts, and R.L. Sutherland High affinity specific antiestrogen binding sites are concentrated in rough microsomal membranes of rat liver Biochem. Biophys. Res. Commun. 120 1984 109 115 (Pubitemid 14138177)