The sphingosine kinaseinhibitor 2-(phyroxyanilino)-4-(pchlorophenyl) thiazole reduces androgen receptor expression via an oxidative stress-dependent mechanism

British Journal of Pharmacology

Volumn 168, Issue 6, 2013, Pages 1497-1505

  Tonelli, Francesca ^a   Alossaimi, Manal ^a   Williamson, Leon ^a   Tate, Rothwelle J ^a   Watson, David G ^a   Chan, Edmond ^a   Bittman, Robert ^b   Pyne, Nigel J ^a   Pyne, Susan ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

androgen receptor; prostate cancer; reactive oxygen species; sphingosine 1 phosphate; sphingosine kinase

Indexed keywords

2 (4 HYDROXYANILINO) 4 (4 CHLOROPHENYL)THIAZOLE; ACETYLCYSTEINE; ANDROGEN RECEPTOR; FINGOLIMOD; FINGOLIMOD METHYL ETHER; FUMONISIN B1; PHOSPHOTRANSFERASE INHIBITOR; PROSTATE SPECIFIC ANTIGEN; PROTEIN P53; REACTIVE OXYGEN METABOLITE; SPHINGOSINE KINASE 1; SPHINGOSINE KINASE 2; UNCLASSIFIED DRUG; 4 (4 (4 CHLORO PHENYL)THIAZOL 2 YLAMINO)PHENOL; 4-(4-(4-CHLORO-PHENYL)THIAZOL-2-YLAMINO)PHENOL; ANDROGEN RECEPTOR ANTAGONIST; ANTINEOPLASTIC AGENT; AR PROTEIN, HUMAN; DRUG DERIVATIVE; ENZYME INHIBITOR; ISOENZYME; MESSENGER RNA; PHOSPHOTRANSFERASE; PROPANEDIOL DERIVATIVE; SCAVENGER; SPHINGOSINE; SPHINGOSINE KINASE; THIAZOLE DERIVATIVE; TUMOR PROTEIN;

ARTICLE; CANCER CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOWN REGULATION; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME INHIBITION; GENE EXPRESSION; HUMAN; HUMAN CELL; NUCLEOTIDE SEQUENCE; OXIDATIVE STRESS; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; PROTEIN PROCESSING; RNA TRANSLATION; SIGNAL TRANSDUCTION; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; GENETICS; MALE; METABOLISM; PROSTATE TUMOR; PROTEIN STABILITY; TUMOR CELL LINE;

ANDROGEN RECEPTOR ANTAGONISTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DOWN-REGULATION; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; HUMANS; ISOENZYMES; MALE; NEOPLASM PROTEINS; OXIDATIVE STRESS; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PROPYLENE GLYCOLS; PROSTATE-SPECIFIC ANTIGEN; PROSTATIC NEOPLASMS; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEIN STABILITY; RECEPTORS, ANDROGEN; RNA, MESSENGER; SPHINGOSINE; THIAZOLES;

EID: 84874425286     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/bph.12035     Document Type: Article

References (39)

1. Akao Y, Banno Y, Nakagawa Y, Hasegawa N, Kim T, Murate T, et al. (2006). High expression of sphingosine kinase 1 and S1P receptors in chemotherapy-resistant prostate cancer PC-3 cells and their camptothecin-induced up-regulation. Biochem Biophys Res Commun 342: 1284-1290.
2. Alderton F, Rakhit S, Kong K-C, Palmer T, Sambi S, Pyne S, et al. (2001). Tethering of the platelet-derived growth factor beta receptor to G-protein-coupled receptors. A novel platform for integrative signaling by these receptor classes in mammalian cells. J Biol Chem 276: 28578-28585.
3. Alimirah F, Panchanathan R, Chen J, Zhang X, Ho SM, Choubey D, (2007). Restoration of p53 expression in human cancer cell lines upregulates the expression of Notch 1: implications for cancer cell fate determination after genotoxic stress. Neoplasia 9: 1152-1159.
4. Arnold HK, Sears RC, (2008). A tumor suppressor role for PP2A-B56alpha through negative regulation of c-Myc and other key oncoproteins. Cancer Metastasis Rev 27: 147-158.
5. Barr RK, Lynn HE, Moretti PA, Khew-Goodall Y, Pitson SM, (2008). Deactivation of sphingosine kinase 1 by protein phosphatase 2A. J Biol Chem 283: 34994-35002.
6. de Boer W, Bolt J, Kuiper GG, Brinkmann AO, Mulder E, (1987). Analysis of steroid- and DNA-binding domains of the calf uterine androgen receptor by limited proteolysis. J Steroid Biochem 28: 9-19.
7. Bouchier-Hayes L, (2010). The role of caspase-2 in stress-induced apoptosis. J Cell Mol Med 14: 1212-1224.
8. Dayon A, Brizuela L, Martin C, Mazerolles C, Pirot N, Doumerc N, et al. (2009). Sphingosine kinase-1 is central to androgen-regulated prostate cancer growth and survival. PLoS One. 4: e8048.
9. Fajardo AM, Mackenzie DA, Ji M, Deck LM, Jagt DL, Thompson TA, et al. (2012). The curcumin analog ca27 down-regulates androgen receptor through an oxidative stress mediated mechanism in human prostate cancer cells. Prostate 72: 612-625.
10. French KJ, Schrecengost RS, Lee BD, Zhuang Y, Smith SN, Eberly JLM, et al. (2003). Discovery and evaluation of inhibitors of human sphingosine kinase. Cancer Res 63: 5962-5969.
11. French KJ, Zhuang Y, Maines LW, Gao P, Wang W, Beljanski V, et al. (2010). Pharmacology and antitumor activity of ABC294640 a selective inhibitor of sphingosine kinase-2. J Pharmacol Exp Ther 333: 129-139.
12. Gao P, Smith CD, (2011). Ablation of sphingosine kinase 2 inhibits tumor cell proliferation and migration. Mol Cancer Res 9: 1509-1519.
13. Gregory CW, He B, Wilson EM, (2001). The putative androgen receptor-A form results from in vitro proteolysis. J Mol Endocrinol 27: 309-319.
14. Halkidou K, Gnanapragasam VJ, Mehta PB, Logan IR, Brady ME, Cook S, et al. (2003). Expression of Tip60, an androgen receptor coactivator, and its role in prostate cancer development. Oncogene 22: 2466-2477.
15. Heffernan-Stroud LA, Helke KL, Jenkins RW, De Costa AM, Hannun YA, Obeid LM, (2011). Defining a role for sphingosine kinase 1 in p53-dependent tumors. Oncogene 31: 1166-1175.
16. Huwiler A, Kotelevets N, Xin C, Pastukhov O, Pfeilschifter J, Zangemeister-Wittke U, (2011). Loss of sphingosine kinase-1 in carcinoma cells increases formation of reactive oxygen species and sensitivity to doxorubicin-induced DNA damage. Br J Pharmacol 162: 532-543.
17. Kapitonov D, Allegood JC, Mitchell C, Hait NC, Almenara JA, Adams JK, et al. (2009). Targeting sphingosine kinase 1 inhibits Akt signaling, induces apoptosis and suppresses growth of human glioblastoma cells and xenografts. Cancer Res 69: 6915-6923.
18. Leclercq TM, Moretti PA, Pitson SM, (2011). Guanine nucleotides regulate sphingosine kinase 1 activation by eukaryotic elongation factor 1A and provide a mechanism for eEF1A-associated oncogenesis. Oncogene 30: 372-378.
19. Li J, Guan HY, Gong LY, Song LB, Zhang N, Wu J, et al. (2008). Clinical significance of sphingosine kinase-1 expression in human astrocytomas progression and overall patient survival. Clin Cancer Res 14: 6996-7003.
20. Libertini SJ, Tepper CG, Rodriguez V, Asmuth DM, Kung HJ, Mudryj M, (2007). Evidence for calpain-mediated androgen receptor cleavage as a mechanism for androgen independence. Cancer Res 67: 9001-9005.
21. Lim KG, Tonelli F, Li Z, Lu X, Bittman R, Pyne S, et al. (2011a). FTY720 analogues as sphingosine kinase 1 inhibitors: enzyme inhibition kinetics, allosterism, proteasomal degradation, and actin rearrangement in MCF-7 breast cancer cells. J Biol Chem 286: 18633-18640.
22. Lim KG, Sun C, Bittman R, Pyne NJ, Pyne S, (2011b). (R)-FTY720 methyl ether is a specific sphingosine kinase 2 inhibitor: effect on sphingosine kinase 2 expression in HEK 293 cells and actin rearrangement and survival of MCF-7 breast cancer cells. Cell Signal 23: 1590-1595.
23. Long JS, Edwards J, Watson C, Tovey S, Mair K, Schiff R, et al. (2010). Sphingosine kinase 1 induces tolerance to human epidermal growth factor receptor 2 and prevents formation of a migratory phenotype in response to sphingosine 1-phosphate in estrogen receptor positive breast cancer cells. Mol Cell Biol 30: 3827-3841.
24. Loveridge C, Tonelli F, Leclercq T, Lim KG, Long S, Berdyshev E, et al. (2010). The sphingosine kinase 1 inhibitor 2-(p-hydroxyanilino)-4-(p- chlorophenyl)thiazole induces proteasomal degradation of sphingosine kinase 1 in mammalian cells. J Biol Chem 285: 38841-38852.
25. Lu X, Sun C, Valentine WJ, Shuyu E, Liu J, Tigyi G, et al. (2009). Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720. J Org Chem 74: 3192-3195.
26. Nava VE, Cuvillier O, Edsall LC, Kimura K, Milstien S, Gelmann EP, et al. (2000). Sphingosine enhances apoptosis of radiation-resistant prostate cancer cells. Cancer Res 60: 4468-4474.
27. Pchejetski D, Golzio M, Bonhoure E, Calvet C, Doumerc N, Garcia V, et al. (2005). Sphingosine kinase-1 as a chemotherapy sensor in prostate adenocarcinoma cell and mouse models. Cancer Res 65: 11667-11675.
28. Pchejetski D, Doumerc N, Golzio M, Naymark M, Teissié J, Kohama T, et al. (2008). Chemosensitizing effects of sphingosine kinase-1 inhibition in prostate cancer cell and animal models. Mol Cancer Ther 7: 1836-1845.
29. Pitman MR, Barr RK, Gliddon BL, Magarey AM, Moretti PA, Pitson SM, (2011). A critical role for the protein phosphatase 2A B'α regulatory subunit in dephosphorylation of sphingosine kinase 1. Int J Biochem Cell Biol 43: 342-347.
30. Pyne NJ, Pyne S, (2010). Sphingosine 1-phosphate and cancer. Nat Rev Cancer 10: 489-503.
31. Pyne S, Pyne NJ, (2001). Sphingosine 1-phosphate signaling in mammalian cells. Biochem J 349: 385-402.
32. Pyne S, Bittman R, Pyne NJ, (2011). Sphingosine kinase inhibitors and cancer: seeking the golden sword of Hercules. Cancer Res 71: 6576-6582.
33. Raje MR, Knott K, Kharel Y, Bissel P, Lynch KR, Santos WL, (2012). Design, synthesis and biological activity of sphingosine kinase 2 selective inhibitors. Bioorg Med Chem 20: 183-194.
34. Sankala HM, Hait NC, Paugh SW, Shida D, Lépine S, Elmore LW, et al. (2007). Involvement of sphingosine kinase 2 in p53-independent induction of p21 by the chemotherapeutic drug doxorubicin. Cancer Res 67: 10466-10474.
35. Takabe K, Paugh SW, Milstien S, Spiegel S, (2008). 'Inside-out' signaling of sphingosine-1-phosphate: therapeutic targets. Pharmacol Rev 60: 181-195.
36. Tonelli F, Lim KG, Loveridge C, Long J, Pitson SM, Tigyi G, et al. (2010). FTY720 and (S)-FTY720 vinylphosphonate inhibit sphingosine kinase 1 and promote its proteasomal degradation in human pulmonary artery smooth muscle, breast cancer and androgen-independent prostate cancer cells. Cell Signal 22: 1536-1542.
37. 3 sphingosine kinase 1 and extracellular signal-regulated kinase-1/2 is associated with development of tamoxifen resistance in estrogen receptor-positive breast cancer patients. Am J Pathol 177: 2205-2215.
38. Wilson CM, McPhaul MJ, (1994). A and B forms of the androgen receptor are present in human genital skin fibroblasts. Proc Natl Acad Sci U S A 91: 1234-1238.
39. Xia P, Gamble JR, Wang L, Pitson SM, Moretti PA, Wattenberg BW, et al. (2000). An oncogenic role of sphingosine kinase. Curr Biol 10: 1527-1530.