In vitro and in vivo anticancer effects of the novel vitamin E ether analogue RRR-α-Tocopheryloxybutyl sulfonic acid in prostate cancer

Clinical Cancer Research

Volumn 15, Issue 3, 2009, Pages 898-906

  Ni, Jing ^a   Mai, Tiejun ^a   Pang, See Tong ^b   Haque, Imranul ^c   Huang, Kaohsing ^a   Dimaggio, Matthew A ^a   Xie, Shaozhen ^a   James, Nadine S ^c   Kasi, Dhanalakshmi ^c   Chemler, Sherry R ^c   Yeh, Shuyuan ^a,d  

^a UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

^b CHANG GUNG MEMORIAL HOSPITAL   (Taiwan)

^c UNIVERSITY AT BUFFALO   (United States)

^d UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ALPHA TOCOPHEROL DERIVATIVE; ALPHA TOCOPHEROL SUCCINATE; ALPHA TOCOPHERYLOXYBUTYL SULFONIC ACID; ANDROGEN RECEPTOR; DNA NUCLEOTIDYLEXOTRANSFERASE; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROSTATE CANCER; TUMOR GROWTH;

ADMINISTRATION, ORAL; ALPHA-TOCOPHEROL; ANIMALS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DRUG EVALUATION, PRECLINICAL; HUMANS; MALE; MICE; MICE, NUDE; PROSTATIC NEOPLASMS; RECEPTORS, ANDROGEN; RECEPTORS, CALCITRIOL; SULFONIC ACIDS; VITAMIN E; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 61349095515     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-08-1087     Document Type: Article

References (37)

1. Zu K, Ip C. Synergy between selenium and vitamin E in apoptosis induction is associated with activation of distinctive initiator caspases in human prostate cancer cells. Cancer Res 2003;63:6988-95.
2. Neuzil J, Weber T, Schroder A, et al. Induction of cancer cell apoptosis by α-tocopheryl succinate: molecular pathways and structural requirements. FASEB J 2001;15:403-15.
3. Zhang Y, Ni J, Messing EM, Chang E, Yang CR, Yeh S. Vitamin E succinate inhibits the function of androgen receptor and the expression of prostate- specific antigen in prostate cancer cells. Proc Natl Acad Sci U S A 2002;99:7408-13.
4. Ni J, Chen M, Zhang Y, Li R, Huang J, Yeh S. Vitamin E succinate inhibits human prostate cancer cell growth via modulating cell cycle regulatory machinery. Biochem Biophys Res Commun 2003;300:357-63.
5. Simmons-Menchaca M, Qian M,Yu W, Sanders BG, Kline K. RRR-α-tocopheryl succinate inhibits DNA synthesis and enhances the production and secretion of biologically active transforming growth factor-β by avian retrovirus-transformed lymphoid cells. Nutr Cancer 1995;24:171 -85.
6. Yu W, Heim K, Qian M, Simmons-Menchaca M, Sanders BG, Kline K. Evidence for role of transforming growth factor-β in RRRα-tocopheryl succinate-induced apoptosis of human MDA-MB-435 breast cancer cells. Nutr Cancer 1997;27:267-78.
7. You H,Yu W, Munoz-Medellin D, Brown PH, Sanders BG, Kline K. Role of extracellular signal-regulated kinase pathway in RRR-α-tocopheryl succinate-induced differentiation of human MDA-MB- 435 breast cancer cells. Mol Carcinog 2002;33:228-36.
8. 2-terminal kinase but not p38 mitogen-activated protein kinases is required for RRR-α-tocopheryl succinate-induced apoptosis of human breast cancer cells. Cancer Res 2001;61:6569-76.
9. Neuzil J,WeberT, Gellert N,Weber C. Selective cancer cell killing by α-tocopheryl succinate. Br J Cancer 2001;84:87-9.
10. Malafa MP, Fokum FD, Andoh J, et al. Vitamin Esuccinate suppresses prostate tumor growth by inducing apoptosis. Int J Cancer 2006;118:2441 -7.
11. Weber T, Lu M, Andera L, et al. Vitamin E succinate is a potent novel antineoplastic agent with high selectivity and cooperativity with tumor necrosis factor- related apoptosis-inducing ligand (Apo2 ligand) in vivo. Clin Cancer Res 2002;8:863-9.
12. Lawson KA, Anderson K, Simmons-Menchaca M, et al. Comparison of vitamin E derivatives α-TEAand VES in reduction of mouse mammary tumor burden and metastasis. Exp Biol Med (Maywood) 2004; 229:954-63.
13. Anderson K, Simmons-Menchaca M, Lawson KA, Atkinson J, Sanders BG, Kline K. Differential response of human ovarian cancer cells to induction of apoptosis by vitamin E Succinate and vitamin E analogue, α-TEA. Cancer Res 2004;64:4263-9.
14. Ni J, Wen X,Yao J, et al. Tocopherol-associated protein suppresses prostate cancer cell growth by inhibition of the phosphoinositide 3-kinase pathway. Cancer Res 2005;65:9807-16.
15. Lin HK, Yeh S, Kang HY, Chang C. Akt suppresses androgen-induced apoptosis by phosphorylating and inhibiting androgen receptor. Proc Natl Acad Sci U S A 2001;98:7200-5.
16. Ni J, Pang ST, Yeh S. Differential retention of α-vitamin E is correlated with its transporter gene expression and growth inhibition efficacy in prostate cancer cells. Prostate 2007;67:463-71.
17. Greenberg NM, De Mayo F, Finegold MJ, et al. Prostate cancer in a transgenic mouse. Proc Natl Acad Sci U S A1995;92:3439-43.
18. Plymate SR, Haugk KH, Sprenger CC, et al. Increased manganese superoxide dismutase (SOD-2) is part of the mechanism for prostate tumor suppression byMac25/insulin-like growth factorbinding-protein-related protein-1. Oncogene 2003;22:1024-34.
19. YinY, Ni J, Chen M, Dimaggio MA,Guo Y, Yeh S. The therapeutic and preventive effect of RRR-α-vitamin e succinate on prostate cancer via induction of insulinlike growth factor binding protein-3. Clin Cancer Res 2007;13:2271 -80.
20. Kogure K, Hama S, Kisaki M, et al. Structural characteristic of terminal dicarboxylic moiety required for apoptogenic activity of α-tocopheryl esters. Biochim Biophys Acta 2004;1672:93-9.
21. Birringer M, EyTina JH, Salvatore BA, Neuzil J. Vitamin E analogues as inducers of apoptosis: structure-function relation. Br J Cancer 2003;88:1948-55.
22. Chang E, Ni J, Yin Y, et al. α-Vitamin E derivative, RRR-α-tocopheryloxybutyric acid inhibits the proliferation of prostate cancer cells. Asian J Androl 2007; 9:31-9.
23. Shiau CW, Huang JW, Wang DS, et al. α-Tocopheryl succinate induces apoptosisin prostate cancer cells in part through inhibition of Bcl-xL/Bcl-2 function. J Biol Chem 2006;281:11819-25.
24. Tomic-VaticA, Eytina J, Chapman J, Mahdavian E, Neuzil J, Salvatore BA. Vitamin E amides, a new class of vitamin E analogues with enhanced proapoptotic activity. Int J Cancer 2005;117:188-93.
25. Neuzil J, Zhao M, Ostermann G, et al. α-Tocopheryl succinate, an agent with in vivo anti-tumour activity, induces apoptosis by causing lysosomal instability. Biochem J 2002;362:709-15.
26. Wike-Hooley JL, Haveman J, Reinhold HS. The relevance of tumour pH to the treatment of malignant disease. Radiother Oncol 1984;2:343-66.
27. Kozin SV, Shkarin P, Gerweck LE. The cell transmembrane pH gradient in tumors enhances cytotoxicity of specific weak acid chemotherapeutics. Cancer Res 2001;61:4740 - 3.
28. Gerweck LE,Vijayappa S, Kozin S. Tumor pH controls the in vivo efficacy of weak acid and base chemotherapeutics. Mol Cancer Ther 2006;5:1275-9.
29. Wu W, Luo Y, Sun C, et al. Targeting cell-impermeable prodrug activation to tumor microenvironment eradicates multiple drug-resistant neoplasms. Cancer Res 2006;66:970-80.
30. Lawson KA, Anderson K, Menchaca M, et al. Novel vitamin E analogue decreases syngeneic mouse mammary tumor burden and reduces lung metastasis. Mol Cancer Ther 2003;2:437-44.
31. Fariss MW, Fortuna MB, Everett CK, Smith JD, Trent DF, Djuric Z. The selective antiproliferative effects of α-tocopheryl hemisuccinate and cholesteryl hemisuccinate on murine leukemia cells result from the action of the intact compounds. Cancer Res 1994;54:3346-51.
32. Hahn T, Szabo L, Gold M, Ramanathapuram L, Hurley LH, Akporiaye ET. Dietary administration of the proapoptotic vitamin E analogue α-tocopheryloxy- acetic acid inhibits metastatic murine breast cancer. Cancer Res 2006;66:9374-8.
33. Lanvers-Kaminsky C, Bremer A, Dirksen U, Jurgens H, Boos J. Cytotoxicity of treosulfan and busulfan on pediatric tumor cell lines. Anticancer Drugs 2006;17: 657-62.
34. Kawasaki Y, Suzuki J, Suzuki H. Efficacy of methylprednisolone and urokinase pulse therapy combined with or without cyclophosphamide in severe Henoch-Schoenlein nephritis: a clinical and histopathological study. Nephrol Dial Transplant 2004; 19:858-64.
35. Freedman LD, Doak GO. The preparation and properties of phosphonic acids. Chem Rev 1957; 57:479-523.
36. Serjeant EP, Dempsey B. Ionization constants of organic acids in solution. IUPAC Chemical Data Series No. 23. Oxford (UK): Pergamon Press; 1979.
37. Hoppe PP, Krennrich G. Bioavailability and potency of natural-source and all-racemic α-tocopherol in the human: a dispute. Eur J Nutr 2000;39:183-93.