Alpha-tocopheryl phosphate is a novel apoptotic agent

Frontiers in Bioscience

Volumn 12, Issue 6, 2007, Pages 2013-2019

  Rezk, Bashir M ^a   Van Der Vijgh, Wim J F ^b,c   Bast, Aalt ^a   Haenen, Guido R M M ^b  

^a LOUISIANA STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b MAASTRICHT UNIVERSITY   (Netherlands)

^c VU UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

Alpha tocopheryl phosphate; Alpha tocopheryl succinate; Apoptosis; Osteosarcoma cell line

Indexed keywords

TOSCANA VIRUS;

ALPHA TOCOPHEROL; ALPHA TOCOPHEROL PHOSPHATE; ALPHA TOCOPHEROL SUCCINATE; ALPHA-TOCOPHEROL PHOSPHATE; DRUG DERIVATIVE; GROWTH INHIBITOR;

APOPTOSIS; ARTICLE; CHEMISTRY; DRUG EFFECT; HEMOLYSIS; HUMAN; MEMBRANE FLUIDITY; TUMOR CELL LINE;

ALPHA-TOCOPHEROL; APOPTOSIS; CELL LINE, TUMOR; GROWTH INHIBITORS; HEMOLYSIS; HUMANS; MEMBRANE FLUIDITY; VITAMIN E;

EID: 36049017294     PISSN: 27686701     EISSN: 27686698     Source Type: Journal    
DOI: 10.2741/2206     Document Type: Article

References (32)

1. Ogru E, R. Gianello, R. Libinaki, A. Smallridge, R. Bak, S. Geytenbeck, D. Kannar, S. West: Vitamin E phosphate: An endogenous form of vitamin E. Medimond Med. Pub, Englewood, NJ (2003)
2. Gianello R, R. Libinaki, A. Azzi, P.D. Gavin, Y. Negis, J.M. Zingg, P. Holt, H.H. Keah, A. Griffey, A. Smallridge, S.M. West, E. Ogru: Alpha-tocopheryl phosphate: a novel, natural form of vitamin E. Free Radic Biol Med 39, 970-976 (2005)
3. Negis Y, J.M. Zingg, E. Ogru, R. Gianello, R. Libinaki, A. Azzi: On the existence of cellular tocopheryl phosphate, its synthesis, degradation and cellular roles: a hypothesis. IUBMB Life 57, 23-25 (2005) (Pubitemid 40637697)
4. Rezk BM, G.R.M.M. Haenen, W.J.F. van der Vijgh, A. Bast: The extraordinary antioxidant activity of vitamin E phosphate. Biochem Biophys Acta 1683, 16-21 (2004) (Pubitemid 38844655)
5. Prasad KN, J. Edwards-Prasad: Effects of tocopherol (vitamin E)acid succinate on morphological alterations and growth inhibition in melanoma cells in culture. Cancer Res 42, 550-555 (1982) (Pubitemid 12173594)
6. Kline K, G.S. Cochran, B.G. Sanders: Growth-inhibitory effects of vitamin E succinate on retrovirus-transformed tumor cells in vitro. Nutr Cancer 14, 27-41 (1990) (Pubitemid 20202872)
7. Turley JM, F.W. Ruscetti, S.J. Kim, T. Fu, F.V. Gou, M.C. Birchenall-Roberts: Vitamin E succinate inhibits proliferation of BT-20 human breast cancer cells: increased binding of cyclin A negatively regulates E2F transactivation activity. Cancer Res 57, 2668-2675 (1997) (Pubitemid 27283778)
8. Yamamoto S, H. Tamai, R. Ishisaka, T. Kanno, K. Arita, H. Kobuchi, K. Utsumi. Mechanism of alpha-tocopheryl succinate-induced apoptosis of promyelocytic leukemia cells. Free Radic Res 33, 407-418 (2000)
9. Neuzil J, T. Weber, N. Gellert, C. Weber: Selective cancer cell killing by alpha-tocopheryl succinate. Br J Cancer 84, 87-89 (2001) (Pubitemid 32102509)
10. Neuzil J, M. Zhao, G. Ostermann, M. Sticha, N. Gellert, C. Weber, J.W. Eaton, U.T. Brunk: Alpha-tocopheryl succinate, an agent with in vivo anti-tumour activity, induces apoptosis by causing lysosomal instability. Biochem J 362, 709-715 (2002) (Pubitemid 34242323)
11. Birringer M, J.H. EyTina, B.A. Salvatore, J. Neuzil: Vitamin E analogues as inducers of apoptosis: structure-function relation. Br J Cancer 88, 1948-1955 (2003) (Pubitemid 36829673)
12. Alleva R, M.S. Benassi, M. Tomasetti, N. Gellert, F. Ponticelli, B. Borghi, P. Picci, J. Neuzil: Alpha-tocopheryl succinate induces cytostasis and apoptosis in osteosarcoma cells: the role of E2F1. Biochem Biophys Res Commun 331, 1515-1521 (2005) (Pubitemid 40692526)
13. Alleva R, M.S. Benassi, L. Pazzaglia, M. Tomasetti, N. Gellert, B. Borghi, J. Neuzil, P. Picci: Alpha-Tocopheryl succinate alters cell cycle distribution sensitising human osteosarcoma cells to methotrexate-induced apoptosis. Cancer Lett 232, 226-235 (2006) (Pubitemid 43170972)
14. Wu K, Y. Zhao, G.C. Li, W.P. Yu: c-Jun N-terminal kinase is required for vitamin E succinate-induced apoptosis in human gastric cancer cells. World J Gastroenterol 10, 1110-1114 (2004) (Pubitemid 38559383)
15. Kogure K, S. Hama, M. Kisaki, H. Takemasa, A. Tokumura, I. Suzuki, K. Fukuzawa: Structural characteristic of terminal dicarboxylic moiety required for apoptogenic activity of alpha-tocopheryl esters. Biochim Biophys Acta 1672, 93-99 (2004) (Pubitemid 38515860)
16. Neuzil J, T. Weber, A. Schroder, M. Lu, G. Ostermann, N. Gellert, G.C. Mayne, B. Olejnicka, A. Negre-Salvayre, M. Sticha, R.J. Coffey, C. Weber: Induction of cancer cell apoptosis by alpha-tocopheryl succinate: molecular pathways and structural requirements. FASEB J 15, 403-415 (2001) (Pubitemid 32141432)
17. Weber T, M. Lu, L. Andera, H. Lahm, N. Gellert, M.W. Fariss, V. Korinek, W. Sattler, D.S. Ucker, A. Terman, A. Schroder, W. Erl, U.T. Brunk, R.J. Coffey, C. Weber, J. Neuzil: 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 8, 863-869 (2002) (Pubitemid 34742119)
18. Barnett KT, F.D. Fokum, M.P. Malafa: Vitamin E succinate inhibits colon cancer liver metastases. J Surg Res 106, 292-298 (2002)
19. Tomasetti M, N. Gellert, A. Procopio, J. Neuzil: A vitamin E analogue suppresses malignant mesothelioma in a preclinical model: a future drug against a fatal neoplastic disease? Int J Cancer 109, 641-642 (2004) (Pubitemid 38405608)
20. Burton GW, A. Webb, K.U. Ingold: A mild, rapid, and efficient method of lipid extraction for use in determining vitamin E/lipid ratios. Lipids 20, 29-39 (1985) (Pubitemid 15168820)
21. Tsuda K, K. Kimura, I. Nishio: Leptin improves membrane fluidity of erythrocytes in humans via a nitric oxide-dependent mechanism-an electron paramagnetic resonance investigation. Biochem Biophys Res Commun 297, 672-681 (2002)
22. Nakayama S, E.M. Katoh, T. Tsuzuki, S. Kobayashi: Protective effect of alpha-tocopherol-6-O-phosphate against ultraviolet B-induced damage in cultured mouse skin. Invest Dermatol 121, 406-411 (2003) (Pubitemid 36969916)
23. Orditura M, F. De Vita, A. Roscigno, S. Infusino, A. Auriemma, P. Iodice, F. Ciaramella, G. Abbate, G. Catalano: Amifostine: A selective cytoprotective agent of normal tissues from chemo-radiotherapy induced toxicity (Review). Oncol Rep 6, 1357-1362 (1999)
24. Azzi A, A. Stocker: Vitamin E: non-antioxidant roles. Prog Lipid Res 39, 231-255 (2000) (Pubitemid 30224705)
25. Tomic-Vatic A, J. Eytina, J. Chapman, E. Mahdavian, J. Neuzil, B.A. Salvatore: Vitamin E amides, a new class of vitamin E analogues with enhanced proapoptotic activity. Int J Cancer 117, 188-193 (2005) (Pubitemid 41377437)
26. Gerweck LE, K. Seetharaman: Cellular pH gradient in tumor versus normal tissue: potential exploitation for the treatment of cancer. Cancer Res 56, 1194-1198 (1996) (Pubitemid 26080953)
27. Libinaki R, E. Ogru, R. Gianello, L. Bolton, S. Geytenbeek: Evaluation of the safety of mixed tocopheryl phosphates (MTP)-A formulation of alpha-tocopheryl phosphate plus alpha-di-tocopheryl phosphate. Food Chem Toxicol 44, 916-932 (2006) (Pubitemid 43850063)
28. Felemovicius I, M.E. Bonsack, M.L. Baptista, J.P. Delaney: Intestinal radioprotection by vitamin E (alphatocopherol). Ann Surg 222, 504-508, discussion 508-510 (1995)
29. Pérez-Pé R, J.A. Cebrián-Pérez, T. Muiño-Blanco: Semen plasma proteins prevent cold-shock membrane damage to ram spermatozoa. Theriogenology 56, 425-434 (2001) (Pubitemid 32730816)
30. Guarnieri C, E. Giordano, C. Muscari, L. Grossi, C.M. Caldarera: Alpha-tocopherol pretreatment improves endothelium-dependent vasodilation in aortic strips of young and aging rats exposed to oxidative stress. Mol Cell Biochem 157, 223-228 (1996) (Pubitemid 26142456)
31. Negis Y, N. Aytan, N. Ozer, E. Ogru, R. Libinaki, R. Gianello, A. Azzi, J.M. Zingg: The effect of tocopheryl phosphates on atherosclerosis progression in rabbits fed with a high cholesterol diet. Arch Biochem Biophys 450, 63-66 (2006) (Pubitemid 43782742)
32. Munteanu A, J.M. Zingg, E. Ogru, R. Libinaki, R. Gianello, S. West, Y. Negis, A. Azzi: Modulation of cell proliferation and gene expression by alpha-tocopheryl phosphates: relevance to atherosclerosis and inflammation. Biochem Biophys Res Commun. 318, 311-316 (2004) (Pubitemid 38526281)