α-Tocopheryl phosphate-An activated form of vitamin E important for angiogenesis and vasculogenesis?

BioFactors

Volumn 38, Issue 1, 2012, Pages 24-33

  Zingg, Jean Marc ^a   Meydani, Mohsen ^a   Azzi, Angelo ^a  

^a TUFTS UNIVERSITY   (United States)

Author keywords

Tocopherol; Tocopheryl phosphate; Vascular endothelial growth factor; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL; ALPHA TOCOPHERYL PHOSPHATE; ASCORBIC ACID; BETA CAROTENE; HYPOXIA INDUCIBLE FACTOR 1ALPHA; LOW DENSITY LIPOPROTEIN; PHOSPHATIDYLINOSITOL 3 KINASE; PHOSPHORIC ACID DERIVATIVE; PROTEIN KINASE B; SELENIUM; UNCLASSIFIED DRUG; VASCULOTROPIN; VASCULOTROPIN RECEPTOR 2;

ANGIOGENESIS; ANTIANGIOGENIC ACTIVITY; ANTIOXIDANT ACTIVITY; BRAIN ISCHEMIA; CANCER PREVENTION; CANCER RISK; FETUS RESORPTION; HEART INFARCTION; HEART MUSCLE ISCHEMIA; HUMAN; HYPERCHOLESTEROLEMIA; HYPOXIA; LIPID PEROXIDATION; MACROPHAGE; MONOCYTE; NEUROPROTECTION; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; REPERFUSION INJURY; REVIEW; SIGNAL TRANSDUCTION; UMBILICAL VEIN ENDOTHELIAL CELL;

ALPHA-TOCOPHEROL; ANGIOGENESIS INDUCING AGENTS; ANIMALS; FEMALE; GENE EXPRESSION REGULATION; HUMANS; NEOVASCULARIZATION, PHYSIOLOGIC; PLACENTA; PREGNANCY; VASCULAR ENDOTHELIAL GROWTH FACTOR A; VITAMINS;

RATTUS;

EID: 84857648875     PISSN: 09516433     EISSN: 18728081     Source Type: Journal    
DOI: 10.1002/biof.198     Document Type: Review

References (130)

1. Mason, K. E. (1977) The first two decades of vitamin E. Fed. Proc. 36, 1906-1910.
2. Ricciarelli, R., Zingg, J. M., and Azzi, A. (2002) The 80th anniversary of vitamin E: beyond its antioxidant properties. Biol. Chem. 383, 457-465.
3. Wolf, G. (2005) The discovery of the antioxidant function of vitamin E: the contribution of Henry A. Mattill. J. Nutr. 135, 363-366.
4. Zingg, J. M. (2007) Vitamin E: an overview of major research directions. Mol. Aspects. Med. 28, 400-422.
5. Evans, H. M. and Bishop, K. S. (1922) On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science 56, 650-651.
6. Mattill, H. A. (1927) The oxidative destruction of vitamins A and E and the protective action of certain vegetable oils. J. Am. Med. Assoc. 89, 1505-1508.
7. Cummings, M. J. and Mattill, H. A. (1931) The auto-oxidation of fats with reference to their destructive effect on vitamin E. Eur. J. Nutr. 3, 421-432.
8. Evans, H. M., Emerson, O. H., and Emerson, G. A. (1935) The isolation from wheat germ oil of an alcohol, alpha-tocopherol, having the properties of vitamin E. J. Biol. Chem. 113, 319-332.
9. Zingg, J. M. (2007) Molecular and cellular activities of vitamin E analogues. Mini Rev. Med. Chem. 7, 543-558.
10. Sato, Y., Hagiwara, K., Arai, H., and Inoue, K. (1991) Purification and characterization of the alpha-tocopherol transfer protein from rat liver. FEBS Lett. 288, 41-45.
11. Sato, Y., Arai, H., Miyata, A., Tokita, S., Yamamoto, K., Tanabe, T., and Inoue, K. (1993) Primary structure of alpha-tocopherol transfer protein from rat liver. Homology with cellular retinaldehyde-binding protein. J. Biol. Chem. 268, 17705-17710.
12. Hentati, A., Deng, H. X., Hung, W. Y., Nayer, M., Ahmed, M. S., He, X., Tim, R., Stumpf, D. A., Siddique, T., and Ahmed (1996) Human alpha-tocopherol transfer protein: gene structure and mutations in familial vitamin E deficiency. Ann. Neurol. 39, 295-300.
13. Dersjant-Li, Y. and Peisker, M. (2010) Utilization of stereoisomers from alpha-tocopherol in livestock animals. J. Anim. Physiol. Anim. Nutr. (Berl) 94, 413-421.
14. Meydani, M., Koga, T., and Ali, S. (2001) In Encyclopedia of Life Sciences. Nature Publishing Group, Hoboken, pp. 1-6.
15. Traber, M. G. and Atkinson, J. (2007) Vitamin E, antioxidant and nothing more. Free Radic. Biol. Med. 43, 4-15.
16. Brigelius-Flohe, R., Kelly, F. J., Salonen, J. T., Neuzil, J., Zingg, J. M., and Azzi, A. (2002) The European perspective on vitamin E: current knowledge and future research. Am. J. Clin. Nutr. 76, 703-716.
17. Rimbach, G., Minihane, A. M., Majewicz, J., Fischer, A., Pallauf, J., Virgli, F., and Weinberg, P. D. (2002) Regulation of cell signalling by vitamin E. Proc. Nutr. Soc. 61, 415-425.
18. Zingg, J. M. and Azzi, A. (2004) Non-antioxidant activities of vitamin E. Curr. Med. Chem. 11, 1113-1133.
19. Azzi, A. (2007) Molecular mechanism of alpha-tocopherol action. Free Radic. Biol. Med. 43, 16-21.
20. Atkinson, J., Harroun, T., Wassall, S. R., Stillwell, W., and Katsaras, J. (2010) The location and behavior of alpha-tocopherol in membranes. Mol. Nutr. Food Res. 54, 641-651.
21. Evans, H. M., Emerson, G. A., and Emerson, O. H. (1938) The chemistry of vitamin E. II. Biological assays of various synthetic compounds. Science 88, 38-39.
22. Weiser, H. and Vecchi, M. (1982) Stereoisomers of alpha-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, individually or in mixtures, as determined by rat resorption-gestation tests. Int. J. Vitam. Nutr. Res. 52, 351-370.
23. Muller, P. Y., Netscher, T., Frank, J., Stoecklin, E., Rimbach, G., and Barella, L. (2005) Comparative quantification of pharmacodynamic parameters of chiral compounds (RRR- vs. all-rac-alpha tocopherol) by global gene expression profiling. J. Plant. Physiol. 162, 811-817.
24. Muller, D. P., Manning, J. A., Mathias, P. M., and Harries, J. T. (1976) Studies on the intestinal hydrolysis of tocopheryl esters. Int. J. Vitam. Nutr. Res. 46, 207-210.
25. Mathias, P. M., Harries, J. T., Peters, T. J., and Muller, D. P. (1981) Studies on the in vivo absorption of micellar solutions of tocopherol and tocopheryl acetate in the rat: demonstration and partial characterization of a mucosal esterase localized to the endoplasmic reticulum of the enterocyte. J. Lipid Res. 22, 829-837.
26. Nierenberg, D. W., Lester, D. C., and Colacchio, T. A. (1987) Determination of tocopherol and tocopherol acetate concentrations in human feces using high-performance liquid chromatography. J. Chromatogr. 413, 79-89.
27. Lauridsen, C., Hedemann, M. S., and Jensen, S. K. (2001) Hydrolysis of tocopheryl and retinyl esters by porcine carboxyl ester hydrolase is affected by their carboxylate moiety and bile acids. J. Nutr. Biochem. 12, 219-224.
28. Birringer, M., EyTina, J. H., Salvatore, B. A., and Neuzil, J. (2003) Vitamin E analogues as inducers of apoptosis: structure-function relation. Br. J. Cancer 88, 1948-1955.
29. Rezk, B. M., van, der Vijgh, W. J., Bast, A., and Haenen, G. R. (2007) Alpha-tocopheryl phosphate is a novel apoptotic agent. Front Biosci. 12, 2013-2019.
30. Birringer, M. (2010) Analysis of vitamin E metabolites in biological specimen. Mol. Nutr. Food Res. 54, 588-598.
31. Urano, S., Inomori, Y., Sugawara, T., Kato, Y., Kitahara, M., Hasegawa, Y., Matsuo, M., and Mukai, K. (1992) Vitamin E: inhibition of retinol-induced hemolysis and membrane-stabilizing behavior. J. Biol. Chem. 267, 18365-18370.
32. Azzi, A. and Zingg, J. M. (2006) The role and importance of vitamin E for general health. Clin. Dermatol.; Retinoids Other Treat. 22, 26-29.
33. Ouahchi, K., Arita, M., Kayden, H., Hentati, F., Ben Hamida, M., Sokol, R., Arai, H., Inoue, K., Mandel, J. L., and Koenig, M. (1995) Ataxia with isolated vitamin E deficiency is caused by mutations in the alpha-tocopherol transfer protein. Nat. Genet. 9, 141-145.
34. Ben Hamida, C., Doerflinger, N., Belal, S., Linder, C., Reutenauer, L., Dib, C., Gyapay, G., Vignal, A., Le Paslier, D., and Cohen, D. (1993) Localization of Friedreich ataxia phenotype with selective vitamin E deficiency to chromosome 8q by homozygosity mapping (see comments). Nat. Genet. 5, 195-200.
35. Terasawa, Y., Ladha, Z., Leonard, S. W., Morrow, J. D., Newland, D., Sanan, D., Packer, L., Traber, M. G., and Farese, R. V. Jr. (2000) Increased atherosclerosis in hyperlipidemic mice deficient in alpha-tocopherol transfer protein and vitamin E. Proc. Natl. Acad. Sci. USA 97, 13830-13834.
36. Jishage, K., Arita, M., Igarashi, K., Iwata, T., Watanabe, M., Ogawa, M., Ueda, O., Kamada, N., Inoue, K., Arai, H., and Suzuki, H. (2001) Alpha-tocopherol transfer protein is important for the normal development of placental labyrinthine trophoblasts in mice. J. Biol. Chem. 276, 1669-1672.
37. Yokota, T., Igarashi, K., Uchihara, T., Jishage, K., Tomita, H., Inaba, A., Li, Y., Arita, M., Suzuki, H., Mizusawa, H., and Arai, H. (2001) Delayed-onset ataxia in mice lacking alpha -tocopherol transfer protein: model for neuronal degeneration caused by chronic oxidative stress. Proc. Natl. Acad. Sci. USA 98, 15185-15190.
38. Gohil, K., Schock, B. C., Chakraborty, A. A., Terasawa, Y., Raber, J., Farese, R. V. Jr., Packer, L., Cross, C. E., and Traber, M. G. (2003) Gene expression profile of oxidant stress and neurodegeneration in transgenic mice deficient in alpha-tocopherol transfer protein. Free Radic. Biol. Med. 35, 1343-1354.
39. Suarna, C., Wu, B. J., Choy, K., Mori, T., Croft, K., Cynshi, O., and Stocker, R. (2006) Protective effect of vitamin E supplements on experimental atherosclerosis is modest and depends on preexisting vitamin E deficiency. Free Radic. Biol. Med. 41, 722-730.
40. Viana, M., Barbas, C., Castro, M., Herrera, E., and Bonet, B. (1999) Alpha-tocopherol concentration in fetal and maternal tissues of pregnant rats supplemented with alpha-tocopherol. Ann. Nutr. Metab. 43, 107-112.
41. Kaempf-Rotzoll, D. E., Horiguchi, M., Hashiguchi, K., Aoki, J., Tamai, H., Linderkamp, O., and Arai, H. (2003) Human placental trophoblast cells express alpha-tocopherol transfer protein. Placenta 24, 439-444.
42. Viana, M., Castro, M., Barbas, C., Herrera, E., and Bonet, B. (2003) Effect of different doses of vitamin E on the incidence of malformations in pregnant diabetic rats. Ann. Nutr. Metab. 47, 6-10.
43. Muller-Schmehl, K., Beninde, J., Finckh, B., Florian, S., Dudenhausen, J. W., Brigelius-Flohe, R., and Schuelke, M. (2004) Localization of alpha-tocopherol transfer protein in trophoblast, fetal capillaries' endothelium and amnion epithelium of human term placenta. Free Radic. Res. 38, 413-420.
44. Zingg, J. M., Kempna, P., Paris, M., Reiter, E., Villacorta, L., Cipollone, R., Munteanu, A., De Pascale, C., Menini, S., Cueff, A., Arock, M., Azzi, A., and Ricciarelli, R. (2008) Characterization of three human sec14p-like proteins: alpha-tocopherol transport activity and expression pattern in tissues. Biochimie 90, 1703-1715.
45. Narushima, K., Takada, T., Yamanashi, Y., and Suzuki, H. (2008) Niemann-pick C1-like 1 mediates alpha-tocopherol transport. Mol. Pharmacol. 74, 42-49.
46. Zingg, J. M., Azzi, A., and Meydani, M. (2008) Genetic polymorphisms as determinants for disease-preventive effects of vitamin E. Nutr. Rev. 66, 406-414.
47. Carter, A. M. and Enders, A. C. (2004) Comparative aspects of trophoblast development and placentation. Reprod. Biol. Endocrinol. 2, 46.
48. Kim, H. Y., Pratt, D. A., Seal, J. R., Wijtmans, M., and Porter, N. A. (2005) Lipid-soluble 3-pyridinol antioxidants spare alpha-tocopherol and do not efficiently mediate peroxidation of cholesterol esters in human low-density lipoprotein. J. Med. Chem. 48, 6787-6789.
49. Sen, A., Ghosh, P. K., and Mukherjea, M. (1998) Changes in lipid composition and fluidity of human placental basal membrane and modulation of bilayer protein functions with progress of gestation. Mol. Cell. Biochem. 187, 183-190.
50. Sen, A. and Mukherjea, M. (1998) Modulation of bilayer fluidity by lipid peroxidation of human placental syncytiotrophoblast membranes during embryogenesis. Indian J. Biochem. Biophys. 35, 216-223.
51. Jauniaux, E., Watson, A. L., Hempstock, J., Bao, Y. P., Skepper, J. N., and Burton, G. J. (2000) Onset of maternal arterial blood flow and placental oxidative stress. A possible factor in human early pregnancy failure. Am. J. Pathol. 157, 2111-2122.
52. Burton, G. J., Hempstock, J., and Jauniaux, E. (2003) Oxygen, early embryonic metabolism and free radical-mediated embryopathies. Reprod. Biomed. Online 6, 84-96.
53. Jauniaux, E., Hempstock, J., Greenwold, N., and Burton, G. J. (2003) Trophoblastic oxidative stress in relation to temporal and regional differences in maternal placental blood flow in normal and abnormal early pregnancies. Am. J. Pathol. 162, 115-125.
54. Rotzoll, D. E., Scherling, R., Etzl, R., Stepan, H., Horn, L. C., and Poschl, J. M. (2008) Immunohistochemical localization of alpha-tocopherol transfer protein and lipoperoxidation products in human first-trimester and term placenta. Eur. J. Obstet. Gynecol. Reprod. Biol. 140, 183-191.
55. Roberts, L. J.II, Oates, J. A., Linton, M. F., Fazio, S., Meador, B. P., Gross, M. D., Shyr, Y., and Morrow, J. D. (2007) The relationship between dose of vitamin E and suppression of oxidative stress in humans. Free Radic. Biol. Med. 43, 1388-1393.
56. Guzy, R. D. and Schumacker, P. T. (2006) Oxygen sensing by mitochondria at complex III: the paradox of increased reactive oxygen species during hypoxia. Exp. Physiol. 91, 807-819.
57. Kasimanickam, R. K., Kasimanickam, V. R., Rodriguez, J. S., Pelzer, K. D., Sponeneberg, P. D., and Thatcher, C. D. (2010) Tocopherol induced angiogenesis in placental vascular network in late pregnant ewes. Reprod. Biol. Endocrinol. 8, 86.
58. Sengupta, J., Lalitkumar, P. G., Najwa, A. R., Charnock-Jones, D. S., Evans, A. L., Sharkey, A. M., Smith, S. K., and Ghosh, D. (2007) Immunoneutralization of vascular endothelial growth factor inhibits pregnancy establishment in the rhesus monkey (Macaca mulatta). Reproduction 133, 1199-1211.
59. Zhang, B., Tanaka, J., Yang, L., Sakanaka, M., Hata, R., Maeda, N., and Mitsuda, N. (2004) Protective effect of vitamin E against focal brain ischemia and neuronal death through induction of target genes of hypoxia-inducible factor-1. Neuroscience 126, 433-440.
60. Daghini, E., Zhu, X. Y., Versari, D., Bentley, M. D., Napoli, C., Lerman, A., and Lerman, L. O. (2007) Antioxidant vitamins induce angiogenesis in the normal pig kidney. Am. J. Physiol. Renal. Physiol. 293, F371-F381.
61. Nespereira, B., Perez-Ilzarbe, M., Fernandez, P., Fuentes, A. M., Paramo, J. A., and Rodriguez, J. A. (2003) Vitamins C and E downregulate vascular VEGF and VEGFR-2 expression in apolipoprotein-E-deficient mice. Atherosclerosis 171, 67-73.
62. Schindler, R. and Mentlein, R. (2006) Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells. J. Nutr. 136, 1477-1482.
63. Tang, F. Y. and Meydani, M. (2001) Green tea catechins and vitamin E inhibit angiogenesis of human microvascular endothelial cells through suppression of IL-8 production. Nutr. Cancer 41, 119-125.
64. Shibata, A., Nakagawa, K., Sookwong, P., Tsuduki, T., Oikawa, S., and Miyazawa, T. (2009) delta-Tocotrienol suppresses VEGF induced angiogenesis whereas alpha-tocopherol does not. J. Agric. Food Chem. 57, 8696-8704.
65. Rodriguez, J. A., Nespereira, B., Perez-Ilzarbe, M., Eguinoa, E., and Paramo, J. A. (2005) Vitamins C and E prevent endothelial VEGF and VEGFR-2 overexpression induced by porcine hypercholesterolemic LDL. Cardiovasc. Res. 65, 665-673.
66. 2 in angiotensin II-induced vascular hypertrophy. Hypertension 32, 488-495.
67. 2 generation play a key role in flow-mediated dilation in human coronary resistance arteries. Circ. Res. 93, 573-580.
68. Dong, L. F., Swettenham, E., Eliasson, J., Wang, X. F., Gold, M., Medunic, Y., Stantic, M., Low, P., Prochazka, L., Witting, P. K., Turanek, J., Akporiaye, E. T., Ralph, S. J., and Neuzil, J. (2007) Vitamin E analogues inhibit angiogenesis by selective induction of apoptosis in proliferating endothelial cells: the role of oxidative stress. Cancer Res. 67, 11906-11913.
69. Neuzil, J., Rohlena, J., Dong, L., Kluckova, K., Zobalova, R., Goodwin, J., Tilly, D., Stursa, J., Pecinova, A., Philimonenko, A., Hozak, P., Banerjee, J., Ledvina, M., Sen, C. K., and Coster, M. (2011) Mitochondrially targeted -tocopheryl succinate is antiangiogenic: potential benefit against tumor angiogenesis but caution against wound healing. Antioxid. Redox. Signal. 15, 2923-2935.
70. Zingg, J. M., Libinaki, R., Lai, C. Q., Meydani, M., Gianello, R., Ogru, E., and Azzi, A. (2010) Modulation of gene expression by alpha-tocopherol and alpha-tocopheryl phosphate in THP-1 monocytes. FRBM 49, 1989-2000.
71. Munteanu, A., Taddei, M., Tamburini, I., Bergamini, E., Azzi, A., and Zingg, J. M. (2006) Antagonistic effects of oxidized low density lipoprotein and {alpha}-tocopherol on CD36 scavenger receptor expression in monocytes: involvement of protein kinase B and peroxisome proliferator-activated receptor-{gamma}. J. Biol. Chem. 281, 6489-6497.
72. Kempna, P., Reiter, E., Arock, M., Azzi, A., and Zingg, J. M. (2004) Inhibition of HMC-1 mast cell proliferation by vitamin E: involvement of the protein kinase B pathway. J. Biol. Chem. 279, 50700-50709.
73. Numakawa, Y., Numakawa, T., Matsumoto, T., Yagasaki, Y., Kumamaru, E., Kunugi, H., Taguchi, T., and Niki, E. (2006) Vitamin E protected cultured cortical neurons from oxidative stress-induced cell death through the activation of mitogen-activated protein kinase and phosphatidylinositol 3-kinase. J. Neurochem. 97, 1191-1202.
74. Siragusa, M., Katare, R., Meloni, M., Damilano, F., Hirsch, E., Emanueli, C., and Madeddu, P. (2010) Involvement of phosphoinositide 3-kinase gamma in angiogenesis and healing of experimental myocardial infarction in mice. Circ. Res. 106, 757-768.
75. Morrish, D. W., Dakour, J., and Li, H. (2001) Life and death in the placenta: new peptides and genes regulating human syncytiotrophoblast and extravillous cytotrophoblast lineage formation and renewal. Curr. Protein Pept. Sci. 2, 245-259.
76. Li, H., Dakour, J., Guilbert, L. J., Winkler-Lowen, B., Lyall, F., and Morrish, D. W. (2005) PL74, a novel member of the transforming growth factor-beta superfamily, is overexpressed in preeclampsia and causes apoptosis in trophoblast cells. J. Clin. Endocrinol. Metab. 90, 3045-3053.
77. Mukherjee, S., Lekli, I., Das, M., Azzi, A., and Das, D. K. (2008) Cardioprotection with alpha-tocopheryl phosphate: amelioration of myocardial ischemia reperfusion injury is linked with its ability to generate a survival signal through Akt activation. Biochim. Biophys. Acta. 1782, 498-503.
78. Jin, K., Mao, X. O., and Greenberg, D. A. (2006) Vascular endothelial growth factor stimulates neurite outgrowth from cerebral cortical neurons via Rho kinase signaling. J. Neurobiol. 66, 236-242.
79. Sakowski, S. A., Heavener, S. B., Lunn, J. S., Fung, K., Oh, S. S., Spratt, S. K., Hogikyan, N. D., and Feldman, E. L. (2009) Neuroprotection using gene therapy to induce vascular endothelial growth factor-A expression. Gene Ther. 16, 1292-1299.
80. Ogru, E., Gianello, R., Libinaki, R., Smallridge, A., Bak, R., Geytenbeck, S., Kannar, D., and West, S., Eds. (2003) Vitamin E Phosphate: An Endogenous Form of Vitamin E. Medimond S.r.l. (Bologna), 109-113.
81. Gianello, R., Libinaki, R., Azzi, A., Gavin, P. D., Negis, Y., Zingg, J. M., Holt, P., Keah, H. H., Griffey, A., Smallridge, A., West, S. M., and Ogru, E. (2005) Alpha-tocopheryl phosphate: a novel, natural form of vitamin E. Free Radic. Biol. Med. 39, 970-976.
82. Libinaki, R., Ogru, E., Gianello, R., Bolton, L., and Geytenbeek, S. (2005) 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.
83. Gianello, R., Hall, W. C., Kennepohl, E., Libinaki, R., and Ogru, E. (2007) Subchronic oral toxicity study of mixed tocopheryl phosphates in rats. Int. J. Toxicol. 26, 475-490.
84. Mustacich, D. J., Vo, A. T., Elias, V. D., Payne, K., Sullivan, L., Leonard, S. W., and Traber, M. G. (2007) Regulatory mechanisms to control tissue alpha-tocopherol. Free Radic. Biol. Med. 43, 610-618.
85. Lippman, S. M., Klein, E. A., Goodman, P. J., Lucia, M. S., Thompson, I. M., Ford, L. G., Parnes, H. L., Minasian, L. M., Gaziano, J. M., Hartline, J. A., Parsons, J. K., Bearden, J. D.III, Crawford, E. D., Goodman, G. E., Claudio, J., Winquist, E., Cook, E. D., Karp, D. D., Walther, P., Lieber, M. M., Kristal, A. R., Darke, A. K., Arnold, K. B., Ganz, P. A., Santella, R. M., Albanes, D., Taylor, P. R., Probstfield, J. L., Jagpal, T. J., Crowley, J. J., Meyskens, F. L. Jr., Baker, L. H., and Coltman, C. A. Jr. (2009) Effect of selenium and vitamin E on risk of prostate cancer and other cancers: the Selenium and Vitamin E Cancer Prevention Trial (SELECT). JAMA 301, 39-51.
86. Klein, E. A., Thompson, I. M. Jr., Tangen, C. M., Crowley, J. J., Lucia, M. S., Goodman, P. J., Minasian, L. M., Ford, L. G., Parnes, H. L., Gaziano, J. M., Karp, D. D., Lieber, M. M., Walther, P. J., Klotz, L., Parsons, J. K., Chin, J. L., Darke, A. K., Lippman, S. M., Goodman, G. E., Meyskens, F. L. Jr., and Baker, L. H. (2011) Vitamin E and the risk of prostate cancer: the Selenium and Vitamin E Cancer Prevention Trial (SELECT). JAMA 306, 1549-1556.
87. Mondul, A. M., Rager, H. C., Kopp, W., Virtamo, J., and Albanes, D. (2011) Supplementation with {alpha}-tocopherol or {beta}-carotene reduces serum concentrations of vascular endothelial growth factor-D, but Not -A or -C, in male smokers. J. Nutr. 141, 2030-2034.
88. Ohno-Matsui, K. (2011) Parallel findings in age-related macular degeneration and Alzheimer's disease. Prog. Retin. Eye Res. 30, 217-238.
89. Munteanu, A., Zingg, J. M., Ogru, E., Libinaki, R., Gianello, R., West, S., Negis, Y., and Azzi, A. (2004) Modulation of cell proliferation and gene expression by alpha-tocopheryl phosphates: relevance to atherosclerosis and inflammation. Biochem. Biophys. Res. Commun. 318, 311-316.
90. Saitoh, Y., Yumoto, A., and Miwa, N. (2009) alpha-Tocopheryl phosphate suppresses tumor invasion concurrently with dynamic morphological changes and delocalization of cortactin from invadopodia. Int. J. Oncol. 35, 1277-1288.
91. Arany, Z., Foo, S. Y., Ma, Y., Ruas, J. L., Bommi-Reddy, A., Girnun, G., Cooper, M., Laznik, D., Chinsomboon, J., Rangwala, S. M., Baek, K. H., Rosenzweig, A., and Spiegelman, B. M. (2008) HIF-independent regulation of VEGF and angiogenesis by the transcriptional coactivator PGC-1alpha. Nature 451, 1008-1012.
92. Thangarajah, H., Yao, D., Chang, E. I., Shi, Y., Jazayeri, L., Vial, I. N., Galiano, R. D., Du, X. L., Grogan, R., Galvez, M. G., Januszyk, M., Brownlee, M., and Gurtner, G. C. (2009) The molecular basis for impaired hypoxia-induced VEGF expression in diabetic tissues. Proc. Natl. Acad. Sci. USA 106, 13505-13510.
93. Prior, S. J., Hagberg, J. M., Paton, C. M., Douglass, L. W., Brown, M. D., McLenithan, J. C., and Roth, S. M. (2006) DNA sequence variation in the promoter region of the VEGF gene impacts VEGF gene expression and maximal oxygen consumption. Am. J. Physiol. Heart Circ. Physiol. 290, H1848-H1855.
94. Josko, J. and Mazurek, M. (2004) Transcription factors having impact on vascular endothelial growth factor (VEGF) gene expression in angiogenesis. Med. Sci. Monit. 10, RA89-RA98.
95. Pages, G. and Pouyssegur, J. (2005) Transcriptional regulation of the vascular endothelial growth factor gene-a concert of activating factors. Cardiovasc. Res. 65, 564-573.
96. Heo, K., Park, K. A., Kim, Y. H., Kim, S. H., Oh, Y. S., Kim, I. H., Ryu, S. H., and Suh, P. G. (2009) Sphingosine 1-phosphate induces vascular endothelial growth factor expression in endothelial cells. BMB Rep. 42, 685-690.
97. Kranenburg, O., Gebbink, M. F., and Voest, E. E. (2004) Stimulation of angiogenesis by Ras proteins. Biochim. Biophys. Acta. 1654, 23-37.
98. Akiri, G., Nahari, D., Finkelstein, Y., Le, S. Y., Elroy-Stein, O., and Levi, B. Z. (1998) Regulation of vascular endothelial growth factor (VEGF) expression is mediated by internal initiation of translation and alternative initiation of transcription. Oncogene 17, 227-236.
99. Tischer, E., Mitchell, R., Hartman, T., Silva, M., Gospodarowicz, D., Fiddes, J. C., and Abraham, J. A. (1991) The human gene for vascular endothelial growth factor. Multiple protein forms are encoded through alternative exon splicing. J. Biol. Chem. 266, 11947-11954.
100. Levy, N. S., Chung, S., Furneaux, H., and Levy, A. P. (1998) Hypoxic stabilization of vascular endothelial growth factor mRNA by the RNA-binding protein HuR. J. Biol. Chem. 273, 6417-6423.
101. Shim, J. and Karin, M. (2002) The control of mRNA stability in response to extracellular stimuli. Mol. Cells 14, 323-331.
102. Basu, A., Datta, D., Zurakowski, D., and Pal, S. (2010) Altered VEGF mRNA stability following treatments with immunosuppressive agents: implications for cancer development. J. Biol. Chem. 285, 25196-25202.
103. Hua, Z., Lv, Q., Ye, W., Wong, C. K., Cai, G., Gu, D., Ji, Y., Zhao, C., Wang, J., Yang, B. B., and Zhang, Y. (2006) MiRNA-directed regulation of VEGF and other angiogenic factors under hypoxia. PLoS One 1, e116.
104. Long, J., Wang, Y., Wang, W., Chang, B. H., and Danesh, F. R. (2010) Identification of microRNA-93 as a novel regulator of vascular endothelial growth factor in hyperglycemic conditions. J. Biol. Chem. 285, 23457-23465.
105. Ghosh, R., Lipson, K. L., Sargent, K. E., Mercurio, A. M., Hunt, J. S., Ron, D., and Urano F. (2010) Transcriptional regulation of VEGF-A by the unfolded protein response pathway. PLoS One 5, e9575.
106. Munteanu, A., Ricciarelli, R., Massone, S., and Zingg, J. M. (2007) Modulation of proteasome activity by vitamin E in THP-1 monocytes. IUBMB Life 59, 771-780.
107. Watson, A. L., Skepper, J. N., Jauniaux, E., and Burton, G. J. (1998) Changes in concentration, localization and activity of catalase within the human placenta during early gestation. Placenta 19, 27-34.
108. Watson, A. L., Skepper, J. N., Jauniaux, E., and Burton, G. J. (1998) Susceptibility of human placental syncytiotrophoblastic mitochondria to oxygen-mediated damage in relation to gestational age. J. Clin. Endocrinol. Metab. 83, 1697-1705.
109. Dyatlov, V. A., Makovetskaia, V. V., Leonhardt, R., Lawrence, D. A., and Carpenter, D. O. (1998) Vitamin E enhances Ca(2+)-mediated vulnerability of immature cerebellar granule cells to ischemia. Free Radic. Biol. Med. 25, 793-802.
110. Zingg, J. M., Meydani, M., and Azzi, A. (2010) alpha-Tocopheryl phosphate-an active lipid mediator? Mol. Nutr. Food Res. 54, 1-14.
111. Nishio, K., Ishida, N., Saito, Y., Ogawa-Akazawa, Y., Shichiri, M., Yoshida, Y., Hagihara, Y., Noguchi, N., Chirico, J., Atkinson, J., and Niki, E. (2011) alpha-Tocopheryl phosphate: uptake, hydrolysis, and antioxidant action in cultured cells and mouse. Free Radic. Biol. Med. 50, 1794-1800.
112. Watson, J. C., Redmann, J. G., Meyers, M. O., Alperin-Lea, R. C., Gebhardt, B. M., Delcarpio, J. B., and Woltering, E. A. (1997) Breast cancer increases initiation of angiogenesis without accelerating neovessel growth rate. Surgery 122, 508-513; discussion 513-504.
113. West, D. C., Thompson, W. D., Sells, P. G., and Burbridge, M. F. (2001) Angiogenesis Assays Using Chick Chorioallantoic Membrane. Humana Press Inc., Totowa, NJ. Methods Mol. Med. 46, 107-129.
114. Leeson, S. and Caston, L. J. (2003) Vitamin Enrichment of Eggs. J. Appl. Poult. Res. 12, 24-26.
115. Baal, N., Widmer-Teske, R., McKinnon, T., Preissner, K. T., and Zygmunt, M. T. (2009) In vitro spheroid model of placental vasculogenesis: does it work? Lab. Invest. 89, 152-163.
116. Serbedzija, G. N., Flynn, E., and Willett, C. E. (1999) Zebrafish angiogenesis: a new model for drug screening. Angiogenesis 3, 353-359.
117. West, D. C. and Burbridge, M. F. (2009) Three-dimensional in vitro anglogenesis in the rat aortic ring model. Methods Mol. Biol. 467, 189-210.
118. Greenway, F. L., Liu, Z., Yu, Y., Caruso, M. K., Roberts, A. T., Lyons, J., Schwimer, J. E., Gupta, A. K., Bellanger, D. E., Guillot, T. S., and Woltering, E. A. (2007) An assay to measure angiogenesis in human fat tissue. Obes. Surg. 17, 510-515.
119. Negis, Y., Zingg, J. M., Ogru, E., Gianello, R., Libinaki, R., and Azzi, A. (2005) On the existence of cellular tocopheryl phosphate, its synthesis, degradation and cellular roles: a hypothesis. IUBMB Life 57, 23-25.
120. Negis, Y., Aytan, N., Ozer, N., Ogru, E., Libinaki, R., Gianello, R., Azzi, A., and Zingg, J. M. (2006) The effect of tocopheryl phosphates on atherosclerosis progression in rabbits fed with a high cholesterol diet. Arch. Biochem. Biophys. 450, 63-66.
121. English, D., Kovala, A. T., Welch, Z., Harvey, K. A., Siddiqui, R. A., Brindley, D. N., and Garcia, J. G. (1999) Induction of endothelial cell chemotaxis by sphingosine 1-phosphate and stabilization of endothelial monolayer barrier function by lysophosphatidic acid, potential mediators of hematopoietic angiogenesis. J. Hematother. Stem Cell Res. 8, 627-634.
122. Crouzin, N., de Jesus Ferreira, M. C., Cohen-Solal, C., M'Kadmi, C., Bernad, N., Martinez, J., Barbanel, G., Vignes, M., and Guiramand, J. (2011) alpha-Tocopherol and alpha-tocopheryl phosphate interact with the cannabinoid system in the rodent hippocampus. Free Radic. Biol. Med. 51, 1643-1655.
123. Zingg, J. M. (2007) Modulation of signal transduction by vitamin E. Mol. Aspects. Med. 28, 481-506.
124. Hait, N. C., Allegood, J., Maceyka, M., Strub, G. M., Harikumar, K. B., Singh, S. K., Luo, C., Marmorstein, R., Kordula, T., Milstien, S., and Spiegel, S. (2009) Regulation of histone acetylation in the nucleus by sphingosine-1-phosphate. Science 325, 1254-1257.
125. Alvarez, S. E., Harikumar, K. B., Hait, N. C., Allegood, J., Strub, G. M., Kim, E. Y., Maceyka, M., Jiang, H., Luo, C., Kordula, T., Milstien, S., and Spiegel, S. (2010) Sphingosine-1-phosphate is a missing cofactor for the E3 ubiquitin ligase TRAF2. Nature 465, 1084-1088.
126. Strub, G. M., Paillard, M., Liang, J., Gomez, L., Allegood, J. C., Hait, N. C., Maceyka, M., Price, M. M., Chen, Q., Simpson, D. C., Kordula, T., Milstien, S., Lesnefsky, E. J., and Spiegel, S. (2011) Sphingosine-1-phosphate produced by sphingosine kinase 2 in mitochondria interacts with prohibitin 2 to regulate complex IV assembly and respiration. FASEB J. 25, 600-612.
127. Dam, H. and Glavind, J. (1942) Factors Influencing Capillary Permeability in the Vitamin E Deficient Chick. Science 96, 235-236.
128. Lobato, K. R., Cardoso, C. C., Binfare, R. W., Budni, J., Wagner, C. L., Brocardo, P. S., de Souza, L. F., Brocardo, C., Flesch, S., Freitas, A. E., Dafre, A. L., and Rodrigues, A. L. (2010) alpha-Tocopherol administration produces an antidepressant-like effect in predictive animal models of depression. Behav. Brain Res. 209, 249-259.
129. Nowacka, M. M. and Obuchowicz, E. (2011) Vascular endothelial growth factor (VEGF) and its role in the central nervous system: a new element in the neurotrophic hypothesis of antidepressant drug action. Neuropeptides, doi:10.1016/j.npep.2011.1005.1005.
130. Gavard, J., Hou, X., Qu, Y., Masedunskas, A., Martin, D., Weigert, R., Li, X., and Gutkind, J. S. (2009) A role for a CXCR2/phosphatidylinositol 3-kinase gamma signaling axis in acute and chronic vascular permeability. Mol. Cell. Biol. 29, 2469-2480.