Publication Cover
Redox Report
Communications in Free Radical Research
Volume 6, 2001 - Issue 3
264
Views
39
CrossRef citations to date
0
Altmetric
Reviews

Vitamin E analogues as inducers of apoptosis: implications for their potential antineoplastic role

, , , &
Pages 143-151 | Published online: 19 Jul 2013

  • Burton GW, Traber MG. Vitamin E: antioxidant activity, biokinetics, and bioavailability. Annu Rev Nutr 1990; 10: 357–382.
  • Azzi A, Stocker A. Vitamin E: non-antioxidant roles. Progr Lipid Res 2000; 39: 231–255.
  • Neuzil J, Thomas SR, Stocker R. Requirement for, promotion, or inhibition by a-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation. Free Radic Biol Med 1997; 22: 57–71.
  • Haendeler J, Zeiher AM, Dimmeler S. Vitamin C and E prevent lipopolysaccharide-induced apoptosis in human endothelial cells by modulation of Bc1-2 and Bax. Eur J Pharmacol 1996; 317: 407–411.
  • Neuzil J, Weber T, Schroder A et al. Induction of apoptosis in cancer cells by a-tocopheryl succinate: molecular pathways and structural requirements. FASEB J 2001; 15: 403–415.
  • Qian M, Kralova J, Yu W et al. c-Jun involvement in vitamin E succinate induced apoptosis of reticuloendotheliosis virus transformed avian lymphoid cells. Oncogene 1997; 15: 223–230.
  • Neuzil J, Svensson I, Weber T, Weber C, Brunk UT. a-Tocopheryl succinate-induced apoptosis in Jurkat T cells involves caspase-3 activation, and both lysosomal and mitochondria' destabilisation. FEBS Lett 1999; 445: 295–300.
  • Djuric Z, Heilbrun LK, Lababidi S, Everett-Bauer CK, Fariss MW. Growth inhibition of MCF-7 and MCF-10A human breast cells by a-tocopheryl hemisuccinate, cholesteryl hemisuccinate and their ether analogs. Cancer Lett 1997; 111: 133–139.
  • Jha MN, Bedford JS, Cole WC, Edward-Prasad J, Prasad KN. Vitamin E (d-a-tocopheryl succinate) decreases mitotic accumulation in 7-irradiated human tumor but not in normal cells. Nutr Cancer 1999; 35: 189–194.
  • Neuzil J, Weber T, Gellert N, Weber C. Selective cancer cell killing by a-tocopheryl succinate. Br J Cancer 2001; 84: 87–89.
  • Vaux DL, Strasser A. The molecular biology of apoptosis. Proc Natl Acad Sci USA 1996; 93: 2239–2244.
  • Nathan I, Dizdaroglu M, Bernstein L, Junker U, Lee CK, Muegge K, Durum SK. Induction of oxidative DNA damage in U937 cells by TNF or anti-Fas stimulation. Cytokine 2000; 12: 881–887.
  • Suzuki Y, Ono Y, Hirabayashi Y. Rapid and specific reactive oxygen species generation via NADPH oxidase activation during Fas-mediated apoptosis. FEBS Lett 1998; 425: 209–212.
  • Mabile L, Fitoussi G, Periquet B, Schmitt A, Salvayre R, Negre-Salvayre A. a-Tocopherol and Trolox block the early intracellular events elicited by oxidized low density lipoproteins in cultured endothelial cells. Free Radic Biol Med 1995; 19: 177–187.
  • de Nigris F, Franconi F, Maida I, Palumbo G, Anania V, Napoli C. Modulation by a- and 7-tocopherol and oxidized low-density lipoprotein of apoptotic signaling in human coronary smooth muscle cells. Biochem Pharmacol 2000; 59: 1477–1487.
  • Lizard G, Miguet C, Bessede Get al. Impairment with various antioxidants of the loss of mitochondria' transmembrane potential and of the cytosolic release of cytochrome c occuring during 7-ketocholesterol-induced apoptosis. Free Radic Biol Med 2000; 28: 743–753.
  • Chen Q, Cederbaum Al. Cytotoxicity and apoptosis produced by cytochrome P450 2E1 in HepG2 cells. Mol Pharmacol 1998; 53: 638–648.
  • Chan SL, Tammariello SP, Estus S, Mattson MP. Prostate apoptosis response-4 mediates trophic factor withdrawal-induced apoptosis of hippocampal neurons: actions prior to mitochondria' dysfunction and caspase activation. J Neurochem 1999; 73: 502–512.
  • Tagami M, Ikeda K, Yamagata K et al. Vitamin E prevents apoptosis in hippocampal neurons caused by cerebral ischemia and reperfusion in stroke prone spontaneously hypertensive rats. Lab Invest 1999; 79: 609–615.
  • Weber T, Dalen H, Terman A et al. Mitochondria play a central role in a-tocopheryl succinate-induced apoptosis in malignant cells. 2001: Submitted.
  • Fariss MW, Fortuna MB, Everett CK, Smith JD, Trent DF, Djuric Z. The selective antiproliferative effects of a-tocopheryl hemisuccinate and cholesteryl hemisuccinate on murine leukemia cells result from the action of the intact compounds. Cancer Res 1994; 54: 3346–3351.
  • Tirmenstein MA, Ge X, Elkins CR, Fariss MW. Administration of the Tris salt of a-tocopheryl hemisuccinate inactivates CYP2E1, enhances microsomal a-tocopherol levels and protects against carbon tetrachloride-induced hepatotoxicity. Free Radic Biol Med 1999; 26: 825–835.
  • Zhao B, Yu W, Qian M et al. Involvement of activator protein-1 (AP-1) in induction of apoptosis by vitamin E succinate in human breast cancer cells. Mol Carcinog 1997; 19: 180–190.
  • Yu W, Simmons-Menchaca M, You H et al. RRR-a-tocopheryl succinate induction of prolonged activation of c-jun amino-terminal kinase and c-jun during induction of apoptosis in human MDA-MB-435 breast cancer cells. Mol Carcinog 1998; 22: 247–257.
  • Turley JM, Funakoshi S, Ruscetti FW et al. Growth inhibition and apoptosis of RL human B lymphoma cells by vitamin E succinate and retinoic acid: role for transforming growth factor-P. Cell Growth Differ 1995; 6: 655–663.
  • Ottino P, Duncan JR. Effect of a-tocopherol succinate on free radical and lipid peroxidation levels in BL6 melanoma cells. Free Radic Biol Med 1997; 22: 1145–1151.
  • Mignotte B, Vayssiere JL. Mitochondria and apoptosis. Eur J Biochem 1998; 252: 1–15.
  • Susin SA, Daugas E, Ravagnan L et al. Two distinct pathways leading to nuclear apoptosis. J Exp Med 2000; 192: 571–580:
  • Luo X, Budihardjo I, Zou H, Slaughter C, Wang X. Bid, a Bc1-2 interacting protein, mediates cytochrome c release from mitochondria in response to activation of cell surface death receptors. Cell 1998; 94: 481–490.
  • Li P, Nijhawan D, Budihardjo I et al. Cytochrome c and dATP-dependent formation of Apaf-l/caspase-9 complex initiates an apoptotic protease cascade. Cell 1997; 91: 479–489.
  • Wolf BB, Green DR. Suicidal tendencies: apoptotic cell death by caspase family proteinases. J Biol Chem 1999; 274: 20049–20052.
  • Ferrari D, Stepczynska A, Los M, Wesselborg S, Schulze-Osthoff K. Differential regulation and ATP requirement for caspase-8 and caspase-3 activation during CD95- and anticancer drug-induced apoptosis. J Exp Med 1998; 188: 979–984.
  • Roberg K, 011inger K. Oxidative stress causes relocation of the lysosomal enzyme cathepsin D with ensuing apoptosis in neonatal rat cardiomyocytes. Am J Pathol 1998; 152: 1151–1156.
  • O11inger K, Brunk UT. Cellular injury induced by oxidative stress is mediated through lysosomal damage. Free Radic Biol Med 1995; 19: 565–574.
  • Shibata M, Kanamori S, Isahara K et al. Participation of cathepsins B and D in apoptosis of PC12 cells following serum deprivation. Biochem Biophys Res Commun 1998; 251: 199–203.
  • Ishisaka R, Utsumi T, Yabuki M et al. Activation of caspase-3-like protease by digitonin-treated lysosomes. FEBS Lett 1998; 435: 233–236.
  • Monney L, Olivier R, Otter I, Jansen B, Poirier GO, Borner C. Role of an acidic compartment in tumor-necrosis-factor-a-induced production of ceramide, activation of caspase-3 and apoptosis. Eur J Biochem 1998; 251: 295–303.
  • Wu GS, Saftig P, Peters C, El-Deiry WS. Potential role for cathepsin D in p53-dependent tumor suppression and chemosensitivity. Oncogene 1998; 16: 2177–2183.
  • Roberg K, Johansson U, 011inger K. Lysosomal release of cathepsin D precedes relocation of cytochrome c and loss of mitochondrial transmembrane potential during apoptosis induced by oxidative stress. Free Radic Biol Med 1999; 27: 1228–1237.
  • Li W, Yuan X, Nordgren Get al. Induction of cell death by the lysosomotropic detergent MSDH. FEBS Lett 2000; 470: 35–39.
  • Heinrich M, Wickel M, Winoto-Morbach S et al. Ceramide as an activator lipid of cathepsin D. Adv Exp Med Biol 2000; 477: 305–315.
  • Mellor H, Parker PJ. The extended protein kinase C superfamily. Biochem J 1998; 332: 281–292.
  • Ron D, Kazanietz MG. New insights into the regulation of protein kinase C and novel phorbol ester receptors. FASEB J 1999; 13: 1658–1676.
  • Millward TA, Zolnierowicz S, Hemmings BA. Regulation of protein kinase cascades by protein phosphatase 2A. Trends Biochem Sci 1999; 24: 186–191.
  • Haimovitz-Friedman A, Balaban N, McLoughlin M et al. Protein kinase C mediates basic fibroblast growth factor protection of endothelial cells against radiation-induced apoptosis. Cancer Res 1994; 54: 2591–2597.
  • Chen CY, Faller DV. Selective inhibition of protein kinase C isozymes by Fos ligation. J Biol Chem 1999; 274: 15320–15328.
  • Santoro MF, Armand RR, Robertson MM et al. Regulation of protein phosphatase 2A activity by caspase-3 during apoptosis. J Biol Chem 1998; 273: 13119–13128.
  • Lee JY, Hannun YA, Obeid LM. Ceramide inactivates cellular protein kinase C-a. J Biol Chem 1996; 271: 13169–13174.
  • Ruvolo PP, Deng X, Ito T, Can BK, May WS. Ceramide induces bc1-2 dephosphorylation via a mechanism involving mitochondrial PP2A. J Biol Chem 1999; 274: 20296–20300.
  • Ruiz-Ruiz C, Robledo G, Font J, Izquierdo M, Lopez-Rivas A. Protein kinase C inhibits CD95 (Fas/AP0-1)-mediated apoptosis by at least two different mechanisms in Jurkat T cells. J Immunol 1999; 163: 4737–4746.
  • Whelan RD, Parker PJ. Loss of protein kinase C function induces an apoptotic response. Oncogene 1998; 16: 1939–1944.
  • Mayne GC, Murray AW. Evidence that protein kinase C-E mediates phorbol ester inhibition of calphostin C- and tumour necrosis factor-a-induced apoptosis in U937 histiocytic lymphoma cells. J Biol Chem 1998; 273: 24115–24121.
  • Ruvolo PP, Deng X, Can BK, May WS. A functional role for mitochondrial protein kinase C-a in bc1-2 phosphorylation and suppression of apoptosis. J Biol Chem 1998; 273: 25436–25442.
  • Watters DJ, Parsons PG. Critical targets of protein kinase C in differentiation of tumour cells. Biochem Pharmacol 1999; 58: 383–388.
  • Ways DK, Kukoly CA, deVente J et al. MCF-7 breast cancer cells transfected with protein kinase C-a exhibit altered expression of other protein kinase C isoforms and display a more aggressive neoplastic phenotype. J Clin Invest 1995; 95: 1906–1915.
  • Kolch W, Heidecker G, Kochs G et al. Protein kinase C-a activates RAF-1 by direct phosphorylation. Nature 1993; 364: 249–252.
  • Livneh E, Fishman DD. Linking protein kinase C to cell-cycle control. Eur J Biochem 1997; 248: 1–9.
  • Nakaigawa N, Hirai S, Mizuno K, Shuin T, Hosaka M, Ohno S. Differential effects of overexpression of PKCa and PKCS/E on cellular E2F activity in late G1 phase. Biochem Biophys Res Commun 1996; 222: 95–100.
  • de Vente JE, Kukoly CA, Bryant WO et al. Phorbol esters induce death in MCF-7 breast cancer cells with altered expression of protein kinase C isoforms. Role for p53-independent induction of gadd-45 in initiating death. J Clin Invest 1995; 96: 1874–1886.
  • Frey MR, Saxon ML, Zhao X, Rollins A, Evans SS, Black JD. Protein kinase C isozyme-mediated cell cycle arrest involves induction of p21WmP-1 and p27K'Pl and hypophosphorylation of the retinoblastoma protein in intestinal epithelial cells. J Biol Chem 1997; 272: 9424–9435.
  • O'Connor L, Huang DC, O'Reilly LA, Strasser A. Apoptosis and cell division. Curr Opinion Cell Biol 2000; 12: 257–263.
  • Harvey KJ, Lukovic D, Ucker DS. Caspase-dependent Cdk activity is a requisite effector of apoptotic death events. J Cell Biol 2000; 148: 59–72.
  • Turley JM, Ruscetti FW, Kim SJ, Fu T, Gou FV, Birchenall-Roberts MC .Vitamin E succinate inhibits proliferation of BT-20 human breast cancer cells: increased binding of cyclin A negatively regulates E2F transactivation activity. Cancer Res 1997; 57: 2668–2675.
  • Mazel S, Burtrum D, Petrie HT. Regulation of cell division cycle progression by bc1-2 expression: a potential mechanism for inhibition of programmed cell death. J Exp Med 1996; 183: 2219–2226.
  • Tasinato A, Boscoboinik D, Bartoli GM, Maroni P, Azzi A. d-a-Tocopherol inhibition of vascular smooth muscle cell proliferation occurs at physiological concentrations, correlates with protein kinase C inhibition, and is independent of its antioxidant properties. Proc Natl Acad Sci USA 1995; 92: 12190–12194.
  • Cachia 0, El Benna J, Perduzzi E, Descombs B, Gougerot-Pocidalo MA, Leger CL. a-Tocopherol inhibits the respiratory burst in human monocytes. Attenuation of p47Ph0” membrane translocation and phosphorylation. J Biol Chem 1998; 273: 32801–32805.
  • Li Q, Subbulakshmi V, Fields AP, Murray NR, Cathcart MK. Protein kinase C-a regulates human monocyte 02- production and low density lipoprotein lipid oxidation. J Biol Chem 1999; 274: 3764–3771.
  • Ricciarelli R, Tasinato A, Clement S, Ozer NK, Boscoboinik D, Azzi A. a-Tocopherol specifically inactivates cellular protein kinase C-a by changing its phosphorylation state. Biochem J 1998; 334: 243–249.
  • Neuzil J, Weber T, Lu M et al. Vitamin E succinate: a potent new anti-neoplastic agent with high tumor selectivity. 2001; Submitted.
  • Gogu SR, Lertora JJ, George WJ, Hyslop NE, Agrawal KC. Protection of zidovudine-induced toxicity against murine erythroid progenitor cells by vitamin E. Exp Hematol 1991; 19: 649–652.
  • Albanes D, Malila N, Taylor PR et al. Effects of supplemental a-tocopherol and 3-carotene on colorectal cancer: results from a controlled trial. Cancer Causes Control 2000; 11: 197–205.
  • Factor VM, Laskowska D, Jensen MR, Woitach JT, Popescu NC, Thorgeirsson SS. Vitamin E reduces chromosomal damage and inhibits hepatic tumor formation in a transgenic mouse model. Proc Natl Acad Sci USA 2000; 97: 2196–2201.
  • Chinery R, Brockman JA, Peeler MO, Shyr Y, Beauchamp RD, Coffey RJ. Antioxidants enhance the toxicity of chemotherapeutic agents in colorectal cancer: a p53-independent induction of p21Maic'P-1 via C/EBPP. Nat Med 1997; 3: 1233–1241.
  • Malafa MP, Neitzel LT. Vitamin E succinate promotes breast cancer tumor dormancy. J Surg Res 2000; 93: 163–170.
  • Pussinen PJ, Lindner H, Glatter 0 et al. Lipoprotein-associated a-tocopheryl-succinate inhibits cell growth and induces apoptosis in human MCF-7 and HBL-100 breast cancer cells. Biochim Biophys Acta 2000; 1485: 129–144.
  • Fariss MW, Bryson KF, Hylton EE, Lippman HR, Stubin CH, Thao XG. Protection against carbon tetrachloride-induced hepatotoxicity by pretreating rats with the hemisuccinate esters of tocopherol and cholesterol. Environ Health Perspect 1993; 101: 528–536.
  • Traber MG, Ramakrishnan R, Kayden HJ. Human plasma vitamin E kinetics demonstrate rapid recycling of plasma RRR-a-tocopherol. Proc Natl Acad Sci USA 1994; 91: 10005–10008.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.