Sterol superlattice affects antioxidant potency and can be used to assess adverse effects of antioxidants

Analytical Biochemistry

Volumn 382, Issue 1, 2008, Pages 1-8

  Olsher, Michelle ^a   Chong, Parkson Lee Gau ^a  

^a TEMPLE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antioxidants; Fluorescence; Lipids; Membrane lateral organization; Membranes; Oxidation; Sterol; Sterol superlattice; Vitamin C

Indexed keywords

ALCOHOLS; ASCORBIC ACID; ASCORBYL PALMITATE; FLUORESCENCE; FREE RADICALS; LIPIDS; MEMBRANES; OXIDATION; PALMITIC ACID;

ACID CONCENTRATIONS; ANTIOXIDANT CONCENTRATION; FLUORESCENCE METHOD; MEMBRANE BILAYERS; RADICAL-INDUCED STEROL; STEROL; SUPERLATTICE FORMATION; VITAMIN C;

ANTIOXIDANTS;

ANTIOXIDANT; ASCORBIC ACID; ASCORBYL PALMITATE; RADICAL; STEROL;

ARTICLE; CONCENTRATION (PARAMETERS); FLUORESCENCE; LIPID BILAYER; LIPID OXIDATION; LIPID VESICLE; MEMBRANE STRUCTURE; PRIORITY JOURNAL;

EID: 51249102129     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2008.07.021     Document Type: Article

References (53)

1. Collin B., Busseuil D., Zeller M., Perrin C., Barthez O., Duvillard L., Vergely C., Bardou M., Dumas M., Cottin Y., and Rochette L. Increased superoxide anion production is associated with early atherosclerosis and cardiovascular dysfunctions in a rabbit model. Mol. Cell Biochem. 294 (2007) 225-235
2. Pelicano H., Carney D., and Huang P. ROS stress in cancer cells and therapeutic implications. Drug. Resist. Updat. 7 (2004) 97-110
3. Stocker R., and Jr Keaney J.F. Role of oxidative modifications in atherosclerosis. Physiol. Rev. 84 (2004) 1381-1478
4. Brown N.S., and Bicknell R. Hypoxia and oxidative stress in breast cancer. Oxidative stress: Its effects on the growth, metastatic potential and response to therapy of breast cancer. Breast Cancer. Res. 3 (2001) 323-327
5. Panini S.R., and Sinensky M.S. Mechanisms of oxysterol-induced apoptosis. Curr. Opin. Lipidol. 12 (2001) 529-533
6. Moslen M.T. Free Radicals in Diagnostic Medicine (1994), Plenum Press, New York
7. Ames B.N., Shigenaga M.K., and Hagen T.M. Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl Acad. Sci. USA 90 (1993) 7915-7922
8. Stampfer M.J., Hennekens C.H., Manson J.E., Colditz G.A., Rosner B., and Willett W.C. Vitamin E consumption and the risk of coronary disease in women. N. Engl. J. Med. 328 (1993) 1444-1449
9. Rimm E.B., Stampfer M.J., Ascherio A., Giovannucci E., Colditz G.A., and Willett W.C. Vitamin E consumption and the risk of coronary heart disease in men. N. Engl. J. Med. 328 (1993) 1450-1456
10. Sigounas G., Anagnostou A., and Steiner M. Dl-alpha-tocopherol induces apoptosis in erythroleukemia, prostate, and breast cancer cells. Nutr. Cancer 28 (1997) 30-35
11. Zhang Y., Ni J., Messing E.M., Chang E., Yang C.R., and 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. USA 99 (2002) 7408-7413
12. Zu K., and 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. 63 (2003) 6988-6995
13. Lonn E., Bosch J., Yusuf S., Sheridan P., Pogue J., Arnold J.M., Ross C., Arnold A., Sleight P., Probstfield J., and Dagenais G.R. And HOPE and HOPE-TOO Trial Investigators, Effects of long-term vitamin E supplementation on cardiovascular events and cancer: a randomized controlled trial. JAMA 293 (2005) 1338-1347
14. Uneri C., Sari M., Baglam T., Polat S., and Yuksel M. Effects of vitamin E on cigarette smoke induced oxidative damage in larynx and lung. Laryngoscope 116 (2006) 97-100
15. Miller E.R., Pastor-Barriuso R., Dalal D., Riemersma R.A., Appel L.J., and Guallar E. Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann. Intern. Med. 142 (2005) 37-46
16. Waters D.D., Alderman E.L., Hsia J., Howard B.V., Cobb F.R., Rogers W.J., Ouyang P., Thompson P., Tardif J.C., Higginson L., Bittner V., Steffes M., Gordon D.J., Proschan M., Younes N., and Verter J.I. Effects of hormone replacement therapy and antioxidant vitamin supplements on coronary atherosclerosis in postmenopausal women: a randomized controlled trial. JAMA 288 (2002) 2432-2440
17. Pham D.Q., and Plakogiannis R. Vitamin E supplementation in cardiovascular disease and cancer prevention. 1 Ann. Pharmacother. 39 (2005) 1870-1878
18. Gaziano J.M., Manson J.E., Branch L.G., Colditz G.A., Willett W.C., and Buring J.E. A prospective study of consumption of carotenoids in fruits and vegetables and decreased cardiovascular mortality in the elderly. Ann. Epidemiol. 5 (1995) 255-260
19. Osganian S.K., Stampfer M.J., Rimm E., Spiegelman D., Manson J.E., and Willett W.C. Dietary carotenoids and risk of coronary artery disease in women. Am. J. Clin. Nutr. 77 (2003) 1390-1399
20. Tung K.H., Wilkens L.R., Wu A.H., McDuffie K., Hankin J.H., Nomura A.M., Kolonel L.N., and Goodman M.T. Association of dietary vitamin A, carotenoids, and other antioxidants with the risk of ovarian cancer. Cancer Epidemiol. Biomarkers. Prev. 14 (2005) 669-676
21. Briviba K., Schnabele K., Schwertle E., Blockhaus M., and Rechkemmer G. Beta-Carotene inhibits growth of human colon carcinoma cells in vitro by induction of apoptosis. Biol. Chem. 382 (2001) 1663-1668
22. Sesso H.D. Carotenoids and cardiovascular disease: what research gaps remain?. Curr. Opin. Lipidol. 17 (2006) 11-16
23. Pokorski M., and Marczak M. Stability of ascorbyl palmitate molecule in the rat brain. J. Physiol. Pharmacol. 56 Suppl. 4 (2005) 197-201
24. Pokorski M., Marczak M., Dymecka A., and Suchocki P. Ascorbyl palmitate as a carrier of ascorbate into neural tissues. J. Biomed. Sci. 10 (2003) 193-198
25. Smart R.C., and Crawford C.L. Effect of ascorbic acid and its synthetic lipophilic derivative ascorbyl palmitate on phorbol ester-induced skin-tumor promotion in mice. Am. J. Clin. Nutr. 54 (1991) 1266S-1273S
26. Ross D., Mendiratta S., Qu Z.C., Cobb C.E., and May J.M. Ascorbate 6-palmitate protects human erythrocytes from oxidative damage. Free Radic. Biol. Med. 26 (1999) 81-89
27. Jonker D., Lee V.S., Hargreaves R.J., and Lake B.G. Comparison of the effects of ascorbyl palmitate and L-ascorbic acid on paracetamol-induced hepatotoxicity in the mouse. Toxicology 52 (1988) 287-295
28. Smart R.C., Huang M.T., Han Z.T., Kaplan M.C., Focella A., and Conney A.A.H. Inhibition of 12-O-tetradecanoylphorbol-13-acetate induction of ornithine decarboxylase activity, DNA synthesis, and tumor promotion in mouse skin by ascorbic acid and ascorbyl palmitate. Cancer Res. 47 (1987) 6633-6638
29. Perricone N.V., Nagy K., Horvath F., Dajko G., Uray I., and Zs-Nagy I. The hydroxyl free radical reactions of ascorbyl palmitate as measured in various in vitro models. Biochem. Biophys. Res. Commun. 262 (1999) 661-665
30. Meves A., Stock S.N., Beyerle A., Pittelkow M.R., and Peus D. Vitamin C derivative ascorbyl palmitate promotes ultraviolet-B-induced lipid peroxidation and cytotoxicity in keratinocytes. J. Invest. Dermatol. 119 (2002) 1103-1108
31. 2+-dependent phosphatase activity. Biochem. Pharmacol. 67 (2004) 919-926
32. Pinnell S.R. Ascorbyl-6-palmitate is not ascorbic acid. J. Invest. Dermatol. 119 (2002) 991
33. Schroeder F., Jefferson J.R., Kier A.B., Knittel J., Scallen T.J., Wood W.G., and Hapala I. Membrane cholesterol dynamics: cholesterol domains and kinetic pools. Proc. Soc. Exp. Biol. Med. 196 (1991) 235-252
34. Chong P.L.-G. Evidence for regular distribution of sterols in liquid crystalline phosphatidylcholine bilayers. Proc. Natl Acad. Sci. USA 91 (1994) 10069-10073
35. Radhakrishnan A., Anderson T.G., and McConnell H.M. Condensed complexes, rafts, and the chemical activity of cholesterol in membranes. Proc. Natl Acad. Sci. USA 97 (2000) 12422-12427
36. Virtanen J.A., Ruonala M., Vauhkonen M., and Somerharju P. Lateral organization of liquid-crystalline cholesterol-dimyristoylphosphatidylcholine bilayers: Evidence for domains with hexagonal and centered rectangular cholesterol superlattices. Biochemistry 34 (1995) 11568-11581
37. Chong P.L.-G., and Sugar I.P. Fluorescence studies of lipid regular distribution in membranes. Chem. Phys. Lipids 116 (2002) 153-175
38. Chong P.L.-G., and Olsher M. Fluorescence studies of the existence and functional importance of regular distributions in liposomal membranes. Soft Materials 2 (2004) 85-108
39. Somerharju P., Virtanen J.A., and Cheng K.H. Lateral organization of membrane lipids. The superlattice view. Biochim. Biophys. Acta 1440 (1999) 32-48
40. Venegas B., Sugar I.P., and Chong P.L.-G. Critical factors for detection of biphasic changes in membrane properties at specific sterol mole fractions for maximal superlattice formation. J. Phys. Chem. B 111 (2007) 5180-5192
41. Wang M.M., Sugar I.P., and Chong P.L.-G. Role of the sterol superlattice in the partitioning of the antifungal drug nystatin into lipid membranes. Biochemistry 37 (1998) 11797-11805
42. Liu F., and Chong P.L.-G. Evidence for a regulatory role of cholesterol superlattices in the hydrolytic activity of secretory phospholipase A2 in lipid membranes. Biochemistry 38 (1999) 3867-3873
43. Wang M.M., Olsher M., Sugar I.P., and Chong P.L.-G. Cholesterol superlattice modulates the activity of cholesterol oxidase in lipid membranes. Biochemistry 43 (2004) 2159-2166
44. Olsher M., Yoon S.-I., and Chong P.L.-G. Role of sterol superlattice in free radical-induced sterol oxidation in lipid membranes. Biochemistry 44 (2005) 2080-2087
45. Cannon B., Hermansson M., Gyorke S., Somerharju P., Virtanen J.A., and Cheng K.H. Regulation of calcium channel activity by lipid domain formation in planar lipid bilayers. Biophys. J. 85 (2003) 933-942
46. +-ATPase activity by cholesterol in endogenous lipid vesicles: role of lipid domains. Biochemistry 45 (2006) 13855-13868
47. Bartlett G.R. Phosphorus assay in column chromatography. J. Biol. Chem. 234 (1959) 466-468
48. Liu F., Sugar I.P., and Chong P.L.-G. Cholesterol and ergosterol superlattices in three-component liquid crystalline lipid bilayers as revealed by dehydroergosterol fluorescence. Biophys. J. 72 (1997) 2243-2254
49. Simons K., and Ikonen E. Functional rafts in cell membranes. Nature 387 (1997) 569-572
50. Kusumi A., Koyama-Honda I., and Suzuki K. Molecular dynamics and interactions for creation of stimulation-induced stabilized rafts from small unstable steady-state rafts. Traffic 5 (2004) 213-230
51. Brown D.A., and London E. Functions of lipid rafts in biological membranes. Annu. Rev. Cell Dev. Biol. 14 (1998) 111-136
52. Chong P.L.-G., Liu F., Wang M.M., Truong K., Sugar I.P., and Brown R.E. Fluorescence evidence for cholesterol regular distribution in phosphatidylcholine and in sphingomyelin lipid bilayers. J. Fluorescence 6 (1996) 221-230
53. Huang J. Exploration of molecular interactions in cholesterol superlattices: effect of multibody interactions. Biophys. J. 83 (2002) 1014-1025