Eicosapentaenoic acid and docosahexaenoic acid have distinct membrane locations and lipid interactions as determined by X-ray diffraction

Chemistry and Physics of Lipids

Volumn 212, Issue , 2018, Pages 73-79

  Sherratt, Samuel C R ^a   Mason, R Preston ^a,b  

^a ELUCIDA RESEARCH LLC   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Membrane structure; Omega 3 fatty acids; X ray diffraction

Indexed keywords

2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE; CHOLESTEROL; DOCOSAHEXAENOIC ACID; ICOSAPENTAENOIC ACID; PHOSPHOLIPID; 1-PALMITOYL-2-OLEOYLPHOSPHATIDYLCHOLINE; LIPOSOME; PHOSPHATIDYLCHOLINE;

ARTICLE; ARTIFICIAL MEMBRANE; CHEMICAL INTERACTION; CONTROLLED STUDY; ELECTRON; HIGH TEMPERATURE; HYDRATION; ISOMERIZATION; MEMBRANE STRUCTURE; MEMBRANE VESICLE; PRIORITY JOURNAL; REDUCTION (CHEMISTRY); X RAY DIFFRACTION; CHEMISTRY; ISOMERISM; MEMBRANE FLUIDITY; METABOLISM; SMALL ANGLE SCATTERING; TEMPERATURE;

CHOLESTEROL; DOCOSAHEXAENOIC ACIDS; EICOSAPENTAENOIC ACID; ISOMERISM; MEMBRANE FLUIDITY; PHOSPHATIDYLCHOLINES; SCATTERING, SMALL ANGLE; TEMPERATURE; UNILAMELLAR LIPOSOMES; X-RAY DIFFRACTION;

EID: 85041688221     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2018.01.002     Document Type: Article

References (35)

1. Allam-Ndoul, B., Guenard, F., Barbier, O., Vohl, M.C., Effect of n-3 fatty acids on the expression of inflammatory genes in THP-1 macrophages. Lipids Health Dis., 15, 2016, 69.
2. Bangham, A.D., Standish, M.M., Watkins, J.C., Diffusion of univalent ions across the lamellae of swollen phospholipids. J. Mol. Biol. 13 (1965), 238–252.
3. Bhatt, D.L., Steg, P.G., Brinton, E.A., Jacobson, T.A., Miller, M., Tardif, J.C., Ketchum, S.B., Doyle, R.T. Jr., Murphy, S.A., Soni, P.N., Braeckman, R.A., Juliano, R.A., Ballantyne, C.M., Investigators, R.-I., Rationale and design of REDUCE-IT: reduction of cardiovascular events with icosapent ethyl-Intervention trial. Clin. Cardiol. 40 (2017), 138–148.
4. Borow, K.M., Nelson, J.R., Mason, R.P., Biologic plausibility, cellular effects, and molecular mechanisms of eicosapentaenoic acid (EPA) in atherosclerosis. Atherosclerosis 242 (2015), 357–366.
5. Brzustowicz, M.R., Cherezov, V., Caffrey, M., Stillwell, W., Wassall, S.R., Molecular organization of cholesterol in polyunsaturated membranes: microdomain formation. Biophys. J. 82 (2002), 285–298.
6. Calder, P.C., The role of marine omega-3 (n-3) fatty acids in inflammatory processes, atherosclerosis and plaque stability. Mol. Nutr. Food Res. 56 (2012), 1073–1080.
7. Daviglus, M.L., Stamler, J., Orencia, A.J., Dyer, A.R., Liu, K., Greenland, P., Walsh, M.K., Morris, D., Shekelle, R.B., Fish consumption and the 30-year risk of fatal myocardial infarction. N. Engl. J. Med. 336 (1997), 1046–1053.
8. Doi, M., Nosaka, K., Miyoshi, T., Iwamoto, M., Kajiya, M., Okawa, K., Nakayama, R., Takagi, W., Takeda, K., Hirohata, S., Ito, H., Early eicosapentaenoic acid treatment after percutaneous coronary intervention reduces acute inflammatory responses and ventricular arrhythmias in patients with acute myocardial infarction: a randomized, controlled study. Int. J. Cardiol. 176 (2014), 577–582.
9. Hashimoto, M., Hossain, S., Yamasaki, H., Yazawa, K., Masumura, S., Effects of eicosapentaenoic acid and docosahexaenoic acid on plasma membrane fluidity of aortic endothelial cells. Lipids 34 (1999), 1297–1304.
10. Innis, S.M., Dietary (n-3) fatty acids and brain development. J. Nutr. 137 (2007), 855–859.
11. Kucerka, N., Marquardt, D., Harroun, T.A., Nieh, M.P., Wassall, S.R., Katsaras, J., The functional significance of lipid diversity: orientation of cholesterol in bilayers is determined by lipid species. J. Am. Chem. Soc. 131 (2009), 16358–16359.
12. Kucerka, N., Marquardt, D., Harroun, T.A., Nieh, M.P., Wassall, S.R., de Jong, D.H., Schafer, L.V., Marrink, S.J., Katsaras, J., Cholesterol in bilayers with PUFA chains: doping with DMPC or POPC results in sterol reorientation and membrane-domain formation. Biochemistry 49 (2010), 7485–7493.
13. Mason, R.P., Jacob, R.F., X-ray diffraction analysis of membrane structure changes with oxidative stress. Armstrong, D., (eds.) Methods in Molecular Biology: Ultrastructural and Molecular Biology Protocols., 2002, Humana Press Inc., Totowa, NJ, 71–80.
14. Mason, R.P., Jacob, R.F., Eicosapentaenoic acid inhibits glucose-induced membrane cholesterol crystalline domain formation through a potent antioxidant mechanism. Biochim. Biophys. Acta 1848 (2015), 502–509.
15. Mason, R.P., Gonye, G.E., Chester, D.W., Herbette, L.G., Partitioning and location of Bay K 8644, 1,4-dihydropyridine calcium channel agonist, in model and biological membranes. Biophys. J. 55 (1989), 769–778.
16. Mason, R.P., Moisey, D.M., Shajenko, L., Cholesterol alters the binding of Ca2+ channel blockers to the membrane lipid bilayer. Mol. Pharmacol. 41 (1992), 315–321.
17. Mason, R.P., Walter, M.F., Day, C.A., Jacob, R.F., Active metabolite of atorvastatin inhibits membrane cholesterol domain formation by an antioxidant mechanism. J. Biol. Chem. 281 (2006), 9337–9345.
18. Mason, R.P., Jacob, R.F., Shrivastava, S., Sherratt, S.C.R., Chattopadhyay, A., Eicosapentaenoic acid reduces membrane fluidity, inhibits cholesterol domain formation, and normalizes bilayer width in atherosclerotic-like model membranes. Biochim. Biophys. Acta 1858 (2016), 3131–3140.
19. Mason, R.P., Sherratt, S.C.R., Jacob, R.F., Eicosapentaenoic acid inhibits oxidation of ApoB-containing lipoprotein particles of different size in vitro when administered alone or in combination with atorvastatin active metabolite compared with other triglyceride-lowering agents. J. Cardiovasc. Pharmacol. 68 (2016), 33–40.
20. Mason, R.P., Use of X-ray and neutron diffraction to study small molecule interactions with model and native membranes. Comments Mol. Cell. Biophys. 7 (1991), 209–233.
21. Moody, M.F., X-ray diffraction pattern of nerve myelin: a method for determining the phases. Science 142 (1963), 1173–1174.
22. Mozaffarian, D., Wu, J.H., Omega-3 fatty acids and cardiovascular disease: effects on risk factors, molecular pathways, and clinical events. J. Am. Coll. Cardiol. 58 (2011), 2047–2067.
23. Nelson, J.R., Wani, O., May, H.T., Budoff, M., Potential benefits of eicosapentaenoic acid on atherosclerotic plaques. Vascul. Pharmacol. 91 (2017), 1–9.
24. Nosaka, K., Miyoshi, T., Iwamoto, M., Kajiya, M., Okawa, K., Tsukuda, S., Yokohama, F., Sogo, M., Nishibe, T., Matsuo, N., Hirohata, S., Ito, H., Doi, M., Early initiation of eicosapentaenoic acid and statin treatment is associated with better clinical outcomes than statin alone in patients with acute coronary syndromes: 1-year outcomes of a randomized controlled study. Int. J. Cardiol. 228 (2017), 173–179.
25. Ruocco, M.J., Shipley, G.G., Interaction of cholesterol with galactocerebroside and galactocerebroside-phosphatidylcholine bilayer membranes. Biophys. J. 46 (1984), 695–707.
26. Shaikh, S.R., Kinnun, J.J., Leng, X., Williams, J.A., Wassall, S.R., How polyunsaturated fatty acids modify molecular organization in membranes: insight from NMR studies of model systems. Biochim. Biophys. Acta 1848 (2015), 211–219.
27. Shaikh, S.R., Biophysical and biochemical mechanisms by which dietary N-3 polyunsaturated fatty acids from fish oil disrupt membrane lipid rafts. J. Nutr. Biochem. 23 (2012), 101–105.
28. Soni, S.P., LoCascio, D.S., Liu, Y., Williams, J.A., Bittman, R., Stillwell, W., Wassall, S.R., Docosahexaenoic acid enhances segregation of lipids between: 2H-NMR study. Biophys. J. 95 (2008), 203–214.
29. Soubias, O., Gawrisch, K., Docosahexaenoyl chains isomerize on the sub-nanosecond time scale. J. Am. Chem. Soc. 129 (2007), 6678–6679.
30. Tulenko, T.N., Chen, M., Mason, P.E., Mason, R.P., Physical effects of cholesterol on arterial smooth muscle membranes: evidence of immiscible cholesterol domains and alterations in bilayer width during atherogenesis. J. Lipid Res. 39 (1998), 947–956.
31. Uauy, R., Dangour, A.D., Nutrition in brain development and aging: role of essential fatty acids. Nutr. Rev. 64 (2006), S24–S33 discussion S72-91.
32. Wassall, S.R., Stillwell, W., Docosahexaenoic acid domains: the ultimate non-raft membrane domain. Chem. Phys. Lipids 153 (2008), 57–63.
33. Watanabe, T., Ando, K., Daidoji, H., Otaki, Y., Sugawara, S., Matsui, M., Ikeno, E., Hirono, O., Miyawaki, H., Yashiro, Y., Nishiyama, S., Arimoto, T., Takahashi, H., Shishido, T., Miyashita, T., Miyamoto, T., Kubota, I., CHERRY study investigators, A randomized controlled trial of eicosapentaenoic acid in patients with coronary heart disease on statins. J. Cardiol. 70 (2017), 537–544.
34. Williams, J.A., Batten, S.E., Harris, M., Rockett, B.D., Shaikh, S.R., Stillwell, W., Wassall, S.R., Docosahexaenoic and eicosapentaenoic acids segregate differently between raft and nonraft domains. Biophys. J. 103 (2012), 228–237.
35. Yokoyama, M., Origasa, H., Matsuzaki, M., Matsuzawa, Y., Saito, Y., Ishikawa, Y., Oikawa, S., Sasaki, J., Hishida, H., Itakura, H., Kita, T., Kitabatake, A., Nakaya, N., Sakata, T., Shimada, K., Shirato, K., Effects of eicosapentaenoic acid on major coronary events in hypercholesterolaemic patients (JELIS): a randomised open-label, blinded endpoint analysis. Lancet 369 (2007), 1090–1098.