Relationship between the action of reactive oxygen and nitrogen species on bilayer membranes and antioxidants

Chemistry and Physics of Lipids

Volumn 132, Issue 2, 2004, Pages 197-208

  De Lima, Vânia Rodrigues ^a   Morfim, Marcos Paulo ^a   Teixeira, Adriana ^a   Creczynski Pasa, Tânia Beatriz ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Antioxidants; Differential scanning calorimetry; Lipid peroxidation; Melatonin; Reactive nitrogen species; Reactive oxygen species

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; AZOLECTIN; HYDROXYL GROUP; LIPOSOME; MELATONIN; PEROXYNITRITE; PHOSPHATIDIC ACID; PHOSPHATIDYLCHOLINE; PYRIDOXINE; QUERCETIN; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE;

ANTIOXIDANT ACTIVITY; ARTICLE; BILAYER MEMBRANE; DRUG EFFECT; ENTHALPY; IC 50; LIPID PEROXIDATION; LIVER MICROSOME; MOLECULAR DYNAMICS; PRIORITY JOURNAL;

ANIMALS; ANTIOXIDANTS; CALORIMETRY, DIFFERENTIAL SCANNING; EGG YOLK; FREE RADICALS; LIPID BILAYERS; LIPID PEROXIDATION; LIPOSOMES; MEMBRANE LIPIDS; MICROSOMES, LIVER; PHOSPHATIDIC ACIDS; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; RATS; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 8844266198     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2004.07.003     Document Type: Article

References (80)

1. H. Ahsan, A. Ali, and R. Ali Oxygen free radicals and systemic autoimmunity Clin. Exp. Immunol. 131 2003 398 404
2. A. Arora, M.G. Nair, and G. Strasburg Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system Free Radic. Biol. Med. 24 1998 845 850
3. L.R.C. Barclay, and M.R. Vinqvist Membrane peroxidation: inhibiting effects of water-soluble antioxidants on phospholipids of different charge types Free Radic. Biol. Med. 16 1994 779 788
4. R.P. Bird, and A.H. Draper Comparative studies on different methods of malondyaldehyde determination Methods Enzymol. 105 1984 295 305
5. E. Bombardelli, and M. Spetta Phospholipid-polyphenol complexes: a new concept in skin care ingredients Cosmet. Toiletries 106 1991 69 76
6. W. Bors, W. Heller, C. Michel, and M. Saran Flavonoids as antioxidants, determination of radical-scavenging efficiencies Methods Enzymol. 186 1990 343 355
7. W. Bors, C. Michel, and S. Schikora Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: a pulse radiolysis study Free Radic. Biol. Med. 19 1995 845 850
8. E. Casalino, C. Sblano, and C. Landriscina A possible mechanism for inhibition of lipid peroxidation by ascorbate in rat liver microsomes Int. J. Biochem. Cell Biol. 28 1996 137 149
9. F. Castelli, D. Trombetta, A. Tomaiano, F. Bonina, G. Romeo, N. Uccella, and A. Saija Dipalmitoylphosphatidylcholine/linoleic acid mixed unilamellar vesicles as model membranes for studies on novel free-radical scavengers JPM 37 1997 135 141
10. J.S. Choi, H.Y. Chung, S.S. Kang, M.J. Jung, J.W. Kim, J.K. No, and H.A. Jung The structure-activity relationship of flavonoids as scavengers of peroxynitrite Phytother. Res. 16 2002 232 235
11. S.M. Colles, and G.M. Chisolm Lysophosphatidylcholine-induced cellular injury in cultured fibroblasts involves oxidative events J. Lipid Res. 41 2000 1188 1198
12. P. Cos, M. Calomme, J.B. Sindambiwe, T. de Bruyne, K. Cimanga, L. Pieters, A.J. Vlietinck, and D.V. Berghe Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids Planta Med. 67 2001 515 519
13. E.J. Costa, C.S. Shida, M.H. Biaggi, A.S. Ito, and M.T. Lamy-Freund How melatonin interacts with lipid bilayers: a study by fluorescence and ESR spectroscopies FEBS Lett. 416 1997 103 106
14. +-ATPase from chloroplasts FEBS Lett. 350 1994 195 198
15. +-ATPase from chloroplasts Biochim. Biophys. Acta 1320 1997 58 64
16. 1 Arch Biochem. Biophys. 376 2000 141 148
17. R.F. Epand, J.C. Martinou, S. Montessuit, and R.M. Epand Fatty acids enhance membrane permeabilization by pro-apoptotic Bax Biochem. J. 377 2004 509 516
18. H.W. Gardner Oxygen radical chemistry of polyunsaturated fatty acids Free Radic. Biol. Med. 7 1989 65 86
19. S.P.A. Goss, N. Hogg, and B. Kalyanaraman The effect of nitric oxide release rates on the oxidation of human low density lipoprotein J. Biol. Chem. 272 1997 21647 21653
20. G.R. Gourley, W. Mogilevsky, and G.B. Odell Hepatic microsomal composition studies in the Gunn rats Biochim. Biophys. Acta 750 1983 419 423
21. B. Halliwell, and M.C. Gutteridge Mechanism of damage targets by oxidative stress: lipid peroxidation In: Free Radicals in Biology and Medicine 2000 Oxford Science Publications New York 291-293
22. B. Halliwell, M.C. Gutteridge, and O.I. Aruoma The deoxyribose method: a simple test-tube assay for determination of rate constants for reactions of hydroxyl radicals Anal. Biochem. 165 1987 215 219
23. L.G. Herbette, C. Favreau, K. Segalman, C.A. Napolitano, and J. Watras Mechanisms of fatty acid effects on sarcoplasmic reticulum. II. Structural changes induced by oleic and palmitic acids J. Biol. Chem. 259 1984 1325 1335
24. R.A. Hoover, R.D. Lynch, and M.J. Karnovsky Decrease in adhesion of cells cultured in polyunsaturated fatty acids Cell 12 1977 295 300
25. K.L. Horan, B.S. Lutzke, A.R. Cazers, J.M. McCall, and D.E. Epps Kinetic evaluation of lipophilic inhibitors of lipid peroxidation in DLPC liposomes Free Radic. Biol. Med. 17 1994 587 596
26. M.L. Hu, Y.K. Chen, and Y.F. Lin The antioxidant and prooxidant activity of some B vitamins and vitamin-like compounds Chem. Biol. Interact. 97 1995 63 73
27. M.L. Hu, and A.L. Tappel GSH and antioxidants protect against LPO and protein damage Lipids 27 1992 42 45
28. M. Huang, J. Li, H. Teoh, and R.Y.K. Man Low concentrations of 17β-estradiol reduce oxidative modification of low-density lipoproteins in the presence of vitamin C and vitamin E Free Radic. Biol. Med. 27 1999 438 441
29. C.A. Hubel, V.E. Kagan, E.R. Kosin, M. McLaughlin, and J.M. Roberts Increased ascorbate radical formation in skin: an electron paramagnetic resonance study Photochem. Photobiol. 59 1997 1 4
30. F. Itoh, Y. Minamide, T. Horie, and S. Awazu Time dependent changes in rat liver microsomes upon lipid peroxidation Lipids 24 1989 905 908
31. +) ATPase activity reduction in high glucose-treated human erythrocytes Free Radic. Biol. Med. 30 2001 232 237
32. O.R. Justo, and A.M. Moraes Incorporation of antibiotics in liposomes designed for tuberculosis therapy by inhalation Drug Deliv. 10 2003 201 207
33. 2-treated U937 monocytes Free Radic. Biol. Med. 36 2004 423 428
34. R.F. Khairutdinov, J.W. Coddington, and J.K. Hurst Permeation of phospholipid membranes by peroxynitrite Biochemistry 39 2000 14238 14249
35. H.A. Kleinveld, J.G. Swaaka, and C.E. Hack Interactions between oxygen free radicals and proteins. Implications for rheumatoid arthritis. An overview Scand. J. Rheumatol. 18 1989 341 352
36. A. Kontush, S. Meyer, B. Finckh, A. Kohlschutter, and U. Beisiegel Alpha-tocopherol as a reductant for Cu(II) in human lipoproteins. Triggering role in the initiation of lipoprotein oxidation J. Biol. Chem. 271 1996 11106 11112
37. W.H. Koppenol Oxyradical reactions: from bond-dissociation energies to reduction potentials FEBS Lett. 264 1990 165 167
38. W.H. Koppenol The Haber-Weiss cycle - 71 years later Redox Rep. 7 2002 59 60
39. W.H. Koppenol, R. Kissner, and J.S. Beckman Synthesis of peroxynitrite: to go with flow or on solid grounds? Methods Enzymol. 269 1996 296 302
40. J.W. Ledbetter, and S. Schaertel Pyridinyl and ketyl radicals of pyridoxal-5′-phosphate on micellar and liposomal surfaces J. Photochem. Photobiol. B: Biol. 47 1998 12 21
41. S.I. Liochev, and I. Fridovich The Haber-Weiss cycle - 70 years later: an alternative view Redox Rep. 7 2002 55 56
42. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the Folin phenol reagent J. Biol. Chem. 193 1951 265 275
43. D.V. Lynch, and P.L. Steponkus Lyotropic phase behavior of unsaturated phosphatidylcholine species: relevance to the mechanism of plasma membrane destabilization and freezing injury Biochim. Biophys. Acta 984 1989 267 272
44. S. Mabrey, and J.M. Sturtevant Incorporation of saturated fatty acids into phosphatidylcholine bilayers Biochim. Biophys. Acta 486 1977 444 450
45. T.J. McIntosh Differences in hydrocarbon chain tilt between hydrated phosphatidylethanolamine and phosphatidylcholine bilayers. A molecular packing model Biophys. J. 29 1980 237 245
46. L. Montanari, P. Fantozzi, J.M. Snyder, and J.W. King Selective extraction of phospholipids from soybeans with supercritical carbon dioxide and ethanol J. Supercrit. Fluids 14 1999 87 93
47. P. Muangman, M.L. Spenny, R.N. Tamura, and N.S. Gibran Fatty acids and glucose increase neutral endopeptidase activity in human microvascular endothelial cells Shock 19 2003 508 512
48. H. Ohkawa, N. Ohishi, and K. Yagi Assay for lipid peroxides in animal-tissues by thiobarbituric acid reaction Anal. Biochem. 95 1979 351 358
49. J.W. Park Liposome-based drug delivery in breast cancer treatment Breast Cancer Res. 4 2002 95 99
50. K.P. Pauls, A.L. MacKay, and M. Bloom Deuterium nuclear magnetic resonance study of the effects of palmitic acid on dipalmitoylphosphatidylcholine bilayers Biochemistry 22 1983 6101 6109
51. 2+ permeability of cardiac sarcolemmal vesicles J. Biol. Chem. 260 1985 9666 9671
52. I. Pinchuk, and D. Lichtenberg The mechanism of action of antioxidants against lipoprotein peroxidation, evaluation based on kinetic experiments Prog. Lipid Res. 41 2002 279 314
53. P.L. Privalov, V.V. Plotnikov, and V.V. Filimonov Precision scanning microcalorimeter for the study of liquids J. Chem. Thermodyn. 7 1975 41 47
54. R. Radi, J.S. Beckman, K.M. Bush, and B.A Freeman Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide Arch. Biochem. Biophys. 288 1991 481 487
55. R.J. Reiter Pineal melatonin: cell biology of its synthesis and of its physiological interactions Endocr. Rev. 12 1991 151 180
56. R.J. Reiter, D. Acuna-Castroviejo, D.X. Tan, and S. Burkhardt Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system Ann. N. Y. Acad. Sci. 939 2001 200 215
57. K.L. Retsky, and B. Frei Vitamin C prevents metal ion-dependent initiation and propagation of lipid peroxidation in human low-density lipoprotein Biochim. Biophys. Acta 1257 1995 279 287
58. A. Roland, R.A. Patterson, and D.S. Leake Measurement of copper-binding sites on low-density lipoprotein Arterioscler. Thromb. Vasc. Biol. 21 2001 594 602
59. A. Saija, M. Scalese, M. Lanza, D. Marzullo, F. Bonina, and F. Castelli Flavonoids as antioxidant agents: importance of their interaction with biomembranes Free Radic. Biol. Med. 19 1995 481 486
60. A.M. Samuni, A. Lipman, and Y. Barenholz Damage to liposomal lipids: protection by antioxidants and cholesterol-mediated dehydration Chem. Phys. Lipids 105 2000 121 134
61. J.B. Schenkman, and D.L. Cinti Preparation of microssomes with calcium Methods Enzymol. 52 1978 83 89
62. P.G. Scherer, and J. Seelig Electric charge effects on phospholipid headgroups. Phosphatidylcholine in mixtures with cationic and anionic amphiphiles Biochemistry 28 1989 7720 7728
63. J.K. Seydel Nuclear magnetic resonance and differential scanning calorimetry as tools for studying drug-membrane interactions Trends Pharmacol. Sci. 12 1991 368 370
64. N. Sone, M. Yoshida, H. Hirata, and Y. Kagawa Reconstitution of vesicles capable of energy transformation from phospholipids and adenosine triphosphatase of thermophilic bacterium J. Biochem. 81 1977 519 528
65. W.D. Stanbro Modeling the interaction of peroxynitrite with low-density lipoproteins. I. Plasma levels of peroxynitrite J. Theor. Biol. 205 2000 457 464
66. W.E. Teague, N.L. Fuller, R.P. Rand, and K. Gawrisch Polyunsaturated lipids in membrane fusion events Cell Mol. Biol. Lett. 7 2002 262 264
67. A. Teixeira, M.P. Morfim, C.A.S. de Cordova, C.C.T. Charão, V.R. de Lima, and T.B. Creczynski-Pasa Melatonin protects against pro oxidant enzymes and reduces LPO in distinct membranes induced by the hydroxyl and ascorbyl radicals and by peroxynitrite J. Pineal Res. 35 2003 262 268
68. C.E. Thomas, and S.D. Aust Rat liver microsomal NADPH-dependent release of iron from ferritin and lipid peroxidation Free Radic. Biol. Med. 1 1985 293 300
69. O. Tirosh, R. Kohen, J. Katzhendler, A. Alon, and Y. Barenholz Oxidative stress effect on the integrity of lipid bilayers is modulated by cholesterol level of bilayers Chem. Phys. Lipids 87 1997 17 22
70. A. Tokumura A family of phospholipids autacoids: occurrence, metabolism and bioactions Prog. Lipid Res. 34 1995 151 184
71. F. Tolgyesi, and G. Monticelli pH and chain length dependence of phosphatidic acid phase transition parameters Bioelectrochem. Bioenergy 17 1987 309 317
72. A.S. Ulrich, M. Sami, and A. Watts Hydration of DOPC bilayers by differential scanning calorimetry Biochim. Biophys. Acta 1191 1994 225 230
73. R. Verlengia, R. Gorjão, C.C. Kanunfre, S. Bordin, T. Martins de Lima, and R. Curi Effects of arachidonic acid on proliferation cytokines production and pleiotropic genes expression in Jurkat cells - a comparison with oleic acid Life Sci. 73 2003 2939 2951
74. P. Viani, G. Cervato, A. Fiorilli, E. Rigamonti, and B. Cestaro Studies on peroxidation processes of model membranes and synaptosomes: role of phosphatidic acid Chem. Phys. Lipids 52 1990 49 55
75. B.A. Wagner, G.R. Buettner, and C.P. Burns Free radical-mediated lipid peroxidation in cells: oxidizability is a function of cell lipid bis-allylic hydrogen content Biochemistry 33 1994 4449 4453
76. 2+-ATPase of human erythrocyte membranes Biochim. Biophys. Acta 730 1983 196 200
77. P.L. Yeagle The Membranes of Cells 1993 Academic Press California 349
78. 2 and phospholipids in neural membranes in an experimental epilepsy model Acta Neurol. Scand. 106 2002 258 262
79. 1 on lipid peroxidation in membranes Biochim. Biophys. Acta 1371 1998 134 142
80. Y.C. Zhou, and R.L. Zheng Phenolic compounds and an analog as superoxide anion scavengers and antioxidants Biochem. Pharmacol. 42 1991 1177 1179