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Volumn 5, Issue 10, 2014, Pages 1653-1658

Lipid peroxidation in membranes: The peroxyl radical does not "float"

Author keywords

autoxidation; hydroperoxide; MD simulations; peroxyl; phospholipid bilayers

Indexed keywords

CELL MEMBRANES; CYTOLOGY; LIPID BILAYERS; OXIDATION; PHOSPHOLIPIDS; REACTION KINETICS;

EID: 84901049582     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz500502q     Document Type: Article
Times cited : (71)

References (45)
  • 1
    • 84876582559 scopus 로고    scopus 로고
    • A Perspective on Free Radical Autoxidation: The Physical Organic Chemistry of Polyunsaturated Fatty Acid and Sterol Peroxidation
    • Porter, N. A. A Perspective on Free Radical Autoxidation: The Physical Organic Chemistry of Polyunsaturated Fatty Acid and Sterol Peroxidation J. Org. Chem. 2013, 78, 3511-3524
    • (2013) J. Org. Chem. , vol.78 , pp. 3511-3524
    • Porter, N.A.1
  • 2
    • 79959460547 scopus 로고    scopus 로고
    • Free Radical Oxidation of Polyunsaturated Lipids: New Mechanistic Insights and the Development of Peroxyl Radical Clocks
    • Pratt, D. a.; Tallman, K. a.; Porter, N. A. Free Radical Oxidation of Polyunsaturated Lipids: New Mechanistic Insights and the Development of Peroxyl Radical Clocks Acc. Chem. Res. 2011, 44, 458-467
    • (2011) Acc. Chem. Res. , vol.44 , pp. 458-467
    • Pratt, D.A.1    Tallman, K.A.2    Porter, N.A.3
  • 3
    • 80054089650 scopus 로고    scopus 로고
    • Free Radical Lipid Proxidation: Mechanisms and Analysis
    • Yin, H.; Xu, L.; Porter, N. A. Free Radical Lipid Proxidation: Mechanisms and Analysis Chem. Rev. 2011, 111, 5944-5972
    • (2011) Chem. Rev. , vol.111 , pp. 5944-5972
    • Yin, H.1    Xu, L.2    Porter, N.A.3
  • 4
    • 84878376045 scopus 로고    scopus 로고
    • Vitamin Currency in a Lipid Exchange Market
    • Mesmin, B.; Antonny, B. Vitamin Currency in a Lipid Exchange Market Science 2013, 340, 1051-1052
    • (2013) Science , vol.340 , pp. 1051-1052
    • Mesmin, B.1    Antonny, B.2
  • 5
    • 0036086130 scopus 로고    scopus 로고
    • Free Radicals in the Physiological Control of Cell Function
    • Dröge, W. Free Radicals in the Physiological Control of Cell Function Physiol. Rev. 2002, 82, 47-95
    • (2002) Physiol. Rev. , vol.82 , pp. 47-95
    • Dröge, W.1
  • 8
    • 67649216515 scopus 로고    scopus 로고
    • CD36, a Scavenger Receptor Involved in Immunity, Metabolism, Angiogenesis, and Behavior
    • Silverstein, R. L.; Febbraio, M. CD36, a Scavenger Receptor Involved in Immunity, Metabolism, Angiogenesis, and Behavior Sci. Signaling 2009, 2, re3
    • (2009) Sci. Signaling , vol.2 , pp. 3
    • Silverstein, R.L.1    Febbraio, M.2
  • 14
    • 0037411282 scopus 로고    scopus 로고
    • 4-Hydroxy-2-nonenal: A Product and Mediator of Oxidative Stress
    • Uchida, K. 4-Hydroxy-2-nonenal: a Product and Mediator of Oxidative Stress Prog. Lipid Res. 2003, 42, 318-343
    • (2003) Prog. Lipid Res. , vol.42 , pp. 318-343
    • Uchida, K.1
  • 15
    • 47049095632 scopus 로고    scopus 로고
    • Routes to 4-Hydroxynonenal: Fundamental Issues in the Mechanisms of Lipid Peroxidation
    • Schneider, C.; Porter, N. A.; Brash, A. R. Routes to 4-Hydroxynonenal: Fundamental Issues in the Mechanisms of Lipid Peroxidation J. Biol. Chem. 2008, 283, 15539-15543
    • (2008) J. Biol. Chem. , vol.283 , pp. 15539-15543
    • Schneider, C.1    Porter, N.A.2    Brash, A.R.3
  • 16
    • 0025814980 scopus 로고
    • Chemistry and Biochemistry of 4-Hydroxynonenal, Malonaldehyde and Related Aldehydes
    • Esterbauer, H.; Schaur, R. J.; Zollner, H. Chemistry and Biochemistry of 4-Hydroxynonenal, Malonaldehyde and Related Aldehydes Free Radic. Biol. Med. 1991, 11, 81-128
    • (1991) Free Radic. Biol. Med. , vol.11 , pp. 81-128
    • Esterbauer, H.1    Schaur, R.J.2    Zollner, H.3
  • 17
    • 0033535371 scopus 로고    scopus 로고
    • Lipid Peroxidation-DNA Damage by Malondialdehyde
    • Marnett, L. J. Lipid Peroxidation-DNA Damage by Malondialdehyde Mutat. Res. 1999, 424, 83-95
    • (1999) Mutat. Res. , vol.424 , pp. 83-95
    • Marnett, L.J.1
  • 18
    • 33644514643 scopus 로고    scopus 로고
    • Endogenous Reactive Intermediates as Modulators of Cell Signaling and Cell Death
    • West, J. D.; Marnett, L. J. Endogenous Reactive Intermediates as Modulators of Cell Signaling and Cell Death Chem. Res. Toxicol. 2006, 19, 173-194
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 173-194
    • West, J.D.1    Marnett, L.J.2
  • 19
    • 37349055140 scopus 로고    scopus 로고
    • Effect of Lipid Peroxidation on the Properties of Lipid Bilayers: A Molecular Dynamics Study
    • Wong-Ekkabut, J.; Xu, Z.; Triampo, W.; Tang, I.-M.; Tieleman, D. P.; Monticelli, L. Effect of Lipid Peroxidation on the Properties of Lipid Bilayers: A Molecular Dynamics Study Biophys. J. 2007, 93, 4225-4236
    • (2007) Biophys. J. , vol.93 , pp. 4225-4236
    • Wong-Ekkabut, J.1    Xu, Z.2    Triampo, W.3    Tang, I.-M.4    Tieleman, D.P.5    Monticelli, L.6
  • 20
    • 84863984081 scopus 로고    scopus 로고
    • Biophysics of Lipid Bilayers Containing Oxidatively Modified Phospholipids: Insights from Fluorescence and EPR Experiments and from MD Simulations
    • Jurkiewicz, P.; Olz̀yńska, A.; Cwiklik, L.; Conte, E.; Jungwirth, P.; Megli, F. M.; Hof, M. Biophysics of Lipid Bilayers Containing Oxidatively Modified Phospholipids: Insights from Fluorescence and EPR Experiments and from MD Simulations Biochim. Biophys. Acta 2012, 1818, 2388-2402
    • (2012) Biochim. Biophys. Acta , vol.1818 , pp. 2388-2402
    • Jurkiewicz, P.1    Olz̀yńska, A.2    Cwiklik, L.3    Conte, E.4    Jungwirth, P.5    Megli, F.M.6    Hof, M.7
  • 22
    • 84880549841 scopus 로고    scopus 로고
    • Molecular Dynamics Study of Oxidized Lipid Bilayers in NaCl Solution
    • Jarerattanachat, V.; Karttunen, M.; Wong-Ekkabut, J. Molecular Dynamics Study of Oxidized Lipid Bilayers in NaCl Solution J. Phys. Chem. B 2013, 117, 8490-8501
    • (2013) J. Phys. Chem. B , vol.117 , pp. 8490-8501
    • Jarerattanachat, V.1    Karttunen, M.2    Wong-Ekkabut, J.3
  • 23
    • 0001016776 scopus 로고
    • Autoxidation of Model Membranes. The Kinetics and Mechanism of Autoxidation of Mixed Phospholipid Bilayers
    • Barclay, L. R. C.; Baskin, K. A.; Kong, D.; Locke, S. J. Autoxidation of Model Membranes. The Kinetics and Mechanism of Autoxidation of Mixed Phospholipid Bilayers Can. J. Chem. 1987, 65, 2541-2550
    • (1987) Can. J. Chem. , vol.65 , pp. 2541-2550
    • Barclay, L.R.C.1    Baskin, K.A.2    Kong, D.3    Locke, S.J.4
  • 24
    • 0027232771 scopus 로고
    • 1992 Syntex Award Lecture Model Biomembranes: Quantitative Studies of Peroxidation, Antioxidant Action, Partitioning, and Oxidative Stress
    • Barclay, L. R. C. 1992 Syntex Award Lecture Model Biomembranes: Quantitative Studies of Peroxidation, Antioxidant Action, Partitioning, and Oxidative Stress Can. J. Chem. 1993, 71, 1-16
    • (1993) Can. J. Chem. , vol.71 , pp. 1-16
    • Barclay, L.R.C.1
  • 25
    • 70349116511 scopus 로고    scopus 로고
    • Rate Constants for Peroxidation of Polyunsaturated Fatty Acids and Sterols in Solution and in Liposomes
    • Xu, L.; Davis, T. a.; Porter, N. A. Rate Constants for Peroxidation of Polyunsaturated Fatty Acids and Sterols in Solution and in Liposomes J. Am. Chem. Soc. 2009, 131, 13037-13044
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 13037-13044
    • Xu, L.1    Davis, T.A.2    Porter, N.A.3
  • 26
    • 33845557804 scopus 로고
    • Autoxidation of Biological Molecules. 2. Autoxidation of a Model Membrane. Comparison of the Autoxidation of Egg Lecithin Phosphatidylcholine in Water and in Chlorobenzene
    • Barclay, L.; Ingold, K. Autoxidation of Biological Molecules. 2. Autoxidation of a Model Membrane. Comparison of the Autoxidation of Egg Lecithin Phosphatidylcholine in Water and in Chlorobenzene J. Am. Chem. Soc. 1981, 103, 6478-6485
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6478-6485
    • Barclay, L.1    Ingold, K.2
  • 27
    • 39149099088 scopus 로고    scopus 로고
    • Tocopherols and Tocotrienols in Membranes: A Critical Review
    • Atkinson, J.; Epand, R. F.; Epand, R. M. Tocopherols and Tocotrienols in Membranes: A Critical Review Free Radic. Biol. Med. 2008, 44, 739-764
    • (2008) Free Radic. Biol. Med. , vol.44 , pp. 739-764
    • Atkinson, J.1    Epand, R.F.2    Epand, R.M.3
  • 28
    • 0027251053 scopus 로고
    • The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate
    • Buettner, G. R. The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate Arch. Biochem. Biophys. 1993, 300, 535-543
    • (1993) Arch. Biochem. Biophys. , vol.300 , pp. 535-543
    • Buettner, G.R.1
  • 29
    • 84862509068 scopus 로고    scopus 로고
    • How Lipid Unsaturation, Peroxyl Radical Partitioning, and Chromanol Lipophilic Tail Affect the Antioxidant Activity of α-Tocopherol: Direct Visualization via High-Throughput Fluorescence Studies Conducted with Fluorogenic α-Tocopherol Analogues
    • Krumova, K.; Friedland, S.; Cosa, G. How Lipid Unsaturation, Peroxyl Radical Partitioning, and Chromanol Lipophilic Tail Affect the Antioxidant Activity of α-Tocopherol: Direct Visualization via High-Throughput Fluorescence Studies Conducted with Fluorogenic α-Tocopherol Analogues J. Am. Chem. Soc. 2012, 134, 10102-10113
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 10102-10113
    • Krumova, K.1    Friedland, S.2    Cosa, G.3
  • 30
    • 72449141707 scopus 로고    scopus 로고
    • Partition of Indicaxanthin in Membrane Biomimetic Systems. A Kinetic and Modeling Approach
    • Turco Liveri, M. L.; Sciascia, L.; Allegra, M.; Tesoriere, L.; Livrea, M. A. Partition of Indicaxanthin in Membrane Biomimetic Systems. A Kinetic and Modeling Approach J. Agric. Food Chem. 2009, 57, 10959-10963
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 10959-10963
    • Turco Liveri, M.L.1    Sciascia, L.2    Allegra, M.3    Tesoriere, L.4    Livrea, M.A.5
  • 31
    • 2342598922 scopus 로고    scopus 로고
    • Diffusion of α-Tocopherol in Membrane Models: Probing the Kinetics of Vitamin e Antioxidant Action by Fluorescence in Real Time
    • Gramlich, G.; Zhang, J.; Nau, W. M. Diffusion of α-Tocopherol in Membrane Models: Probing the Kinetics of Vitamin E Antioxidant Action by Fluorescence in Real Time J. Am. Chem. Soc. 2004, 126, 5482-5492
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5482-5492
    • Gramlich, G.1    Zhang, J.2    Nau, W.M.3
  • 32
    • 9544238226 scopus 로고    scopus 로고
    • Radical-Initiated Lipid Peroxidation in Low Density Lipoproteins: Insights Obtained from Kinetic Modeling
    • Waldeck, A. R.; Stocker, R. Radical-Initiated Lipid Peroxidation in Low Density Lipoproteins: Insights Obtained from Kinetic Modeling Chem. Res. Toxicol. 1996, 9, 954-964
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 954-964
    • Waldeck, A.R.1    Stocker, R.2
  • 34
    • 80051668513 scopus 로고    scopus 로고
    • Vitamins C and E: Beneficial Effects from a Mechanistic Perspective
    • Traber, M. G.; Stevens, J. F. Vitamins C and E: Beneficial Effects from a Mechanistic Perspective Free Radic. Biol. Med. 2011, 51, 1000-1013
    • (2011) Free Radic. Biol. Med. , vol.51 , pp. 1000-1013
    • Traber, M.G.1    Stevens, J.F.2
  • 35
    • 84878034660 scopus 로고    scopus 로고
    • Molecular Dynamics Simulations of Depth Distribution of Spin-Labeled Phospholipids within Lipid Bilayer
    • Kyrychenko, A.; Ladokhin, A. S. Molecular Dynamics Simulations of Depth Distribution of Spin-Labeled Phospholipids within Lipid Bilayer J. Phys. Chem. B 2013, 117, 5875-5885
    • (2013) J. Phys. Chem. B , vol.117 , pp. 5875-5885
    • Kyrychenko, A.1    Ladokhin, A.S.2
  • 36
    • 0008901450 scopus 로고
    • Relative Partition Coefficients for Organic Solutes from Fluid Simulations
    • Jorgensen, W. L.; Briggs, J. M.; Contreras, M. L. Relative Partition Coefficients for Organic Solutes from Fluid Simulations J. Phys. Chem. 1990, 94, 1683-1686
    • (1990) J. Phys. Chem. , vol.94 , pp. 1683-1686
    • Jorgensen, W.L.1    Briggs, J.M.2    Contreras, M.L.3
  • 38
    • 66349120487 scopus 로고    scopus 로고
    • Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions
    • Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions J. Phys. Chem. B 2009, 113, 6378-6396
    • (2009) J. Phys. Chem. B , vol.113 , pp. 6378-6396
    • Marenich, A.V.1    Cramer, C.J.2    Truhlar, D.G.3
  • 41
    • 84881224703 scopus 로고    scopus 로고
    • Insights about α-Tocopherol and Trolox Interaction with Phosphatidylcholine Monolayers under Peroxidation Conditions through Brewster Angle Microscopy
    • Castro, C. M.; Pinheiro, M.; Lúcio, M.; Giner-Casares, J. J.; Camacho, L.; Lima, J. L.; Reis, S.; Segundo, M. A. Insights about α-Tocopherol and Trolox Interaction with Phosphatidylcholine Monolayers under Peroxidation Conditions through Brewster Angle Microscopy Colloids Surf., B 2013, 111, 626-635
    • (2013) Colloids Surf., B , vol.111 , pp. 626-635
    • Castro, C.M.1    Pinheiro, M.2    Lúcio, M.3    Giner-Casares, J.J.4    Camacho, L.5    Lima, J.L.6    Reis, S.7    Segundo, M.A.8
  • 43
    • 0025689941 scopus 로고
    • The Antioxidant Activities of Phenolic Antioxidants in Free Radical Peroxidation of Phospholipid Membranes
    • Barclay, L. R. C.; Baskin, K. A.; Dakin, K. A.; Locke, S. J.; Vinqvist, M. R. The Antioxidant Activities of Phenolic Antioxidants in Free Radical Peroxidation of Phospholipid Membranes Can. J. Chem. 1990, 68, 2258-2269
    • (1990) Can. J. Chem. , vol.68 , pp. 2258-2269
    • Barclay, L.R.C.1    Baskin, K.A.2    Dakin, K.A.3    Locke, S.J.4    Vinqvist, M.R.5
  • 45
    • 84887985179 scopus 로고    scopus 로고
    • Reactive Oxygen Species at Phospholipid Bilayers: Distribution, Mobility and Permeation
    • Cordeiro, R. M. Reactive Oxygen Species at Phospholipid Bilayers: Distribution, Mobility and Permeation Biochim. Biophys. Acta 2014, 1838, 438-444
    • (2014) Biochim. Biophys. Acta , vol.1838 , pp. 438-444
    • Cordeiro, R.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.