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1
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0024603895
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Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity
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33845374568
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Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function
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The role of vitamin e in atherosclerosis
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(b) Upston, J. M.; Kritharides, L.; Stocker, R. A. The role of vitamin E in atherosclerosis. Prog. Lipid Res. 2003, 42, 405-422.
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Upston, J.M.1
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Is the oxidative modification hypothesis relevant to human atherosclerosis? Do the antioxidant trials conducted to date refute the hypothesis?
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(c) Steinberg, D.; Witzum, J. L. Is the oxidative modification hypothesis relevant to human atherosclerosis? Do the antioxidant trials conducted to date refute the hypothesis? Circulation 2002, 105, 2107-11.
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Steinberg, D.1
Witzum, J.L.2
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6
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Vitamin E in human low-density lipoprotein: When and how this antioxidant becomes a pro-oxidant
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(a) Bowry, V. W.; Ingold, K. U.; Stocker, R. Vitamin E in human low-density lipoprotein: When and how this antioxidant becomes a pro-oxidant. Biochem. J. 1992, 288, 341-344.
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Bowry, V.W.1
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7
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Tocopherol-mediated peroxidation. The prooxidant effect of vitamin e on the radical-initiated oxidation of human low-density lipoprotein
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(b) Bowry, V. W.; Stocker, R. Tocopherol-mediated peroxidation. The prooxidant effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. J. Am. Chem. Soc. 1993, 115, 6029-6044.
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and references therein
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(c) Ingold, K. U.; Bowry, V. W.; Stocker, R.; Walling, C. Autoxidation of lipids and antioxidation by α-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids: Unrecognized consequences of lipid particle size as exemplified by oxidation of human low density lipoprotein. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 45-49 and references therein.
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9
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0141645551
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6-Amino-3-pyridinols: Towards diffusion-controlled antioxidants
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(a) Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. 6-Amino-3-pyridinols: towards diffusion-controlled antioxidants. Angew. Chem. Int. Ed. 2003, 42, 4370-3.
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Porter, N.A.6
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10
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10844262564
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Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants
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(b) Wijtmans, M.; Pratt, D. A.; Brinkhorst, J.; Swerza, R.; Valgimigli, L.; Pedulli, G. F.; Porter, N. A. Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants. J. Org. Chem. 2004, 69, 9215-9223.
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Wijtmans, M.1
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11
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0034810395
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5-Pyrimidinols: Novel chain-breaking antioxidants more effective than phenols
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(a) Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. 5-Pyrimidinols: novel chain-breaking antioxidants more effective than phenols. J. Am. Chem. Soc. 2001, 123, 4625-4626.
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Pratt, D.A.1
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12
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0142228953
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The effect of ring nitrogen atoms on the homolytic reactivity of phenolic compounds: Understanding the radical-scavenging ability of 5-pyrimidinols
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(b) Valgimigli, L.; Brigati, G.; Pedulli, G. F.; DiLabio, G. A.; Mastragostino, M.; Arbizzani, C.; Pratt, D. A. The effect of ring nitrogen atoms on the homolytic reactivity of phenolic compounds: Understanding the radical-scavenging ability of 5-pyrimidinols. Chem.-Eur. J. 2003, 9, 4997-5010.
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Valgimigli, L.1
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Mastragostino, M.5
Arbizzani, C.6
Pratt, D.A.7
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13
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27444441299
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note
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For brevity, we include here only the results obtained with 5. See the Supporting Information for representative results obtained with 6.
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14
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0034600255
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Unsymmetrical azo initiators increases efficiency of radical generation in aqueous dispersions, liposomal membranes, and lipoproteins
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(a) Culbertson, S. M.; Porter, N. A. Unsymmetrical azo initiators increases efficiency of radical generation in aqueous dispersions, liposomal membranes, and lipoproteins. J. Am. Chem. Soc. 2000, 122, 4032-4038.
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0035913748
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Minimizing tocopherol oxidation of low density lipoprotein with an amphiphilic unsymmetrical azo initiator
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(b) Culbertson, S. M.; Vinqvist, M. R.; Barclay, L. R. C.; Porter, N. A. Minimizing tocopherol oxidation of low density lipoprotein with an amphiphilic unsymmetrical azo initiator. J. Am. Chem. Soc. 2001, 123, 8951-8960.
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Porter, N.A.4
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16
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27444435907
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note
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It should be noted that similar results were obtained in separate experiments with LDL obtained from different individuals.
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17
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0030641128
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Requirement for, promotion, or inhibition by α-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation
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Neuzil, J.; Thomas, S. R.; Stocker, R. Requirement for, promotion, or inhibition by α-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation. Free Radical Biol. Med. 1997, 22, 57-71.
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0343238361
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Oxidized phospholipids, linked to apolipoprotein B of oxidized LDL, are ligands for macrophage scavenger receptors
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Gillotte, K. L.; Hörkkö, S.; Witztum, J. L.; Steinberg, D. Oxidized phospholipids, linked to apolipoprotein B of oxidized LDL, are ligands for macrophage scavenger receptors. J. Lipid Res. 2000, 41, 824-833.
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13944251985
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Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins
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Milne, G. L.; Seal, J. R.; Havrilla, C. M.; Wijtmans, M.; Porter, N. A. Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins. J. Lipid Res. 2005, 46, 307-319.
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20
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0001230161
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Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation
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Giessauf, A.; van Wickern, B.; Simat, T.; Steinhart, H.; Esterbauer, H. Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation. FEBS Lett. 1996, 389, 136-140.
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21
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0033619720
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Identification of modified tryptophan residues in apolipoprotein B-100 derived from copper ion-oxidized low-density lipoprotein
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Analysis of apoB-100 digests were found to contain Trp oxidation products N-formylkynurenine, kynurenine, and tryptamine, leading the authors to conclude that the fluorescence is not simply quenched by a peroxidation-derived product. These oxidation products have different absorption and emission maxima compared with Trp itself. See also the following: Yang, C.; Gu, Z.-W.; Yang, M.; Lin, S.-N.; Siuzdak, G.; Smith, C. V. Identification of modified tryptophan residues in apolipoprotein B-100 derived from copper ion-oxidized low-density lipoprotein. Biochemistry 1999, 38, 15903-15908.
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The damaging effect of UV-C irradiation on lens α-crystallin
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Fujii, N.; Uchida, H. Saito, T. The damaging effect of UV-C irradiation on lens α-crystallin. Mol. Vision 2004, 10, 814-820.
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2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: Design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation
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(a) Noguchi, N.; Iwaki, Y.; Takahashi, M.; Komuro, E.; Kato, Y.; Tamura, K.; Cynshi, O.; Kodama, T.; Niki, E. 2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di- tert-butylbenzofuran: design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation. Arch. Biochem. Biophys. 1997, 342, 236-243.
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Noguchi, N.1
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Tamura, K.6
Cynshi, O.7
Kodama, T.8
Niki, E.9
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24
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0031282293
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Inhibition of oxidation of low-density lipoprotein by a novel antioxidant, BO-653, prepared by theoretical design
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(b) Noguchi, N.; Okimoto, Y.; Tsuchiya, J.; Cynshi, O.; Kodama, T.; Niki, E. Inhibition of oxidation of low-density lipoprotein by a novel antioxidant, BO-653, prepared by theoretical design. Arch. Biochem. Biophys. 1997, 347, 141-147.
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25
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13144251127
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Antiatherogenic effects of the antioxidant BO-653 in three different animal models
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(c) Cynshi, O.; Kawabe, Y.; Suzuki, T.; Takashima, Y.; Kaise, H.; Nakamura, M.; Ohba, Y.; Kato, Y.; Tamura, K.; Hayasaka, A.; Higashida, A.; Sakaguchi, H.; Takeya, M.; Takahashi, K.; Inoue, K.; Noguchi, N.; Niki, E.; Kodama, T. Antiatherogenic effects of the antioxidant BO-653 in three different animal models. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10123-10128.
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Ohba, Y.7
Kato, Y.8
Tamura, K.9
Hayasaka, A.10
Higashida, A.11
Sakaguchi, H.12
Takeya, M.13
Takahashi, K.14
Inoue, K.15
Noguchi, N.16
Niki, E.17
Kodama, T.18
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26
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0038460842
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Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants
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(d) Tamura, K.; Kato, Y.; Ishikawa, A.; Kato, Y.; Himori, M.; Yoshida, M.; Takashima, Y.; Suzuki, T.; Kawabe, Y.; Cynshi, O.; Kodama, T.; Niki, E.; Shimizu, M. Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5- benzofuranols as a novel series of antiatherogenic antioxidants. J. Med. Chem. 2003, 46, 3083-3093.
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Tamura, K.1
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Takashima, Y.7
Suzuki, T.8
Kawabe, Y.9
Cynshi, O.10
Kodama, T.11
Niki, E.12
Shimizu, M.13
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27
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27444433634
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note
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Studies of pyridinol oxidation to be published in due course suggest that quinone-imines are among the products formed. The reactivity of these compounds is important with regard to the in vivo efficacy of the compounds.
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