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Volumn 48, Issue 22, 2005, Pages 6787-6789

Lipid-soluble 3-pyridinol antioxidants spare α-tocopherol and do not efficiently mediate peroxidation of cholesterol esters in human low-density lipoprotein

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYPYRIDINE; ALPHA TOCOPHEROL; ANTIOXIDANT; CHOLESTEROL ESTER; LOW DENSITY LIPOPROTEIN CHOLESTEROL; TRYPTOPHAN;

EID: 27444435355     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0507173     Document Type: Article
Times cited : (30)

References (27)
  • 1
    • 0024603895 scopus 로고
    • Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity
    • Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 1989, 320, 915-924.
    • (1989) N. Engl. J. Med. , vol.320 , pp. 915-924
    • Steinberg, D.1    Parthasarathy, S.2    Carew, T.E.3    Khoo, J.C.4    Witztum, J.L.5
  • 2
    • 33845374568 scopus 로고
    • Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function
    • Burton, G. W.; Ingold, K. U. Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function. Acc. Chem. Res. 1986, 19, 194-201.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 194-201
    • Burton, G.W.1    Ingold, K.U.2
  • 3
    • 0036566151 scopus 로고    scopus 로고
    • Oxidized lipid accumulates in the presence of alpha-tocopherol in atherosclerosis
    • (a) Upston, J. M.; Terentis, A. C.; Morris, K.; Keaney, J. F., Jr.; Stocker, R. Oxidized lipid accumulates in the presence of alpha-tocopherol in atherosclerosis. Biochem. J. 2002, 363, 753-760.
    • (2002) Biochem. J. , vol.363 , pp. 753-760
    • Upston, J.M.1    Terentis, A.C.2    Morris, K.3    Keaney Jr., J.F.4    Stocker, R.5
  • 5
    • 0037197722 scopus 로고    scopus 로고
    • Is the oxidative modification hypothesis relevant to human atherosclerosis? Do the antioxidant trials conducted to date refute the hypothesis?
    • (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.
    • (2002) Circulation , vol.105 , pp. 2107-2111
    • Steinberg, D.1    Witzum, J.L.2
  • 6
    • 0026460826 scopus 로고
    • Vitamin E in human low-density lipoprotein: When and how this antioxidant becomes a pro-oxidant
    • (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.
    • (1992) Biochem. J. , vol.288 , pp. 341-344
    • Bowry, V.W.1    Ingold, K.U.2    Stocker, R.3
  • 7
    • 0027213625 scopus 로고
    • Tocopherol-mediated peroxidation. The prooxidant effect of vitamin e on the radical-initiated oxidation of human low-density lipoprotein
    • (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.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6029-6044
    • Bowry, V.W.1    Stocker, R.2
  • 8
    • 0027397359 scopus 로고
    • 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
    • and references therein
    • (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.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 45-49
    • Ingold, K.U.1    Bowry, V.W.2    Stocker, R.3    Walling, C.4
  • 10
    • 10844262564 scopus 로고    scopus 로고
    • Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants
    • (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.
    • (2004) J. Org. Chem. , vol.69 , pp. 9215-9223
    • Wijtmans, M.1    Pratt, D.A.2    Brinkhorst, J.3    Swerza, R.4    Valgimigli, L.5    Pedulli, G.F.6    Porter, N.A.7
  • 11
    • 0034810395 scopus 로고    scopus 로고
    • 5-Pyrimidinols: Novel chain-breaking antioxidants more effective than phenols
    • (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.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4625-4626
    • Pratt, D.A.1    Dilabio, G.A.2    Brigati, G.3    Pedulli, G.F.4    Valgimigli, L.5
  • 12
    • 0142228953 scopus 로고    scopus 로고
    • The effect of ring nitrogen atoms on the homolytic reactivity of phenolic compounds: Understanding the radical-scavenging ability of 5-pyrimidinols
    • (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.
    • (2003) Chem.-Eur. J. , vol.9 , pp. 4997-5010
    • Valgimigli, L.1    Brigati, G.2    Pedulli, G.F.3    Dilabio, G.A.4    Mastragostino, M.5    Arbizzani, C.6    Pratt, D.A.7
  • 13
    • 27444441299 scopus 로고    scopus 로고
    • note
    • For brevity, we include here only the results obtained with 5. See the Supporting Information for representative results obtained with 6.
  • 14
    • 0034600255 scopus 로고    scopus 로고
    • Unsymmetrical azo initiators increases efficiency of radical generation in aqueous dispersions, liposomal membranes, and lipoproteins
    • (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.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4032-4038
    • Culbertson, S.M.1    Porter, N.A.2
  • 15
    • 0035913748 scopus 로고    scopus 로고
    • Minimizing tocopherol oxidation of low density lipoprotein with an amphiphilic unsymmetrical azo initiator
    • (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.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8951-8960
    • Culbertson, S.M.1    Vinqvist, M.R.2    Barclay, L.R.C.3    Porter, N.A.4
  • 16
    • 27444435907 scopus 로고    scopus 로고
    • note
    • It should be noted that similar results were obtained in separate experiments with LDL obtained from different individuals.
  • 17
    • 0030641128 scopus 로고    scopus 로고
    • Requirement for, promotion, or inhibition by α-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation
    • 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.
    • (1997) Free Radical Biol. Med. , vol.22 , pp. 57-71
    • Neuzil, J.1    Thomas, S.R.2    Stocker, R.3
  • 18
    • 0343238361 scopus 로고    scopus 로고
    • Oxidized phospholipids, linked to apolipoprotein B of oxidized LDL, are ligands for macrophage scavenger receptors
    • 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.
    • (2000) J. Lipid Res. , vol.41 , pp. 824-833
    • Gillotte, K.L.1    Hörkkö, S.2    Witztum, J.L.3    Steinberg, D.4
  • 19
    • 13944251985 scopus 로고    scopus 로고
    • Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins
    • 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.
    • (2005) J. Lipid Res. , vol.46 , pp. 307-319
    • Milne, G.L.1    Seal, J.R.2    Havrilla, C.M.3    Wijtmans, M.4    Porter, N.A.5
  • 20
    • 0001230161 scopus 로고    scopus 로고
    • Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation
    • 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.
    • (1996) FEBS Lett. , vol.389 , pp. 136-140
    • Giessauf, A.1    Van Wickern, B.2    Simat, T.3    Steinhart, H.4    Esterbauer, H.5
  • 21
    • 0033619720 scopus 로고    scopus 로고
    • Identification of modified tryptophan residues in apolipoprotein B-100 derived from copper ion-oxidized low-density lipoprotein
    • 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.
    • (1999) Biochemistry , vol.38 , pp. 15903-15908
    • Yang, C.1    Gu, Z.-W.2    Yang, M.3    Lin, S.-N.4    Siuzdak, G.5    Smith, C.V.6
  • 22
    • 16644388652 scopus 로고    scopus 로고
    • The damaging effect of UV-C irradiation on lens α-crystallin
    • Fujii, N.; Uchida, H. Saito, T. The damaging effect of UV-C irradiation on lens α-crystallin. Mol. Vision 2004, 10, 814-820.
    • (2004) Mol. Vision , vol.10 , pp. 814-820
    • Fujii, N.1    Uchida, H.2    Saito, T.3
  • 23
    • 0031570723 scopus 로고    scopus 로고
    • 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
    • (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.
    • (1997) Arch. Biochem. Biophys. , vol.342 , pp. 236-243
    • Noguchi, N.1    Iwaki, Y.2    Takahashi, M.3    Komuro, E.4    Kato, Y.5    Tamura, K.6    Cynshi, O.7    Kodama, T.8    Niki, E.9
  • 24
    • 0031282293 scopus 로고    scopus 로고
    • Inhibition of oxidation of low-density lipoprotein by a novel antioxidant, BO-653, prepared by theoretical design
    • (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.
    • (1997) Arch. Biochem. Biophys. , vol.347 , pp. 141-147
    • Noguchi, N.1    Okimoto, Y.2    Tsuchiya, J.3    Cynshi, O.4    Kodama, T.5    Niki, E.6
  • 27
    • 27444433634 scopus 로고    scopus 로고
    • note
    • 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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