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Volumn 10, Issue 12, 1997, Pages 1387-1396

(Carboxyalkyl)pyrroles in human plasma and oxidized low-density lipoproteins

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYNONENAL; ARACHIDONIC ACID; CHOLESTEROL ESTER; EPITOPE; FREE RADICAL; HUMAN SERUM ALBUMIN; KEYHOLE LIMPET HEMOCYANIN; LINOLENIC ACID; OXIDIZED LOW DENSITY LIPOPROTEIN; PHOSPHOLIPID; POLYUNSATURATED FATTY ACID; PYRROLE DERIVATIVE; TRIACYLGLYCEROL;

EID: 0031472489     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970112c     Document Type: Article
Times cited : (96)

References (37)
  • 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., and Witztum, J. L. (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 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
    • 0026631158 scopus 로고
    • The role of oxidized low-density lipoproteins in the pathogenesis of atherosclerosis
    • Parthasarathy, S., Steinberg, D., and Witztum, J. L. (1992) The role of oxidized low-density lipoproteins in the pathogenesis of atherosclerosis. Annu. Rev. Med. 43, 219-225.
    • (1992) Annu. Rev. Med. , vol.43 , pp. 219-225
    • Parthasarathy, S.1    Steinberg, D.2    Witztum, J.L.3
  • 3
    • 0023198480 scopus 로고
    • Autoxidation of low-density lipoprotein: Loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes
    • Esterbauer, H., Jürgens, G., Quehenberger, O., and Koller, E. (1987) Autoxidation of low-density lipoprotein: Loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes. J. Lipid Res. 28, 495-509.
    • (1987) J. Lipid Res. , vol.28 , pp. 495-509
    • Esterbauer, H.1    Jürgens, G.2    Quehenberger, O.3    Koller, E.4
  • 4
    • 0026657363 scopus 로고
    • The role of lipid peroxidation and antioxidants in oxidative modification of LDL
    • Esterbauer, H., Gebicki, J., Puhl, H., and Jürgens, G. (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biol. Med. 13, 341-390.
    • (1992) Free Radical Biol. Med. , vol.13 , pp. 341-390
    • Esterbauer, H.1    Gebicki, J.2    Puhl, H.3    Jürgens, G.4
  • 5
    • 0022633583 scopus 로고
    • Modification of human low-density lipoprotein by the lipid peroxidation product 4-hydroxynonenal
    • Jürgens, G. J., Lang, J., and Esterbauer, H. (1986) Modification of human low-density lipoprotein by the lipid peroxidation product 4-hydroxynonenal. Biochim. Biophys. Acta 875, 103-114.
    • (1986) Biochim. Biophys. Acta , vol.875 , pp. 103-114
    • Jürgens, G.J.1    Lang, J.2    Esterbauer, H.3
  • 6
    • 0023221153 scopus 로고
    • Oxidation of human low-density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products
    • Steinbrecher, U. P. (1987) Oxidation of human low-density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products. J. Biol. Chem. 262, 3603-3608.
    • (1987) J. Biol. Chem. , vol.262 , pp. 3603-3608
    • Steinbrecher, U.P.1
  • 9
    • 0016864008 scopus 로고
    • Peroxy radical cyclization as a model for prostaglandin biosynthesis
    • Porter, N. A., and Funk, M. O. (1975) Peroxy radical cyclization as a model for prostaglandin biosynthesis. J. Org. Chem. 40, 3614-3615.
    • (1975) J. Org. Chem. , vol.40 , pp. 3614-3615
    • Porter, N.A.1    Funk, M.O.2
  • 10
    • 0021162288 scopus 로고
    • 2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution
    • 2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution. J. Am. Chem. Soc. 106, 6049-6060.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6049-6060
    • Salomon, R.G.1    Miller, D.B.2    Zagorski, M.G.3    Coughlin, D.J.4
  • 11
    • 0039046560 scopus 로고
    • Pyrroles
    • Barton, D., and Ollis, D. W., Eds. Pergamon, New York
    • Jackson, A. H. (1980) Pyrroles. In Comprehensive Organic Chemistry (Barton, D., and Ollis, D. W., Eds.) Vol. 4, pp 275-320, Pergamon, New York.
    • (1980) Comprehensive Organic Chemistry , vol.4 , pp. 275-320
    • Jackson, A.H.1
  • 13
    • 0029862568 scopus 로고    scopus 로고
    • Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal
    • Sayre, L. M., Sha, W., Xu, G., Kaur, K., Nadkarni, D., Subbanagounder, G., and Salomon, R. G. (1996) Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 9, 1194-1201.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1194-1201
    • Sayre, L.M.1    Sha, W.2    Xu, G.3    Kaur, K.4    Nadkarni, D.5    Subbanagounder, G.6    Salomon, R.G.7
  • 14
    • 0000197246 scopus 로고
    • Aldehydes formed by lipid peroxidation: Mechanisms of formation, occurrence, and determination
    • Virgo-Pelfrey, C., Ed. CRC Press, Boca Raton, FL
    • Esterbauer, H., Zollner, H., and Schaur, R. J. (1990) Aldehydes formed by lipid peroxidation: Mechanisms of formation, occurrence, and determination. In Membrane Lipid Oxidation Volume I (Virgo-Pelfrey, C., Ed.) pp 239-268, CRC Press, Boca Raton, FL.
    • (1990) Membrane Lipid Oxidation , vol.1 , pp. 239-268
    • Esterbauer, H.1    Zollner, H.2    Schaur, R.J.3
  • 15
    • 0024521694 scopus 로고
    • Hydrolysis of phosphatidylcholine during LDL oxidation is mediated by platelet-activating factor acetylhydrolase
    • Steinbrecher, U. P., and Pritchard, P. H. (1989) Hydrolysis of phosphatidylcholine during LDL oxidation is mediated by platelet-activating factor acetylhydrolase. J. Lipid Res. 30, 305-315.
    • (1989) J. Lipid Res. , vol.30 , pp. 305-315
    • Steinbrecher, U.P.1    Pritchard, P.H.2
  • 18
    • 0030054125 scopus 로고    scopus 로고
    • Previously unknown aldehydic lipid peroxidation compounds of arachidonic acid
    • Mlakar, A., and Spiteller, G. (1996) Previously unknown aldehydic lipid peroxidation compounds of arachidonic acid. Chem. Phys. Lipids 79, 47-53.
    • (1996) Chem. Phys. Lipids , vol.79 , pp. 47-53
    • Mlakar, A.1    Spiteller, G.2
  • 19
    • 0028175960 scopus 로고
    • Generation of α-hydroxyaldehydic compounds in the course of lipid peroxidation
    • Loidl-Stahlhofen, A., Hannemann, K., and Spiteller, G. (1994) Generation of α-hydroxyaldehydic compounds in the course of lipid peroxidation. Biochim. Biophys. Acta 1213, 140-148.
    • (1994) Biochim. Biophys. Acta , vol.1213 , pp. 140-148
    • Loidl-Stahlhofen, A.1    Hannemann, K.2    Spiteller, G.3
  • 20
    • 0000061171 scopus 로고
    • Modification of low-density lipoprotein by endothelial cells involves lipid peroxidation and degradation of low-density lipoprotein phospholipids
    • Steinbrecher, U. P., Parthasarathy, S., Leake, D. S., Witztum, J. L., and Steinberg, D. (1984) Modification of low-density lipoprotein by endothelial cells involves lipid peroxidation and degradation of low-density lipoprotein phospholipids. Proc. Natl. Acad. Sci. U.S.A. 81, 3883-3887.
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 3883-3887
    • Steinbrecher, U.P.1    Parthasarathy, S.2    Leake, D.S.3    Witztum, J.L.4    Steinberg, D.5
  • 21
    • 0023213632 scopus 로고
    • Decrease in reactive amino groups during oxidation or endothelial cell modification of LDL. Correlation with changes in receptor-mediated catabolism
    • Steinbrecher, U. P., Witztum, J. L., Parthasarathy, S., and Steinberg, D. (1987) Decrease in reactive amino groups during oxidation or endothelial cell modification of LDL. Correlation with changes in receptor-mediated catabolism. Atherosclerosis 7, 135-143.
    • (1987) Atherosclerosis , vol.7 , pp. 135-143
    • Steinbrecher, U.P.1    Witztum, J.L.2    Parthasarathy, S.3    Steinberg, D.4
  • 22
    • 0014379086 scopus 로고
    • Practical methods for plasma lipoprotein analysis
    • Hatch, F. T., and Lees, R. S. (1968) Practical methods for plasma lipoprotein analysis. Adv. Lipid Res. 6, 1-68.
    • (1968) Adv. Lipid Res. , vol.6 , pp. 1-68
    • Hatch, F.T.1    Lees, R.S.2
  • 23
    • 37049098124 scopus 로고
    • The biosynthesis of calendic acid, octadeca-(8E,10E,12)-trienoic acid, by developing marigold seeds: Origins of (E,E,Z) and (Z,E,Z) conjugated triene acids in higher plants
    • Crombie, L., and Holloway, S. J. (1985) The biosynthesis of calendic acid, octadeca-(8E,10E,12)-trienoic acid, by developing marigold seeds: Origins of (E,E,Z) and (Z,E,Z) conjugated triene acids in higher plants. J. Chem. Soc., Perkin Trans. 1 2425-32.
    • (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 2425-2432
    • Crombie, L.1    Holloway, S.J.2
  • 24
    • 0025772868 scopus 로고
    • Expeditious synthesis of the four isomers of methyl mimorphecolate
    • Duffault, J. M., Einhorn, J., and Alexakis, A. (1991) Expeditious synthesis of the four isomers of methyl mimorphecolate. Tetrahedron Lett. 30, 3701.
    • (1991) Tetrahedron Lett. , vol.30 , pp. 3701
    • Duffault, J.M.1    Einhorn, J.2    Alexakis, A.3
  • 25
    • 2642617942 scopus 로고
    • Eine einfache synthese des laevulinaldehyds
    • Mondon, A. (1952) Eine einfache synthese des laevulinaldehyds. (A simple synthesis of levulinaldehyde.) Angew. Chem. 64, 224.
    • (1952) Angew. Chem. , vol.64 , pp. 224
    • Mondon, A.1
  • 26
    • 2642711033 scopus 로고
    • A new method for the synthesis of γ-keto aldehydes
    • Kulinkovich, O. G., Tischenko, I. G., and Masalov, N. V. (1984) A new method for the synthesis of γ-keto aldehydes. Synthesis 886-887.
    • (1984) Synthesis , pp. 886-887
    • Kulinkovich, O.G.1    Tischenko, I.G.2    Masalov, N.V.3
  • 27
    • 84987541992 scopus 로고
    • A short route to 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one
    • Boga, C., Savoia, D., Trombini, C., and Umani-Ronchi, A. (1986) A short route to 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one. Synthesis 212-213.
    • (1986) Synthesis , pp. 212-213
    • Boga, C.1    Savoia, D.2    Trombini, C.3    Umani-Ronchi, A.4
  • 28
    • 0001223273 scopus 로고
    • Mass spectra of acetaltype compounds
    • Friedal, R. A., and Sharley, A. G. (1956) Mass spectra of acetaltype compounds. Anal. Chem. 28, 940.
    • (1956) Anal. Chem. , vol.28 , pp. 940
    • Friedal, R.A.1    Sharley, A.G.2
  • 29
    • 0029096670 scopus 로고
    • Improved synthesis of various isotope labeled 4-hydroxyalkenals and peroxidation intermediates
    • Rees, M. S., van Kuijik, F. J. G. M., Siakotos, A. N., and Mundy, B. P. (1995) Improved synthesis of various isotope labeled 4-hydroxyalkenals and peroxidation intermediates. Synth. Commun. 25 (20), 3225-3236.
    • (1995) Synth. Commun. , vol.25 , Issue.20 , pp. 3225-3236
    • Rees, M.S.1    Van Kuijik, F.J.G.M.2    Siakotos, A.N.3    Mundy, B.P.4
  • 31
    • 0022186670 scopus 로고    scopus 로고
    • Pierce, Rockford, IL
    • Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., and Klenk, D. C. (1985) Measurements of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85. See also BCA Protein Assay Reagent Instructions, Pierce, Rockford, IL 61105.
    • BCA Protein Assay Reagent Instructions , pp. 61105
  • 32
    • 0023483391 scopus 로고
    • Mechanism of formation and quantitation of imines, pyrroles, and stable nonpyrrole adducts in 2,5-hexanedione-treated protein
    • DeCaprio, A. P., Jackowshi, S. J., and Regan, K. A. (1987) Mechanism of formation and quantitation of imines, pyrroles, and stable nonpyrrole adducts in 2,5-hexanedione-treated protein. Mol. Pharmacol. 32, 542-548.
    • (1987) Mol. Pharmacol. , vol.32 , pp. 542-548
    • Decaprio, A.P.1    Jackowshi, S.J.2    Regan, K.A.3
  • 35
    • 0027972543 scopus 로고
    • The mechanism of nucleophilic substitution of alkyl pyrroles in the presence of oxygen
    • Amarnath, V., Valentine, W. M., Amarnath, K., Eng, M. A., and Grahm, D. G. (1994) The mechanism of nucleophilic substitution of alkyl pyrroles in the presence of oxygen. Chem. Res. Toxicol. 7, 56-61.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 56-61
    • Amarnath, V.1    Valentine, W.M.2    Amarnath, K.3    Eng, M.A.4    Grahm, D.G.5
  • 37
    • 0030976980 scopus 로고    scopus 로고
    • Inactivation of cathepsin B by oxidized LDL involves complex formation induced by binding of putative reactive sites exposed at low pH to thiols on the enzyme
    • O'Neil, J., Hoppe, G., Sayre, L. M., and Hoff, H. F. (1997) Inactivation of cathepsin B by oxidized LDL involves complex formation induced by binding of putative reactive sites exposed at low pH to thiols on the enzyme. Free Radical Biol. Med. 23, 215-225.
    • (1997) Free Radical Biol. Med. , vol.23 , pp. 215-225
    • O'Neil, J.1    Hoppe, G.2    Sayre, L.M.3    Hoff, H.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.