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Volumn 11, Issue 4, 1998, Pages 317-328

Reactions of 4-hydroxy-2(E)-nonenal and related aldehydes with proteins studied by carbon-13 nuclear magnetic resonance spectroscopy

Author keywords

[No Author keywords available]

Indexed keywords

2 HEXENAL; 4 HYDROXYNONENAL; 4 OXOPENTANAL; BOVINE SERUM ALBUMIN; UNCLASSIFIED DRUG;

EID: 0031924992     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970176n     Document Type: Article
Times cited : (53)

References (40)
  • 1
    • 0026795635 scopus 로고
    • Protein oxidation and aging
    • Stadtman, E. R. (1992) Protein oxidation and aging. Science 257, 1220-1224.
    • (1992) Science , vol.257 , pp. 1220-1224
    • Stadtman, E.R.1
  • 2
    • 0028359702 scopus 로고
    • Inhibition of glycolytic enzymes by endogenous aldehydes: A possible relation to diabetic neuropathies
    • Novotny, M., Yancey, M. F., Stuart, R., Wiesler, D., and Peterson, R. G. (1994) Inhibition of glycolytic enzymes by endogenous aldehydes: a possible relation to diabetic neuropathies. Biochim. Biophys. Acta 1226, 145-150.
    • (1994) Biochim. Biophys. Acta , vol.1226 , pp. 145-150
    • Novotny, M.1    Yancey, M.F.2    Stuart, R.3    Wiesler, D.4    Peterson, R.G.5
  • 3
    • 0026602073 scopus 로고
    • Oxidation of low density lipoprotein leads to particle aggregation and altered macrophage recognition
    • Hoff, H. F., Whitaker, T. E., and O'Neil, J. (1992) Oxidation of low density lipoprotein leads to particle aggregation and altered macrophage recognition. J. Biol. Chem. 267, 602-609.
    • (1992) J. Biol. Chem. , vol.267 , pp. 602-609
    • Hoff, H.F.1    Whitaker, T.E.2    O'Neil, J.3
  • 4
    • 0031028437 scopus 로고    scopus 로고
    • Immunochemical detection of 4-hydroxy-2-nonenal adducts in Alzheimer's disease is associated with inheritance of APOE4
    • Montine, K. S., Olson, S. J., Amarnath, V., Whetsell, W. O., Graham, D. G., and Montine, T. J. (1997) Immunochemical detection of 4-hydroxy-2-nonenal adducts in Alzheimer's disease is associated with inheritance of APOE4. Am. J. Pathol. 150, 437-443.
    • (1997) Am. J. Pathol. , vol.150 , pp. 437-443
    • Montine, K.S.1    Olson, S.J.2    Amarnath, V.3    Whetsell, W.O.4    Graham, D.G.5    Montine, T.J.6
  • 5
    • 0025814980 scopus 로고
    • Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde, and related aldehydes
    • Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde, and related aldehydes. Free Radical Biol. Med. 11, 81-128.
    • (1991) Free Radical Biol. Med. , vol.11 , pp. 81-128
    • Esterbauer, H.1    Schaur, R.J.2    Zollner, H.3
  • 6
    • 0027535124 scopus 로고
    • Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal
    • Szweda, L. I., Uchida, K., Tsai, L., and Stadtman, E. R. (1993) Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. J. Biol. Chem. 268, 3342-3347.
    • (1993) J. Biol. Chem. , vol.268 , pp. 3342-3347
    • Szweda, L.I.1    Uchida, K.2    Tsai, L.3    Stadtman, E.R.4
  • 7
    • 0030040310 scopus 로고    scopus 로고
    • E-4-Hydroxy-2-nonenal is cytotoxic and cross-links cytoskeletal proteins in P19 neuroglial cultures
    • Montine, T. J., Amarnath, V., Martin, M. E., Strittmatter, W. J., and Graham, D. G. (1996).E-4-Hydroxy-2-nonenal is cytotoxic and cross-links cytoskeletal proteins in P19 neuroglial cultures. Am. J. Pathol. 148, 89-93.
    • (1996) Am. J. Pathol. , vol.148 , pp. 89-93
    • Montine, T.J.1    Amarnath, V.2    Martin, M.E.3    Strittmatter, W.J.4    Graham, D.G.5
  • 8
    • 0002460909 scopus 로고
    • Mechanisms of cell injury
    • Craighead, J. E., Ed., Mosby, St. Louis, MO
    • Farber, J. L. (1995) Mechanisms of cell injury. In Pathology of Environmental and Occupational Disease (Craighead, J. E., Ed.) pp 287-302, Mosby, St. Louis, MO.
    • (1995) Pathology of Environmental and Occupational Disease , pp. 287-302
    • Farber, J.L.1
  • 9
    • 0031010333 scopus 로고    scopus 로고
    • Reactive oxygen-mediated protein oxidation in aging and disease
    • Stadtman, E. R., and Berlett, B. S. (1997) Reactive oxygen-mediated protein oxidation in aging and disease. Chem. Res. Toxicol. 10, 485-494.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 485-494
    • Stadtman, E.R.1    Berlett, B.S.2
  • 10
  • 11
    • 0027480753 scopus 로고
    • Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase
    • Uchida, K., and Stadtman, E. R. (1993) Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. J. Biol. Chem. 268, 6388-6393.
    • (1993) J. Biol. Chem. , vol.268 , pp. 6388-6393
    • Uchida, K.1    Stadtman, E.R.2
  • 12
    • 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., Subbana-goundar, 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    Subbana-goundar, G.6    Salomon, R.G.7
  • 13
    • 0028897831 scopus 로고
    • Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal
    • Nadkarni, D. V., and Sayre, L. M. (1995) Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem. Res. Toxicol. 8, 284-291.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 284-291
    • Nadkarni, D.V.1    Sayre, L.M.2
  • 14
    • 0028997880 scopus 로고
    • Direct characterization of the lipid peroxidation product 4-hydroxy-2-nonenenal using electrospray mass spectrometry
    • Bruenner, B. A., Jones, A. D., and German, J. B. (1995) Direct characterization of the lipid peroxidation product 4-hydroxy-2-nonenenal using electrospray mass spectrometry. Chem. Res. Toxicol. 8, 552-559.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 552-559
    • Bruenner, B.A.1    Jones, A.D.2    German, J.B.3
  • 15
    • 0028930878 scopus 로고
    • Characterization of protein adducts produced by N-methyldithiocarbamate and AT-methyldithiocarbamate esters
    • Valentine, W. M., Amarnath, V., Amarnath, K., and Graham, D. G. (1995) Characterization of protein adducts produced by N-methyldithiocarbamate and AT-methyldithiocarbamate esters. Chem. Res. Toxicol. 8, 254-261.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 254-261
    • Valentine, W.M.1    Amarnath, V.2    Amarnath, K.3    Graham, D.G.4
  • 17
    • 0028141716 scopus 로고
    • Formation and structure of cross-linking and monomeric pyrrole autoxidation products in 2,5-hexanedione-treated amino acids, peptides, and proteins
    • Zhu, M., Spink, D. C., Yan, B., Bank, S., and DeCaprio, A. P. (1994) Formation and structure of cross-linking and monomeric pyrrole autoxidation products in 2,5-hexanedione-treated amino acids, peptides, and proteins. Chem. Res. Toxicol. 7, 551-558.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 551-558
    • Zhu, M.1    Spink, D.C.2    Yan, B.3    Bank, S.4    DeCaprio, A.P.5
  • 18
    • 0029003573 scopus 로고
    • Determination of aldehydic lipid peroxidation products with dabsylhydrazine by high-performance liquid chromatography
    • Wu, H. Y., and Lin, J. K. (1995) Determination of aldehydic lipid peroxidation products with dabsylhydrazine by high-performance liquid chromatography. Anal. Chem. 67, 1603-1612.
    • (1995) Anal. Chem. , vol.67 , pp. 1603-1612
    • Wu, H.Y.1    Lin, J.K.2
  • 20
    • 37049070565 scopus 로고
    • Synthesis and chemistry of azolenines. Part 16. Preparation of 3H- And 2H-Pyrroles from 2,2-disubstituted 1,4-diketones via the Paal-Knorr reaction, and isolation of intermediate 2-hydroxy-3,3-dihydro-2H-pyrroles
    • Lui, K. H., and Sammes, M. P. (1990) Synthesis and chemistry of azolenines. Part 16. Preparation of 3H- and 2H-Pyrroles from 2,2-disubstituted 1,4-diketones via the Paal-Knorr reaction, and isolation of intermediate 2-hydroxy-3,3-dihydro-2H-pyrroles. J. Chem. Soc., Perkin Trans. I 457-468.
    • (1990) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 457-468
    • Lui, K.H.1    Sammes, M.P.2
  • 21
    • 0002042838 scopus 로고
    • Facile and inexpensive synthesis of 4-oxoalkanoic acids from primary nitroalkanes and acrolein
    • Ballini, R., and Petrini, M. (1986) Facile and inexpensive synthesis of 4-oxoalkanoic acids from primary nitroalkanes and acrolein. Synthesis 1024-1026.
    • (1986) Synthesis , pp. 1024-1026
    • Ballini, R.1    Petrini, M.2
  • 22
    • 37049096818 scopus 로고
    • The synthesis and ring-contraction of halogenated hydroxyquinones; a new synthesis of cryptosporiopsin
    • Henderson, G. B., and Hill, R. A. (1983) The synthesis and ring-contraction of halogenated hydroxyquinones; a new synthesis of cryptosporiopsin. J. Chem. Soc., Perkin Trans. I 2595-2599.
    • (1983) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2595-2599
    • Henderson, G.B.1    Hill, R.A.2
  • 23
    • 0020425779 scopus 로고
    • Synthesis of carbon-13 labeled 5-(diethylphosphono)-2-pentanone ethylene ketal. A reagent for synthesis of multi C-13 labeled steroids
    • DeGraw, J. I., Christie, P. H., and Cairns, T. (1982) Synthesis of carbon-13 labeled 5-(diethylphosphono)-2-pentanone ethylene ketal. A reagent for synthesis of multi C-13 labeled steroids. J. Labelled Compd. Radiopharm. 19, 945-952.
    • (1982) J. Labelled Compd. Radiopharm. , vol.19 , pp. 945-952
    • DeGraw, J.I.1    Christie, P.H.2    Cairns, T.3
  • 24
    • 0026648682 scopus 로고
    • A facile synthesis of 4-hydroxy-2(E)-nonenal
    • Gardner, H. W., Bartelt, R. J., and Weisleder, D. (1992) A facile synthesis of 4-hydroxy-2(E)-nonenal. Lipids 27, 686-689.
    • (1992) Lipids , vol.27 , pp. 686-689
    • Gardner, H.W.1    Bartelt, R.J.2    Weisleder, D.3
  • 26
    • 2642617032 scopus 로고
    • Synthesis of (±)-dictyoprolene through (Z)-3-nonenol, a pheromonal component of Anastrepha ludens
    • Vig, O. P., Kad, G. L., Sabharwal, A., Sharma, S., and Dogra, V. (1989) Synthesis of (±)-dictyoprolene through (Z)-3-nonenol, a pheromonal component of Anastrepha ludens. J. Indian Chem. Soc, 66, 28-29.
    • (1989) J. Indian Chem. Soc , vol.66 , pp. 28-29
    • Vig, O.P.1    Kad, G.L.2    Sabharwal, A.3    Sharma, S.4    Dogra, V.5
  • 27
    • 0009012849 scopus 로고
    • Modification of histidine residues in bovine serum albumin by reaction with (E)-2-octenal
    • Alaiz, M., and Giron, J. (1994) Modification of histidine residues in bovine serum albumin by reaction with (E)-2-octenal. J. Agric. Food Chem. 42, 2094-2098.
    • (1994) J. Agric. Food Chem. , vol.42 , pp. 2094-2098
    • Alaiz, M.1    Giron, J.2
  • 28
    • 0017710580 scopus 로고
    • Antiproteolytic aldehydes and ketones: Substituent and secondary deuterium isotope effects on equilibrium addition of water and other nucleophiles
    • Lewis, C. A., and Wolfenden, R. (1977) Antiproteolytic aldehydes and ketones: substituent and secondary deuterium isotope effects on equilibrium addition of water and other nucleophiles. Biochemistry 16, 4886-4890.
    • (1977) Biochemistry , vol.16 , pp. 4886-4890
    • Lewis, C.A.1    Wolfenden, R.2
  • 30
    • 0029078659 scopus 로고
    • Changes induced in bovine serum albumin following interaction with the lipid peroxidation product (E)-2-octenal
    • Alaiz, M., and Barragan, S. (1995) Changes induced in bovine serum albumin following interaction with the lipid peroxidation product (E)-2-octenal. Chem. Phys. Lipids 77, 217-223.
    • (1995) Chem. Phys. Lipids , vol.77 , pp. 217-223
    • Alaiz, M.1    Barragan, S.2
  • 31
    • 0000894635 scopus 로고
    • An H-1, C-13, and N-15 NMR study of the Paal-Knorr condensation of acetonylacetone with primary amines
    • Katritzky, A. R., Yousaf, T. I., and Chen, B. C. (1986) An H-1, C-13, and N-15 NMR study of the Paal-Knorr condensation of acetonylacetone with primary amines. Tetrahedron 42, 623-628.
    • (1986) Tetrahedron , vol.42 , pp. 623-628
    • Katritzky, A.R.1    Yousaf, T.I.2    Chen, B.C.3
  • 35
    • 0027972543 scopus 로고
    • The mechanism of nucleophilic substitution of alkylpyrroles in the presence of oxygen
    • Amarnath, V., Valentine, W. M., Amarnath, K., Eng, M. A., and Graham, D. G. (1994) The mechanism of nucleophilic substitution of alkylpyrroles 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    Graham, D.G.5
  • 36
    • 0030181297 scopus 로고    scopus 로고
    • Determination of the site of 4-hydroxy-2-nonenal adduction to protein by electrospray tandem mass spectrometry
    • Bolgar, M. S., and Gaskell, S. J. (1996) Determination of the site of 4-hydroxy-2-nonenal adduction to protein by electrospray tandem mass spectrometry. Anal. Chem. 68, 2325-2330.
    • (1996) Anal. Chem. , vol.68 , pp. 2325-2330
    • Bolgar, M.S.1    Gaskell, S.J.2
  • 38
    • 0030989545 scopus 로고    scopus 로고
    • 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease
    • Sayre, L. M., Zelasko, D. A., Harris, P. L. R., Parry, G., Salomon, R. G., and Smith, M. A. (1997) 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease. J. Neurochem. 68, 2092-2097.
    • (1997) J. Neurochem. , vol.68 , pp. 2092-2097
    • Sayre, L.M.1    Zelasko, D.A.2    Harris, P.L.R.3    Parry, G.4    Salomon, R.G.5    Smith, M.A.6
  • 39
    • 0029986692 scopus 로고    scopus 로고
    • Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: Immunochemical detection in mitochondria exposed to oxidative stress
    • Cohn, J. A., Tsai, L., Friguet, B., and Szweda, L. I. (1996) Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: Immunochemical detection in mitochondria exposed to oxidative stress. Arch. Biochem. Biophys. 328, 158-164.
    • (1996) Arch. Biochem. Biophys. , vol.328 , pp. 158-164
    • Cohn, J.A.1    Tsai, L.2    Friguet, B.3    Szweda, L.I.4
  • 40
    • 0342415324 scopus 로고
    • NMR Spectra
    • Rappoport, Z., Ed., John Wiley, Chichester, U.K.
    • Chiara, J. L., and Gomez-Sanchez. (1994) NMR Spectra. In Enamines (Rappoport, Z., Ed.) pp 280-293, John Wiley, Chichester, U.K.
    • (1994) Enamines , pp. 280-293
    • Chiara, J.L.1    Gomez-Sanchez2


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