REFERENCES
- Alderton A. L., Faustman C., Liebler D. C., Hill D. W. Induction of redox instability of bovine myoglobin by adduction with 4-hydroxy-2-nonenal. Biochemistry 2003; 42: 4398–4405, [INFOTRIEVE], [CSA]
- Aldini G., Dalle-Donne I., Vistoli G., Maffei Facino R., Carini M. Covalent modification of actin by 4-hydroxy-trans-2-nonenal (HNE): LC-ESI-MS/MS evidence for Cys374 Michael adduction. J. Mass Spectrom. 2005; 40: 946–954, [INFOTRIEVE], [CSA], [CROSSREF]
- Baker A., Zidek L., Wiesler D., Chmelik J., Pagel M., Novotny M. V. Reaction of N-acetylglycyllysine methyl ester with 2-alkenals: an alternative model for covalent modification of proteins. Chem. Res. Toxicol. 1998; 11: 730–740, [INFOTRIEVE], [CSA], [CROSSREF]
- Bolgar M. S., Gaskell S. J. Tandem mass spectrometric characterization of modified peptides and proteins. Biochem. Soc. Trans. 1995; 23: 907–910, [INFOTRIEVE], [CSA]
- Bolgar M. S., Yang C. Y., Gaskell S. J. First direct evidence for lipid/protein conjugation in oxidized human low density lipoprotein. J. Biol. Chem. 1996; 271: 27999–28001, [INFOTRIEVE], [CSA], [CROSSREF]
- Bruenner B. A., Jones A. D., German J. B. Direct characterization of protein adducts of the lipid peroxidation product 4-hydroxy-2-nonenal using electrospray mass spectrometry. Chem. Res. Toxicol. 1995; 8: 552–559, [INFOTRIEVE], [CSA], [CROSSREF]
- Burcham P. C., Kuhan Y. T. Introduction of carbonyl groups into proteins by the lipid peroxidation product, malondialdehyde. Biochem. Biophys. Res. Commun. 1996; 220: 996–1001, [INFOTRIEVE], [CSA], [CROSSREF]
- Calingasan N. Y., Uchida K., Gibson G. E. Protein-bound acrolein: a novel marker of oxidative stress in Alzheimer's disease. J. Neurochem. 1999; 72: 751–756, [INFOTRIEVE], [CSA], [CROSSREF]
- Carini M., Aldini G., Facino R. M. Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins. Mass Spectrom. Rev. 2004; 23: 281–305, [INFOTRIEVE], [CSA], [CROSSREF]
- Chio K. S., Tappel A. L. Synthesis and characterization of the fluorescent products derived from malonaldehyde and amino acids. Biochemistry 1969; 8: 2821–2826, [INFOTRIEVE], [CSA], [CROSSREF]
- Cohn J. A., Tsai L., Friguet B., Szweda L. I. Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: immunochemical detection in mitochondria exposed to oxidative stress. Arch. Biochem. Biophys. 1996; 328: 158–164, [INFOTRIEVE], [CSA], [CROSSREF]
- Deng Y., Salomon R. G. Total synthesis of oxidized phospholipids. 3. The (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine. J. Org. Chem. 2000; 65: 6660–6665, [INFOTRIEVE], [CSA], [CROSSREF]
- Doorn J. A., Petersen D. R. Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal. Chem. Res. Toxicol. 2002; 15: 1445–1450, [INFOTRIEVE], [CSA], [CROSSREF]
- Esterbauer H., Ertl A., Scholz N. The reaction of cysteine with α,β-unsaturated aldehydes. Tetrahedron 1976; 32: 285–289, [CSA], [CROSSREF]
- Esterbauer H., Schaur R. J., Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde and related aldehydes. Free Radical Biol. Med. 1991; 11: 81–128, [CSA], [CROSSREF]
- Fenaille F., Guy P. A., Tabet J. C. Study of protein modification by 4-hydroxy-2-nonenal and other short chain aldehydes analyzed by electrospray ionization tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2003; 14: 215–226, [INFOTRIEVE], [CSA], [CROSSREF]
- Friguet B., Stadtman E. R., Szweda L. I. Modification of glucose-6-phosphate dehydrogenase by 4-hydroxynonenal. J. Biol. Chem. 1994; 269: 21639–21643, [INFOTRIEVE], [CSA]
- Frye E. B., Degenhardt T. P., Thorpe S. R., Baynes J. W. Role of the Maillard reaction in aging of tissue proteins. Advanced glycation end product-dependent increase in imidazolium cross-links in human lens proteins. J. Biol. Chem. 1998; 273: 18714–18719, [INFOTRIEVE], [CSA], [CROSSREF]
- Furuhata A., Ishii T., Kumazawa S., Yamada T., Nakayama T., Uchida K. Nϵ-(3-methylpyridinium)lysine, a major antigenic adduct generated in acrolein-modified protein. J. Biol. Chem. 2003; 278: 48658–48665, [INFOTRIEVE], [CSA], [CROSSREF]
- Goodfriend T. L., Ball D. L., Egan B. M., Campbell W. B., Nithipatikom K. Epoxy-keto derivative of linoleic acid stimulates aldosterone secretion. Hypertension 2004; 43: 358–363, [INFOTRIEVE], [CSA], [CROSSREF]
- Hashimoto M., Sibata T., Wasada H., Toyokuni S., Uchida K. Structural basis of protein-bound endogenous aldehydes. Chemical and immunochemical characterizations of configurational isomers of a 4-hydroxy-2-nonenal-histidine adduct. J. Biol. Chem. 2003; 278: 5044–5051, [INFOTRIEVE], [CSA], [CROSSREF]
- Isom A. L., Barnes S., Wilson L., Kirk M., Coward L., Darley-Usmar V. Modification of cytochrome c by 4-hydroxy- 2-nonenal: evidence for histidine, lysine, and arginine-aldehyde adducts. J. Am. Soc. Mass. Spectrom. 2004; 15: 1136–1147, [INFOTRIEVE], [CSA], [CROSSREF]
- Itakura K., Furuhata A., Shibata N., Kobayashi M., Uchida K. Maillard reaction-like lysine modification by a lipid peroxidation product: immunochemical detection of protein-bound 2-hydroxyheptanal in vivo. Biochem. Biophys. Res. Commun. 2003; 308: 452–457, [INFOTRIEVE], [CSA], [CROSSREF]
- Itakura K., Osawa T., Uchida K. Structure of a fluorescent compound formed from 4-hydroxy-2-nonenal and Nα-hippuryllysine: A model for fluorophores derived from protein modification by lipid peroxidation. J. Org. Chem. 1998; 63: 185–187, [INFOTRIEVE], [CSA], [CROSSREF]
- Itakura K., Uchida K. Evidence that malondialdehyde-derived aminoenimine is not a fluorescent age pigment. Chem. Res. Toxicol. 2001; 14: 473–475, [INFOTRIEVE], [CSA], [CROSSREF]
- Itakura K., Uchida K., Osawa T. A novel fluorescent malondialdehyde-lysine adduct. Chem. Phys. Lipids 1996; 84: 75–79, [CSA], [CROSSREF]
- Kamido H., Kuksis A., Marai L., Myher J. J. Lipid ester-bound aldehydes among copper-catalyzed peroxidation products of human plasma lipoproteins. J. Lipid Res. 1995; 36: 1876–1886, [INFOTRIEVE], [CSA]
- Kikugawa K., Beppu M. Involvement of lipid oxidation products in the formation of fluorescent and cross-linked proteins. Chem. Phys. Lipids 1987; 44: 277–296, [INFOTRIEVE], [CSA], [CROSSREF]
- Kurtz A. J., Lloyd R. S. 1,N2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage. J. Biol. Chem. 2003; 278: 5970–5976, [INFOTRIEVE], [CSA], [CROSSREF]
- Lee S. H., Blair I. A. Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chem. Res. Toxicol. 2000; 13: 698–702, [INFOTRIEVE], [CSA], [CROSSREF]
- Lee S. H., Oe T., Blair I. A. Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins. Science 2001; 292: 2083–2086, [INFOTRIEVE], [CSA], [CROSSREF]
- Levine R. L., Williams J. A., Stadtman E. R., Schacter E. Carbonyl assays for determination of oxidatively modified proteins. Methods Enzymol. 1994; 233: 346–357, [INFOTRIEVE], [CSA]
- Lin D., Lee H.-G., Liu Q., Perry G., Smith M. A., Sayre L. M. 4-Oxo-2-nonenal is both more neurotoxic and more protein reactive than 4-hydroxy-2-nonenal. Chem Res Toxicol 2005; 18: 1219–1231, [INFOTRIEVE], [CSA], [CROSSREF]
- Liu Z., Minkler P. E., Sayre L. M. Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal. Chem. Res. Toxicol. 2003; 16: 901–911, [INFOTRIEVE], [CSA]
- Liu Z., Sayre L. M. Model studies on the modification of proteins by lipoxidation-derived 2-hydroxyaldehydes. Chem. Res. Toxicol. 2003; 16: 232–241, [INFOTRIEVE], [CSA], [CROSSREF]
- Monnier V. M., Mustata G. T., Biemel K. L., Reihl O., Lederer M. O., Zhenyu D., Sell D. R. Cross-linking of the extracellular matrix by the maillard reaction in aging and diabetes: an update on “a puzzle nearing resolution”. Ann. N. Y. Acad. Sci. 2005; 1043: 533–544, [INFOTRIEVE], [CSA], [CROSSREF]
- Montine T. J., Amarnath V., Martin M. E., Strittmatter W. J., Graham D. G. E-4-Hydroxy-2-nonenal is cytotoxic and crosslinks cytoskeletal proteins in P19 neuroglial cultures. Am. J. Pathol. 1996a; 148: 89–93, [INFOTRIEVE], [CSA]
- Montine T. J., Huang D. Y., Valentine W. M., Amarnath V., Saunders A., Weisgraber K. H., Graham D. G., Strittmatter W. J. Crosslinking of apolipoprotein E by products of lipid peroxidation. J. Neuropathol. Exp. Neurol. 1996b; 55: 202–210, [INFOTRIEVE], [CSA]
- Musatov A., Hebert E., Carroll C. A., Weintraub S. T., Robinson N. C. Specific modification of two tryptophans within the nuclear-encoded subunits of bovine cytochrome c oxidase by hydrogen peroxide. Biochemistry 2002; 43: 1003–1009, [CSA]
- Nadkarni D. V., Sayre L. M. Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem. Res. Toxicol. 1995; 8: 284–291, [INFOTRIEVE], [CSA], [CROSSREF]
- Nair V., Offerman R. J., Turner G. A., Pryor A. N., Baenziger N. C. Fluorescent 1,4-dihydropyridines: the malondialdehyde connection. Tetrahedron 1988; 44: 2793–2803, [CSA]
- Oe T., Arora J. S., Lee S. H., Blair I. A. A novel lipid hydroperoxide-derived cyclic covalent modification to histone H4. J. Biol. Chem. 2003a; 278: 42098–42105, [INFOTRIEVE], [CSA], [CROSSREF]
- Oe T., Lee S. H., Silva Elipe M. V., Arison B. H., Blair I. A. A novel lipid hydroperoxide-derived modification to arginine. Chem. Res. Toxicol. 2003b; 16: 1598–1605, [INFOTRIEVE], [CSA], [CROSSREF]
- Orioli M., Aldini G., Beretta G., Facino R. M., Carini M. LC-ESI-MS/MS determination of 4-hydroxy-trans-2-nonenal Michael adducts with cysteine and histidine-containing peptides as early markers of oxidative stress in excitable tissues. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2005; 827: 109–118, [INFOTRIEVE], [CSA]
- Pollack M., Oe T., Lee S. H., Silva Elipe M. V., Arison B. H., Blair I. A. Characterization of 2′-deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product. Chem. Res. Toxicol. 2003; 16: 893–900, [INFOTRIEVE], [CSA]
- Requena J. R., Fu M. X., Ahmed M. U., Jenkins A. J., Lyons T. J., Baynes J. W., Thorpe S. R. Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein. Biochem. J. 1997; 322: 317–325, [INFOTRIEVE], [CSA]
- Salomon R. G., Kaur K., Podrez E., Hoff H. F., Krushinsky A. V., Sayre L. M. HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques. Chem. Res. Toxicol. 2000; 13: 557–564, [INFOTRIEVE], [CSA], [CROSSREF]
- Sayre L. M., Arora P. K., Iyer R. S., Salomon R. G. Pyrrole formation from 4-hydroxynonenal and primary amines. Chem. Res. Toxicol. 1993; 6: 19–22, [INFOTRIEVE], [CSA], [CROSSREF]
- Sayre L. M., Perry G., Smith M. A. In situ methods for detection and localization of markers of oxidative stress: application in neurodegenerative disorders. Methods Enzymol. 1999; 309: 133–152, [INFOTRIEVE], [CSA]
- Sayre L. M., Sha W., Xu G., Kaur K., Nadkarni D., Subbanagounder G., Salomon R. G. Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 1996; 9: 1194–1201, [INFOTRIEVE], [CSA], [CROSSREF]
- Sayre L. M., Smith M. A., Perry G. Chemistry and biochemistry of oxidative stress in neurodegenerative disease. Curr. Med. Chem. 2001; 8: 721–738, [INFOTRIEVE], [CSA]
- Sayre L. M., Zelasko D. A., Harris P. L., Perry G., Salomon R. G., Smith M. A. 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease. J. Neurochem. 1997; 68: 2092–2097, [INFOTRIEVE], [CSA]
- Slatter D. A., Avery N. C., Bailey A. J. Identification of a new cross-link and unique histidine adduct from bovine serum albumin incubated with malondialdehyde. J. Biol. Chem. 2004; 279: 61–69, [INFOTRIEVE], [CSA], [CROSSREF]
- Slatter D. A., Murray M., Bailey A. J. Formation of a dihydropyridine derivative as a potential cross-link derived from malondialdehyde in physiological systems. FEBS Lett. 1998; 421: 180–184, [INFOTRIEVE], [CSA], [CROSSREF]
- Sodum R. S., Chung F. L. 1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 1988; 48: 320–323, [INFOTRIEVE], [CSA]
- Sowell J., Frei B., Stevens J. F. Vitamin C conjugates of genotoxic lipid peroxidation products: Structural characterization and detection in human plasma. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 17964–17969, [INFOTRIEVE], [CSA], [CROSSREF]
- Spiteller P., Kern W., Reiner J., Spiteller G. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim. Biophys. Acta 2001; 1531: 188–208, [INFOTRIEVE], [CSA]
- Tsai L., Szweda P. A., Vinogradova O., Szweda L. I. Structural characterization and immunochemical detection of a fluorophore derived from 4-hydroxy-2-nonenal and lysine. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 7975–7980, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K. Current status of acrolein as a lipid peroxidation product. Trends Cardiovasc. Med. 1999; 9: 109–113, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K. 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress. Prog. Lipid Res. 2003; 42: 318–343, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K., Itakura K., Kawakishi S., Hiai H., Toyokuni S., Stadtman E. R. Characterization of epitopes recognized by 4-hydroxy-2-nonenal specific antibodies. Arch. Biochem. Biophys. 1995; 324: 241–248, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K., Kanematsu M., Sakai K., Matsuda T., Hattori N., Mizuno Y., Suzuki D., Miyata T., Noguchi N., Niki E., Osawa T. Protein-bound acrolein: potential markers for oxidative stress. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 4882–4887, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K., Sakai K., Tiakura K., Osawa T., Toyokuni S. Protein modification by lipid peroxidation products: formation of malondialdehyde-derived Nϵ-(2-propenal)lysine in proteins. Arch. Biochem. Biophys. 1997; 346: 45–52, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K., Stadtman E. R. Modification of histidine residues in proteins by reaction with 4-hydroxynonenal. Proc. Natl. Acad. Sci. U.S.A. 1992; 89: 4544–4548, [INFOTRIEVE], [CSA], [CROSSREF]
- Uchida K., Stadtman E. R. Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. J. Biol. Chem. 1993; 268: 6388–6393, [INFOTRIEVE], [CSA]
- Uchida K., Szweda L. I., Chae H.-Z., Stadtman E. R. Immunochemical detection of 4-hydroxynonenal protein adducts in oxidized hepatocytes. Proc. Natl. Acad. Sci. U.S.A. 1993; 90: 8742–8746, [INFOTRIEVE], [CSA], [CROSSREF]
- Wang H., Kozekov I. D., Harris T. M., Rizzo C. J. Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. J. Am. Chem. Soc. 2003; 125: 5687–5700, [INFOTRIEVE], [CSA], [CROSSREF]
- Wu S., Pérez M. D., Puyol P., Sawyer L. beta-Lactoglobulin binds palmitate within its central cavity. J. Biol. Chem. 1998; 274: 170–174, [CSA], [CROSSREF]
- Xu D., Thiele G. M., Kearley M. L., Haugen M. D., Klassen L. W., Sorrell M. F., Tuma D. J. Epitope characterization of malondialdehyde-acetaldehyde adducts using an enzyme-linked immunosorbent assay. Chem. Res. Toxicol. 1997; 10: 978–986, [INFOTRIEVE], [CSA], [CROSSREF]
- Xu G., Liu Y., Kansal M. M., Sayre L. M. Rapid cross-linking of proteins by 4-ketoaldehydes and 4-hydroxy-2-alkenals does not arise from the lysine-derived monoalkylpyrroles. Chem. Res. Toxicol. 1999a; 12: 855–861, [INFOTRIEVE], [CSA], [CROSSREF]
- Xu G., Liu Y., Sayre L. M. Independent synthesis, solution behavior, and studies on the mechanism of formation of a primary amine-derived fluorophore representing crosslinking of proteins by (E)-4-hydroxy-2-nonenal (HNE). J. Org. Chem. 1999b; 64: 5732–5745, [CSA], [CROSSREF]
- Xu G., Liu Y., Sayre L. M. Polyclonal antibodies to a fluorescent 4-hydroxy-2-nonenal (HNE)-derived lysine-lysine cross-link: characterization and application to HNE-treated protein and in vitro oxidized low-density lipoprotein. Chem. Res. Toxicol. 2000; 13: 406–413, [INFOTRIEVE], [CSA], [CROSSREF]
- Xu G., Sayre L. M. Structural characterization of a 4-hydroxy-2-alkenal-derived fluorophore that contributes to lipoperoxidation-dependent protein crosslinking in aging and degenerative disease. Chem. Res. Toxicol. 1998; 11: 247–251, [INFOTRIEVE], [CSA], [CROSSREF]
- Yan L. -J., Lodge J. K., Traber M. G., Packer L. Apolipoprotein B carbonyl formation is enhanced by lipid peroxidation during copper-mediated oxidation of human low-density lipoprotein. Arch. Biochem. Biophys. 1997; 339: 165–171, [INFOTRIEVE], [CSA], [CROSSREF]
- Yi P., Zhan D., Samokyszyn V. M., Doerge D. R., Fu P. P. Synthesis and 32P-postlabeling/high-performance liquid chromatography separation of diastereomeric 1,N2-(1,3-propano)-2′-deoxyguanosine 3′-phosphate adducts formed from 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 1997; 10: 1259–1265, [INFOTRIEVE], [CSA], [CROSSREF]
- Yuan Q. Modifications of biomolecules by lipoxidation derived aldehydes. Ph.D. Thesis, Case Western Reserve University. 2006
- Zhang W. H., Liu J., Xu G., Yuan Q., Sayre L. M. Model studies on protein side chain modification by 4-oxo-2-nonenal. Chem. Res. Toxicol. 2003; 16: 512–523, [INFOTRIEVE], [CSA], [CROSSREF]