The immunological and chemical detection of N-(hexanoyl)phosphatidylethanolamine and N-(hexanoyl)phosphatidylserine in an oxidative model induced by carbon tetrachloride

Biochemical and Biophysical Research Communications

Volumn 393, Issue 4, 2010, Pages 631-636

  Hisaka, Shinsuke ^a   Yamada, Naomi ^a   Naito, Kentaro ^a   Osawa, Toshihiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Amide type adduct; Aminophospholipid; Lipid peroxidation; Monoclonal antibody; Oxidative modification

Indexed keywords

2 (HEXANOYL)PHOSPHATIDYLSERINE; CARBON TETRACHLORIDE; GLYCEROPHOSPHOLIPID; MONOCLONAL ANTIBODY; N (HEXANOYL)PHOSPHATIDYLETHANOLAMINE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIGEN RECOGNITION; ARTICLE; CONTROLLED STUDY; ERYTHROCYTE GHOST; ERYTHROCYTE MEMBRANE; EXPERIMENTAL MODEL; LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT; TANDEM MASS SPECTROMETRY;

ANIMALS; ANTIBODIES, MONOCLONAL; CARBON TETRACHLORIDE; ERYTHROCYTE MEMBRANE; FLUORESCENT ANTIBODY TECHNIQUE; LIPID PEROXIDATION; MALE; MODELS, ANIMAL; OXIDATIVE STRESS; PHOSPHATIDYLETHANOLAMINES; PHOSPHATIDYLSERINES; RATS; RATS, WISTAR; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

RATTUS;

EID: 77949491800     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2010.02.043     Document Type: Article

References (27)

1. Stadtman E.R. Protein oxidation and aging. Science 257 (1992) 1220-1224
2. Marnett L.J., Riggins J.N., and West J.D. Endogenous generation of reactive oxidants and electrophiles and their reactions with DNA and protein. J. Clin. Invest. 111 (2003) 583-593
3. ε-(hexanonyl)lysine in protein exposed to lipid hydroperoxide A plausible marker for lipid hydroperoxide-derived protein modification. J. Biol. Chem. 274 (1999) 20406-20414
4. Kawai Y., Kato Y., Nakae D., Kusuoka O., Konishi Y., Uchida K., and Osawa T. Immunohistochemical detection of a substituted 1, N(2)-ethenodeoxyguanosine adduct by ω-6 polyunsaturated fatty acid hydroperoxides in the liver of rats fed a choline-deficient, L-amino acid-defined diet. Carcinogenesis 23 (2002) 485-489
5. ε-(hexanoyl)ethanolamine, a novel phosphatidylethanolamine adduct, during the oxidation of erythrocyte membrane and low-density lipoprotein. Biochem. Biophys. Res. Commun. 306 (2003) 706-711
6. Esterbauer H., Schaur R.J., and Zollner H. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free. Radic. Biol. Med. 11 (1991) 81-128
7. Szweda L.I., Uchida K., Tsai L., and Stadtman E.R. Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. Selective modification of an active-site lysine. J. Biol. Chem. 268 (1993) 3342-3347
8. Requena J.R., Fu M.X., Ahmed M.U., Jenkins A.J., Lyons T.J., Baynes J.W., and Thorpe S.R. Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein. Biochem. J. 322 (1997) 317-325
9. Uchida K., Kanematsu M., Morimitsu Y., Osawa T., Noguchi N., and Niki E. Acrolein is a product of lipid peroxidation reaction. Formation of free acrolein and its conjugate with lysine residues in oxidized low-density lipoproteins. J. Biol. Chem. 273 (1998) 16058-16066
10. Kawai Y., Kato Y., Fujii H., Makino Y., Mori Y., Naito M., and Osawa T. Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modified protein. J. Lipid Res. 44 (2003) 1124-1131
11. ε-(hexanoyl)lysine in human urine by liquid chromatography/tandem mass spectrometry. Free Radic. Biol. Med. 37 (2004) 1864-1874
12. Hisaka S., Kato Y., Kitamoto N., Yoshida A., Kubushiro Y., Naito M., and Osawa T. Chemical and immunochemical identification of propanoyllysine derived from oxidized n-3 polyunsaturated fatty acid. Free Radic. Biol. Med. 46 (2009) 1463-1471
13. Guichardant M., Taibi-Tronche P., Fay L.B., and Lagarde M. Covalent modifications of aminophospholipids by 4-hydroxynonenal. Free Radic. Biol. Med. 25 (1998) 1049-1056
14. Requena J.R., Ahmed M.U., Fountain C.W., Degenhardt T.P., Reddy S., Perez C., Lyons T.J., Jenkins A.J., Baynes J.W., and Thorpe S.R. Carboxymethylethanolamine, a biomarker of phospholipid modification during the Maillard reaction in vivo. J. Biol. Chem. 272 (1997) 17473-17479
15. Breitling-Utzmann C.M., Unger A., Friedl D.A., and Lederer M.O. Identification and quantification of phosphatidylethanolamine derived glucosylamines and aminoketoses from human erythrocytes-influence of glycation products on lipid peroxidation. Arch. Biochem. Biophys. 391 (2001) 245-254
16. Jain S.K. Evidence for membrane lipid peroxidation during the in vivo aging of human erythrocytes. Biochim. Biophys. Acta 937 (1988) 205-210
17. ε-(hexanoyl)lysine: application to the evaluation of protective effects of flavonoid supplementation against exercise-induced oxidative stress in rat skeletal muscle. Biochem. Biophys. Res. Commun. 274 (2000) 389-393
18. Petersen G., Chapman K.D., and Hansen H.S. A rapid phospholipase D assay using zirconium precipitation of anionic substrate phospholipids: application to N-acylethanolamine formation in vitro. J. Lipid Res. 41 (2000) 1532-1538
19. Dodge J.T., Mitchell C., and Hanahan D.J. The preparation and chemical characteristics of hemoglobin-free ghosts of human erythrocytes. Arch. Biochem. Biophys. 100 (1963) 119-130
20. Tiano L., Ballarini P., Santoni G., Wozniak M., and Falcioni G. Morphological and functional changes of mitochondria from density separated trout erythrocytes. Biochim. Biophys. Acta 1457 (2000) 118-128
21. ε-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. J. Lipid Res. 47 (2006) 1386-1398
22. Linderkamp O., Frienderichs E., Boehler T., and Ludwig A. Age dependency of red blood cell deformability and density: studies in transient erythroblastopenia of childhood. Br. J. Haematol. 83 (1993) 125-129
23. Bratosin D., Mazurier J., Tissier J.P., Estaquier J., Huart J.J., Ameisen J.C., Aminoff D., and Montreuil J. Cellular and molecular mechanisms of senescent erythrocyte phagocytosis by macrophages. Biochimie 80 (1998) 173-195
24. Noguchi T., Fong K.L., Lai E.K., Alexander S.S., King M.M., Olson L., Poyer J.L., and McCay P.B. Specificity of a phenobarbital-induced cytochrome P-450 for metabolism of carbon tetrachloride to the trichloromethyl radical. Biochem. Pharmacol. 31 (1982) 615-624
25. 2 -isoprostanes) in carbon tetrachloride hepatotoxicity. J. Clin. Invest. 90 (1992) 2502-2507
26. Podrez E.A., Poliakov E., Shen Z., Zhang R., Deng Y., Sun M., Finton P.J., Shan L., Gugiu B., Fox P.L., Hoff H.F., Salomon R.G., and Hazen S.L. Identification of a novel family of oxidized phospholipids that serve as ligands for the macrophage scavenger receptor CD36. J. Biol. Chem. 277 (2002) 38503-38516
27. Chaurio R.A., Janko C., Muñoz L.E., Frey B., Herrmann M., and Gaipl U.S. Phospholipids: key players in apoptosis and immune regulation. Molecules 30 (2009) 4892-4914