A method for detection of 4-hydroxy-2-nonenal adducts in proteins

Free Radical Biology and Medicine

Volumn 51, Issue 1, 2011, Pages 1-4

  Wakita, Chika ^a   Honda, Kazuya ^a   Shibata, Takahiro ^a   Akagawa, Mitsugu ^b   Uchida, Koji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

4 Hydroxy 2 nonenal; Free radicals; Pyridylamination; Reductive amination

Indexed keywords

4 HYDROXYNONENAL; ALDEHYDE; FLUORESCENT DYE;

AMINATION; ARTICLE; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION;

EID: 79957962280     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2011.02.037     Document Type: Short Survey

References (32)

1. E.R. Stadtman, and R.L. Levine Protein oxidation Ann. N.Y. Acad. Sci. 899 2000 191 208 (Pubitemid 30352787)
2. E. Shacter Quantification and significance of protein oxidation in biological samples Drug Metab. Rev. 32 2000 307 326 (Pubitemid 32001909)
3. K. Uchida Role of reactive aldehyde in cardiovascular diseases Free Radic. Biol. Med. 28 2000 1685 1696 (Pubitemid 30628655)
4. H. Esterbauer, R.J. Schaur, and H. Zollner Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes Free Radic. Biol. Med. 11 1991 81 128 (Pubitemid 121003917)
5. K. Uchida 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress Prog. Lipid Res. 42 2003 318 343 (Pubitemid 36411689)
6. D. Steinberg, S. Parthasarathy, T.E. Carew, J.C. Khoo, and J.L. Witztum Low-density lipoprotein and atherogenesis N. Engl. J. Med. 320 1989 915 924
7. D. Steinberg Role of oxidized LDL and antioxidants in atherosclerosis Adv. Exp. Med. Biol. 369 1995 39 48
8. I. Dalle-Donne, R. Rossi, D. Giustarini, A. Milzani, and R. Colombo Protein carbonyl groups as biomarkers of oxidative stress Clin. Chim. Acta 329 2003 23 38 (Pubitemid 36187411)
9. T. Nyström Role of oxidative carbonylation in protein quality control and senescence EMBO J. 24 2005 1311 1317 (Pubitemid 40593052)
10. R.L. Levine Carbonyl modified proteins in cellular regulation, aging and disease Free Radic. Biol. Med. 32 2002 790 796 (Pubitemid 34439249)
11. E.R. Stadtman Protein oxidation and aging Science 257 1992 1220 1224
12. E.R. Stadtman Protein oxidation in aging and age-related diseases Ann. N.Y. Acad. Sci. 928 2001 22 38 (Pubitemid 32386064)
13. K. Uchida, L.I. Szweda, H.Z. Chae, and E.R. Stadtman Immunochemical detection of 4-hydroxy-2-nonenal modified proteins in oxidized hepatocytes Proc. Natl. Acad. Sci. U. S. A. 90 1993 8742 8746 (Pubitemid 23277746)
14. A. Furuhata, M. Nakamura, T. Osawa, and K. Uchida Thiolation of protein-bound carcinogenic aldehyde: an electrophilic acrolein-lysine adduct that covalently binds to thiols J. Biol. Chem. 277 2002 27919 27926 (Pubitemid 34966739)
15. K. Ichihashi, T. Osawa, S. Toyokuni, and K. Uchida Endogenous formation of protein adducts with carcinogenic aldehydes: implication for oxidative stress J. Biol. Chem. 276 2001 23903 23913
16. S. Yamada, S. Kumazawa, T. Ishii, T. Nakayama, K. Itakura, N. Shibata, M. Kobayashi, K. Sakai, T. Osawa, and K. Uchida Immunochemical detection of a lipofuscin-like fluorophore derived from malondialdehyde and lysine J. Lipid Res. 42 2001 1187 1196 (Pubitemid 32744241)
17. J. Liggins, and A.J. Furth Role of protein-bound carbonyl groups in the formation of advanced glycation endproducts Biochim. Biophys. Acta 1361 1997 123 130 (Pubitemid 27362085)
18. R.L. Levine, J.A. Williams, E.R. Stadtman, and E. Shacter Carbonyl assays for determination of oxidatively modified proteins Methods Enzymol. 233 1994 346 357
19. J. Choi, C.A. Malakowsky, J.M. Talent, C.C. Conrad, and R.W. Gracy Identification of oxidized plasma proteins in Alzheimer's disease Biochem. Biophys. Res. Commun. 293 2002 1566 1570 (Pubitemid 34681057)
20. J. Choi, H.D. Rees, S.T. Weintraub, A.I. Levey, L.S. Chin, and L. Li Oxidative modifications and aggregation of Cu, Zn-superoxide dismutase associated with Alzheimer and Parkinson diseases J. Biol. Chem. 280 2005 11648 11655 (Pubitemid 40418479)
21. D. Mantle, G. Falkous, and D. Walker Quantification of protease activities in synovial fluid from rheumatoid and osteoarthritis cases: comparison with antioxidant and free radical damage markers Clin. Chim. Acta 284 1999 45 58 (Pubitemid 29324864)
22. A.C. Bowling, J.B. Schulz, R.H. Brown Jr., and M.F. Beal Superoxide dismutase activity, oxidative damage, and mitochondrial energy metabolism in familial and sporadic amyotrophic lateral sclerosis J. Neurochem. 61 1993 2322 2325 (Pubitemid 23354097)
23. I. Grattagliano, G. Vendemiale, F. Boscia, T. Micelli-Ferrari, L. Cardia, and E. Altomare Oxidative retinal products and ocular damages in diabetic patients Free Radic. Biol. Med. 25 1998 369 372 (Pubitemid 28326213)
24. S. Hase, T. Ikenaka, and Y. Matsushima Structure analyses of oligosaccharides by tagging of the reducing end sugars with a fluorescent compound Biochem. Biophys. Res. Commun. 85 1978 257 263 (Pubitemid 9073177)
25. L. De Montarby, P. Mosset, and R. Gree Sorbic acid iron tricarbonyl complex as resolving agent: chiral syntheses of 4-hydroxy nonenal and cariolic acid Tetrahedron Lett. 29 1988 3895
26. M. Hashimoto, T. Shibata, H. Wasada, S. Toyokuni, and K. Uchida 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. 278 2003 5044 5051 (Pubitemid 36801014)
27. C. Wakita, T. Maeshima, A. Yamazaki, T. Shibata, S. Ito, M. Akagawa, M. Ojika, J. Yodoi, and K. Uchida Stereochemical configuration of 4-hydroxy-2-nonenal-cysteine adducts and their stereoselective formation in a redox-regulated protein J. Biol. Chem. 284 2009 28810 28822
28. L.M. Sayre, P.K. Arora, R.S. Iyer, and R.G. Salomon Pyrrole formation from 4-hydroxynonenal and primary amines Chem. Res. Toxicol. 6 1993 19 22 (Pubitemid 23040366)
29. D.V. Nadkarni, and L.M. Sayre Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal Chem. Res. Toxicol. 8 1995 284 291
30. K. Itakura, T. Osawa, and K. Uchida Structure of a fluorescent compound formed from 4-hydroxy-2-nonenal and Na-hippuryllysine: a model for fluorophores derived from protein modifications by lipid peroxidation J. Org. Chem. 63 1998 185 187
31. G. Xu, and L.M. Sayre Structural characterization of a 4-hydroxy-2-alkenal-derived fluorophore that contributes to lipoperoxidation- dependent protein cross-linking in aging and degenerative disease Chem. Res. Toxicol. 11 1998 247 251 (Pubitemid 28194347)
32. N. Breusing, T. Grune, L. Andrisic, M. Atalay, G. Bartosz, F. Biasi, S. Borovic, L. Bravo, I. Casals, R. Casillas, A. Dinischiotu, J. Drzewinska, H. Faber, N.M. Fauzi, A. Gajewska, J. Gambini, D. Gradinaru, T. Kokkola, A. Lojek, W. Luczaj, D. Margina, C. Mascia, R. Mateos, A. Meinitzer, M.T. Mitjavila, L. Mrakovcic, M.C. Munteanu, M. Podborska, G. Poli, P. Sicinska, E. Skrzydlewska, J. Vina, I. Wiswedel, N. Zarkovic, S. Zelzer, and C.M. Spickett An inter-laboratory validation of methods of lipid peroxidation measurement in UVA-treated human plasma samples Free Radic. Res. 44 2010 1203 1215