Long-lived 4-oxo-2-enal-derived apparent Lysine Michael adducts are actually the isomeric 4-ketoamides

Chemical Research in Toxicology

Volumn 20, Issue 2, 2007, Pages 165-170

  Zhu, Xiaochun ^a   Sayre, Lawrence M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYNONENAL; 4 KETOAMIDE; 4 OXO 2 NONENAL; ALDEHYDE; AMIDE; LINOLEIC ACID; LYSINE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICHAEL ADDITION; OXIDATION; TANDEM MASS SPECTROMETRY;

ALDEHYDES; AMIDES; ANIMALS; BOROHYDRIDES; CATTLE; LACTOGLOBULINS; LINOLEIC ACID; LYSINE; MOLECULAR STRUCTURE; STEREOISOMERISM; TIME FACTORS;

EID: 33947170583     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx600295j     Document Type: Article

References (26)

1. Uchida, K. (2003) 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress. Prog. Lipid Res. 42, 318-343.
2. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biol. Med. 11, 81-128.
3. Spiteller, P., Kern, W., Reiner, J., and Spiteller, G. (2001) Aldehydic lipid peroxidation products derived from linoleic acid. Biochim. Biophvs. Acta 1531, 188-208.
4. Lee, S. H., and Blair, I. A. (2000) Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chem. Res. Toxicol. 13, 698-702.
5. Xu, G., and Sayre, L. M. (1998) 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. 11, 247-251.
6. Xu, G., Liu, Y., and Sayre, L. M. (1999) 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. 64, 5732-5745.
7. Zhang, W. H., Liu, J., Xu, G., Yuan, Q., and Sayre, L. M. (2003) Model studies on protein side chain modification by 4-oxo-2-nonenal. Chem. Res. Toxicol. 16, 512-523.
8. Oe, T., Arora, J. S., Lee, S. H., and Blair, I. A. (2003) A novel lipid hydroperoxide-derived cyclic covalent modification to histone H4. J. Biol. Chem. 278, 42098-42105.
9. Lin, D., Lee, H. G., Liu, Q., Perry, G., Smith, M. A., and Sayre, L. M. (2005) 4-Oxo-2-nonenal is both more neurotoxic and more protein reactive than 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 18, 1219-1231.
10. Doorn, J. A., and Petersen, D. R. (2002) Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal. Chem. Res. Toxicol. 15, 1445-1450.
11. Doorn, J. A., and Petersen, D. R (2003) Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal. Chem.-Biol. Interact. 143-144, 93-100.
12. Liu, Z., Minkler, P. E., and Sayre, L. M. (2003) Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal. Chem. Res. Toxicol. 16, 901-911.
13. Zhu, X., and Sayre, L. M. (2007) Mass spectrometric evidence for long-lived protein adducts of 4-oxo-2-nonenal. Redox Rep., 12, 45-49.
14. Yuan, Q. (2006) Modification of Biomolecules by Lipoxidation-Derived Aldehydes. Ph.D. Thesis, Case Western Reserve University, Cleveland, OH.
15. 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. (2002) Identification of a novel family of oxidized phospholipids that serve as ligands for the macrophage scavenger receptor CD36. J. Biol. Chem. 277, 38503-38516.
16. Lee, S. H., Silva Elipe, M. V., Arora, J. S., and Blair, I. A (2005) Dioxododecenoic acid: a lipid hydroperoxide-derived bifunctional electrophile responsible for etheno DNA adduct formation. Chem. Res. Toxicol. 18, 566-578.
17. Sowell, J., Frei, B., and Stevensk, J. F. (2004) Vitamin C conjugates of genotoxic lipid peroxidation products: structural characterization and detection in human plasma. Proc. Natl. Acad. Sci. U.S.A. 101, 17964-17969.
18. West, J. D., Ji, C., Duncan, S. T., Amarnath, V., Schneider, C., Rizzo, C. J., Brash, A. R., and Marnett, L. J. (2004) Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation. Chem. Res. Toxicol. 17, 453-462.
19. Jian, W., Arora, J. S., Oc, T., Shuvaev, V. V., and Blair, I. A. (2005) Induction of endothelial cell apoptosis by lipid hydroperoxide-derived bifunctional electrophiles. Free Radical Biol. Med. 39, 1162-1176.
20. Carbone, D. L., Doorn, J. A., Kiebler, Z., Ickes, B. R., and Petersen, D. R. (2005) Modification of heat shock protein 90 by 4-hydroxynonenal in a rat model of chronic alcoholic liver disease. J. Pharmacol. Exp. Ther. 315, 8-15.
21. Doorn, J. A., Hurley, T. D., and Petersen, D. R. (2006) Inhibition of human mitochondrial aldehyde dehydrogenase by 4-hydroxynon-2-enal and 4-oxonon-2-enal. Chem. Res. Toxicol. 19, 102-110.
22. Shibata, T., Iio, K., Kawai, Y., Shibata, N., Kawaguchi, M., Toi, S., Kobayashi, M., Kobayashi, M., Yamamoto, K., and Uchida, K. (2006) Identification of a lipid peroxidation product as a potential trigger of the p53 pathway. J. Biol. Chem. 281, 1196-1204.
23. Wagner, T. M., Mullally, J. E., and Fitzpatrick, F. A. (2006) Reactive lipid species from cyclooxygenase-2 inactivate tumor suppressor LKB1/STK11: cyclopentenone prostaglandins and 4-hydroxy-2-nonenal covalently modify and inhibit the AMP-kinase kinase that modulates cellular energy homeostasis and protein translation. J. Biol. Chem. 281, 2598-2604.
24. 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.
25. Birtwistle, D. H., Brown, J. M., Herbert, R. H., James, A. P., Lee, K. F., and Taylor, R. J. (1989). Conformational analysis in the directed hydrogenation of homoallylic alcohols. J. Chem. Soc., Chem. Commun. 194-196.
26. Takabe, K., Iida, Y., Hiyoshi, H., Ono, M., Hirose, Y., Fukui, Y., Yoda, H., and Mase, N. (2000) Reverse enantioselectivity in the lipase-catalyzed desymmetrization of prochiral 2-carbamoylmethyl-1,3-propanediol derivatives. Tetrahedron: Asymmetry 11, 4825-4829.