Scavenging 4-Oxo-2-nonenal

Chemical Research in Toxicology

Volumn 28, Issue 10, 2015, Pages 1888-1890

  Amarnath, Venkataraman ^a   Amarnath, Kalyani ^b  

^a Department of Pathology Microbiology and Immunology ^*  (United States)

^b VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 OXO 2 NONENAL; ALDEHYDE; LYSINE; OXAZINE DERIVATIVE; PHENOL DERIVATIVE; PROTEIN; PYRIDOXAMINE; UNCLASSIFIED DRUG; 4-OXO-2-NONENAL; PYRROLE DERIVATIVE; SCAVENGER;

ARTICLE; LIPID OXIDATION; MICHAEL ADDITION; REACTION ANALYSIS; CHEMISTRY; LIPID PEROXIDATION; METABOLISM;

ALDEHYDES; FREE RADICAL SCAVENGERS; LIPID PEROXIDATION; LYSINE; PROTEINS; PYRIDOXAMINE; PYRROLES;

EID: 84944746671     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/acs.chemrestox.5b00301     Document Type: Article

References (21)

1. Uchida, K. (2000) Role of reactive aldehyde in cardiovascular diseases Free Radical Biol. Med. 28, 1685-1696 10.1016/S0891-5849(00)00226-4
2. Doorn, J. A. and Peterson, 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 10.1021/tx025590o
3. Lee, S. H., Takahashi, R., Goto, T., and Oe, T. (2010) Mass spectrometric characterization of modifications to angiotensin II by lipid peroxidation products, 4-oxo-2(E)-nonenal and 4-hydroxy-2(E)-nonenal Chem. Res. Toxicol. 23, 1771-1785 10.1021/tx100228q
4. Shimozu, Y., Shibata, T., Ojika, M., and Uchida, K. (2009) Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts Chem. Res. Toxicol. 22, 957-964 10.1021/tx900059k
5. Oe, T., Lee, S. H., Silva Elipe, M. V., Arison, B. H., and Blair, I. A. (2003) A novel lipid hydroperoxide-derived modification to arginine Chem. Res. Toxicol. 16, 1598-1605 10.1021/tx034178l
6. Chou, P.-H. et al. 2010, Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues Chem. Res. Toxicol. 23, 1442-1448 10.1021/tx100047d
7. Galligan, J. J., Rose, K. L., Beavers, W. N., Hill, S., Tallman, K. A., Tansey, W. P., and Marnett, L. J. (2014) Stable histone adduction by 4-oxo-2-nonenal: A potential link between oxidative stress and epigenetics J. Am. Chem. Soc. 136, 11864-11866 10.1021/ja503604t
8. 2-isoprostane pathway Chem. Phys. Lipids 128, 85-99 10.1016/j.chemphyslip.2003.10.007
9. 2 via the levuglandin pathway Biochemistry 38, 9389-9396 10.1021/bi990470+
10. Amarnath, V., Amarnath, K., Amarnath, K., Davies, S., and Roberts, L. J. (2004) Pyridoxamine: An extremely potent scavenger of 1,4-dicarbonyls Chem. Res. Toxicol. 17, 410-415 10.1021/tx0300535
11. 2-mediated cytotoxicity Biochemistry 45, 15756-13767 10.1021/bi061860g
12. Amarnath, V., Amarnath, K., Avance, J., Stec, D. F., and Voziyan, P. (2015) 5′-O-Alkylpyridoxamines: lipophilic analogs of pyridoxamine are potent scavengers of 1,2-dicarbonyls Chem. Res. Toxicol. 28, 1469-1475 10.1021/acs.chemrestox.5b00148
13. Liu, Y., Xu, G., and Sayre, L. M. (2003) Carnosine inhibits (E)-4-hydroxy-2-nonenal-induced protein cross-linking: structural characterization of carnosine-HNE adducts Chem. Res. Toxicol. 16, 1589-1597 10.1021/tx034160a
14. Colzani, M., Criscuolo, A., De Maddis, D., Garzon, D., Yeum, K.-J., Vistoli, G., Carini, N., and Aldini, G. (2014) A novel high reolution MS approach for the screening of 4-hydroxy-trans-2-nonenal sequestering agents J. Pharm. Biomed. Anal. 91, 108-118 10.1016/j.jpba.2013.12.024
15. Picklo, M. J., Azenkeng, A., and Hoffmann, M. R. (2011) Trans-4-oxo-2-nonenal potently alters mitochondrial function Free Radical Biol. Med. 50, 400-407 10.1016/j.freeradbiomed.2010.11.014
16. Zhu, X., Gallogly, M. M., Mieyal, J. J., Anderson, V. E., and Sayre, L. M. (2009) Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal Chem. Res. Toxicol. 22, 1050-1059 10.1021/tx9000144
17. Aluise, C. D., Camarillo, J. M., Shimozu, Y., Gallagan, J. J., Rose, K. L., Tallman, K. A., and Marnett, L. J. (2015) Site-specific, intramolecular cross-linking of Pin1 active site residues by the lipid electrophile 4-oxo-2-nonenal Chem. Res. Toxicol. 28, 817-827 10.1021/acs.chemrestox.5b00038
18. Zagol-Ikapitte, I., Amarnath, V., Bala, M., Roberts, L. J., Oates, J. A., and Boutaud, O. (2010) Characterization of scavengers of γ-ketoaldehydes that do not inhibit prostaglandin biosynthesis Chem. Res. Toxicol. 23, 240-250 10.1021/tx900407a
19. Sayre, L. M., Arora, P. K., Iyer, R. S., and Salomon, R. G. (1993) Pyrrole formation from 4-hydroxynonenal and primary amines Chem. Res. Toxicol. 6, 19-22 10.1021/tx00031a002
20. Lin, D., Lee, H., 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 10.1021/tx050080q
21. Carrier, C. J., Zagol-Ikapitte, I., Amarnath, V., Boutaud, O., and Oates, J. A. (2014) Levuglandin forms adducts with Histone H4 in a cyclooxygenase-2-dependent manner, altering its interaction with DNA Biochemistry 53, 2436-2441 10.1021/bi401673b