Cayman Chemical | 4-oxo-2-Nonenal | Description • 4-ONE (CAS 103560-62-9)

10185 4-oxo-2-Nonenal

4-ONE (CAS 103560-62-9)

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4-hydroxy Nonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid and linoleic acid.^1,2 It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity and has been widely used as a marker of lipid peroxidation.^1,2,3 4-oxo-2-Nonenal is a more recently identified product of lipid peroxidation.^4,5,6 It actively modifies histidine and lysine residues on proteins and causes protein cross-linking.^7,8 4-oxo-2-Nonenal also modifies 2'-deoxyguanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.⁴

1 Pryor, W.A., Porter, N.A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic Biol Med 8 541-543 (1990).

2 Esterbauer, H., Schaur, R.J., Zoliner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radic Biol Med 11 81-128 (1991).

3 Sodum, R.S., Chung, F. 1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res 48 320-323 (1988).

4 Rindgen, D., Nakajima, M., Wehrli, S., et al. Covalent modifications to 2'-deoxyguanosine by 4-oxo-nonenal, a novel product of lipid peroxidation. Chem Res Toxicol 12 1195-1204 (1999).

5 Lee, S.H., Blair, I.A. Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chem Res Toxicol 13 698-702 (2000).

6 Spiteller, P., Kern, W., Reiner, J., et al. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim Biophys Acta 1531 188-208 (2001).

7 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 16 901-911 (2003).

8 Zhang, W., Liu, J., Xu, G., et al. Model studies on protein side chain modification by 4-oxo-2-nonenal. Chem Res Toxicol 16 512-523 (2003).

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Pricing updated 2010-03-19.
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