4- oxo-2-nonenal

In a similar biochemically oriented vein, several papers were published during 2003 in the journal Chemical Research in Toxicology, representing yet another area of applicability of 3 mm NMR probe capabilities. In the first of these reports, Hankin et al.159 described the results of an investigation into the covalent binding of leukotriene A4 to DNA and RNA. Later in 2003, Blair and co-workers160 reported on the characterization of 2 -deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product. Two of the adducts characterized, Ai and A2, were consistent with substituted ethano-deoxycytidine structures. The third adduct, B, was characterized as a 7-heptanone-etheno-deoxycytidine adduct (78). 

Rindgen, D., Lee, S.H., Nakajima, M., and Blair, I.A. (2000) Formation of a substituted l,N6-etheno-2 -deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-nonenal. Chem. Res. Toxicol., 13, 846-852. 

Lee and Blair provided a critical link from lipid peroxidation to the formation of etheno adducts by demonstrating the reactivity of 4-hydroperoxy-2-nonenal, 4-oxo-2-nonenal, and 4,5-epoxy-2-decenal with nucleosides. Both 4-hydroperoxy-... 

The third type of oxidative damage that can occur in DNA would result from the addition of bifunctional electrophiles (4-hydroxy-2-nonenal and 4-oxo-2-none-nal) that result from lipid peroxidation to the nucleobases. The etheno adducts formed with 4-hydroxy-2-nonenal can also be derived from vinyl chloride however, the heptano-etheno adducts derived from 4-oxo-2-nonenal can only be derived from lipid peroxidation [115], Thus far no attempt has been made to measure these adducts as a result of the AKR pathway of PAH activation. 

Behr etal. (231) 2,6-Dimethyl-10-oxo-3,6-undecadien-2-ol, 3-methyl-4-oxo-2-nonen-8-ol... 

Doom, J. A. and Petersen, D. R. Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal. Chem. Res. Toxicol. 15 2002 1445-1450. 

Shimozu, Y., Shibata, T., Ojika, M., and Uchida, K. Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts. Chem. Res. Toxicol. 22 2009 957-964. 

Picklo, M. J., A. Azenkeng, and M. R. Hoffmann. Trans-4-oxo-2-nonenal potently alters mitochondrial function. Free RatUc Biol Med 50(2), 2011 400-7. 

Lipid peroxidation of polyunsaturated fatty acids yields a group of reactive unsaturated aldehydic compounds (enals) such as 2-alkenals (acrolein [Acr], crotonaldehyde [Cro], 2-hexenal), 4-hydroxy-2-alkenals (4-hydroxy-2-nonenal [HNE], 4-hydroxy-2-hexenal [HHE]), and ketoaldehydes (malondialdehyde [MDA], glyoxal, 4-oxo-2-nonenal [ONE]) (Uchida 2003) (Eigure 18.1). 

Jian W, Lee SH, Mesaros C, Oe T, Elipe MV, Blair lA. A novel 4-oxo-2( )-nonenal-derived endogenous thiadiazabicyclo glutathione adduct formed during cellular oxidative stress. Chem Res Toxicol 2007 20 1008-1018. 

Lee SH, Blair lA. Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chem Res Toxicol 2000 13 698-702. 

It should be noted that protein carbonylations occur via many different pathways. The hydrazide-coated glass beads are capable of enriching peptides harboring carbonyl modihcations other than those by HNE (e.g., 4-hydroxy-2-hexenal, 4-oxo-2-nonenal, metal-catalyzed oxidation, and others). These modifications can be included in the database search algorithms for in-depth mining of posttranslational protein carbonylations. 

Octadienoic acid Me ester, in 0-80011 Octahydro-17 -2-benzopyran-1 -one, 0-80012 Octahydro-7//-l-benzopyran-7-one, 0-60011 4-Oxo-2-nonenal, 0-70097... 

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