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Detoxification of 4-hydroxynonenal (HNE) in keratinocytes: characterization of conjugated metabolites by liquid chromatography/electrospray ionization tandem mass spectrometry.
Aldini G, Granata P, Orioli M, Santaniello E, Carini M. Aldini G, et al. J Mass Spectrom. 2003 Nov;38(11):1160-8. doi: 10.1002/jms.533. J Mass Spectrom. 2003. PMID: 14648823
The GSH-HNE conjugates were (a) S-(4-hydroxynonanal-3-yl)glutathione, (b) S-(1,4-dihydroxy-nonane-3-yl)glutathione, (c) S-(4-oxononanal-3-yl)glutathione and (d) S-(4-oxo-nonan-1-ol-3-yl)glutathione, and accounted for 52.3 +/- 5.8% of the HNE dose (35 nmol mg(-1) pro …
The GSH-HNE conjugates were (a) S-(4-hydroxynonanal-3-yl)glutathione, (b) S-(1,4-dihydroxy-nonane-3-yl)glutathione, (c) S-(4-oxono …
Pyrrole formation from 4-hydroxynonenal and primary amines.
Sayre LM, Arora PK, Iyer RS, Salomon RG. Sayre LM, et al. Chem Res Toxicol. 1993 Jan-Feb;6(1):19-22. doi: 10.1021/tx00031a002. Chem Res Toxicol. 1993. PMID: 8448343
We now show that 4-HNE reacts with primary amines in aqueous acetonitrile at pH 7.8 to afford after workup, in 14-23% yield, the corresponding pyrroles, which were characterized by independent synthesis from 4-oxononanal. Additional, mostly unstable adducts are also …
We now show that 4-HNE reacts with primary amines in aqueous acetonitrile at pH 7.8 to afford after workup, in 14-23% yield, the correspondi …
Human carbonyl reductase catalyzes reduction of 4-oxonon-2-enal.
Doorn JA, Maser E, Blum A, Claffey DJ, Petersen DR. Doorn JA, et al. Biochemistry. 2004 Oct 19;43(41):13106-14. doi: 10.1021/bi049136q. Biochemistry. 2004. PMID: 15476404
GC/MS analysis confirmed 4HNE and 1HNO and identified the unknown reaction product as 4-oxononanal (4ONA). Analysis of oxime derivatives of the reaction products via LC/MS confirmed the unknown as 4ONA. ...
GC/MS analysis confirmed 4HNE and 1HNO and identified the unknown reaction product as 4-oxononanal (4ONA). Analysis of oxime d …
Rapid cross-linking of proteins by 4-ketoaldehydes and 4-hydroxy-2-alkenals does not arise from the lysine-derived monoalkylpyrroles.
Xu G, Liu Y, Kansal MM, Sayre LM. Xu G, et al. Chem Res Toxicol. 1999 Sep;12(9):855-61. doi: 10.1021/tx990056a. Chem Res Toxicol. 1999. PMID: 10490508
Exposure of proteins to 4-hydroxy-2-nonenal (HNE) results in conversion of lysines in part to 2-pentylpyrroles that can be formed in higher yield by exposure to the isomeric 4-oxononanal. Since both HNE and 4-oxononanal cause protein cross-linking, and …
Exposure of proteins to 4-hydroxy-2-nonenal (HNE) results in conversion of lysines in part to 2-pentylpyrroles that can be formed in higher …
Localization of isoketal adducts in vivo using a single-chain antibody.
Davies SS, Talati M, Wang X, Mernaugh RL, Amarnath V, Fessel J, Meyrick BO, Sheller J, Roberts LJ 2nd. Davies SS, et al. Free Radic Biol Med. 2004 May 1;36(9):1163-74. doi: 10.1016/j.freeradbiomed.2004.02.014. Free Radic Biol Med. 2004. PMID: 15082070
Recognition of isoketal adduct by this anti-isoketal adduct single-chain antibody was essentially independent of the amino acid sequence of adducted peptides or proteins. The antibody did not cross-react with 4-hydroxynonenal or 4-oxononanal adducts or with 15-F2t-i …
Recognition of isoketal adduct by this anti-isoketal adduct single-chain antibody was essentially independent of the amino acid sequence of …
The lipid peroxidation product 4-hydroxynonenal inhibits neurite outgrowth, disrupts neuronal microtubules, and modifies cellular tubulin.
Neely MD, Sidell KR, Graham DG, Montine TJ. Neely MD, et al. J Neurochem. 1999 Jun;72(6):2323-33. doi: 10.1046/j.1471-4159.1999.0722323.x. J Neurochem. 1999. PMID: 10349841 Free article.
HNE can react with target proteins by forming either Michael adducts or pyrrole adducts. 4-Oxononanal, an HNE analogue that can form only pyrrole adducts but not Michael adducts, had no effect on the microtubules. ...
HNE can react with target proteins by forming either Michael adducts or pyrrole adducts. 4-Oxononanal, an HNE analogue that ca …
Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal.
Sayre LM, Sha W, Xu G, Kaur K, Nadkarni D, Subbanagounder G, Salomon RG. Sayre LM, et al. Chem Res Toxicol. 1996 Oct-Nov;9(7):1194-201. doi: 10.1021/tx960094j. Chem Res Toxicol. 1996. PMID: 8902276
Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH) directly with 4-oxononanal and the other by preformation of 6-(2-pentylpyrrol-1-yl)hexanoic acid from 6-aminocaproic acid and 4-oxononanal, followed by carbod …
Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH) directly with 4-oxononanal and t …