Document Detail

Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein.
MedLine Citation:
PMID:  9078279     Owner:  NLM     Status:  MEDLINE    
Malondialdehyde (MDA) and 4-hydroxynonenal (HNE) are major end-products of oxidation of polyunsaturated fatty acids, and are frequently measured as indicators of lipid peroxidation and oxidative stress in vivo. MDA forms Schiff-base adducts with lysine residues and cross-links proteins in vitro; HNE also reacts with lysines, primarily via a Michael addition reaction. We have developed methods using NaBH4 reduction to stabilize these adducts to conditions used for acid hydrolysis of protein, and have prepared reduced forms of lysine-MDA [3-(N epsilon-lysino)propan-1-ol (LM)], the lysine-MDA-lysine iminopropene cross-link [1,3-di(N epsilon-lysino)propane (LML)] and lysine-HNE [3-(N epsilon-lysino)-4-hydroxynonan-l-ol (LHNE)]. Gas chromatography/MS assays have been developed for quantification of the reduced compounds in protein. RNase incubated with MDA or HNE was used as a model for quantification of the adducts by gas chromatography/MS. There was excellent agreement between measurement of MDA bound to RNase as LM and LML, and as thiobarbituric acid-MDA adducts measured by HPLC; these adducts accounted for 70-80% of total lysine loss during the reaction with MDA. LM and LML (0.002-0.12 mmol/ mol of lysine) were also found in freshly isolated low-density lipoprotein (LDL) from healthy subjects. LHNE was measured in RNase treated with HNE, but was not detectable in native LDL. LM, LML and LHNE increased in concert with the formation of conjugated dienes during the copper-catalysed oxidation of LDL, but accounted for modification of < 1% of lysine residues in oxidized LDL. These results are the first report of direct chemical measurement of MDA and HNE adducts to lysine residues in LDL. LM, LML and LHNE should be useful as biomarkers of lipid peroxidative modification of protein and of oxidative stress in vitro and in vivo.
J R Requena; M X Fu; M U Ahmed; A J Jenkins; T J Lyons; J W Baynes; S R Thorpe
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Biochemical journal     Volume:  322 ( Pt 1)     ISSN:  0264-6021     ISO Abbreviation:  Biochem. J.     Publication Date:  1997 Feb 
Date Detail:
Created Date:  1997-04-15     Completed Date:  1997-04-15     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  2984726R     Medline TA:  Biochem J     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  317-25     Citation Subset:  IM    
Department of Chemistry and Biochemistry, University of South Carolina, Columbia 29208, USA.
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MeSH Terms
Aldehydes / metabolism*
Amino Acids / chemistry
Collagen / metabolism
Copper / metabolism
Crystallins / metabolism
Drug Stability
Gas Chromatography-Mass Spectrometry
Lipid Peroxidation
Lipoproteins, LDL / metabolism*
Lysine / chemistry,  metabolism*
Malondialdehyde / metabolism*
Schiff Bases
Skin / metabolism
Grant Support
Reg. No./Substance:
0/Aldehydes; 0/Amino Acids; 0/Crystallins; 0/Lipoproteins, LDL; 0/Schiff Bases; 0/oxidized low density lipoprotein; 29343-52-0/4-hydroxy-2-nonenal; 542-78-9/Malondialdehyde; 56-87-1/Lysine; 7440-50-8/Copper; 9007-34-5/Collagen; EC 3.1.-/Ribonucleases

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