Document Detail


Identification of a new cross-link and unique histidine adduct from bovine serum albumin incubated with malondialdehyde.
MedLine Citation:
PMID:  14570889     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Malondialdehyde, acetaldehyde, acrolein, and 4-hydroxynonenal are all products of fatty acid oxidation found in the fatty streaks of atherosclerotic arteries due to a lack of antioxidants and an increase in glycation products. Previously identified cross-links derived from these molecules have nearly always required more than one molecule of each type, although this is physiologically less likely than a reaction involving a single molecule. Here we provide indirect but strong evidence for a malondialdehyde-derived cross-link requiring just one malondialdehyde molecule to link arginine and lysine, giving 2-ornithinyl-4-methyl(1epsilon-lysyl)1,3-imidazole following a 4-day incubation of albumin with 8 mm malondialdehyde. This cross-link was identified as its partial degradation product Nepsilon-(2-carboxyl,2-aminoethane)-Nepsilon-methanoyl-lysine by NMR and mass spectrometry. Analysis of plasma from treated diabetic patients revealed that one patient levels had as high as 0.46%, 0.67% of their lysine/arginine residues modified by this cross-link, although others had lower levels. Alkaline hydrolysis of serum albumin also revealed two acid-labile malondialdehyde adducts of histidine in significant quantities, the isomers 4- and 2-ethylidene-histidine. These constituted up to 0.93% of the histidines in treated diabetic patients. Although collagen is readily cross-linked by malondialdehyde, none of these particular products could be found in incubations of collagen with malondialdehyde.
Authors:
David A Slatter; Nicholas C Avery; Allen J Bailey
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2003-10-21
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  279     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  2004 Jan 
Date Detail:
Created Date:  2003-12-25     Completed Date:  2004-03-03     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  61-9     Citation Subset:  IM    
Affiliation:
Collagen Research Group, Division of Molecular and Cellular Biology, University of Bristol, Bristol BS40 5DS, UK. das55@cam.ac.uk
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MeSH Terms
Descriptor/Qualifier:
Animals
Arginine / analogs & derivatives,  blood
Binding Sites
Cattle
Cross-Linking Reagents / pharmacology
Diabetes Mellitus / blood
Guinea Pigs
Histidine*
Humans
Lysine / analogs & derivatives,  blood
Magnetic Resonance Spectroscopy
Malondialdehyde / pharmacology*
Mass Spectrometry
Serum Albumin, Bovine / chemistry*,  drug effects
Chemical
Reg. No./Substance:
0/Cross-Linking Reagents; 0/Serum Albumin, Bovine; 542-78-9/Malondialdehyde; 56-87-1/Lysine; 71-00-1/Histidine; 74-79-3/Arginine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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