| Identification of a new cross-link and unique histidine adduct from bovine serum albumin incubated with malondialdehyde. | |
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MedLine Citation:
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PMID: 14570889 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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David A Slatter; Nicholas C Avery; Allen J Bailey |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2003-10-21 |
Journal Detail:
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Title: The Journal of biological chemistry Volume: 279 ISSN: 0021-9258 ISO Abbreviation: J. Biol. Chem. Publication Date: 2004 Jan |
Date Detail:
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Created Date: 2003-12-25 Completed Date: 2004-03-03 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985121R Medline TA: J Biol Chem Country: United States |
Other Details:
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Languages: eng Pagination: 61-9 Citation Subset: IM |
Affiliation:
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Collagen Research Group, Division of Molecular and Cellular Biology, University of Bristol, Bristol BS40 5DS, UK. das55@cam.ac.uk |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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