Behavior of 4-hydroxynonenal in phospholipid membranes
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
22577896
DOI
10.1021/jp3044219
Knihovny.cz E-resources
- MeSH
- Aldehydes chemistry MeSH
- Fluorescence MeSH
- Phosphatidylcholines chemistry MeSH
- Lipid Bilayers chemistry MeSH
- Membranes, Artificial * MeSH
- Models, Molecular MeSH
- Molecular Structure MeSH
- Molecular Dynamics Simulation MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 1-palmitoyl-2-oleoylphosphatidylcholine MeSH Browser
- 4-hydroxy-2-nonenal MeSH Browser
- Aldehydes MeSH
- Phosphatidylcholines MeSH
- Lipid Bilayers MeSH
- Membranes, Artificial * MeSH
Under conditions of oxidative stress, 4-hydroxy-2-nonenal (4-HNE) is commonly present in vivo. This highly reactive and cytotoxic compound is generated by oxidation of lipids in membranes and can be easily transferred from a membrane to both cytosol and the extracellular space. Employing time-dependent fluorescence shift (TDFS) method and molecular dynamics simulations, we found that 4-HNE is stabilized in the carbonyl region of a 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) bilayer. 4-HNE is thus able to react with cell membrane proteins and lipids. Stabilization in the membrane is, however, moderate and a transfer of 4-HNE to either extra- or intracellular space occurs on a microsecond time scale. These molecular-level details of 4-HNE behavior in the lipid membrane rationalize the experimentally observed reactivity of 4-HNE with proteins inside and outside the cell. Furthermore, these results support the view that 4-HNE may play an active role in cell signaling pathways.
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