Journal
JOURNAL OF PHYSICAL CHEMISTRY B
Volume 116, Issue 22, Pages 6411-6415Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp3044219
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Funding
- Granting Agency of the Czech Republic (ESF EUROMEMBRANE) [MEM/09/E006]
- Czech Science Foundation [P203/08/0114, P208/10/0376]
- Academy of Sciences of the Czech Republic
- Ministry of Education [LH12001]
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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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