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pubmed-article:11371432pubmed:dateCreated2001-5-23lld:pubmed
pubmed-article:11371432pubmed:abstractTextValproic acid (VPA) is a short, branched fatty acid with broad-spectrum anticonvulsant activity. It has been suggested that VPA acts directly on the plasma membrane. We calculated the free energy of interaction of VPA with a model lipid bilayer using simulated annealing and the continuum solvent model. Our calculations indicate that VPA is likely to partition into the bilayer both in its neutral and charged forms, as expected from such an amphipathic molecule. The calculations also show that VPA may migrate (flip-flop) across the membrane; according to our (theoretical) study, the most likely flip-flop path at neutral pH involves protonation of VPA pending its insertion into the lipid bilayer and deprotonation upon departure from the other side of the bilayer. Recently, the flip-flop of long fatty acids across lipid bilayers was studied using fluorescence and NMR spectroscopies. However, the measured value of the flip-flop rate appears to depend on the method used in these studies. Our calculated value of the flip-flop rate constant, 20/s, agrees with some of these studies. The limitations of the model and the implications of the study for VPA and other fatty acids are discussed.lld:pubmed
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pubmed-article:11371432pubmed:issn0006-3495lld:pubmed
pubmed-article:11371432pubmed:authorpubmed-author:MusafiaBBlld:pubmed
pubmed-article:11371432pubmed:authorpubmed-author:KesselAAlld:pubmed
pubmed-article:11371432pubmed:authorpubmed-author:Ben-TalNNlld:pubmed
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pubmed-article:11371432pubmed:volume80lld:pubmed
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pubmed-article:11371432pubmed:pagination2536-45lld:pubmed
pubmed-article:11371432pubmed:dateRevised2009-11-18lld:pubmed
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pubmed-article:11371432pubmed:year2001lld:pubmed
pubmed-article:11371432pubmed:articleTitleContinuum solvent model studies of the interactions of an anticonvulsant drug with a lipid bilayer.lld:pubmed
pubmed-article:11371432pubmed:affiliationDepartment of Biochemistry, George S. Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv 69978 Israel.lld:pubmed
pubmed-article:11371432pubmed:publicationTypeJournal Articlelld:pubmed
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