Structural and dynamical details of cholesterol-lipid interaction as revealed by deuterium NMR

Dufourc, Érick J.; Parish, Edward J.; Chitrakorn, Sarawanee; Smith, Ian C. P.

doi:10.1021/bi00320a025

Cited by 238 publications

(285 citation statements)

References 28 publications

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“…In this plot, C20 corresponds to the first atom in the chain, and Ciso is the last atom for which an order parameter is calculated. Although S CD inequivalence for the two hydrogen atoms has been reported in cholesterol for C24 72 and also for other methylene groups in the cholesterol side chain, 73 this difference cannot be resolved when calculating using the above described method. Therefore, the order parameters corresponding to these positions should be viewed as average values.…”

Section: Sterol Tilt and The Popc Acyl Chain Ordermentioning

confidence: 97%

Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study

Robalo

Ramalho

Huster

et al. 2015

Phys. Chem. Chem. Phys.

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Following a recent experimental investigation of the effect of the length of the alkyl side chain in a series of cholesterol analogues (Angew. Chem., Int. Ed., 2013, 52, 12848-12851), we report here an atomistic molecular dynamics characterization of the behaviour of methyl-branched side chain sterols (iso series) in POPC bilayers. The studied sterols included androstenol (i-C0-sterol) and cholesterol (i-C8-sterol), as well as four other derivatives (i-C5, i-C10, i-C12 and i-C14-sterol). For each sterol, both subtle local effects and more substantial differential alterations of membrane properties along the iso series were investigated. The location and orientation of the tetracyclic ring system is almost identical in all compounds. Among all the studied sterols, cholesterol is the sterol that presents the best matching with the hydrophobic length of POPC acyl chains, whereas longer-chained sterols interdigitate into the opposing membrane leaflet. In accordance with the experimental observations, a maximal ordering effect is observed for intermediate sterol chain length (i-C5, cholesterol, i-C10). Only for these sterols a preferential interaction with the saturated sn-1 chain of POPC (compared to the unsaturated sn-2 chain) was observed, but not for either shorter or longer-chained derivatives. This work highlights the importance of the sterol alkyl chain in the modulation of membrane properties and lateral organization in biological membranes.

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Section: Sterol Tilt and The Popc Acyl Chain Ordermentioning

confidence: 97%

Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study

Robalo

Ramalho

Huster

et al. 2015

Phys. Chem. Chem. Phys.

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“…The same effect is reported using independently chain-labeled phospholipids or ring-labeled cholesterol. Using deuterium-labeled cholesterol offers the advantage of determining the average orientation of the fused ring system with respect to the bilayer normal [18,19]. Cholesterol sits perpendicular to the membrane surface and keeps this orientation independent of temperature [18].…”

Section: Effect Of Mammalian Sterols On Model Membranesmentioning

confidence: 99%

“…Using deuterium-labeled cholesterol offers the advantage of determining the average orientation of the fused ring system with respect to the bilayer normal [18,19]. Cholesterol sits perpendicular to the membrane surface and keeps this orientation independent of temperature [18]. The depth of embedment in the membrane has been also determined: cholesterol is buried in the bilayer with the OH group facing the carbonyl of the fatty acid lipid chains [20].…”

Section: Effect Of Mammalian Sterols On Model Membranesmentioning

confidence: 99%

Sterols and membrane dynamics

2008

Self Cite

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The effect of sterols from mammals, plants, fungi, and bacteria on model and natural membrane dynamics are reviewed, in the frame of ordering-disordering properties of membranes. It is shown that all sterols share a common property: the ability to regulate dynamics in order to maintain membranes in a microfluid state where it can convey important biological processes. Depending on the sterol class, this property is modulated by molecular modifications that have occurred during evolution. The role of sterols in rafts, antibiotic complexes, and in protecting membranes from the destructive action of amphipathic toxins is also discussed.

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“…An interesting system to study in this way would be a-cholesterol-phospholipid mixtures. Dufourc et al (55) have shown that the a-cholesterol molecule adopts a tilted conformation in phospholipid bilayer model membranes while the P-cholesterol ring structure lies with its plane parallel to the bilayer normal. They have speculated that this is why the P-cholesterol molecule occurs in natural systems while the a-cholesterol molecule does not.…”

Section: Experimental Considerationsmentioning

confidence: 99%

The evolution of membranes

Bloom¹,

Mouritsen²

1988

Can. J. Chem.

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. J. Chem. 66, 706 (1988).Consideration of the influence of cholesterol on the physical properties of biological membranes leads to the conclusion that cholesterol increases the thickness of fluid membrane bilayers without appreciably increasing the microviscosity component of membrane fluidity. At sufficiently high cholesterol concentrations, the gel-liquid crystalline phase transition is completely eliminated in phospholipid-cholesterol mixtures and the system has the properties of a two-dimensional liquid over a wide range of temperatures. It is proposed that with the evolution of cholesterol and related sterols in an oxygen-rich atmosphere, the resulting modification of physical constraints on membrane properties made it possible for new evolutionary driving forces to manifest themselves leading to the peculiar properties of plasma membranes of eucaryotic cells.MYER BLOOM et OLE G. MOURITSEN. Can. J. Chem. 66, 706 (1988).Si on examine l'influence du cholestCro1 sur les propriCtCs physiques des membranes biologiques, on est amen6 B conclure que le cholesterol augmente 1'Cpaisseur des doubles couches des membranes fluides sans alfgmenter d'une facon appriciable la composante de la microviscosit6 de la fluidit6 de la membrane. A des concentrations de cholestCro1 suffisamment ClevCes, la transition de la phase cristalline gel-liquide est complktement CliminCe des mClanges phospholipide-cholestCro1 et, pour un grand intervalle de tempiratures, le systkme posskde les propriCtCs d'une liquide bi-dimensionnel. On est amen6 B proposer que, avec 1'Cvolution du cholestCro1 et des stCrols apparentCs dans un atmosphkre riche en oxygkne, la modification qui rCsulte de contraintes physiques sur les propriCtCs de la membrane fait qu'il est possible pour de nouvelles forces Cvolutionnaires de se manifester; ceci provoque l'apparition de propriitis particulikres pour les membranes plasmatiques des cellules eucaryotices.[Traduit par la revue]

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Structural and dynamical details of cholesterol-lipid interaction as revealed by deuterium NMR

Cited by 238 publications

References 28 publications

Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study

Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study

Sterols and membrane dynamics

The evolution of membranes

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