The effect of variations in phospholipid and sterol structure on the nature of lipid–sterol interactions in lipid bilayer model membranes

Mannock, David A.; Lewis, Richard L.; McMullen, Todd; McElhaney, Ronald N.

doi:10.1016/j.chemphyslip.2010.03.011

Cited by 141 publications

(120 citation statements)

References 347 publications

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“…In the paper, they reported that the pretransition is completely abolished at X ch > 0.05 for all the CnPC-Chol binary bilayers (n = [14][15][16][17][18][19][20]. However, in the recent papers by Mannock et al [32,33], they have noted that later studies using high-sensitivity DSC instruments revealed that the pretransition persists to X ch = 0.10 in the C16PC-Chol binary bilayer. Taking this recent result into account, our results about the X ch values of the abolition of the pretransition for the CnPC-Chol binary bilayers (n = 14-16) are reasonable.…”

Section: Dsc Measurementsmentioning

confidence: 87%

How does acyl chain length affect thermotropic phase behavior of saturated diacylphosphatidylcholine–cholesterol binary bilayers?

Tamai¹,

Izumikawa²,

Fukui³

et al. 2013

Biochimica et Biophysica Acta (BBA) - Biomembranes

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Thermotropic phase behavior of diacylphosphatidylcholine (CnPC)-cholesterol binary bilayers (n=14-16) was examined by fluorescence spectroscopy using 6-propionyl-2-(dimethylamino)naphthalene (Prodan) and differential scanning calorimetry. The former technique can detect structural changes of the bilayer in response to the changes in polarity around Prodan molecules partitioned in a relatively hydrophilic region of the bilayer, while the latter is sensitive to the conformational changes of the acyl chains. On the basis of the data from both techniques, we propose possible temperature T-cholesterol composition Xch phase diagrams for these binary bilayers. A notable feature of our phase diagrams, including our previous results for diheptadecanoylphosphatidylcholine (C17PC) and distearoylphosphatidylcholine (C18PC), is that there is a peritectic-like point around Xch=0.15, which can be interpreted as indicating the formation of a 1:6-complex of cholesterol and CnPCs within the binary bilayer irrespective of the acyl chain length. We could give a reasonable explanation for such complex formation using the modified superlattice view. Our results also showed that the Xch value of the abolition of the main transition is almost constant for n=14-17 (ca. 0.33), while it increases to ca. 0.50 for n=18. By contrast, a biphasic n-dependence of Xch was observed for the abolition of the pretransition, suggesting that there are at least two antagonistic n-dependent factors. We speculate that this could be explained by the enhancement of the van der Waals interaction with increases in n and the weakening of the repulsion between the neighboring headgroups with decreases in n.

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Section: Dsc Measurementsmentioning

confidence: 87%

How does acyl chain length affect thermotropic phase behavior of saturated diacylphosphatidylcholine–cholesterol binary bilayers?

Tamai¹,

Izumikawa²,

Fukui³

et al. 2013

Biochimica et Biophysica Acta (BBA) - Biomembranes

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“…An inverse relationship between y and the ordering effects of a given sterol has been verified in subsequent studies, for diverse molecules such as intrinsically 13,14 or extrinsically 15,16 fluorescent sterols, 25-hydroxycholesterol, 17 cholesteryl hemisuccinate, 18 or b-sitosterol. 19 While a direct relationship between sterol tilt and ordering capability appears to be clear, it should be recognized that the tilt itself depends on the sterol structure, and numerous types of chemical modifications affect sterol orientation within membranes, 20 as evident from the above examples. Sterol tilt itself is also influenced by the overall order of the membrane, which in turn depends on the phospholipid composition and sterol content as well as on the structure of the latter.…”

Section: Introductionmentioning

confidence: 99%

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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“…Accordingly, optically resolvable imaging in lipid bilayer membranes involving at least three components reported the coexistence of a liquid-disordered (L d ) phase, formed mainly from unsaturated phospholipids (9 -14), with a liquid-ordered (L o ) phase formed from saturated phospholipids and sphingolipids in the presence of cholesterol (8,15,16). In the latter, a higher degree of conformational order is imposed on the acyl tails of lipids by the rigid ring structure of cholesterol (17), increasing the thickness of the lipid bilayer and lipid packing, although lipids remain laterally mobile. Sterols (18) and sphingolipid/sterol interactions (19 -24) have recently emerged as essential determinants of lipid partitioning within membranes.…”

mentioning

confidence: 99%

Differential Effect of Plant Lipids on Membrane Organization

Grosjean

Mongrand

Beney

et al. 2015

Journal of Biological Chemistry

104

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Background: The effect of the wide variety of plant lipids on membrane organization is still poorly understood. Results: The local amounts of phytosphingolipids and free and conjugated phytosterols control the relative proportion and spatial distribution of ordered domains. Conclusion: Plant lipids differently modulate, alone or in combination, membrane heterogeneity. Significance: Our results highlight how plant lipid diversity might drive the plasma membrane subcompartmentalization.

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The effect of variations in phospholipid and sterol structure on the nature of lipid–sterol interactions in lipid bilayer model membranes

Cited by 141 publications

References 347 publications

How does acyl chain length affect thermotropic phase behavior of saturated diacylphosphatidylcholine–cholesterol binary bilayers?

How does acyl chain length affect thermotropic phase behavior of saturated diacylphosphatidylcholine–cholesterol binary bilayers?

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

Differential Effect of Plant Lipids on Membrane Organization

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