Hexagonal phase with ordered acyl chains formed by a short chain asymmetric ceramide

Dupuy, Fernando Gabriel; Bordín, Santiago P. Fernandez; Maggio, Bruno; Oliveira, Rafael G.

doi:10.1016/j.colsurfb.2016.10.009

Cited by 9 publications

(9 citation statements)

References 48 publications

(62 reference statements)

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“…The large discrepancy from the value reported here points to the subtleties in data analysis. We also note that the formation of a H II phase was claimed for C10:0 Cer [40]. However, close inspection of the reported experimental data suggest rather the formation of lamellar gel phases, consistent also with MD simulations [41].…”

Section: Discussionsupporting

confidence: 87%

“…Applying shape arguments for lipid mixing instead allowed us to derive a simple model for nonlinear mixing of lipids in H II phases that can be exploited experimentally. We also alude to the possibility of non-additive mixing, leading to a variation of C 0 of a lipids with its concentration, which has been implied to occur for cholesterol 40 and sphingomyelin [20].…”

Section: Introductionmentioning

confidence: 81%

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Intrinsic Lipid Curvatures of Mammalian Plasma Membrane Outer Leaflet Lipids and Ceramides

Kaltenegger

Kremser

Frewein

et al. 2021

Preprint

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We developed a global X-ray data analysis method to determine the intrinsic curvatures of lipids hosted in inverted hexagonal phases. In particular, we combined compositional modelling with molecular shape-based arguments to account for non-linear mixing effects of guest-in-host lipids on intrinsic curvature. The technique was verified by all-atom molecular dynamics simulations and applied to sphingomyelin and a series of phosphatidylcholines and ceramides with differing composition of the hydrocarbon chains. We report positive lipid curvatures for sphingomyelin and all phosphatidylcholines with disaturated and monounsaturated hydrocarbons. Substitution of the second saturated hydrocarbon with an unsaturated acyl chain in turn shifted the intrinsic lipid curvatures to negative values. All ceramides, with chain lengths varying between C2:0 and C24:0, displayed significant negative lipid curvature values. Moreover, we report non-additive mixing for C2:0 ceramide and sphingomyelin. Our findings manifest the high and manifold potential of lipids to modulate physiological membrane function.

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Section: Discussionsupporting

confidence: 87%

Section: Introductionmentioning

confidence: 81%

Intrinsic Lipid Curvatures of Mammalian Plasma Membrane Outer Leaflet Lipids and Ceramides

Kaltenegger

Kremser

Frewein

et al. 2021

Preprint

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“…This allows to hypothesize that at very high V-Cer concentrations, there may be areas of the membrane where such Cer organize in hexagonal type II or even cubic bicontinuous phases. A recent study using a combination of X-ray diffraction techniques and infrared spectroscopy has shown for the first time that another asymmetric Cer species (10:0 Cer), in its pure state, is indeed able to self-organize into a hexagonal lattice.…”

Section: Discussionmentioning

confidence: 99%

Membrane Restructuring Events during the Enzymatic Generation of Ceramides with Very Long-Chain Polyunsaturated Fatty Acids

et al. 2018

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In rat sperm heads, sphingomyelin (SM) species that contain very long-chain polyunsaturated fatty acid (V-SM) become ceramides (V-Cer) after inducing in vitro the acrosomal reaction. The reason for such a specific location of this conversion, catalyzed by a sphingomyelinase (SMase), has received little investigation so far. Here, the effects of SMase were compared in unilamellar vesicles (large unilamellar vesicles (LUVs), giant unilamellar vesicles (GUVs)) containing phosphatidylcholine, and either V-SM or a palmitate-rich SM (P-SM). In uniformly sized LUVs at 37 °C, more V-Cer was generated and more rapidly than P-Cer. Nephelometry and dynamic light scattering showed that LUVs tended to form large lipid particles more intensely, and Förster resonance energy transfer (FRET) increases suggested that lateral lipid mixing was more marked when V-Cer rather than P-Cer was produced. As reported by 6-dodecanoyl-2-dimethyl-aminopnaphthalene (Laurdan) and 1,6-diphenyl-1,3,5,-hexatriene (DPH), the production of V-Cer resulted in higher and faster restriction in lipid mobility than that of P-Cer, implying a stronger increase in membrane dehydration and microviscosity. Moreover, DPH anisotropy suggested a higher solubility of V-Cer than that of P-Cer in the liquid-disordered phase. At room temperature, liquid-condensed lateral domains appeared in P-SM- but not in V-SM-containing GUVs. The former maintained their size while losing their contents gradually during SMase action, whereas the latter became permeable earlier and reduced their size in few minutes until suddenly collapsing. The fast and potent generation of V-Cer may contribute to the membrane restructuring events that occur on the acrosome-reacted sperm head.

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“…Using small-angle X-ray scattering and polarized light microscopy, the fully hydrated 10:0 Cer dispersions, at temperatures below the main transition, are arranged in a tridimensional structure corresponding to an inverted hexagonal phase (Dupuy et al 2017). Infrared spectroscopy and wide angle X-ray diffraction indicate that the acyl chains of Cers exhibit a relatively high order in the hexagonal phase (Fig.…”

Section: Topological Implicationsmentioning

confidence: 99%

“…The remarkable feature of this cartoon is that the sphingosine methyl end practically fit close to the center of the space between the cylinders, relieving packing frustration. Adapted from Dupuy et al (2017) similar chain structures. The area per molecule and compressibility of SM condensed phases depend upon the length of the saturated acyl chain (Fig.…”

Section: Sphingomyelinsmentioning

confidence: 99%

The many faces (and phases) of ceramide and sphingomyelin I – single lipids

Fanani

Maggio

2017

Biophys Rev

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Ceramides, the simplest kind of two-chained sphingolipids, contain a single hydroxyl group in position 1 of the sphingoid base. Sphingomyelins further contain a phosphocholine group at the OH of position 1 of ceramide. Ceramides and sphingomyelins show a variety of species depending on the fatty acyl chain length, hydroxylation, and unsaturation. Because of the relatively high transition temperature of sphingomyelin compared to lecithin and, particularly, of ceramides with 16:0-18:0 saturated chains, a widespread idea on their functional importance refers to formation of rather solid domains enriched in sphingomyelin and ceramide. Frequently, and especially in the cell biology field, these are generally (and erroneously) assumed to occur irrespective on the type of N-acyl chain in these lipids. This is because most studies indicating such condensed ordered domains employed sphingolipids with acyl chains with 16 carbons while scarce attention has been focused on the influence of the N-acyl chain on their surface properties. However, abundant evidence has shown that variations of the N-acyl chain length in ceramides and sphingomyelins markedly affect their phase state, interfacial elasticity, surface topography, electrostatics and miscibility and that, even the usually conceived "condensed" sphingolipids and many of their mixtures, may exhibit liquid-like expanded states. This review is a summarized overview of our work and of related others on some facts regarding membranes composed of single molecular species of ceramide and sphingomyelin. A second part is dedicated to discuss the miscibility properties between species of sphingolipids that differ in N-acyl and oligosaccharide chains.

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Hexagonal phase with ordered acyl chains formed by a short chain asymmetric ceramide

Cited by 9 publications

References 48 publications

Intrinsic Lipid Curvatures of Mammalian Plasma Membrane Outer Leaflet Lipids and Ceramides

Intrinsic Lipid Curvatures of Mammalian Plasma Membrane Outer Leaflet Lipids and Ceramides

Membrane Restructuring Events during the Enzymatic Generation of Ceramides with Very Long-Chain Polyunsaturated Fatty Acids

The many faces (and phases) of ceramide and sphingomyelin I – single lipids

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