Studies on the interaction of cholesterol with diester- and dietherlecithin

Schwarz, Frank; Paltauf, Fritz; Laggner, Peter

doi:10.1016/0009-3084(76)90044-x

Cited by 45 publications

(21 citation statements)

References 30 publications

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“…The condensing effect of cholesterol on these lipids in t h e air-water monolayer was observed to account for only one-half of the effect that was achieved on [ C 1 8 : 1 -C 1 6 : 0 ] phosphatidylcholine molecules (47). Significant differences b e t w e e n diether-and diesterphosphatidylcholine in their interactions with cholesterol have recently been reported; the data support t h e conjecture that an interaction occurs between the carbonyl oxygens of diesterphosphatidylcholine and the ]3-OH group of cholest e r o l (48). Moreover, T 1 relaxation data measured by 13C_NMR show that the largest effect of cholesterol on egg phosphatidylcholine molecules in vesicle bilayers as probed by a Cs nitroxide label occurs at the fatty acyl carbonyl position (41).…”

Section: Cholesterol Phosphatidy|choline Bilayersmentioning

confidence: 65%

A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

Huang

1977

Lipids

216

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Based on the structural properties of phospholipid and cholesterol molecules, and making use of the known structural and motional effects of cholesterol and its analogs on phospholipid bilayers, a model for the cholesterol-phosphatidylcholine complex is proposed. In this model, the 3beta-hydroxyl group of cholesterol is assumed to engage in hydrogen bonding with the carbonyl oxygen of the fatty acyl groups in phospholipids. Some specific configurations of the saturated and unsaturated fatty acyl chains of the phospholipid are suggested to participate in van der Waals attractive interactions with the apha and beta surface of the steroid nucleus.

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Section: Cholesterol Phosphatidy|choline Bilayersmentioning

confidence: 65%

A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

Huang

1977

Lipids

216

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“…Consider their individual effects. Cholesterol alone stabilizes the lamellar phase of PC bilayers and this is usually interpreted as a result of cholesterol inhibiting the motion of the hydrocarbon chains (Demel and de Kruij ff 1976;McIntosh 1978;Schwarz et al 1976). On the other hand, cholesterol alone causes the conversion to the hexagonal structure of PE bilayers (Cullis and de Kruijff 1978, and Fig.…”

Section: Discussionmentioning

confidence: 99%

Effects of cholesterol on the structural transitions induced by diacylglycerol in phosphatidylcholine and phosphatidylethanolamine bilayer systems

Coorssen¹,

Rand²

1990

Biochem. Cell Biol.

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C~R S S E N , J. R., and RAND, R. P. 1990. Effects of cholesterol on the structural transitions induced by diacylglycerol in phosphatidylcholine and phosphatidylethanolamine bilayer systems. Biochem. Cell Biol. 68: 65-69. The transient membrane lipid diacylglycerol (DG) is known to modify and destabilize phospholipid bilayers and can lead to the formation of nonbilayer structures. Since cholesterol forms a major fraction of many plasma membranes, we have investigated how it modifies the structural effects of DG on bilayers of egg phosphatidylcholine (PC) and egg phosphatidylethanolamine (PE). We view these systems as modelling the behaviour of local, DG-containing sites in membranes. Using X-ray diffraction, we have characterized the lamellar (L,) and inverse hexagonal (H,,) structures that these ternary lipid mixtures f~r m in excess aqueous solution. As the DG level increases, the lipid progresses from a single L, structure to a mixture of La and Hi,, and then to a pure Hi, structure. This allows determination of the DG levels at which the PI,, transition begins, which we interpret as those levels that destabilize bilayers. In both PC and PE bilayers, the presence of 30 molvo cholesterol reduces the amounts of DG required to destabilize the bilayer structure. The destabilization can be translated into the number of neighbouring lipid molecules that a DG molecule perturbs, and of bilayer areas that it affects. The data show that the presence of cholesterol greatly enhances the perturbing effects of DG. We examine the possible role of DG in enzyme activation and membrane fusion. COORSSEN, J. R., et RAND, R. P. 1990. Effects of cholesterol on the structural transitions induced by diacylglycerol in phosphatidylcholine and phosphatidylethanolamine bilayer systems. Biochem. Cell Biol. 68 : 65-69. Le diacylglyctrol (DG), lipide membranaire transitoire, est reconnu pour modifier et dtstabiliser les doubles couches phospholipides et peut conduire A la formation de structures non bilamellaires. Comme le cholesterol forme une fraction importante de plusieurs membranes plasmiques, nous avons rechercht comment il modifie les effets structuraux du DG sur les doubles couches de phosphatidylcholine (PG) d'oeuf et de phosphatidyltthanolamine (PE) d'oeuf. Nous considtrons ces syst&mes comme modelant le comportement des sites locaux renfermant le DG dans les membranes.Utilisant la diffraction des rayons X, nous avons caracttrist la structure lamellaire (L,) et la structure hexagonale inverse (His) que ces mtlanges de lipides ternaires forment dans une solution aqueuse en ex&. A mesure que la concentration du DG augmente, le lipide passe de la structure unique L, A un mtlange de structures La et H,, et finalement A une structure HBI. Cela permet de d4terminer A quels t a w de DG commence la transition HI, et nous interprdtons que ces taux sont ceux qui dtstabilisent les doubles couches. Dans les doubles couches de PC et les doubles couches de PE, la prtsence de cholesttrol (30 molvo) rtduit la quantitt de DG requise pour ddstabili...

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“…Although the wide distribution of ether lipids in biological tissues is now well established, and the biochemical pathways leading to ether lipid synthesis have been elucidated (Snyder et al, 1985), very little is known about the biological significance of most ether lipid species. In this regard, a better understanding of the physical properties of ether lipid bilayers should be useful, and towards that end, techniques such as surface balance (Paltauf et al, 1971), differential scanning calorimetry (Vaughan and Keough, 1974;Lee and Fitzgerald, 1980;Boggs et al, 1981;Seddon et al, 1983), x-ray diffraction (Schwarz et al, 1976), fluorescence spectroscopy (Bittman et al, 1981), vibrational spectroscopy (Mushayakarara and Huang et al, 1986;Levin et al, 1985a, Lewis et al, 1986 and NMR spectroscopy (Hauser, 1981;Hauser et al, 1981;Siminovitch et al, 1983; Ruocco et al, 1985a,b;Jarrell et al, 1986) have been used to study the physical properties of ether lipids in bilayers. Despite the diversity of physical techniques that have been used in these studies, the precise role that the ether linkage plays in modulating the physical properties of the lipid bilayer remains unclear.…”

Section: Introductionmentioning

confidence: 99%

“…This lowering of the lamellar-to-inverted hexagonal (HI,) phase-transition temperature, first observed by Boggs et al (1981) in a differential scanning calorimetry (DSC) study of synthetic ether-linked analogues of PE, reflects a destabilization of the lamellar phase by the ether linkage. In the case of the phosphatidylcholines, early investigations of DHPC using physical techniques such as DSC (Vaughan and Keough, 1974), x-ray diffraction (Schwarz et al, 1976), and high-resolution 'H-NMR (Hauser, 1981;Hauser et al, 1981) suggested that the replacement of ester linkages by ether bonds had little effect on thermal behavior, bilayer structure, or conformation of the phosphatidylcholine (PC) headgroup. However, more recent studies using DSC, x-ray diffraction, and solid-state '4N-, 31P_, and 2H-NMR (Siminovitch et al, 1983;Ruocco et al, 1985a,b) clearly indicate that the change in linkage does have a significant effect on structure and dynamics in the low temperature gel phases.…”

Section: Introductionmentioning

confidence: 99%

High-pressure infrared spectroscopy of ether- and ester-linked phosphatidylcholine aqueous dispersions

Siminovitch¹,

Wong²,

Mantsch³

1987

Biophysical Journal

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Infrared spectra of aqueous dispersions of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and its ether-linked analogue, 1,2-dihexadecyl-sn-glycero-3-phosphocholine (DHPC), were measured in a diamond anvil cell at 28 degrees C as a function of pressure up to 20 kbar. Although these two lipids differ only in the linkages to the saturated hydrocarbon chains, significant differences were observed in their barotropic behavior. Most notable were the magnitudes of the pressure-induced correlation field splittings of the methylene scissoring and rocking modes, and the relative intensities of the corresponding component bands. In the case of the scissoring mode, not only can the correlation field component band be resolved at a lower pressure in DHPC (1.2 kbar, as compared with 2.2 kbar in DPPC), but the initial magnitude of the correlation field splitting in DHPC, particularly less than 9 kbar, is significantly greater than that observed in DPPC. These differences are attributed to the presence of an interdigitated lamellar gel phase in DHPC. At all pressures where the correlation field component band delta'CH2 can be resolved, the relative peak height/intensity ratio R = I delta'/I delta is greater in DPPC than in DHPC, suggesting that this parameter may be useful as a test of interdigitation.

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Studies on the interaction of cholesterol with diester- and dietherlecithin

Cited by 45 publications

References 30 publications

A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

Effects of cholesterol on the structural transitions induced by diacylglycerol in phosphatidylcholine and phosphatidylethanolamine bilayer systems

High-pressure infrared spectroscopy of ether- and ester-linked phosphatidylcholine aqueous dispersions

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