Cholesterylphosphate incorporation in egg phosphatidylcholine vesicles : Gel chromatography, and fluorescence polarization studies

Colombat, A.; Motta, Claude; Jouanel, P; Greil, J.D.; Panouse-Perrin, J; Dastugue, B.; Delattre, Jacques

doi:10.1016/s0300-9084(81)80040-5

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…They found the change to be similar to that caused by the same molar ratio of cholesterol. Colombat et al (1981) arrived at a similar conclusion for the effect of cholesteryl phosphate.…”

Section: Discussionmentioning

confidence: 55%

“…Reports in the literature concerning a number of hydrophilic substituents of the /3-OH group of cholesterol indicated that such derivatives in phospholipids membranes behave in many respects like cholesterol (Lyte & Shinitzky, 1979 lombat et al, 1981;Demel et al, 1984). The increase in lipid membrane microviscosity and degree of order caused by cholesterylphosphocholine (Lyte & Shinitzky, 1979) and cholesteryl phosphate (Colombat et al, 1981) is close to that induced by cholesterol. Although the crystal structures of cholesteryl phosphate and cholesteryl sulfate have been elucidated (Pascher & Sundell, 1977, 1982, little additional information is available on the interaction between charged esters of cholesterol or -tocopherol and phospholipids.…”

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confidence: 93%

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Effects of replacement of the hydroxyl group of cholesterol and tocopherol on the thermotropic behavior of phospholipid membranes

Lai¹,

Düzgüneş²,

Szoka³

1985

Biochemistry

118

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The role of the hydroxyl groups of cholesterol and tocopherol in mediating their interaction with phospholipid bilayers has been a subject of considerable interest. We have examined this question by using derivatives of cholesterol and tocopherol in which the hydroxyl group is esterified to succinate. The hemisuccinate esters of cholesterol and alpha-tocopherol can be readily incorporated into phospholipid membranes and in fact can by themselves form closed membrane vesicles as demonstrated by the encapsulation of [3H]sucrose. The thermotropic behavior of mixtures containing each succinate ester and phospholipid was studied by differential scanning calorimetry. The effect of cholesteryl hemisuccinate on the thermotropic properties of dipalmitoylphosphatidylcholine and dimyristoylphosphatidylethanolamine is very similar to that of cholesterol. This indicates that the 3 beta-OH is not required for the formation of a cholesterol-phospholipid complex. In mixtures of tocopherol acid succinate and phospholipids the peak transition temperature is progressively shifted to lower temperatures as the mole fraction of alpha-tocopherol succinate is increased, while the enthalpy of the transition is only slightly affected. At a tocopherol succinate/phospholipid molar ratio of 9/1 a phase transition is still detectable. A comparison between tocopherol succinate and tocopherol indicates that the substitution of the hydroxyl group reduces the interaction of tocopherol with phospholipids to a small but measurable extent. Thus, the hydroxyl group of tocopherol is more important than the hydroxyl group of cholesterol in influencing their interactions with phospholipids.

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“…They found the change to be similar to that caused by the same molar ratio of cholesterol. Colombat et al (1981) arrived at a similar conclusion for the effect of cholesteryl phosphate.…”

Section: Discussionmentioning

confidence: 55%

mentioning

confidence: 93%

Effects of replacement of the hydroxyl group of cholesterol and tocopherol on the thermotropic behavior of phospholipid membranes

Lai¹,

Düzgüneş²,

Szoka³

1985

Biochemistry

118

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“…While it is difficult to accommodate neutral cholesteryl esters into bilayers, a number of charged 3-O-cholesteryl esters can easily be incorporated into a liposome structure and some can even form liposomes by themselves (Colombat et al, 1981;Brockerhoff & Ramsammy, 1982). In this study, we have shown that it is possible to form stable liposomes from TPE or DOPE and the cholesteryl ester CHEMS at pH 7.5.…”

Section: Discussionmentioning

confidence: 72%

pH-Induced destabilization of phosphatidylethanolamine-containing liposomes: role of bilayer contact

Ellens¹,

Bentz²,

Szoka³

1984

Biochemistry

442

343

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The mechanism of pH-induced destabilization of liposomes composed of phosphatidylethanolamine and a charged cholesteryl ester was studied by following the release of encapsulated aqueous contents. The kinetics of release were measured continuously by using the water-soluble fluorophore 8-aminonaphthalene-1,3,6-trisulfonic acid in combination with the water-soluble quencher p- xylylenebis (pyridinium) bromide. With this fluorescence assay, release of contents from liposomes composed of phosphatidylethanolamine and cholesteryl hemisuccinate was shown to be a function of pH, ratio of phosphatidylethanolamine to cholesteryl hemisuccinate, and acyl chain composition of the phosphatidylethanolamine. Leakage was very slow at pH 5.5 and increased dramatically with decreasing pH down to 4.0. Replacing phosphatidylethanolamine by phosphatidylcholine eliminated the effect of pH on leakage. Analysis of the kinetics of release by a mass action model demonstrated that bilayer destabilization and leakage occur subsequent to aggregation. The requirement of bilayer contact for destabilization has been found previously for acidic phospholipid bilayers in the presence of divalent cation and for saturated phosphatidylcholine bilayers below the isothermal phase transition temperature. The phosphatidylethanolamine-containing bilayers examined here satisfy the same requirement.

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“…The increase in order obtained with Chol SO4 exhibited an almost linear relationship to the fraction of the ester in the suspension. Using the same technique, other cholesterol esters, e.g., cholesteryl phosphorylcholine (15), cholesteryl hemisuccinate, cholesteryl betainate (16) and cholesteryl phosphate (17), have also been shown to increase, although to a lesser extent than cholesterol, the degree of order of egg PC liposomes or of lipids from the red blood cell. The use of DPPC enables us to demonstrate that for temperatures below the Tin, Chol SO4 also decreased the order of acyl chains.…”

Section: And Discussionmentioning

confidence: 99%

Cholesteryl sulfate‐phosphatidylcholine interactions

Daigneault

Bleau

Roberts

1984

Lipids

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The effect of cholesteryl sulfate, a natural membrane component, on the physical state of dipalmitoyl phosphatidylcholine multilamellar vesicles was investigated using fluorescence polarization and differential scanning calorimetry techniques. Cholesteryl sulfate increased the order of acyl chains for those temperatures higher than the gel‐to‐liquid crystalline transition temperature while it decreased the order for those temperatures below the phase transition temperature. At equimolar concentrations, cholesteryl sulfate suppressed the crystal liquid‐to‐gel phase transition of dipalmitoyl phosphatidylcholine. These data suggest that sterol sulfates may provide new tools for the elucidation of molecular mechanisms involved in sterollipid interactions.

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Cholesterylphosphate incorporation in egg phosphatidylcholine vesicles : Gel chromatography, and fluorescence polarization studies

Cited by 6 publications

References 18 publications

Effects of replacement of the hydroxyl group of cholesterol and tocopherol on the thermotropic behavior of phospholipid membranes

Effects of replacement of the hydroxyl group of cholesterol and tocopherol on the thermotropic behavior of phospholipid membranes

pH-Induced destabilization of phosphatidylethanolamine-containing liposomes: role of bilayer contact

Cholesteryl sulfate‐phosphatidylcholine interactions

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