The preference of cholesterol for phosphatidylcholine in mixed phosphatidylcholine-phosphatidylethanolamine bilayers

Dijck, P.W.M. Van; Kruijff, Ben de; Deenen, L.L.M. Van; Gier, J. De; Demel, R.A.

doi:10.1016/0005-2736(76)90326-6

Cited by 354 publications

(119 citation statements)

References 21 publications

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“…2A). This difference is no doubt due to the physical state of the molecules in the monolayer, dioleoyl phosphatidylethanolamine being in the liquid crystalline state (transition temperature --10°C) whereas the dipalmitoyl derivative is in the gel state (transition temperature 60 ° C) [17]. A similar result was obtained with the two phosphatidylserines, the reaction occurring with the saturated compound showing a smaller increase in surface pressure than that with the unsaturated compound.…”

Section: Resultssupporting

confidence: 53%

A monolayer study of the reaction of trinitrobenzene sulphonic acid with amino phospholipids

Bishop

Bevers

Meer

et al. 1979

Biochimica et Biophysica Acta (BBA) - Biomembranes

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SummaryThe reaction of trinitrobenzene sulphonic acid with amino phospholipids, and in particular phosphatidylethanolamine has been studied by the monolayer technique. Injection of trinitrobenzene sulphonic acid under a monolayer of amino phospholipid results in an increase in surface pressure. The rate and extent of the pressure change is greatly affected by the initial surface pressure, the fatty acid composition of the lipid, and the presence of other non-reactive lipids, especially negatively charged phospholipids.The extent of the reaction was measured with 32P-labelled phospholipids isolated from Bacillus subtilis. Only about 80% of the phosphatidylethanolamine in the monolayer could be converted to its trinitrophenyl derivative. In the presence of negatively charged phospholipids such as cardiolipin or phosphatidylglycerol, a further 20% decrease in the trinitrophenylation of phosphatidylethanolamine was found. The pressure increase occurring during trinitrophenylation could also be correlated with the extent of the reaction by comparison of the force-area curves of pure phosphatidylethanolamine, its trinitrophenyl derivative and mixtures of both compounds.The data may offer an explanation for the observation that incomplete labelling of amino phospholipids frequently occurs in natural membranes and furthermore indicate that the use of chemical labelling techniques in the study of lipid asymmetry in biological membranes must be approached with great caution.

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Section: Resultssupporting

confidence: 53%

A monolayer study of the reaction of trinitrobenzene sulphonic acid with amino phospholipids

Bishop

Bevers

Meer

et al. 1979

Biochimica et Biophysica Acta (BBA) - Biomembranes

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“…To check the reproducibility of the results, three heating scans were recorded for each sample. Cooling scans yielded thermograms very similar to the heating scans, but and according to the literature [40], the transitions in cooling curves were shifted by about 1³C to lower temperatures. Therefore, due to the supercooling phenomenon, accurate thermotropic transitions are evaluated from heating curves.…”

Section: Di¡erential Scanning Calorimetry (Dsc)supporting

confidence: 72%

Lipid composition and dynamics of cell membranes of Bacillus stearothermophilus adapted to amiodarone

Rosa¹,

Antunes-Madeira²,

Matos³

et al. 2000

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

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Bacillus stearothermophilus, a useful model to evaluate membrane interactions of lipophilic drugs, adapts to the presence of amiodarone in the growth medium. Drug concentrations in the range of 1^2 WM depress growth and 3 WM completely suppresses growth. Adaptation to the presence of amiodarone is reflected in lipid composition changes either in the phospholipid classes or in the acyl chain moieties. Significant changes are observed at 2 WM and expressed by a decrease of phosphatidylethanolamine (relative decrease of 23.3%) and phosphatidylglycerol (17.9%) and by the increase of phosphoglycolipid (162%). The changes in phospholipid acyl chains are expressed by a decrease of straight-chain saturated fatty acids (relative decrease of 12.2%) and anteiso-acids (22%) with a parallel increase of the iso-acids (9.8%). Consequently, the ratio straight-chain/branched iso-chain fatty acids decreases from 0.38 (control cultures) to 0.30 (cultures adapted to 2 WM amiodarone). The physical consequences of the lipid composition changes induced by the drug were studied by fluorescence polarization of diphenylhexatriene and diphenylhexatriene-propionic acid, and by differential scanning calorimetry. The thermotropic profiles of polar lipid dispersions of amiodarone-adapted cells are more similar to control cultures (without amiodarone) than those resulting from a direct interaction of the drug with lipids, i.e., when amiodarone was added directly to liposome suspensions. It is suggested that lipid composition changes promoted by amiodarone occur as adaptations to drug tolerance, providing the membrane with physico-chemical properties compatible with membrane function, counteracting the effects of the drug. ß

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“…Incorporation of cholesterol into saturated or unsaturated phosphatidylethanolamines broadened the melting transition, decreased the heat content of the transition and shifted the transition temperature to lower values [25]. At a concentration of 50 mol% the transition as detected by DSC was completely suppressed.…”

Section: Discussionmentioning

confidence: 97%

Sterol-phospholipid interactions in model membranes Effect of polar group substitutions in the cholesterol side-chain at C20 and C22

Gallay

Kruijff

Demel

1984

Biochimica et Biophysica Acta (BBA) - Biomembranes

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The interactions of phospholipids with four different cholesterol derivatives substituted with one OH or one keto group at position C2o or C22 of the side-chain were studied. The derivatives were the 22,R-hydroxy; 22,S-hydroxy; 22-keto-and 20,S-hydroxycholesterol. Two aspects of the interactions were investigated: (1) the effect of the cholesterol derivatives on the gel--, liquid crystalline phase transition of dipalmitoylphosphatidylcholine (DPPC) and of dielaidoyiphosphatidylethanolamine (DEPE) monitored by differential scanning calorimetry and (2) The effect on the lamellar--, hexagonal H n phase transition of DEPE monitored by DSC and by 3t P-NMR to determine structural changes. The gel ---, liquid crystalline phase transition was affected by the cholesterol derivatives to a much larger extent in the case of DPPC than of DEPE. In both cases, there was a differential effect of the four derivatives, the 22,R-hydroxycholesterol being the less effective. In DPPC-sterol 1 : 1 systems, 22,R-hydroxycholesterol does not suppress the melting transition, the AH values becomes 7.1 kcal. mol-1 as compared to 8.2 kcal. mol-1 for the pure lipid. 22,S-OH cholesterol has a much stronger effect (AH = 3.1 kcai. tool-1) and 22-ketocholesterol suppresses the transition completely. In DEPE mixtures of all these compounds, the melting transition of the phospholipid is still observable. The transition temperature was shifted to lower values (-13.5°C in the presence of 20,S-OH cholesterol). The AH of the transition was lowered by these compounds except in DEPE-22,R-OH cholesterol mixtures and the cooperativity of the transition (reflected by the width at half peak height) was reduced. The lameilar --, hexagonal H t~ phase transition was also affected by the presence of these cholesterol derivatives. The transition temperature value was depressed with all these compounds. 20,S-OH cholesterol was the most effective followed by 22,R-OH cholesterol. The AH of the transition was not strongly affected. The molecular intedacial properties of these derivatives were studied by the monomolecular film technique. It is most likely that 22,R-OH cholesterol due to the hydroxyl groups at the * To whom correspondence should be sent at (present address): E.R. No. 64 du Centre National de la Recherche Scientifique, Unit~ d'Enseignements et de Recherche Biom~dicale des Saints-P~res, 45, rue des Saints-P~res, 75270 Paris C~dex 06, France. Abbreviations: DEPE, 1,2-dielaidoyl-sn-glycero-3-phosphoethanolamine; DOPE, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine; DPPC, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine; DOPC, 1,2-dioleoyl-sn-glycero-3-phosphocholine; EDTA, ethylenediaminetetraacetic acid; 22,R-OH cholesterol, (22,22,(22,20, 22-ketocholesterol, 5-cholestene-3fl-ol-22-one; cytochrome P-450sc¢, cytochrome P-450 specific for the side-chain cleavage of cholesterol.0005-2736/84/$03.00 © 1984 Elsevier Science Publishers B.V. 973~-and 22,R-positions orients with the sterol nucleus lying flat at the air/water interface, since the compression isotherm...

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The preference of cholesterol for phosphatidylcholine in mixed phosphatidylcholine-phosphatidylethanolamine bilayers

Cited by 354 publications

References 21 publications

A monolayer study of the reaction of trinitrobenzene sulphonic acid with amino phospholipids

A monolayer study of the reaction of trinitrobenzene sulphonic acid with amino phospholipids

Lipid composition and dynamics of cell membranes of Bacillus stearothermophilus adapted to amiodarone

Sterol-phospholipid interactions in model membranes Effect of polar group substitutions in the cholesterol side-chain at C20 and C22

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