Correlation between molecular shape and hexagonal H<sub>II</sub> phase promoting ability of sterols

Gallay, Jacques; Kruijff, Ben de

doi:10.1016/0014-5793(82)80289-5

Cited by 62 publications

(38 citation statements)

References 16 publications

(10 reference statements)

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“…The most effective sterol was the 20,S-OH derivative, followed by 22,R-OH cholesterol which in fact exhibited the largest shift at low concentrations. In contrast to what was found for a series of sterol derivatives modified on the polar group at the 3-position [4], there is no clear correlation between the bilayer-destabilizing effect of the sterols used in this study and their molecular surface area. The monolayer studies evidence that these sterols exhibit a larger molecular area than cholesterol at moderate surface pressure (12 mN.…”

Section: Discussioncontrasting

confidence: 99%

“…All the sterol derivatives induced a shift of the bilayer ~ hexagonal H~I phase transition of DEPE to lower temperatures as observed by DSC and 31p_NMR without modifying significantly the A H of the transition. This effect is much more pronounced than in the case of cholesterol itself [4]. The most effective sterol was the 20,S-OH derivative, followed by 22,R-OH cholesterol which in fact exhibited the largest shift at low concentrations.…”

Section: Discussionmentioning

confidence: 83%

“…In addition, cholesterol and derivatives affect also the lipid polymorphism of non-bilayer-forming lipids [2][3][4][5]. This effect is related to their dynamical shape as estimated by their properties in monomolecular films [4].…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Discussioncontrasting

confidence: 99%

Section: Discussionmentioning

confidence: 83%

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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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“…Finally, as previously mentioned the ability of 'helper' lipids such as DOPE and cholesterol to adopt or promote H II organization in mixed lipid systems has been well described elsewhere. 26,38,40 The ability of cationic lipids to induce inverted nonbilayer structures in combination with anionic lipids leads naturally to a model describing intracellular delivery of nucleic acid polymers mediated by cationic lipids. The model is shown in Figure 6 and is an extension of the model previously proposed by Szoka and co-workers.…”

Section: Discussionmentioning

confidence: 99%

“…This is consistent with the previously noted ability of cholesterol to promote the H II phase in a variety of mixed phospholipid systems. [38][39][40] Influence of cationic lipid structure on the polymorphism of mixtures of cationic and anionic lipids It is well known that the chemical structure of cationic lipids can strongly influence the transfection potency of plasmid DNA-cationic lipid complexes formed from them. Although a detailed correlation between the transfection potency of complexes formed from different cationic lipids and the polymorphic phase preferences of these lipids in mixtures with anionic lipids is outside the scope of this study, it is important to point out that the ability of cationic lipids to adopt H II phase structure does offer the possibility of obtaining a measurable parameter to correlate with transfection potency.…”

Section: Gene Therapymentioning

confidence: 99%

On the mechanism whereby cationic lipids promote intracellular delivery of polynucleic acids

2001

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The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

Debieu

Bach

Hugon

et al. 2001

Pest Management Science

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Fenhexamid, a recently developed botryticide, is shown here to inhibit sterol biosynthesis. When the fungus Botryotinia fuckeliana was grown in the presence of fenhexamid, the ergosterol content was reduced, and three 3-keto compounds, 4 alpha-methylfecosterone, fecosterone and episterone, accumulated, suggesting an inhibition of the 3-keto reductase involved in C-4 demethylation. Thus, fenhexamid belongs to a new, promising class of sterol biosynthesis inhibitors not previously used in agriculture or in medicine.

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Correlation between molecular shape and hexagonal H_II phase promoting ability of sterols

Cited by 62 publications

References 16 publications

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

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

On the mechanism whereby cationic lipids promote intracellular delivery of polynucleic acids

The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

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Correlation between molecular shape and hexagonal HII phase promoting ability of sterols

Cited by 62 publications

References 16 publications

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

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

On the mechanism whereby cationic lipids promote intracellular delivery of polynucleic acids

The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

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Correlation between molecular shape and hexagonal H_II phase promoting ability of sterols