Phosphatidylcholine liposomes containing cholesterol analogues with side chains of various lengths

Nakamura, Tatsunosuke; Nishikawa, Masahiko; Inoue, Kazuhide; Nojima, Shoshichi; Akiyama, Tsuyoshi; Sankawa, Ushio

doi:10.1016/0009-3084(80)90014-6

Cited by 41 publications

(14 citation statements)

References 33 publications

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“…Our results showing that only cholesterol-containing BLMs are susceptible to the hemolysin are reminiscent of earlier studies (39) in which it was reported that digitonin induced a noticeable change in glucose permeability of vesicles of egg yolk lecithin containing cholesterol, but not of cholesterol-free vesicles. Digitonin/cholesterol complex formation in the membranes has been established a long time ago (19,20), and these data suggest that complex formation might be related to the hemolytic activity.…”

Section: Discussionsupporting

confidence: 77%

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Yuldasheva

Carvalho

Catanho

et al. 2005

Braz J Med Biol Res

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Plants used in traditional medicine are rich sources of hemolysins and cytolysins, which are potential bactericidal and anticancer drugs. The present study demonstrates for the first time the presence of a hemolysin in the leaves of Passiflora quadrangularis L. This hemolysin is heat stable, resistant to trypsin treatment, has the capacity to froth, and acts very rapidly. The hemolysin activity is dose-dependent, with a slope greater than 1 in a double-logarithmic plot. Polyethylene glycols of high molecular weight were able to reduce the rate of hemolysis, while liposomes containing cholesterol completely inhibited it. In contrast, liposomes containing phosphatidylcholine were ineffective. The Passiflora hemolysin markedly increased the conductance of planar lipid bilayers containing cholesterol but was ineffective in cholesterol-free bilayers. Successive extraction of the crude hemolysin with n-hexane, chloroform, ethyl acetate, and n-butanol resulted in a 10-fold purification, with the hemolytic activity being recovered in the n-butanol fraction. The data suggest that membrane cholesterol is the primary target for this hemolysin and that several hemolysin molecules form a large transmembrane water pore. The properties of the Passiflora hemolysin, such as its frothing ability, positive color reaction with vanillin, selective extraction with n-butanol, HPLC profile, cholesterol-dependent membrane susceptibility, formation of a stable complex with cholesterol, and rapid erythrocyte lysis kinetics indicate that it is probably a saponin.

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Section: Discussionsupporting

confidence: 77%

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Yuldasheva

Carvalho

Catanho

et al. 2005

Braz J Med Biol Res

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“…It has been shown that the complete side-chain was required for maximizing the ordering effect of cholesterol, whereas either a longer or a shorter chain was less effective [20]. At least an isopropyl side-chain is needed to suppress the permeability increase at the phase transition [21]. On the other hand, plant sterols such as ergosterol and stigmasterol exhibit an ordering effect similar to that of cholesterol, despite the substitution by a methyl or ethyl group in the side-chain and the presence of a double bond [12,22].…”

Section: Discussionmentioning

confidence: 99%

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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“…Both model membrane experiments and studies on biological membranes have revealed that the sterol structure is of critical importance for the sterol phospholipid interaction [8,9]. A planar ring system and a side chain at C~7 of at least 4 carbon atoms [10], were found to be prerequisites both for the condensing and liquifying effect. It was, however, found that cholesterol caused the greatest rigidifying effect and that analogues with shorter or longer side chains were less effective [11,12].…”

Section: Introductionmentioning

confidence: 99%

The effect of the sterol oxygen function on the interaction with phospholipids

Demel

Lala

Kumari

et al. 1984

Biochimica et Biophysica Acta (BBA) - Biomembranes

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The effect of cholesteryi ethers (namely cholesteryl methyl ether, cholesteryi ethyl ether, cholesteryl n-propyl ether, cholesteryi isopropyl ether, cholesteryi butyl ether, cholesteryl methoxymethyl ether, cholesteryl (2'-hydroxy)-3-ethyl ether) and cholesteryl ester (namely cholesteryi acetate) is tested on the interaction with phosphatidylcholines in liquid-crystalline and crystalline state. The interfacial properties of sterols are tested at the air-water interface. The cholesteryl ethers show a reduced interracial stability with increasing hydrophobicity of the ether-linked moiety. The interaction between the sterol derivatives and phospholipids in mixed monolayers is indicated by measuring the deviation from the simple addivity rule (condensing effect). An interaction is found only for cholesteryl (2'-hydroxy)-3-ethyl ether, cholesteryl methyl ether and cholesteryl ethyl ether. These sterols also reduce the glucose permeability of liposomal membranes in this order. In this respect cholesteryl (2'-hydroxy)-3-ethyl ether is as effective as cholesterol. Cholesteryl methyl ether and cholesteryl ethyl ether show 62 and 33 percent of the effect observed with cholesterol. The effect of the sterol derivatives on the gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine is measured by differential scanning calorimetry. Cholesteryl methyl ether, cholesteryl ethyl ether, and cholesteryl (2'-hydroxy)-3-ethyl ether reduce the energy content of the phase transition nearly as effective as cholesterol, cholesteryl n-propyl ether has only a small effect. Although cholesteryl acetate, and cholesteryl methoxymethyl ether have no condensing or permeability-reducing effect, they have a considerable effect on the gel-to-liquid-crystalline phase transition. Cholesteryi isopropyl ether and cholesteryl butyl ether have no effect. It is concluded that a free 30-hydroxy group is not a prerequisite to observe a sterol-like effect in membranes. However, the interfacial stability and the orientation of the sterol and oxygen moiety at the sterol 3-position are important.

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Phosphatidylcholine liposomes containing cholesterol analogues with side chains of various lengths

Cited by 41 publications

References 33 publications

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

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

The effect of the sterol oxygen function on the interaction with phospholipids

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