Permeability of cryptands through dihexadecyl phosphate bilayer membranes

Castaing, Madeleine; Kraus, Jean‐Louis; Ponge, Christian

doi:10.1016/0301-4622(91)85003-9

Cited by 4 publications

(6 citation statements)

References 31 publications

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“…The dye leakage approach has proved to be a useful tool in the ®eld of pharmacology (Menassa & Sandorfy 1986;Castaing et al 1991;Sikkema et al 1994;Callaghan & Riordan 1995;Drori et al 1995). Drug±membrane interactions are generally quanti®ed by measuring carboxy¯uorescein leakage through membranes.…”

Section: Discussionmentioning

confidence: 99%

“…An alternative interpretation is that the phospholipid organization in the bilayer may be destabilized when several ligand molecules interact concomitantly at the same site on the membrane. Co-operative processes of this kind have previously been found to exist in the ®eld of liposome (Castaing et al 1991) and cell (Cano-Gauci & Riordan 1987) permeation by structurally unrelated compounds. According to Koshland's induced-®t theory (Korolkovas 1970a), which was put forward to explain the mode of drug action, deep conformational perturbations may occur as the result of the binding of a ligand to a receptor.…”

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confidence: 90%

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Membrane Permeation by Multidrug-resistance-modulators and Non-modulators: Effects of Hydrophobicity and Electric Charge

Castaing

Brouant

Loiseau

et al. 2000

Journal of Pharmacy and Pharmacology

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This study was designed to test the hypothesis that lipophilic cationic drugs with only roughly similar structures mediate the reversal of multidrug-resistance (MDR) by interacting with membrane phospholipids. The permeation properties of MDR-modulators and non-modulators were studied by quantifying their ability to induce the leakage of Sulphan blue through the membrane of negatively charged unilamellar liposomes. Of the 22 compounds under investigation, only those bearing a net positive electric charge per molecule (z) > or = 0.2 induced dye leakage. All these efficient drugs are well-known MDR-modulators: calcium-channel blockers (propranolol, verapamil, diltiazem and dipyridamole), calmodulin antagonists (clomipramine and thioridazine) and antiparasitic agents (mepacrine, thioacridine derivatives and quinine). The non-modulators tested, including antineoplastic agents and steroids, did not induce any membrane permeation. The permeation process was a co-operative one (1.1< Hill coefficient < 4.1) and the permeation doses inducing 50% dye leakage (PD50) were 1.9-11.2 mM. The permeation ability of the MDR-modulators (log(1/PD50)) increased significantly with octanol-buffer distributions per unit net electric charge ((logD)/z). The results provide evidence that a complex interplay occurs between the electric charge and the lipophilicity of the MDR-modulators when a dye leakage is induced through model membranes, and probably also when the MDR is reversed in leukaemic cells.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 90%

Membrane Permeation by Multidrug-resistance-modulators and Non-modulators: Effects of Hydrophobicity and Electric Charge

Castaing

Brouant

Loiseau

et al. 2000

Journal of Pharmacy and Pharmacology

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“…2+ is observed in the basic, negatively charged, form of dihexydecyl phosphate membranes, 58,68 whereas slow leakage is observed in the acidic, neutral, form of the same membranes. These results and observations show that membrane surface charge is an important contributor to membrane permeability in vesicle systems composed of short chain acidic amphiphiles.…”

Section: àmentioning

confidence: 95%

“…2+ has been reported in dihexadecyl phosphate 58 and phospholipid vesicles 59 under certain conditions. The tetraanionic Ru(5,5 0 -dicarboxy-2,2-bpy) 3 4À species was, however, encapsulated in decanoic acid vesicles efficiently for at least 6-12 h after the initial separation from free solute (P > 1 Â 10 À10 cm s À1 ).…”

Section: Solute Permeability and Passive Transport In Mixed Fatty Aci...mentioning

confidence: 95%

“…Charge-charge repulsion between the anionic solutes and the carboxylate headgroups on the membrane surface tends to lead to a high barrier in the first step for anionic solutes, but a low barrier for cationic solutes, which strongly adsorb to the membrane surface. 58,63,68,70,71 The second barrier to transport can be understood in terms of the Born energy for partitioning of the solute into low dielectric region of the bilayers, which can be predicted qualitatively using water : octanol partition coefficients. An additional factor affecting the permeability of cationic species is ion pairing with deprotonated fatty acids followed by trans-membrane diffusion as a net neutral species, although this additional mechanism is at present speculative.…”

Section: àmentioning

confidence: 99%

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Prebiotically relevant mixed fatty acid vesicles support anionic solute encapsulation and photochemically catalyzed trans-membrane charge transport

2011

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The spontaneous assembly of amphiphile-based compartments in aqueous solution is widely viewed as a key step in models for the abiotic formation of primitive cell-like structures. Proposed organic components for such systems consist of mixed short chain fatty acids (FA) and polycyclic aromatic hydrocarbon (PAH) species, the composition of which have been modeled after organic extracts of carbonaceous meteorites. Self-assembly of amphiphiles from these extracts into aqueous suspensions of bilayer structures was long ago demonstrated, although little has since been reported concerning the stability and potential functionality of these complex mixtures. This work explores the thermodynamic and kinetic stability of vesicles prepared from complex mixtures of short chain FA species (CH 3 COOH-C 9 H 19 COOH) with membrane solubilized PAH species. Critical vesicle concentration measurements and ultrafiltration analyses of decanoic acid in the presence of other shorter chain FA species indicate the formation of mixed component vesicle phases composed mainly of C 10 -C 8 FA components. An electrostatic barrier to trans-membrane diffusion of negative charges allows observation of stably encapsulated poly-anionic solutes inside these vesicles. As a model for primitive energy transduction, trans-membrane electron transfer between EDTA and encapsulated ferricyanide was demonstrated, driven catalytically via PAH photochemistry without substantial decomposition of the chromophores or vesicles. These results indicate a plausible role for compartmentalization and catalysis by short chain fatty acids and PAH species in prebiotic vesicle-encapsulated systems.

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Passive permeability of dihexadecyl phosphate vesicles altered by aliphatic alcohols and ω-diols

Castaing

Jallon

Camplo

et al. 1991

Pharmacological Research

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Permeability of cryptands through dihexadecyl phosphate bilayer membranes

Cited by 4 publications

References 31 publications

Membrane Permeation by Multidrug-resistance-modulators and Non-modulators: Effects of Hydrophobicity and Electric Charge

Membrane Permeation by Multidrug-resistance-modulators and Non-modulators: Effects of Hydrophobicity and Electric Charge

Prebiotically relevant mixed fatty acid vesicles support anionic solute encapsulation and photochemically catalyzed trans-membrane charge transport

Passive permeability of dihexadecyl phosphate vesicles altered by aliphatic alcohols and ω-diols

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