Interaction of Basic Drugs with Lipid Bilayers Using Liposome Electrokinetic Chromatography

Carrozzino, Jennifer M.; Khaledi, Morteza G.

doi:10.1007/s11095-004-7685-3

Cited by 55 publications

(40 citation statements)

References 42 publications

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“…The bilayer structure of vesicles resembles that of cell membranes, and although many components of the latter such as peripheral and integral membrane proteins, ionchannels, etc., are typically not included by design in vesicle PSPs for a variety of reasons (increased cost, complexity, lack of commercial availability), both surfactant-and phospholipid-based vesicles have nevertheless proven to be useful for modeling a number of biological and nonbiological processes [50][51][52][53] including the prediction/estimation of drug absorption [54], blood-brain barrier penetration [55], intestinal permeability [56], drug interactions with lipid bilayers [53,57,58], protein-liposome interactions [59], octanolwater partitioning [45,60,61], etc.…”

Section: Introductionmentioning

confidence: 99%

Compositional effects on electrophoretic and chromatographic figures of merit in electrokinetic chromatography with cetyltrimethylammonium bromide/sodium octyl sulfate vesicles as the pseudostationary phase. Part 1: Effect of the phase ratio

et al. 2008

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The effect of the phase ratio on the electrophoretic and chromatographic properties of unilamellar vesicles comprised of cetyltrimethylammonium bromide (CTAB) and sodium octyl sulfate (SOS) was investigated in EKC. The surfactant concentration of the vesicles was 0.9, 1.2, 1.5, and 1.8% w/v, with a mole ratio of 1:3.66 (CTAB/SOS). Results were compared to those obtained using SDS micelles at concentrations of 1.0% (w/v, 35 mM) and 1.5% (52 mM). The CTAB/SOS vesicles (0.9-1.8% w/v) provided a significantly larger elution range (5.7 < or = t(ves)/t(0) < or = 8.7) and greater hydrophobic (methylene) selectivity (2.8 < or = alpha(CH2) < or = 3.1) than SDS micelles (3.1 < or = t(mc)/t(0) < or = 3.3; alpha(CH2) = 2.2). Whereas the larger elution range can be attributed to the 25% reduction in EOF due to the interaction of unaggregated CTAB cations and the negatively charged capillary wall, the higher methylene selectivity is likely due to the lower concentration of water expected in the CTAB/SOS vesicle bilayer compared to the Palisades layer of SDS micelles. For a given phase ratio, CTAB/SOS vesicles are somewhat less retentive than SDS micelles, although retention factors comparable to those observed in 1.0-1.5% SDS can be obtained with 1.5-1.8% CTAB/SOS. A linear relationship was observed between phase ratio and retention factor, confirming the validity of the phase ratio model for these vesicles. Unique polar group selectivities and positional isomer shape selectivities were obtained with CTAB/SOS vesicles, with both types of selectivities being nearly independent of the phase ratio. For four sets of positional isomers, the elution order was always para < ortho < meta. Finally, the thermodynamics of solute retention was qualitatively similar to that reported for other surfactant aggregates (micelles and microemulsions); the enthalpic contribution to retention was consistently favorable for all compounds, whereas the entropic contribution was favorable only to hydrophobic solutes.

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Section: Introductionmentioning

confidence: 99%

Compositional effects on electrophoretic and chromatographic figures of merit in electrokinetic chromatography with cetyltrimethylammonium bromide/sodium octyl sulfate vesicles as the pseudostationary phase. Part 1: Effect of the phase ratio

et al. 2008

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“…For this reason, they can be analyzed by CE, and they proved useful as anionic pseudostationary phases in EKC ( ; for recent reviews see [23,24]. It was found that, besides the pH, the kind of the electrolytes [6,25] and its ionic strength [5,18], and the preparation procedure of the vesicles influences the electrophoretic properties of the particles [23,26]. If their electrophoretic mobility is affected upon attachment of ligands, this change can be used to assess, or even quantify, the interaction in a form of ACE.…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoresis of liposomes functionalized for protein binding

et al. 2006

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CE enabled assessing the attachment of hexa-histidine-tagged proteins to functionalized phospholipid liposomes. The liposomes were made of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, phosphatidyl-ethanolamine, cholesterol and distearoyl-glycero-3-phosphoethanolamine-N-methoxy(polyethylene glycol) in a molar ratio of 29:26:40:5. The unilamellar vesicles, which had an average diameter of 170 nm, were labelled by inclusion of FITC-dextran for fluorescence detection. CE was carried out in poly(vinyl alcohol) (PVA)-coated capillaries at 25 degrees C with a BGE consisting of Tris-HCl (50 mM, pH 8.0). For conjugation of the liposomes with the proteins (soluble synthetic receptor fragments with molecular mass of 60 and 70 kDa, respectively), Ni(2+) was implanted into the vesicle surface by an anchor lipid containing a nitrilotriacetate acid (NTA) group as complexation agent for the metal ions. The difference in surface charge enabled the separation of the different species of interest by CE: plain vesicles, vesicles functionalised with Ni-NTA, vesicle-protein complexes and the species formed upon removal of the Ni-ions by complexation with EDTA. Loss of the Ni-ions resulted in the release of the proteins and the reappearance of the plain Ni-free NTA-liposome species in the electropherograms.

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“…Also, CE has been used to assess liposomal drug delivery systems in a few cases [18][19][20][21][22]. Liposomes have, however, primarily been introduced into capillaries in studies directed at estimating drug lipophilicity in relation to membrane permeability properties [2][3][4][5][23][24][25][26][27][28]. These studies have been conducted using the liposomes as a pseudostationary phase, i.e., by EKC [2-5, 23-26, 28] or by CEC [27].…”

mentioning

confidence: 99%

“…The differences observed between the two lipophilicity estimates at pH 7.4 may at least to some extent be ascribed to electrostatic interactions between the partly charged compounds and the net negatively charged liposomal phase, which are not present in the octanol-water system. Biological membranes are negatively charged and, thus, liposomes with lipid compositions like the one employed in the current study, may be better suited for predicting drug bioavailability and passive transport over epithelia as compared to the octanol-water distribution [3][4][5].…”

mentioning

confidence: 99%

Drug–liposome distribution phenomena studied by capillary electrophoresis‐frontal analysis

et al. 2008

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The potential of using CE frontal analysis (CE-FA) for the study of low-molecular-weight drug-liposome interactions was assessed. The interaction of bupivacaine, brompheniramine, chlorpromazine, imipramine, and ropivacaine with net negatively charged 80/20 mol% 1-oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine/egg yolk phosphatidic acid liposome suspensions in HEPES buffer at pH 7.4 was investigated. The fraction of free drug as a function of lipid concentration was measured and apparent liposome-buffer distribution coefficients were determined for the basic drug substances. The distribution coefficients increased in the order ropivacaine, bupivacaine, brompheniramine, imipramine, and chlorpromazine. The developed CE method was relatively fast allowing estimates of drug-liposome affinity to be obtained within 15 min. CE-FA may have the potential to become a valuable tool for the characterization of drug-liposome interactions in relation to estimation of drug lipophilicity and for the evaluation of drug distribution in liposomal drug delivery systems.

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Interaction of Basic Drugs with Lipid Bilayers Using Liposome Electrokinetic Chromatography

Cited by 55 publications

References 42 publications

Compositional effects on electrophoretic and chromatographic figures of merit in electrokinetic chromatography with cetyltrimethylammonium bromide/sodium octyl sulfate vesicles as the pseudostationary phase. Part 1: Effect of the phase ratio

Compositional effects on electrophoretic and chromatographic figures of merit in electrokinetic chromatography with cetyltrimethylammonium bromide/sodium octyl sulfate vesicles as the pseudostationary phase. Part 1: Effect of the phase ratio

Capillary electrophoresis of liposomes functionalized for protein binding

Drug–liposome distribution phenomena studied by capillary electrophoresis‐frontal analysis

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