Influence of Chain Ordering on the Selectivity of Dipalmitoylphosphatidylcholine Bilayer Membranes for Permeant Size and Shape

Xiang, Tian‐Xiang; Anderson, Bradley D.

doi:10.1016/s0006-3495(98)77711-2

Cited by 140 publications

(178 citation statements)

References 76 publications

(99 reference statements)

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“…We note, however, that the trend is not entirely without precedent; the gel-phase dipalmitolyphosphatidylcholine (DPPC) studies of Xiang and Anderson (14,16,17) also found a decreasing permeation coefficient from acetic to propionic acid, but for larger acids P increased again (17). DPPC is a fully saturated lipid, thus P values are orders of magnitude smaller in the gel phase (17) and so are easier to measure accurately. In constrast, soy lecithin remains in the fluid phase from 3°C to 80°C, because of the high proportion of unsaturated lipids (40).…”

Section: Resultsmentioning

confidence: 77%

“…On the other hand, some weak acid protonophores may also exert detrimental effects on cellular processes such as oxidative phosphorylation, apoptosis (7), and photosynthesis (8). The transport of weak acids across model cell membranes and the determination of permeation rates have consequently been the subject of a considerable number of studies (9)(10)(11)(12)(13)(14)(15)(16)(17)). …”

mentioning

confidence: 99%

“…Investigations of membrane permeation have essentially used two configurations based on either planar bilayer lipid membranes (BLMs) (9)(10)(11)(12)(13)20) or liposomes (10,14,16,17). The former configuration has received the most attention, with flux measurements made between adjacent stirred chambers of different composition separated by the BLM.…”

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confidence: 99%

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Quantitative visualization of passive transport across bilayer lipid membranes

Grime

Edwards

Rudd

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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The ability to predict and interpret membrane permeation coefficients is of critical importance, particularly because passive transport is crucial for the effective delivery of many pharmaceutical agents to intracellular targets. We present a method for the quantitative measurement of the permeation coefficients of protonophores by using laser confocal scanning microscopy coupled to microelectrochemistry, which is amenable to precise modeling with the finite element method. The technique delivers well defined and high mass transport rates and allows rapid visualization of the entire pH distribution on both the cis and trans side of model bilayer lipid membranes (BLMs). A homologous series of carboxylic acids was investigated as probe molecules for BLMs composed of soybean phosphatidylcholine. Significantly, the permeation coefficient decreased with acyl tail length contrary to previous work and to Overton's rule. The reasons for this difference are considered, and we suggest that the applicability of Overton's rule requires re-evaluation.Overton's rule ͉ permeation ͉ ultramicroelectrode ͉ laser confocal scanning microscopy ͉ finite element method

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Section: Resultsmentioning

confidence: 77%

mentioning

confidence: 99%

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Quantitative visualization of passive transport across bilayer lipid membranes

Grime

Edwards

Rudd

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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“…The permeability of a given compound reflects its partition coefficient into the barrier domain, PC barrier/water , and its diffusion coefficient within the barrier, D barrier , as described below 10) where d is the thickness of the barrier. In both bulk solvents (16) and lipid bilayers (17), the diffusion coefficient varies inversely with the minimum crosssectional area of the permeant (ie, D barrier ∝ [molecular volume] 2/3 ). Figure 5 shows the minimum cross-sectional area view for each compound in the series of p-methylhippuric acids, along with the relative surface area normalized to that of the unsubstituted p-methylhippuric acid.…”

Section: Functional Group Contributions To the Standard Free Energy Omentioning

confidence: 99%

Independence of substituent contributions to the transport of small-molecule permeants in lipid bilayer

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Purpose: To explore the independence of functional group contributions to permeability of nonelectrolytes across egg lecithin bilayers. Methods. The transport rates were measured of a series of α-substituted p-methylhippuric acids (-H, -Cl, -OCH 3 , -CN, -OH, -COOH, and -CONH 2 ) across egg lecithin lipid bilayers, in the form of large unilamellar vesicles (LUVs) at 25ΕC. Intrinsic permeability coefficients (P HA ) were calculated from apparent permeability coefficients (P app ) measured as a function of pH. Group contributions to the free energy of transfer from water into the barrier domain, Δ(ΔGΕ) P,X , were calculated for the substituents and compared to the contributions of these groups when attached to p-toluic acid measured earlier. The Δ(ΔGΕ) P,X values from permeability data were also correlated with Δ(ΔGΕ) PC,X values of partitioning from water into organic solvents to determine the physicochemical selectivity of the barrier domain. Results. P app values in LUVs were found to vary approximately linearly with the fraction of neutral permeant over a pH range of 5.5 to 10.5, suggesting that the transport of the ionized species is negligible over this pH range. The Δ(ΔGΕ) P,X values from the 2 series of compounds appear to be the same, indicating that the functional group contributions are independent. 1,9-Decadiene was found to be the most similar to the chemical environment of the barrier domain. Conclusions. Functional group contributions to transport across egg lecithin bilayers appear to be independent of the compound to which they are attached, even though the thickness of the barrier domain in lipid bilayers is approximately the same as the extended length of the permeant.

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“…This is the reason of the non-planar spaces between crystalline lipid lamellae and their adjacent cells outer membrane. Fluid lipids in skin barrier are crucially important for transepidermal diffusion of the lipidic and amphiphilic molecules, occupying those spaces for the insertion and migration through intercellular lipid layers of such molecules [59,60]. The hydrophilic molecules diffuse predominantly "laterally" along surfaces of the less abundant, water filled inter-lamellar spaces or through such volumes; polar molecules can also use the free space between a lamella and a corneocyte outer membrane to the same end [61].…”

Section: Routes Of Drug Penetration Through the Skinmentioning

confidence: 99%

Nanocarrier Systems for Transdermal Drug Delivery

Escobar-Chávez¹,

Rodríguez-Cruz²,

Domínguez-Delgado³

et al. 2012

Recent Advances in Novel Drug Carrier Systems

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is an open discussion, in one hand, the nanotechnologist continue making new and more sophisticated nanocarriers and in the other hand, toxicologist continue evaluating possible damaging effects.Whatever it happens, nanotechnology is the new era and nanomedicine cannot be taking off. New nanocarriers will be created and the entire scientist working in nanomedicine bet for it to be the cure of diseases that in this moment are difficult to deal with [3] The application of preparations to the skin for medical purposes is as old as the history of medicine itself, with references to the use of ointments and salves found in the records of Babylonian and Egyptian medicine. The historical development of permeation research is well described by Hadgraft & Lane [4]. Over time, the skin has become an important route for drug delivery in which topical, regional or systemic effects are desired. Nevertheless, skin constitutes an excellent barrier and presents difficulties for the transdermal delivery of therapeutic agents, since few drugs possess the characteristics required to permeate across the stratum corneum in sufficient quantities to reach a therapeutic concentration in the blood. In order to enhance drug transdermal absorption different methodologies have been investigated developed and patented [5,6]. Improvement in physical permeationenhancement technologies has led to renewed interest in transdermal drug delivery. Some of these novel advanced transdermal permeation enhancement technologies include: iontophoresis, electroporation, ultrasound, microneedles to open up the skin and more recently the use of transdermal nanocarriers [3,[7][8][9][10].A number of excellent reviews that have been published contain detailed discussions concerning many aspects of transdermal nanocarriers [11][12][13][14][15][16][17]. The present chapter shows an updated overview of the use of submicron particles and other nanostructures in the pharmaceutical field, specifically in the area of topical and transdermal drugs. This focus is justified due to the magnitude of the experimental data available with the use of these nanocarriers. The development of submicron particles and other nanostructures in the pharmaceutical and cosmetic fields has been emerged in the last decades for designing best formulations for application through the skin [18][19][20][21]. The skinThe skin is the largest organ of the body [22][23][24], accounting for more than 10% of body mass, and the one that enables the body to interact more intimately with its environment. Essentially, the skin consists of four layers: The SC, that is the outer layer of the skin (nonviable epidermis), and forms the rate-controlling barrier for diffusion for almost all compounds. It is composed of dead flattened, keratin-rich cells, the corneocytes. These dense cells are surrounded by a complex mixture of intercellular lipids, namely, ceramides, free fatty acids, cholesterol, and cholesterol sulphate. Their most important feature is that they are structured as ordered bilayer arrays [25]...

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Influence of Chain Ordering on the Selectivity of Dipalmitoylphosphatidylcholine Bilayer Membranes for Permeant Size and Shape

Cited by 140 publications

References 76 publications

Quantitative visualization of passive transport across bilayer lipid membranes

Quantitative visualization of passive transport across bilayer lipid membranes

Independence of substituent contributions to the transport of small-molecule permeants in lipid bilayer

Nanocarrier Systems for Transdermal Drug Delivery

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