Interaction of menthol with mixed-lipid bilayer of stratum corneum: A coarse-grained simulation study

Wan, Guang; Dai, Xingxing; Yin, Qianqian; Shi, Xinyuan; Qiao, Yanjiang

doi:10.1016/j.jmgm.2015.06.005

Cited by 30 publications

(29 citation statements)

References 44 publications

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“…As a penetration reagent, menthol has an excellent affinity for the hydrophobic lipid tails. The presence of menthol proved to improve the permeability of the cell membrane by interacting with lipids directly, perturbing the lipid tails to varying degrees . We hypothesized that the hydrophobic DESs could first act on the outer membrane, and thus, destabilize its structure.…”

Section: Resultsmentioning

confidence: 99%

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

Cao

Dong

et al. 2019

ChemBioChem

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An efficient and green method is crucial for the recovery of intracellular biological products. The major drawbacks of the conventional cell disruption method are nonselectivity and enzyme denaturation. The permeability of hydrophobic deep eutectic solvents (DESs) to the cell membrane was studied, for the first time, and then hydrophobic DESs were innovatively applied to release intracellular enzymes from recombinant Escherichia coli. After optimization, a DES suspension of l‐menthol/oleic acid (0.5 %, v/v) showed the highest release yield of intracellular enzyme. Compared with that released by sonication, a release yield of phospholipase D (PLD) of up to 114.58 % was achieved, and the specific activity was increased by 1.96 times. The microstructure of the cell membrane under different treatments was observed by using an electron microscope to understand the permeation of DESs to the cell membrane. The feasibility and applicability of the proposed release method in industrial applications were also demonstrated. The effective and green release method of intracellular enzymes developed herein has bright prospects for industrial application to replace traditional cell disruption methods. A preliminary study on the permeability of hydrophobic DESs to the cell membrane showed that there would be a potential application prospect of hydrophobic DESs not only in releasing intracellular contents, but also in seeking new green penetrating agents.

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Section: Resultsmentioning

confidence: 99%

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

Cao

Dong

et al. 2019

ChemBioChem

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“…Free fatty acids, however, can increase the density and compact the ordering of the hydrophobic lipid tails [38,39]. In order to get more accurate results, we used a mixed CG model of SC lipid bilayer comprised of CER NS 24:0, CHOL and FFA 24:0 (2:2:1) [40] (the properties of this molar proportion lipid layer have been validated by Das and coworkers in 2009 [41,42]) to measure the enhanced transdermal permeability effects. We conducted several CG-MD simulations based on Martini force field to investigate the interaction of borneol with the SC lipid model we built before [40].…”

Section: Introductionmentioning

confidence: 99%

Effects of Concentrations on the Transdermal Permeation Enhancing Mechanisms of Borneol: A Coarse-Grained Molecular Dynamics Simulation on Mixed-Bilayer Membranes

Dai

Yin

Wan

et al. 2016

IJMS

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Borneol is a natural permeation enhancer that is effective in drugs used in traditional clinical practices as well as in modern scientific research. However, its molecular mechanism is not fully understood. In this study, a mixed coarse-grained model of stratum corneum (SC) lipid bilayer comprised of Ceramide-N-sphingosine (CER NS) 24:0, cholesterol (CHOL) and free fatty acids (FFA) 24:0 (2:2:1) was used to examine the permeation enhancing mechanism of borneol on the model drug osthole. We found two different mechanisms that were dependent on concentrations levels of borneol. At low concentrations, the lipid system maintained a bilayer structure. The addition of borneol made the lipid bilayer loosen and improved drug permeation. The “pull” effect of borneol also improved drug permeation. However, for a strongly hydrophobic drug like osthole, the permeation enhancement of borneol was limited. When most borneol molecules permeated into bilayers and were located at the hydrophobic tail region, the spatial competition effect inhibited drug molecules from permeating deeper into the bilayer. At high concentrations, borneol led to the formation of water pores and long-lived reversed micelles. This improved the permeation of osthole and possibly other hydrophobic or hydrophilic drugs through the SC. Our simulation results were supported by Franz diffusion tests and transmission electron microscope (TEM) experiments.

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“…Recently, to imitate the complexity and asymmetry of membranes, several CG membrane models have been developed. These include, for example, a model of a generalized plasma membrane [ 21 ], models of thylakoid membranes from cyanobacteria and higher plants [ 22 ], models of stratum corneum [ 23 , 24 ] and red blood cell (RBC) plasma membrane [ 25 ]. The building of an asymmetric membrane model is a challenge due to the difficulty in assigning the number of lipids in each leaflet of the asymmetric bilayer.…”

Section: Introductionmentioning

confidence: 99%

A Coarse Grained Model for a Lipid Membrane with Physiological Composition and Leaflet Asymmetry

et al. 2015

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The resemblance of lipid membrane models to physiological membranes determines how well molecular dynamics (MD) simulations imitate the dynamic behavior of cell membranes and membrane proteins. Physiological lipid membranes are composed of multiple types of phospholipids, and the leaflet compositions are generally asymmetric. Here we describe an approach for self-assembly of a Coarse-Grained (CG) membrane model with physiological composition and leaflet asymmetry using the MARTINI force field. An initial set-up of two boxes with different types of lipids according to the leaflet asymmetry of mammalian cell membranes stacked with 0.5 nm overlap, reliably resulted in the self-assembly of bilayer membranes with leaflet asymmetry resembling that of physiological mammalian cell membranes. Self-assembly in the presence of a fragment of the plasma membrane protein syntaxin 1A led to spontaneous specific positioning of phosphatidylionositol(4,5)bisphosphate at a positively charged stretch of syntaxin consistent with experimental data. An analogous approach choosing an initial set-up with two concentric shells filled with different lipid types results in successful assembly of a spherical vesicle with asymmetric leaflet composition. Self-assembly of the vesicle in the presence of the synaptic vesicle protein synaptobrevin 2 revealed the correct position of the synaptobrevin transmembrane domain. This is the first CG MD method to form a membrane with physiological lipid composition as well as leaflet asymmetry by self-assembly and will enable unbiased studies of the incorporation and dynamics of membrane proteins in more realistic CG membrane models.

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Interaction of menthol with mixed-lipid bilayer of stratum corneum: A coarse-grained simulation study

Cited by 30 publications

References 44 publications

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

Effects of Concentrations on the Transdermal Permeation Enhancing Mechanisms of Borneol: A Coarse-Grained Molecular Dynamics Simulation on Mixed-Bilayer Membranes

A Coarse Grained Model for a Lipid Membrane with Physiological Composition and Leaflet Asymmetry

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