The interaction of eugenol with cell membrane models at the air–water interface is modulated by the lipid monolayer composition

Gonçalves, Giulia Elisa G.; Souza, Fernanda Silva de; Lago, João Henrique G.; Caseli, Luciano

doi:10.1016/j.bpc.2015.07.007

Cited by 12 publications

(4 citation statements)

References 25 publications

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“…This decrease is a consequence of a compressional gain of the mixed monolayer owing to the fact that the rigid structure of the well-packed phospholipid monolayer was smoothed by the presence of thymol. Decrease of values of E for lipid monolayers is reported in the literature for other drug–lipid films at the air–water interface. , …”

Section: Resultsmentioning

confidence: 63%

“…Decrease of values of E for lipid monolayers is reported in the literature for other drug−lipid films at the air−water interface. 19,20 Figure 5 shows the PM-IRRAS spectra for DPPC monolayers with or without thymol at the surface pressure of 30 mN/m. Panel A shows the region corresponding to the main bands of the alkyl tails of the phospholipid.…”

Section: Resultsmentioning

confidence: 99%

“…When this monolayer is constituted of membrane lipids, it can represent a model for half a membrane, and interactions between molecules at the interface can be investigated by a variety of techniques . Interactions of bioactive molecules with lipid Langmuir monolayers have been reported in the literature for synthetic drugs, − natural products, , and metallic nanoparticles . The fact that Langmuir monolayers of lipids may represent a model for half a membrane is extensively defended in the literature (e.g., see ref ).…”

Section: Introductionmentioning

confidence: 99%

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Mechanism of Action of Thymol on Cell Membranes Investigated through Lipid Langmuir Monolayers at the Air–Water Interface and Molecular Simulation

et al. 2016

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A major challenge in the design of biocidal drugs is to identify compounds with potential action on microorganisms and to understand at the molecular level their mechanism of action. In this study, thymol, a monoterpenoid found in the oil of leaves of Lippia sidoides with possible action in biological surfaces, was incorporated in lipid monolayers at the air-water interface that represented cell membrane models. The interaction of thymol with dipalmitoylphosphatidylcholine (DPPC) at the air-water interface was investigated by means of surface pressure-area isotherms, Brewster angle microscopy (BAM), polarization-modulation reflection-absorption spectroscopy (PM-IRRAS), and molecular dynamics simulation. Thymol expands DPPC monolayers, decreases their surface elasticity, and changes the morphology of the lipid monolayer, which evidence the incorporation of this compound in the lipid Langmuir film. Such incorporation could be corroborated by PM-IRRAS since some specific bands for DPPC were changed upon thymol incorporation. Furthermore, potential of mean force obtained by molecular dynamics simulations indicates that the most stable position of the drug along the lipid film is near the hydrophobic regions of DPPC. These results may be useful to understand the interaction between thymol and cell membranes during biochemical phenomena, which may be associated with its pharmaceutical properties at the molecular level.

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Section: Resultsmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mechanism of Action of Thymol on Cell Membranes Investigated through Lipid Langmuir Monolayers at the Air–Water Interface and Molecular Simulation

et al. 2016

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“…Though there are several reports on the antimicrobial function of eugenol by modulating the structural properties of cell membrane, there is limited information on how eugenol modulates the lipid membrane. ,− An interesting work to study the effect of eugenol with lipid monolayers at the air–water interface suggests that the interaction is being modulated by the lipid composition of the monolayer . Therefore, it is of utmost importance to understand the effect of eugenol in synthetic lipid membranes, which provides the opportunity to explore the mechanism of the membrane-modulating properties of any additive. , Generally, membrane lipids under physiologically relevant conditions exist in the liquid-crystalline (fluid) phase, but sometimes lipids may be present in the gel phase .…”

Section: Introductionmentioning

confidence: 99%

Influence of Eugenol on the Organization and Dynamics of Lipid Membranes: A Phase-Dependent Study

Meher

Chakraborty

2018

Langmuir

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Eugenol is known for its antimicrobial effects against microorganisms responsible for infectious diseases in humans, food-borne pathogens, and oral pathogens. In spite of several reports on the antimicrobial function of eugenol by modulating the structural properties of cell membranes, there is limited information on the influence of eugenol in the lipid membrane. In this work, we explored the effect of eugenol on the organization and dynamics of large unilamellar vesicles (LUVs) of DMPC using the intrinsic fluorescence of eugenol and an extrinsic hydrophobic probe, DPH, in varying phases. The organization and dynamics of the bilayers of DMPC vesicles were monitored by utilizing varieties of steady-state and time-resolved fluorescence measurements. Our results show that eugenol stabilizes the gel phase and elevates the phase-transition temperature of DMPC in a concentration-dependent fashion. Fluorescence lifetime measurements demonstrate that higher eugenol-induced water penetration was observed in fluid-phase membranes. Time-resolved anisotropy measurements demonstrate that eugenol reduces the semiangle of DPH wobbling-in-a-cone in gel-phase membranes, whereas the semiangle remains unaffected in fluid-phase membrane. This implies that the eugenol further orders the gel-phase membrane, and this could be a plausible reason for the eugenol-dependent elevation of the phase-transition temperature of DMPC. We envisage that these results will contribute important information to understand the interaction of eugenol with biological membranes.

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Propolis flavonoids and terpenes, and their interactions with model lipid membranes: a review

Šturm

Ulrih

2020

Advances in Biomembranes and Lipid Self-Assembly

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The interaction of eugenol with cell membrane models at the air–water interface is modulated by the lipid monolayer composition

Cited by 12 publications

References 25 publications

Mechanism of Action of Thymol on Cell Membranes Investigated through Lipid Langmuir Monolayers at the Air–Water Interface and Molecular Simulation

Mechanism of Action of Thymol on Cell Membranes Investigated through Lipid Langmuir Monolayers at the Air–Water Interface and Molecular Simulation

Influence of Eugenol on the Organization and Dynamics of Lipid Membranes: A Phase-Dependent Study

Propolis flavonoids and terpenes, and their interactions with model lipid membranes: a review

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