The influence of amphotericin B on the molecular organization and structural properties of DPPC lipid membranes modified by sterols

Kamiński, Daniel; Pociecha, Damian; Górecka, Ewa; Gagoś, Mariusz

doi:10.1016/j.molstruc.2014.10.081

Cited by 3 publications

(3 citation statements)

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“…10 Similarly, amphotericin B, an antifungal agent, disrupts the fungal cell wall by making pores on the membrane that lead to cell death. [11][12][13] Valinomycin and gramicidin A (gA) permeate the bilayer by forming ion channels that alter the membrane electrochemical resistivity. [14][15][16] Molecular lipophilicity is one of the key physicochemical properties considered predictive of passive molecular diffusion across the biological membrane 17 .…”

Section: Introductionmentioning

confidence: 99%

“…The alterations of such species impose on membranes as they associate with and permeate these dynamic structures can have a profound influence on the membrane structure, such as thickness, curvature, permeability, and fluidity. , And, they can affect biological function including the integrity of the membrane barrier effect, cell signaling and adhesion, and thus, the toxicity of the drug. − For example, anesthetic molecules such as chloroform, halothane, and diethyl ether have been shown to induce lateral expansion in the membrane, increasing local disorder in lipid tails adjacent to the intercalating anesthetic molecule . Similarly, amphotericin B, an antifungal agent, disrupts the fungal cell wall by making pores on the membrane that lead to cell death. − Valinomycin and gramicidin A permeate the bilayer by forming ion channels that alter the membrane electrochemical resistivity. − …”

Section: Introductionmentioning

confidence: 99%

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Microcavity-Supported Lipid Bilayers; Evaluation of Drug–Lipid Membrane Interactions by Electrochemical Impedance and Fluorescence Correlation Spectroscopy

et al. 2019

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Many drugs have intracellular or membrane-associated targets thus understanding their interaction with the cell membrane is of value in drug development. Cell-free tools used to predict membrane interactions should replicate the molecular organization of the membrane. Microcavity array supported lipid bilayer (MSLB) platform are versatile biophysical models of the cell membrane that combine liposome-like membrane fluidity with stability and addressability. We used an MSLB herein to interrogate drugmembrane interactions across seven drugs from different classes, including non-steroidal antiinflammatories; Ibuprofen (Ibu) and Diclofenac (Dic), antibiotics; Rifampicin (Rif), Levofloxacin (Levo) and Pefloxacin (Pef), and bisphosphonates; Alendronate (Ale) and Clodronate (Clo). Fluorescence lifetime correlation spectroscopy (FLCS) and electrochemical impedance spectroscopy (EIS) were used to evaluate the impact of drug on DOPC and binary bilayers over physiologically relevant drug concentrations. Whereas FLCS data revealed Ibu, Levo, Pef, Ale and Clo had no impact on lipid lateral

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microcavity-Supported Lipid Bilayers; Evaluation of Drug–Lipid Membrane Interactions by Electrochemical Impedance and Fluorescence Correlation Spectroscopy

et al. 2019

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“…Ergosterol has been proposed as a target molecule in the medical treatment of fungal infections, following mainly two routes: (i) the inhibition of the biosynthesis of ergosterol, as in the case of ketoconazole and clotrimazole drugs action, and (ii) direct interaction, as in the case of amphotericin B, where two reaction mechanisms have been proposed . The first mechanism proposed for direct interaction of ergosterol with amphotericin B has been widely studied.…”

Section: Introductionmentioning

confidence: 99%

Mechanism and kinetics of the oxidative damage to ergosterol induced by peroxyl radicals in lipid media: a theoretical quantum chemistry study

Medina

Iuga

Trigos

2015

J of Physical Organic Chem

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In this work, we have studied the mechanisms and kinetics of the initial damage to ergosterol induced by• OOH and• OOCH 3 peroxyl radicals in a lipid media, using quantum chemistry and computational kinetics methods. The initial damage to ergosterol induced by these radicals occurs predominantly through the hydrogen transfer mechanism (HT) from the allylic position C14 of ergosterol. For the reaction of ergosterol with• OOH, the HT-9 pathway represents~90.8% of the overall rate constant, while in the case of• OOCH 3 , the HT-14 pathway represents more than~97.2% of the overall rate constant. The calculated overall reaction rates for the initial damage to ergosterol caused by the• OOH and • OOCH 3 are 2.05 × 10 6 and 6.26 × 10 4 M À1 s À1 , respectively, indicating that the oxidative damage to ergosterol initiated by these radicals, and probably other alkyl-peroxyl radicals, could be significantly dangerous to their integrity. Taking into account the calculated values of the overall rate coefficients, we can conclude that ergosterol is more susceptible to damage produced by peroxyl radicals than cholesterol and fatty acids. This suggests that fungal cells might be more sensitive to these radicals than animal cells, coinciding with the fact that one of the targets in combating fungi is precisely ergosterol. Finally, theoretical calculations confirm the antioxidant potential of ergosterol and could help explaining the nutraceutical activity of edible and medicinal mushrooms.

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Effect of polyols on the DMPC lipid monolayers and bilayers

Budziak

Arczewska

Sachadyn‐Król

et al. 2018

Biochimica et Biophysica Acta (BBA) - Biomembranes

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The influence of amphotericin B on the molecular organization and structural properties of DPPC lipid membranes modified by sterols

Cited by 3 publications

References 35 publications

Microcavity-Supported Lipid Bilayers; Evaluation of Drug–Lipid Membrane Interactions by Electrochemical Impedance and Fluorescence Correlation Spectroscopy

Microcavity-Supported Lipid Bilayers; Evaluation of Drug–Lipid Membrane Interactions by Electrochemical Impedance and Fluorescence Correlation Spectroscopy

Mechanism and kinetics of the oxidative damage to ergosterol induced by peroxyl radicals in lipid media: a theoretical quantum chemistry study

Effect of polyols on the DMPC lipid monolayers and bilayers

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