Chromone-Containing Allylmorpholines Influence Ion Channels in Lipid Membranes via Dipole Potential and Packing Stress

Herein, we report that chromone-containing allylmorpholines can affect ion channels formed by pore-forming antibiotics in model lipid membranes, which correlates with their ability to influence membrane boundary potential and lipid-packing stress. At 100 µg/mL, allylmorpholines 1, 6, 7, and 8 decrea...

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Bibliographic Details
Published in:International journal of molecular sciences 2022-09, Vol.23 (19), p.11554
Main Authors: Efimova, Svetlana S., Martynyuk, Vera A., Zakharova, Anastasiia A., Yudintceva, Natalia M., Chernov, Nikita M., Yakovlev, Igor P., Ostroumova, Olga S.
Format: Article
Language:English
Subjects:
allylmorpholine
Alzheimer's disease
Amphotericin B
Antibiotics
chromone
Dipoles
Enzymes
Gramicidin
Hexagonal phase
Hydrocarbons
ion channel
Ion channels
Lipid membranes
Lipids
Melt temperature
membrane
Membranes
Phase transitions
Pore formation
Proteins
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Summary:Herein, we report that chromone-containing allylmorpholines can affect ion channels formed by pore-forming antibiotics in model lipid membranes, which correlates with their ability to influence membrane boundary potential and lipid-packing stress. At 100 µg/mL, allylmorpholines 1, 6, 7, and 8 decrease the boundary potential of the bilayers composed of palmitoyloleoylphosphocholine (POPC) by about 100 mV. At the same time, the compounds do not affect the zeta-potential of POPC liposomes, but reduce the membrane dipole potential by 80–120 mV. The allylmorpholine-induced drop in the dipole potential produce 10–30% enhancement in the conductance of gramicidin A channels. Chromone-containing allylmorpholines also affect the thermotropic behavior of dipalmytoylphosphocholine (DPPC), abolishing the pretransition, lowering melting cooperativity, and turning the main phase transition peak into a multicomponent profile. Compounds 4, 6, 7, and 8 are able to decrease DPPC’s melting temperature by about 0.5–1.9 °C. Moreover, derivative 7 is shown to increase the temperature of transition of palmitoyloleoylphosphoethanolamine from lamellar to inverted hexagonal phase. The effects on lipid-phase transitions are attributed to the changes in the spontaneous curvature stress. Alterations in lipid packing induced by allylmorpholines are believed to potentiate the pore-forming ability of amphotericin B and gramicidin A by several times.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms231911554