Phenolic compounds alter the ion permeability of phospholipid bilayers via specific lipid interactions.

Hossain, SI; Saha, SC; Deplazes, E

Phenolic compounds alter the ion permeability of phospholipid bilayers via specific lipid interactions.

Hossain, SI Saha, SC Deplazes, E

Permalink

Publisher:: Royal Society of Chemistry (RSC)
Publication Type:: Journal Article
Citation:: Phys Chem Chem Phys, 2021, 23, (39), pp. 22352-22366
Issue Date:: 2021-10-13

Closed Access

	Filename	Description	Size
	d1cp03250j.pdf	Accepted version	3.86 MB	Adobe PDF	View/Open

Copyright Clearance Process

Recently Added
In Progress
Closed Access

This item is closed access and not available.

Full metadata record

Field	Value	Language
dc.contributor.author	Hossain, SI
dc.contributor.author	Saha, SC
dc.contributor.author	Deplazes, E https://orcid.org/0000-0003-2052-5536
dc.date.accessioned	2022-01-12T06:59:31Z
dc.date.available	2022-01-12T06:59:31Z
dc.date.issued	2021-10-13
dc.identifier.citation	Phys Chem Chem Phys, 2021, 23, (39), pp. 22352-22366
dc.identifier.issn	1463-9076
dc.identifier.issn	1463-9084
dc.identifier.uri	http://hdl.handle.net/10453/152997
dc.description.abstract	This study aims to understand the role of specific phenolic-lipid interactions in the membrane-altering properties of phenolic compounds. We combine tethered lipid bilayer (tBLM) electrical impedance spectroscopy (EIS) with all-atom molecular dynamics (MD) simulations to study the membrane interactions of six phenolic compounds: caffeic acid methyl ester, caffeic acid, 3,4 dihydroxybenzoic acid, chlorogenic acid, syringic acid and p-coumaric acid. tBLM/EIS experiments showed that caffeic acid methyl ester, caffeic acid and 3,4 dihydroxybenzoic acid significantly increase the permeability of phospholipid bilayers to Na+ ions. In contrast, chlorogenic acid, syringic acid and p-coumaric acid showed no effect. Experiments with lipids lacking the phosphate group show a significant decrease in the membrane-altering effects indicating that specific phenolic-lipid interactions are critical in altering ion permeability. MD simulations confirm that compounds that alter ion permeability form stable interactions with the phosphate oxygen. In contrast, inactive phenolic compounds are superficially bound to the membrane surface and primarily interact with interfacial water. Our combined results show that compounds with similar structures can have very different effects on ion permeability in membranes. These effects are governed by specific interactions at the water-lipid interface and show no correlation with lipophilicity. Furthermore, none of the compounds alter the overall structure of the phospholipid bilayer as determined by area per lipid and order parameters. Based on data from this study and previous findings, we propose that phenolic compounds can alter membrane ion permeability by causing local changes in lipid packing that subsequently reduce the energy barrier for ion-induced pores.
dc.format	Electronic
dc.language	eng
dc.publisher	Royal Society of Chemistry (RSC)
dc.relation.ispartof	Phys Chem Chem Phys
dc.relation.isbasedon	10.1039/d1cp03250j
dc.rights	info:eu-repo/semantics/closedAccess
dc.subject	02 Physical Sciences, 03 Chemical Sciences, 09 Engineering
dc.subject.classification	Chemical Physics
dc.subject.mesh	Dielectric Spectroscopy
dc.subject.mesh	Lipid Bilayers
dc.subject.mesh	Molecular Dynamics Simulation
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Permeability
dc.subject.mesh	Phenols
dc.subject.mesh	Phospholipids
dc.subject.mesh	Phenols
dc.subject.mesh	Lipid Bilayers
dc.subject.mesh	Phospholipids
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Permeability
dc.subject.mesh	Molecular Dynamics Simulation
dc.subject.mesh	Dielectric Spectroscopy
dc.title	Phenolic compounds alter the ion permeability of phospholipid bilayers via specific lipid interactions.
dc.type	Journal Article
utslib.citation.volume	23
utslib.location.activity	England
utslib.for	02 Physical Sciences
utslib.for	03 Chemical Sciences
utslib.for	09 Engineering
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Life Sciences
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology/School of Mechanical and Mechatronic Engineering
utslib.copyright.status	closed_access	*
dc.date.updated	2022-01-12T06:59:04Z
pubs.issue	39
pubs.publication-status	Published online
pubs.volume	23
utslib.citation.issue	39

Abstract:

This study aims to understand the role of specific phenolic-lipid interactions in the membrane-altering properties of phenolic compounds. We combine tethered lipid bilayer (tBLM) electrical impedance spectroscopy (EIS) with all-atom molecular dynamics (MD) simulations to study the membrane interactions of six phenolic compounds: caffeic acid methyl ester, caffeic acid, 3,4 dihydroxybenzoic acid, chlorogenic acid, syringic acid and p-coumaric acid. tBLM/EIS experiments showed that caffeic acid methyl ester, caffeic acid and 3,4 dihydroxybenzoic acid significantly increase the permeability of phospholipid bilayers to Na+ ions. In contrast, chlorogenic acid, syringic acid and p-coumaric acid showed no effect. Experiments with lipids lacking the phosphate group show a significant decrease in the membrane-altering effects indicating that specific phenolic-lipid interactions are critical in altering ion permeability. MD simulations confirm that compounds that alter ion permeability form stable interactions with the phosphate oxygen. In contrast, inactive phenolic compounds are superficially bound to the membrane surface and primarily interact with interfacial water. Our combined results show that compounds with similar structures can have very different effects on ion permeability in membranes. These effects are governed by specific interactions at the water-lipid interface and show no correlation with lipophilicity. Furthermore, none of the compounds alter the overall structure of the phospholipid bilayer as determined by area per lipid and order parameters. Based on data from this study and previous findings, we propose that phenolic compounds can alter membrane ion permeability by causing local changes in lipid packing that subsequently reduce the energy barrier for ion-induced pores.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/152997