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Imidazolium Salts Mimicking the Structure of Natural Lipids Exploit Remarkable Properties Forming Lamellar Phases and Giant Vesicles
journal contribution
posted on 2016-11-29, 00:00 authored by Patrick Drücker, Andreas Rühling, David Grill, Da Wang, Annette Draeger, Volker Gerke, Frank Glorius, Hans-Joachim GallaTailor-made
ionic liquids based on imidazolium salts have recently
attracted a large amount of attention because of their extraordinary
properties and versatile functionality. An intriguing ability to interact
with and stabilize membranes has already been reported for 1,3-dialkylimidazolium
compounds. We now reveal further insights into the field by investigating
1,3-dimethyl-4,5-dialkylimidazolium (Cn-IMe·HI, n = 7, 11, 15) and 1,3-dibenzyl-4,5-dialkylimidazolium
(Cn-IBn·HBr, n =
7, 11, 15) salts. Diverse alkyl chain lengths and headgroups differing
in their steric demand were employed for the membrane interface interaction
with bilayer membranes imitating the cellular plasma membrane. Membrane
hydration properties and domain fluidization were analyzed by fluorescent
bilayer probes in direct comparison to established model membranes
in a buffered aqueous environment, which resembles the salt content
and pH of the cytosol of living cells. Membrane binding and insertion
was analyzed via a quartz crystal microbalance and confocal laser
scanning microscopy. We show that short-chain 4,5-dialkylimidazolium
salts with a bulky headgroup were able to disintegrate membranes.
Long-chain imidazolium salts form bilayer membrane vesicles spontaneously
and autonomously without the addition of other lipids. These 4,5-dialkylimidazolium
salts are highly eligible for further biochemical engineering and
drug delivery.
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Imidazolium Salts MimickingNatural Lipids Exploit Remarkable Properties Forming Lamellar PhasesdialkylimidazoliumDiverse alkyl chain lengthsquartz crystal microbalanceLong-chain imidazolium salts form bilayer membrane vesiclesconfocal laser scanning microscopyC nmembrane interface interactionMembrane hydration propertiesGiant Vesicles Tailor-made
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