title: Imidazolium Salts Mimicking the Structure of Natural Lipids Exploit Remarkable Properties Forming Lamellar Phases and Giant Vesicles.
abstract: Tailor-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.
authors.affiliation: Institute of Biochemistry, University of Münster , Wilhelm-Klemm-Str. 2, D-48149 Münster, Germany.|Department of Cell Biology, Institute of Anatomy, University of Bern , Baltzerstrasse 2, 3000 Bern 9, Switzerland.
authors.forename: Patrick
authors.initials: P
authors.lastname: Drücker
authors.affiliation: Organic Chemistry Institute, University of Münster , Corrensstrasse 40, D-48149 Münster, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Rühling
authors.affiliation: Institute of Medical Biochemistry, Center for Molecular Biology of Inflammation, University of Münster , Von-Esmarch-Str. 56, D-48149 Münster, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Grill
authors.affiliation: Institute of Biochemistry, University of Münster , Wilhelm-Klemm-Str. 2, D-48149 Münster, Germany.
authors.forename: Da
authors.initials: D
authors.lastname: Wang
authors.affiliation: Department of Cell Biology, Institute of Anatomy, University of Bern , Baltzerstrasse 2, 3000 Bern 9, Switzerland.
authors.forename: Annette
authors.initials: A
authors.lastname: Draeger
authors.affiliation: Institute of Medical Biochemistry, Center for Molecular Biology of Inflammation, University of Münster , Von-Esmarch-Str. 56, D-48149 Münster, Germany.
authors.forename: Volker
authors.initials: V
authors.lastname: Gerke
authors.affiliation: Organic Chemistry Institute, University of Münster , Corrensstrasse 40, D-48149 Münster, Germany.
authors.forename: Frank
authors.identifier: 0000-0002-0648-956X
authors.initials: F
authors.lastname: Glorius
authors.affiliation: Institute of Biochemistry, University of Münster , Wilhelm-Klemm-Str. 2, D-48149 Münster, Germany.
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Galla
mesh_terms: D015081:2-Naphthylamine / Q000031:analogs & derivatives / Q000737:chemistry; D004161:Diphenylhexatriene / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D007848:Laurates / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000737:chemistry; D010718:Phosphatidylserines / Q000737:chemistry; D044366:Transition Temperature; D053835:Unilamellar Liposomes / Q000737:chemistry*; D055682:Viscoelastic Substances / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D007093:Imidazoles; D052578:Ionic Liquids; D007848:Laurates; D008051:Lipid Bilayers; D010713:Phosphatidylcholines; D010718:Phosphatidylserines; D053835:Unilamellar Liposomes; D055682:Viscoelastic Substances; D004161:Diphenylhexatriene; C050294:1-palmitoyl-2-oleoylglycero-3-phosphoserine; D015081:2-Naphthylamine; C028694:1-palmitoyl-2-oleoylphosphatidylcholine; C065580:laurdan