title: Membrane interactions of ionic liquids: possible determinants for biological activity and toxicity.
abstract: Ionic liquids (ILs) are a class of diverse organic salts with relatively low melting points (below 100°C) which have attracted considerable interest as a promising "green" substitute for organic solvents. The broad solvation properties of ILs and their high solubility in water, however, present health risks, in particular since it was shown that many ILs exhibit cytotoxic properties. In this context, interactions of ILs with the cellular membrane are believed to constitute a primary culprit for toxicity. We present a comprehensive biophysical and microscopy study of membrane interactions of a series of ILs having different side-chain compositions and lengths, and cationic head-group structures and orientations. The experimental data reveal that the ILs studied exhibit distinct mechanisms of membrane binding, insertion, and disruption which could be correlated with their biological activities. The results indicate, in particular, that both the side chain composition and particularly the head-groups of ILs constitute determinants for membrane activity and consequent cell toxicity. This work suggests that tuning membrane interactions of ILs should be an important factor for designing future compounds with benign environmental impact.
authors.affiliation: Department of Chemistry, Ben Gurion University, Beer Sheva 84105, Israel.
authors.forename: Noga
authors.initials: N
authors.lastname: Gal
authors.forename: Danilo
authors.initials: D
authors.lastname: Malferrari
authors.forename: Danilo
authors.initials: D
authors.lastname: Malferarri
authors.forename: Sofiya
authors.initials: S
authors.lastname: Kolusheva
authors.forename: Paola
authors.initials: P
authors.lastname: Galletti
authors.forename: Emilio
authors.initials: E
authors.lastname: Tagliavini
authors.forename: Raz
authors.initials: R
authors.lastname: Jelinek
mesh_terms: D045744:Cell Line, Tumor; D002462:Cell Membrane / Q000378:metabolism*; D002470:Cell Survival; D006801:Humans; D052578:Ionic Liquids / Q000737:chemistry* / Q000378:metabolism*; D012997:Solvents / Q000737:chemistry
chemical_list: D052578:Ionic Liquids; D012997:Solvents