2021
DOI: 10.1021/acsabm.1c00252
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Design Principles of Lipid-like Ionic Liquids for Gene Delivery

Abstract: We developed lipid-like ionic liquids, containing 2mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray analysis, and computational modeling to rationalize the self-assembly and desired physicochemical and biological properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-media… Show more

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Cited by 18 publications
(10 citation statements)
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“…In fact, this is not an unusual phenomenon for ILs because upon cooling, viscous glassy liquids are formed that resist recrystallization. 41 Along with T m , viscosity, a key parameter affecting mass transfer and diffusion, is another fluid characteristic of the ILs in which lower values are favorable for CO 2 capture. Accordingly, the dynamic viscosity, kinetic viscosity, and density of the ILs were measured over the temperature at the range of 20−80 °C at 1 atm (see the SI, Figure S1 42 In light of this consideration, it seemed worthwhile to employ these ILs to serve as readily made materials with discrete structural differences for DAC.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…In fact, this is not an unusual phenomenon for ILs because upon cooling, viscous glassy liquids are formed that resist recrystallization. 41 Along with T m , viscosity, a key parameter affecting mass transfer and diffusion, is another fluid characteristic of the ILs in which lower values are favorable for CO 2 capture. Accordingly, the dynamic viscosity, kinetic viscosity, and density of the ILs were measured over the temperature at the range of 20−80 °C at 1 atm (see the SI, Figure S1 42 In light of this consideration, it seemed worthwhile to employ these ILs to serve as readily made materials with discrete structural differences for DAC.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…melting point or crystallization), as evidenced by the lack of endothermic/exothermic peaks in the differential scanning calorimetry (DSC) curves, reflecting the broad liquid range associated with the ILs. In fact, this is not an unusual phenomenon for ILs because upon cooling, viscous glassy liquids are formed that resist recrystallization …”
Section: Resultsmentioning
confidence: 99%
“…The effectiveness with which LIL‐DNA preparations can deliver DNA to HEK 293T cells in a test tube demonstrates the potential use of LIL cationic lipids in DNA delivery. [ 184 ] ILs have various advantages with regard to the delivery of local nucleic acids: first, ILs successfully transfer nucleic acids into target cells despite the limited permeability of the SC for nucleic acids. Second, ILs can preserve the secondary structure of nucleic acids.…”
Section: Ionic Liquid‐biomacromolecule Formulations For Transdermal D...mentioning
confidence: 99%
“…For example, incorporating a sulfur atom into aliphatic side chains grafted onto imidazolium cations considerably reduces the liquefaction temperatures of ILs relative to congeners bearing fully saturated side chains of equal length. 18 This effect is in part due to the change in torsion angles of the alkyl chains due to the incorporation of the sulfur moiety. Oxygen containing alkyl chains (i.e., ether moieties), were shown to influence thermal properties of ILs via repulsive OÁ Á ÁO interactions in the alkyl chains observed in their crystal structures.…”
Section: Introductionmentioning
confidence: 99%