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|Title: ||Understanding the interactions of imidazolium-based ionic liquids with cell membrane models|
|Authors: ||Mendonça, Carlos M. N.|
Balogh, Debora T.
Barbosa, Simone C.
Sintra, Tânia E.
Ventura, Sónia P. M.
Martins, Luís F. G.
Filipe, Eduardo J. M.
Coutinho, João A. P.
Oliveira Jr., Osvaldo N.
|Keywords: ||Langmuir monolayers|
|Issue Date: ||Dec-2018|
|Publisher: ||Royal Soc Chemistry|
|Citation: ||Carlos M. N. Mendonça, Debora T. Balogh, Simone C. Barbosa,
Tânia E. Sintra, Sónia P. M. Ventura, Luís F. G. Martins, Pedro Morgado,
Eduardo J. M. Filipe, João A. P. Coutinho, Osvaldo N. Oliveira Jr.,
Ana Barros-Timmons, Phys. Chem. Chem. Phys.,
2018, 20, 29764|
|Abstract: ||Cell membrane models have been used to evaluate the interactions of various imidazolium-based ionic
liquids (ILs) with Langmuir monolayers of two types of phospholipids and cholesterol. Data from surface
pressure isotherms, Brewster angle microscopy (BAM) and polarization-modulated infrared reflection
absorption spectroscopy (PM-IRRAS) pointed to significant effects on the monolayers of 1,2-dipalmitoylsn-glycero-3-phosphocholine (DPPC) and cholesterol, used to mimic the membranes of eukaryotic
cells, for ILs containing more than 6 carbon atoms in the alkyl chain (i.e. n 4 6). For ILs with less
hydrophobic tails (n r 6) and low concentrations, the effects were almost negligible, therefore, such ILs
should not be toxic to eukaryotic cells. The hydrophobicity of the anion was also proved to be relevant,
with larger impact from ILs containing tetrafluoroborate ([BF4]
) than chloride (Cl). Molecular dynamics
simulations for DPPC monolayers at the surface of aqueous solutions of alkylimidazolium chloride
([Cnmim]Cl) confirm the penetration of the IL cations with longer alkyl chains into the phospholid
monolayer and provide information on their location and orientation within the monolayer. For
monolayers of dipalmitoylphosphatidyl glycerol (DPPG), which is negatively charged like bacteria cell
membranes, the ILs induced much larger effects. Similarly to the results for DPPC and cholesterol,
effects increased with the number of carbon atoms in the alkyl chain and with a more hydrophobic
. Overall, the approach used can provide relevant information of molecular-level interactions
behind the toxicity mechanisms and support the design of (quantitative) structure–activity relationship
models, which may help design more efficient and environmentally friendly ILs.|
|Appears in Collections:||CQE - Publicações - Artigos em Revistas Internacionais Com Arbitragem Científica|
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