Plasma membrane permeabilisation by ionic liquids

a matter of charge

Diego O. Hartmann, Karina Shimizu, Filipa Siopa, M. Cristina Leitão, Carlos A M Afonso, José N. Canongia Lopes, Cristina Maria Pereira

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Understanding the mechanisms of toxicity of ionic liquids at the molecular level is crucial for their conscious design as to promote higher acceptability as green solvents in a wide range of applications. In this systematic study, we investigated the effects of three families of ionic liquids on the plasma membrane of the filamentous fungus Aspergillus nidulans. Using fluorescence microscopy and gene expression analysis, we were able to demonstrate that the widely studied 1-alkyl-3-methylimidazolium chlorides with long alkyl substituents cause membrane permeabilisation. In opposition, the biocompatibility of cholinium alkanoates was reinforced here, even though their toxicity also increases with the elongation of the anion. Further investigating the effects of charge on membrane permeabilisation, we observed that a series of alkyl-(2-hydroxyethyl)-dimethylammonium bromides led to permeabilisation of the fungal plasma membrane by increasing the length of one alkyl substituent in the cholinium cation. We hypothesise that the chemical nature of the plasma membrane, which presents a heterogeneous charge distribution along its surface, is pivotal for the membrane permeabilising effects of ionic liquids. This study may inspire a new trend in the ionic liquid field: to give preference for the development of compounds carrying functionalised anions as greener alternatives to those carrying functionalized cations.

Original languageEnglish
Pages (from-to)4587-4598
Number of pages12
JournalGreen Chemistry
Volume17
Issue number9
DOIs
Publication statusPublished - 1 Jul 2015

Fingerprint

Ionic Liquids
Cell membranes
Ionic liquids
Cell Membrane
membrane
plasma
Membranes
Anions
Toxicity
Cations
Negative ions
Positive ions
Aspergillus nidulans
anion
Aspergillus
Fluorescence microscopy
Charge distribution
cation
Fungi
Bromides

Cite this

Hartmann, Diego O. ; Shimizu, Karina ; Siopa, Filipa ; Leitão, M. Cristina ; Afonso, Carlos A M ; Canongia Lopes, José N. ; Pereira, Cristina Maria. / Plasma membrane permeabilisation by ionic liquids : a matter of charge. In: Green Chemistry. 2015 ; Vol. 17, No. 9. pp. 4587-4598.
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Hartmann, DO, Shimizu, K, Siopa, F, Leitão, MC, Afonso, CAM, Canongia Lopes, JN & Pereira, CM 2015, 'Plasma membrane permeabilisation by ionic liquids: a matter of charge', Green Chemistry, vol. 17, no. 9, pp. 4587-4598. https://doi.org/10.1039/c5gc01472g

Plasma membrane permeabilisation by ionic liquids : a matter of charge. / Hartmann, Diego O.; Shimizu, Karina; Siopa, Filipa; Leitão, M. Cristina; Afonso, Carlos A M; Canongia Lopes, José N.; Pereira, Cristina Maria.

In: Green Chemistry, Vol. 17, No. 9, 01.07.2015, p. 4587-4598.

Research output: Contribution to journalArticle

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Hartmann DO, Shimizu K, Siopa F, Leitão MC, Afonso CAM, Canongia Lopes JN et al. Plasma membrane permeabilisation by ionic liquids: a matter of charge. Green Chemistry. 2015 Jul 1;17(9):4587-4598. https://doi.org/10.1039/c5gc01472g