Molecular mechanisms of ionic liquid cytotoxicity probed by an integrated experimental and computational approach

Yoo, Brian; Jing, Benxin; Jones, Stuart E.; Lamberti, Gary A.; Zhu, Yingxi; Shah, Jindal K.; Maginn, Edward J.

doi:10.1038/srep19889

Title: Molecular mechanisms of ionic liquid cytotoxicity probed by an integrated experimental and computational approach

Journal Article · Tue Feb 02 04:00:00 UTC 2016 · Scientific Reports

DOI: https://doi.org/10.1038/srep19889 · OSTI ID:1242373

Yoo, Brian ^[1]; Jing, Benxin ^[2]; Jones, Stuart E. ^[2]; Lamberti, Gary A. ^[2]; Zhu, Yingxi ^[3]; Shah, Jindal K. ^[4]; Maginn, Edward J. ^[2]

Univ. of Notre Dame, Notre Dame, IN (United States); Notre Dame University Du Lac
Univ. of Notre Dame, Notre Dame, IN (United States)
Wayne State Univ., Detroit, MI (United States)
Oklahoma State Univ., Stillwater, OK (United States)

Ionic liquids (ILs) are salts that remain liquid down to low temperatures, and sometimes well below room temperature. ILs have been called “green solvents” because of their extraordinarily low vapor pressure and excellent solvation power, but ecotoxicology studies have shown that some ILs exhibit greater toxicity than traditional solvents. A fundamental understanding of the molecular mechanisms responsible for IL toxicity remains elusive. Here we show that one mode of IL toxicity on unicellular organisms is driven by swelling of the cell membrane. Cytotoxicity assays, confocal laser scanning microscopy, and molecular simulations reveal that IL cations nucleate morphological defects in the microbial cell membrane at concentrations near the half maximal effective concentration (EC50) of several microorganisms. Lastly, cytotoxicity increases with increasing alkyl chain length of the cation due to the ability of the longer alkyl chain to more easily embed in, and ultimately disrupt, the cell membrane.

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Research Organization:: Univ. of Notre Dame, Notre Dame, IN (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: FG36-08GO88020

OSTI ID:: 1242373

Journal Information:: Scientific Reports, Journal Name: Scientific Reports Vol. 6; ISSN 2045-2322

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (58)

1-Octanol/Water Partition Coefficients of 1Alkyl-3-methylimidazolium Chloride Domańska, Urszula; Bogel-Łukasik, Ewa; Bogel-Łukasik, Rafał Chemistry - A European Journal, Vol. 9, Issue 13 https://doi.org/10.1002/chem.200204516	journal	July 2003
Membrane interactions of ionic liquids: Possible determinants for biological activity and toxicity Gal, Noga; Malferarri, Danilo; Kolusheva, Sofiya Biochimica et Biophysica Acta (BBA) - Biomembranes, Vol. 1818, Issue 12 https://doi.org/10.1016/j.bbamem.2012.07.025	journal	December 2012
Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity Ranke, Johannes; Müller, Anja; Bottin-Weber, Ulrike Ecotoxicology and Environmental Safety, Vol. 67, Issue 3 https://doi.org/10.1016/j.ecoenv.2006.08.008	journal	July 2007
Environmental fate and toxicity of ionic liquids: A review Thuy Pham, Thi Phuong; Cho, Chul-Woong; Yun, Yeoung-Sang Water Research, Vol. 44, Issue 2 https://doi.org/10.1016/j.watres.2009.09.030	journal	January 2010
g_wham—A Free Weighted Histogram Analysis Implementation Including Robust Error and Autocorrelation Estimates Hub, Jochen S.; de Groot, Bert L.; van der Spoel, David Journal of Chemical Theory and Computation, Vol. 6, Issue 12 https://doi.org/10.1021/ct100494z	journal	November 2010
GROMACS 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation Hess, Berk; Kutzner, Carsten; van der Spoel, David Journal of Chemical Theory and Computation, Vol. 4, Issue 3 https://doi.org/10.1021/ct700301q	journal	February 2008
Computational Study of Room-Temperature Ionic Liquids Interacting with a POPC Phospholipid Bilayer Bingham, Richard J.; Ballone, Pietro The Journal of Physical Chemistry B, Vol. 116, Issue 36 https://doi.org/10.1021/jp306126q	journal	August 2012
Impact of Ionic Liquids in Aqueous Solution on Bacterial Plasma Membranes Studied with Molecular Dynamics Simulations Lim, Geraldine S.; Zidar, Jernej; Cheong, Daniel W. The Journal of Physical Chemistry B, Vol. 118, Issue 35 https://doi.org/10.1021/jp5060952	journal	August 2014
Mutual Solubilities of Water and the [C _n mim][Tf ₂ N] Hydrophobic Ionic Liquids Freire, Mara G.; Carvalho, Pedro J.; Gardas, Ramesh L. The Journal of Physical Chemistry B, Vol. 112, Issue 6 https://doi.org/10.1021/jp7097203	journal	February 2008
Zwitterionic Lipid Assemblies: Molecular Dynamics Studies of Monolayers, Bilayers, and Vesicles Using a New Coarse Grain Force Field Shinoda, Wataru; DeVane, Russell; Klein, Michael L. The Journal of Physical Chemistry B, Vol. 114, Issue 20 https://doi.org/10.1021/jp9107206	journal	May 2010
NIH Image to ImageJ: 25 years of image analysis Schneider, Caroline A.; Rasband, Wayne S.; Eliceiri, Kevin W. Nature Methods, Vol. 9, Issue 7 https://doi.org/10.1038/nmeth.2089	journal	June 2012
(Eco)toxicity of fluoro-organic and cyano-based ionic liquid anions Steudte, Stephanie; Stepnowski, Piotr; Cho, Chul-Woong Chemical Communications, Vol. 48, Issue 75 https://doi.org/10.1039/c2cc34955h	journal	January 2012
Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization Zakrewsky, Michael; Lovejoy, Katherine S.; Kern, Theresa L. Proceedings of the National Academy of Sciences, Vol. 111, Issue 37 https://doi.org/10.1073/pnas.1403995111	journal	August 2014
grofit : Fitting Biological Growth Curves with R Kahm, Matthias; Hasenbrink, Guido; Lichtenberg-Fraté, Hella Journal of Statistical Software, Vol. 33, Issue 7 https://doi.org/10.18637/jss.v033.i07	journal	January 2010
1-Octanol/Water Partition Coefficients of 1Alkyl-3-methylimidazolium Chloride Domańska, Urszula; Bogel-Łukasik, Ewa; Bogel-Łukasik, Rafał Chemistry - A European Journal, Vol. 9, Issue 13 https://doi.org/10.1002/chem.200204516	journal	July 2003
Alternatives for the no-observed-effect level Hoekstra, J. A.; van Ewijk, P. H. Environmental Toxicology and Chemistry, Vol. 12, Issue 1 https://doi.org/10.1002/etc.5620120119	journal	January 1993
GROMACS 3.0: a package for molecular simulation and trajectory analysis Lindahl, Erik; Hess, Berk; van der Spoel, David Journal of Molecular Modeling, Vol. 7, Issue 8 https://doi.org/10.1007/s008940100045	journal	August 2001
Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community Docherty, Kathryn M.; Dixon, JaNeille K.; Kulpa Jr, Charles F. Biodegradation, Vol. 18, Issue 4 https://doi.org/10.1007/s10532-006-9081-7	journal	November 2006
Deoxyribonucleic acid replication in meiosis of Chlamydomonas reinhardi Sueoka, N.; Chiang, K. S.; Kates, J. R. Journal of Molecular Biology, Vol. 25, Issue 1 https://doi.org/10.1016/0022-2836(67)90278-1	journal	April 1967
Alternatives for the no-observed-effect level Hoekstra, J. A.; van Ewijk, P. H. Environmental Pollution, Vol. 87, Issue 3, p. 376 https://doi.org/10.1016/0269-7491(95)90042-x	journal	January 1995
Biomass and Pigments of Benthic Algae Steinman, Alan D.; Lamberti, Gary A.; Leavitt, Peter R. Methods in Stream Ecology https://doi.org/10.1016/B978-012332908-0.50024-3	book	January 2007
Membrane interactions of ionic liquids: Possible determinants for biological activity and toxicity Gal, Noga; Malferarri, Danilo; Kolusheva, Sofiya Biochimica et Biophysica Acta (BBA) - Biomembranes, Vol. 1818, Issue 12 https://doi.org/10.1016/j.bbamem.2012.07.025	journal	December 2012
Room-temperature ionic liquid cations act as short-chain surfactants and disintegrate a phospholipid bilayer Evans, Kervin O. Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 274, Issue 1-3 https://doi.org/10.1016/j.colsurfa.2005.10.007	journal	February 2006
Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity Ranke, Johannes; Müller, Anja; Bottin-Weber, Ulrike Ecotoxicology and Environmental Safety, Vol. 67, Issue 3 https://doi.org/10.1016/j.ecoenv.2006.08.008	journal	July 2007
Environmental fate and toxicity of ionic liquids: A review Thuy Pham, Thi Phuong; Cho, Chul-Woong; Yun, Yeoung-Sang Water Research, Vol. 44, Issue 2 https://doi.org/10.1016/j.watres.2009.09.030	journal	January 2010
Interactions of surfactants with lipid membranes Heerklotz, Heiko Quarterly Reviews of Biophysics, Vol. 41, Issue 3-4 https://doi.org/10.1017/S0033583508004721	journal	November 2008
g_wham—A Free Weighted Histogram Analysis Implementation Including Robust Error and Autocorrelation Estimates Hub, Jochen S.; de Groot, Bert L.; van der Spoel, David Journal of Chemical Theory and Computation, Vol. 6, Issue 12 https://doi.org/10.1021/ct100494z	journal	November 2010
GROMACS 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation Hess, Berk; Kutzner, Carsten; van der Spoel, David Journal of Chemical Theory and Computation, Vol. 4, Issue 3 https://doi.org/10.1021/ct700301q	journal	February 2008
Disruption of Supported Lipid Bilayers by Semihydrophobic Nanoparticles Jing, Benxin; Zhu, Yingxi Journal of the American Chemical Society, Vol. 133, Issue 28 https://doi.org/10.1021/ja2040305	journal	July 2011
Computational Study of Room-Temperature Ionic Liquids Interacting with a POPC Phospholipid Bilayer Bingham, Richard J.; Ballone, Pietro The Journal of Physical Chemistry B, Vol. 116, Issue 36 https://doi.org/10.1021/jp306126q	journal	August 2012
Impact of Ionic Liquids in Aqueous Solution on Bacterial Plasma Membranes Studied with Molecular Dynamics Simulations Lim, Geraldine S.; Zidar, Jernej; Cheong, Daniel W. The Journal of Physical Chemistry B, Vol. 118, Issue 35 https://doi.org/10.1021/jp5060952	journal	August 2014
Semihydrophobic Nanoparticle-Induced Disruption of Supported Lipid Bilayers: Specific Ion Effect Jing, Benxin; Abot, Rosary C. T.; Zhu, Yingxi The Journal of Physical Chemistry B, Vol. 118, Issue 46 https://doi.org/10.1021/jp5074945	journal	November 2014
Structure and Stability of Phospholipid Bilayers Hydrated by a Room-Temperature Ionic Liquid/Water Solution: A Neutron Reflectometry Study Benedetto, Antonio; Heinrich, Frank; Gonzalez, Miguel A. The Journal of Physical Chemistry B, Vol. 118, Issue 42 https://doi.org/10.1021/jp507631h	journal	October 2014
Mutual Solubilities of Water and the [C _n mim][Tf ₂ N] Hydrophobic Ionic Liquids Freire, Mara G.; Carvalho, Pedro J.; Gardas, Ramesh L. The Journal of Physical Chemistry B, Vol. 112, Issue 6 https://doi.org/10.1021/jp7097203	journal	February 2008
Zwitterionic Lipid Assemblies: Molecular Dynamics Studies of Monolayers, Bilayers, and Vesicles Using a New Coarse Grain Force Field Shinoda, Wataru; DeVane, Russell; Klein, Michael L. The Journal of Physical Chemistry B, Vol. 114, Issue 20 https://doi.org/10.1021/jp9107206	journal	May 2010
An auto-inducible mechanism for ionic liquid resistance in microbial biofuel production Ruegg, Thomas L.; Kim, Eun-Mi; Simmons, Blake A. Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4490	journal	March 2014
NIH Image to ImageJ: 25 years of image analysis Schneider, Caroline A.; Rasband, Wayne S.; Eliceiri, Kevin W. Nature Methods, Vol. 9, Issue 7 https://doi.org/10.1038/nmeth.2089	journal	June 2012
Applications of ionic liquids in the chemical industry Plechkova, Natalia V.; Seddon, Kenneth R. Chem. Soc. Rev., Vol. 37, Issue 1 https://doi.org/10.1039/B006677J	journal	January 2008
Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling Couling, David J.; Bernot, Randall J.; Docherty, Kathryn M. Green Chem., Vol. 8, Issue 1 https://doi.org/10.1039/B511333D	journal	January 2006
Toxicity of imidazolium ionic liquids to freshwater algae Kulacki, Konrad J.; Lamberti, Gary A. Green Chem., Vol. 10, Issue 1 https://doi.org/10.1039/B709289J	journal	January 2008
Primary biodegradation of ionic liquid cations, identification of degradation products of 1-methyl-3-octylimidazolium chloride and electrochemical wastewater treatment of poorly biodegradable compounds Stolte, Stefan; Abdulkarim, Salha; Arning, Jürgen Green Chem., Vol. 10, Issue 2 https://doi.org/10.1039/B713095C	journal	January 2008
Unravelling the mechanism of toxicity of alkyltributylphosphonium chlorides in Aspergillus nidulans conidia Petkovic, Marija; Hartmann, Diego O.; Adamová, Gabriela New J. Chem., Vol. 36, Issue 1 https://doi.org/10.1039/C1NJ20470J	journal	January 2012
Biodegradability of 27 pyrrolidinium, morpholinium, piperidinium, imidazolium and pyridinium ionic liquid cations under aerobic conditions Neumann, Jennifer; Steudte, Stephanie; Cho, Chul-Woong Green Chem., Vol. 16, Issue 4 https://doi.org/10.1039/C3GC41997E	journal	January 2014
Amphiphilic interactions of ionic liquids with lipid biomembranes: a molecular simulation study Yoo, Brian; Shah, Jindal K.; Zhu, Yingxi Soft Matter, Vol. 10, Issue 43 https://doi.org/10.1039/C4SM01528B	journal	January 2014
Self-aggregation of ionic liquids: micelle formation in aqueous solution Blesic, Marijana; Marques, Maria Helena; Plechkova, Natalia V. Green Chemistry, Vol. 9, Issue 5 https://doi.org/10.1039/b615406a	journal	January 2007
Nanoscale organization in room temperature ionic liquids: a coarse grained molecular dynamics simulation study Bhargava, B. Lokegowda; Devane, Russell; Klein, Michael L. Soft Matter, Vol. 3, Issue 11 https://doi.org/10.1039/b710801j	journal	January 2007
Exploring fungal activity in the presence of ionic liquids Petkovic, M.; Ferguson, J.; Bohn, A. Green Chemistry, Vol. 11, Issue 6 https://doi.org/10.1039/b823225c	journal	January 2009
Microbial biodegradation and metabolite toxicity of three pyridinium-based cation ionic liquids Docherty, Kathryn M.; Joyce, Michelle V.; Kulacki, Konrad J. Green Chemistry, Vol. 12, Issue 4 https://doi.org/10.1039/b919154b	journal	January 2010
The role of the cell wall in the toxicity of ionic liquids to the alga Chlamydomonas reinhardtii Sena, David W.; Kulacki, Konrad J.; Chaloner, Dominic T. Green Chemistry, Vol. 12, Issue 6 https://doi.org/10.1039/c000899k	journal	January 2010
Coarse-grained force field for ionic surfactants Shinoda, Wataru; DeVane, Russell; Klein, Michael L. Soft Matter, Vol. 7, Issue 13 https://doi.org/10.1039/c1sm05173c	journal	January 2011
(Eco)toxicity of fluoro-organic and cyano-based ionic liquid anions Steudte, Stephanie; Stepnowski, Piotr; Cho, Chul-Woong Chemical Communications, Vol. 48, Issue 75 https://doi.org/10.1039/c2cc34955h	journal	January 2012
Transformations in plasma membranes of cancerous cells and resulting consequences for cation insertion studied with molecular dynamics Klähn, Marco; Zacharias, Martin Physical Chemistry Chemical Physics, Vol. 15, Issue 34 https://doi.org/10.1039/c3cp52085d	journal	January 2013
Polyoxometalate macroion induced phase and morphology instability of lipid membrane Jing, Benxin; Hutin, Marie; Connor, Erin Chemical Science, Vol. 4, Issue 10 https://doi.org/10.1039/c3sc51404h	journal	January 2013
Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization Zakrewsky, Michael; Lovejoy, Katherine S.; Kern, Theresa L. Proceedings of the National Academy of Sciences, Vol. 111, Issue 37 https://doi.org/10.1073/pnas.1403995111	journal	August 2014
Formation of micelles in aqueous solutions of a room temperature ionic liquid: a study using coarse grained molecular dynamics Bhargava, B. L.; L. Klein, Michael Molecular Physics, Vol. 107, Issue 4-6 https://doi.org/10.1080/00268970902810283	journal	February 2009
Multi-property fitting and parameterization of a coarse grained model for aqueous surfactants Shinoda, W.; DeVane, R.; Klein, M. L. Molecular Simulation, Vol. 33, Issue 1-2 https://doi.org/10.1080/08927020601054050	journal	January 2007
grofit : Fitting Biological Growth Curves with R Kahm, Matthias; Hasenbrink, Guido; Lichtenberg-Fraté, Hella Journal of Statistical Software, Vol. 33, Issue 7 https://doi.org/10.18637/jss.v033.i07	journal	January 2010
Acute and Chronic Toxicity of Imidazolium-Based Ionic Liquids on Daphnia Magna Bernot, Randall J.; Brueseke, Michael A.; Evans-White, Michelle A. Environmental Toxicology and Chemistry, Vol. 24, Issue 1 https://doi.org/10.1897/03-635.1	journal	January 2005

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The Use of Liquids Ionic Fluids as Pharmaceutically Active Substances Helpful in Combating Nosocomial Infections Induced by Klebsiella Pneumoniae New Delhi Strain, Acinetobacter Baumannii and Enterococcus Species Miskiewicz, Andrzej; Ceranowicz, Piotr; Szymczak, Mateusz International Journal of Molecular Sciences, Vol. 19, Issue 9 https://doi.org/10.3390/ijms19092779	journal	September 2018
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1-Benzyl-3-cetyl-2-methylimidazolium Iodide (NH125) Is a Broad-Spectrum Inhibitor of Virus Entry with Lysosomotropic Features Moeschler, Sarah; Locher, Samira; Zimmer, Gert Viruses, Vol. 10, Issue 6 https://doi.org/10.3390/v10060306	journal	June 2018
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