Unveiling the Interaction between Fatty-Acid-Modified Membrane and Hydrophilic Imidazolium-Based Ionic Liquid: Understanding the Mechanism of Ionic Liquid Cytotoxicity

Journal of Physical Chemistry B

Volumn 121, Issue 34, 2017, Pages 8162-8170

  Kundu, Niloy ^a   Roy, Shreya ^a   Mukherjee, Devdeep ^a   Maiti, Tapas Kumar ^a   Sarkar, Nilmoni ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CYTOLOGY; CYTOTOXICITY; FATTY ACIDS; FLUIDITY; HYDROPHILICITY; LIQUIDS; MEMBRANES;

IMIDAZOLIUM-BASED; IMIDAZOLIUM-BASED IONIC LIQUID; IONIC LIQUID (ILS); ISOMERIZATION KINETICS; MEMBRANE FLUIDITY; MEMBRANE PERMEABILIZATION; MODIFIED MEMBRANES; MOLECULAR ORIGINS;

IONIC LIQUIDS;

FATTY ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID;

CELL MEMBRANE; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; FLOW CYTOMETRY; HUMAN; K-562 CELL LINE; METABOLISM; SCANNING ELECTRON MICROSCOPY;

CELL MEMBRANE; CELL SURVIVAL; FATTY ACIDS; FLOW CYTOMETRY; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMIDAZOLES; IONIC LIQUIDS; K562 CELLS; MICROSCOPY, ELECTRON, SCANNING;

EID: 85028657512     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.7b06231     Document Type: Article

References (38)

1. Seddon, K. R. Ionic liquids: A Taste of the Future Nat. Mater. 2003, 2, 363-365 10.1038/nmat907
2. Hayes, R.; Warr, G. G.; Atkin, R. Structure and Nanostructure in Ionic Liquids Chem. Rev. 2015, 115, 6357-6426 10.1021/cr500411q
3. Zhang, S.; Zhang, J.; Zhang, Y.; Deng, Y. Nanoconfined Ionic Liquids Chem. Rev. 2017, 117, 6755-6833 10.1021/acs.chemrev.6b00509
4. Goossens, K.; Lava, K.; Bielawski, C. W.; Binnemans, K. Ionic Liquid Crystals: Versatile Materials Chem. Rev. 2016, 116, 4643-4807 10.1021/cr400334b
5. Amarasekara, A. S. Acidic Ionic Liquids Chem. Rev. 2016, 116, 6133-6183 10.1021/acs.chemrev.5b00763
6. Plechkovaa, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37, 123-150 10.1039/B006677J
7. Vekariya, R. L. A Review of Ionic Liquids: Applications towards Catalytic Organic Transformations J. Mol. Liq. 2017, 227, 44-60 10.1016/j.molliq.2016.11.123
8. Ranke, J.; Molter, K.; Stock, F.; Weber, U. B.; Poczobutt, J.; Hoffmann, J.; Ondruschka, B.; Filser, J.; Jastorff, B. Biological Effects of Imidazolium Ionic Liquids with Varying Chain Lengths in Acute Vibrio Fischeri and WST-1 Cell Viability Assays Ecotoxicol. Environ. Saf. 2004, 58, 396-404 10.1016/S0147-6513(03)00105-2
9. Egorova, K. S.; Gordeev, E. G.; Ananikov, V. P. Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine Chem. Rev. 2017, 117, 7132-7189 10.1021/acs.chemrev.6b00562
10. Benedetto, A.; Ballone, P. Room Temperature Ionic Liquids Meet Biomolecules: A Microscopic View of Structure and Dynamics ACS Sustainable Chem. Eng. 2016, 4, 392-412 10.1021/acssuschemeng.5b01385
11. Hartmann, D. O.; Shimizu, K.; Siopa, F.; Leitao, M. C.; Afonso, C. A. M.; Lopes, J. N. C.; Pereira, C. S. Plasma Membrane Permeabilisation by Ionic Liquids: A Matter of Charge Green Chem. 2015, 17, 4587-4598 10.1039/C5GC01472G
12. Ohno, H.; Fujita, K.; Kohno, Y. Is Seven the Minimum Number of Water Molecules per Ion Pair for Assured Biological Activity in Ionic Liquid-Water Mixtures? Phys. Chem. Chem. Phys. 2015, 17, 14454-14460 10.1039/C5CP00768B
13. Bernardes, C. E.; Minas da Piedade, M. E.; Canongia Lopes, J. N. The Structure of Aqueous Solutions of a Hydrophilic Ionic Liquid: the Full Concentration Range of 1-Ethyl-3-methylimidazolium Ethylsulfate and Water J. Phys. Chem. B 2011, 115, 2067-2074 10.1021/jp1113202
14. Bingham, R. J.; Ballone, P. Computational Study of Room- Temperature Ionic Liquids Interacting with a POPC Phospholipid Bilayer J. Phys. Chem. B 2012, 116, 11205-11216 10.1021/jp306126q
15. Lim, G. S.; Zidar, J.; Cheong, D. W.; Jaenicke, S.; Klähn, M. Impact of Ionic Liquids in Aqueous Solution on Bacterial Plasma Membranes Studied with Molecular Dynamics Simulations J. Phys. Chem. B 2014, 118, 10444-10459 10.1021/jp5060952
16. Yoo, B.; Zhu, Y.; Maginn, E. J. Molecular Mechanism of Ionic-Liquid-Induced Membrane Disruption: Morphological Changes to Bilayers, Multilayers, and Vesicles Langmuir 2016, 32, 5403-5411 10.1021/acs.langmuir.6b00768
17. Yoo, B.; Shah, J. K.; Zhu, Y.; Maginn, E. J. Amphiphilic Interactions of Ionic Liquids with Lipid Biomembranes: A Molecular Simulation Study Soft Matter 2014, 10, 8641-8651 10.1039/C4SM01528B
18. Yoo, B.; Jing, B.; Jones, S. E.; Lamberti, G. A.; Zhu, Y.; Shah, J. K.; Maginn, E. J. Molecular Mechanisms of Ionic Liquid Cytotoxicity Probed by an Integrated Experimental and Computational Approach Sci. Rep. 2016, 6 19889 10.1038/srep19889
19. Jing, B.; Lan, N.; Qiu, J.; Zhu, Y. Interaction of Ionic Liquids with a Lipid Bilayer: A Biophysical Study of Ionic Liquid Cytotoxicity J. Phys. Chem. B 2016, 120, 2781-2789 10.1021/acs.jpcb.6b00362
20. Chen, I. A.; Szostak, J. W. A Kinetic Study of the Growth of Fatty Acid Vesicles Biophys. J. 2004, 87, 988-998 10.1529/biophysj.104.039875
21. Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Ionization and Phase Behavior of Fatty Acids in Water: Application of the Gibbs Phase Rule Biochemistry 1988, 27, 1881-1888 10.1021/bi00406a013
22. Morigaki, K.; Walde, P. Fatty Acid Vesicles Curr. Opin. Colloid Interface Sci. 2007, 12, 75-80 10.1016/j.cocis.2007.05.005
23. Wick, R.; Walde, P.; Luisi, P. L. Light Microscopic Investigations of the Autocatalytic Self-Reproduction of Giant Vesicles J. Am. Chem. Soc. 1995, 117, 1435-1436 10.1021/ja00109a031
24. Szostak, J. W.; Bartel, D. P.; Luisi, P. L. Synthesizing life Nature 2001, 409, 387-390 10.1038/35053176
25. Dzieciol, A. J.; Mann, S. Designs for Life: Protocell Models in the Laboratory Chem. Soc. Rev. 2012, 41, 79-85 10.1039/C1CS15211D
26. Walde, P.; Goto, A.; Monnard, P. A.; Wessicken, M.; Luisi, P. L. Oparin's Reactions Revisited: Enzymic Synthesis of Poly(adenylic acid) in Micelles and Self-Reproducing Vesicles J. Am. Chem. Soc. 1994, 116, 7541-7547 10.1021/ja00096a010
27. Adamala, K.; Szostak, J. W. Nonenzymatic Template-Directed RNA Synthesis Inside Model Protocells Science 2013, 342, 1098-1100 10.1126/science.1241888
28. Kundu, N.; Banerjee, P.; Dutta, R.; Kundu, S.; Saini, R. K.; Halder, M.; Sarkar, N. Proton Transfer Pathways of 2,2′-Bipyridine-3,3′-diol in pH Responsive Fatty Acid Self-Assemblies: Multiwavelength Fluorescence Lifetime Imaging in a Single Vesicle Langmuir 2016, 32, 13284-13295 10.1021/acs.langmuir.6b03404
29. Kundu, N.; Banerjee, P.; Kundu, S.; Dutta, R.; Sarkar, N. Sodium Chloride Triggered the Fusion of Vesicle Composed of Fatty Acid Modified Protic Ionic Liquid: A New Insight into the Membrane Fusion Monitored through Fluorescence Lifetime Imaging Microscopy J. Phys. Chem. B 2017, 121, 24-34 10.1021/acs.jpcb.6b09298
30. Kundu, N.; Mukherjee, D.; Maiti, T. K.; Sarkar, N. Protein-Guided Formation of Silver Nanoclusters and Their Assembly with Graphene Oxide as an Improved Bioimaging Agent with Reduced Toxicity J. Phys. Chem. Lett. 2017, 8, 2291-2297 10.1021/acs.jpclett.7b00600
31. Kundu, N.; Banik, D.; Roy, A.; Kuchlyan, J.; Sarkar, N. Modulation of the Aggregation Properties of Sodium Deoxycholate in Presence of Hydrophilic Imidazolium Based Ionic Liquid: Water Dynamics Study to Probe the Structural Alteration of the Aggregates Phys. Chem. Chem. Phys. 2015, 17, 25216-25227 10.1039/C5CP03906A
32. Chernomordik, L. V.; Kozlov, M. M. Membrane Hemifusion: Crossing a Chasm in Two L1eaps Cell 2005, 123, 375-382 10.1016/j.cell.2005.10.015
33. Skarmoutsos, I.; Dellis, D.; Matthews, R. P.; Welton, T.; Hunt, P. A. Hydrogen Bonding in 1-Butyl- and 1-Ethyl-3-methylimidazolium Chloride Ionic Liquids J. Phys. Chem. B 2012, 116, 4921-4933 10.1021/jp209485y
34. Chmyrov, V.; Spielmann, T.; Hevekerl, H.; Widengren, J. Trans-Cis Isomerization of Lipophilic Dyes Probing Membrane Microviscosity in Biological Membranes and in Live Cells Anal. Chem. 2015, 87, 5690-5697 10.1021/acs.analchem.5b00863
35. Onganer, Y.; Quitevis, E. L. Dynamics of Merocyanine 540 in Model Biomembranes: Photoisomerization Studies in Small Unilamellar Vesicles Biochim. Biophys. Acta 1994, 1192, 27-34 10.1016/0005-2736(94)90139-2
36. Widengren, J.; Seidel, C. A. M. Manipulation and Characterization of Photo-Induced Transient States of Merocyanine 540 by Fluorescence Correlation Spectroscopy Phys. Chem. Chem. Phys. 2000, 2, 3435-3441 10.1039/b003268i
37. Kalyanaramn, B.; Feix, J. B.; Sieber, F.; Thomas, J. P.; Girotti, A. W. Photodynamic action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2999-3003 10.1073/pnas.84.9.2999
38. Liang, C. H.; Ho, W. Y.; Yeh, L. H.; Cheng, Y. S.; Chou, T. H. Effects of 1-hexadecyl-3-methylimidazolium Ionic Liquids on the Physicochemical Characteristics and Cytotoxicity of Phosphatidylcholine Vesicles Colloids Surf., A 2013, 436, 1083-1091 10.1016/j.colsurfa.2013.08.040