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Biophysical Reviews

, Volume 10, Issue 3, pp 795–808 | Cite as

Effect of water and ionic liquids on biomolecules

Review

Abstract

The remarkable progress in the field of ionic liquids (ILs) in the last two decades has involved investigations on different aspects of ILs in various conditions. The nontoxic and biocompatible nature of ILs makes them a suitable substance for the storage and application of biomolecules. In this regard, the aqueous IL solutions have attracted a large number of studies to comprehend the role of water in modulating various properties of biomolecules. Here, we review some of the recent studies on aqueous ILs that concern the role of water in altering the behavior of ILs in general and in case of biomolecules solvated in ILs. The different structural and dynamic effects caused by water have been highlighted. We discuss the different modes of IL interaction that are responsible for stabilization and destabilization of proteins and enzymes followed by examples of water effect on this. The role of water in the case of nucleic acid storage in ILs, an area which has mostly been underrated, also has been emphasized. Our discussions highlight the fact that the effects of water on IL behavior are not general and are highly dependent on the nature of the IL under consideration. Overall, we aim to draw attention to the significance of water dynamics in the aqueous IL solutions, a better understanding of which can help in developing superior storage materials for application purposes.

Keywords

IL structure IL dynamics IL protein interactions IL DNA interaction 

Abbreviations

emim

1-Ethyl-3-methylimidazolium

bmim

1-Butyl-3-methylimidazolium

pmim

1-Pentyl-3-methylimidazolium

hmim

1-Hexyl-3-methylimidazolium

omim

1-Octyl-3-methylimidazolium

BPYR

1-butylpyridinium

Notes

Acknowledgments

This work was funded by DST SERB (EMR/2016/001069).

Compliance with ethical standards

Conflict of interest

Debasis Saha declares that he has no conflict of interest. Arnab Mukherjee declares that he has no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

References

  1. Anthony JL, Maginn EJ, Brennecke JF (2001) Solution thermodynamics of imidazolium-based ionic liquids and water. J Phys Chem B 105:10942–10949.  https://doi.org/10.1021/jp0112368 Google Scholar
  2. Araque JC, Daly RP, Margulis CJ (2016) A link between structure, diffusion and rotations of hydrogen bonding tracers in ionic liquids. J Chem Phys 144:204504.  https://doi.org/10.1063/1.4951012 PubMedGoogle Scholar
  3. Araque JC, Yadav SK, Shadeck M, Maroncelli M, Margulis CJ (2015) How is diffusion of neutral and charged tracers related to the structure and dynamics of a room-temperature ionic liquid? Large deviations from Stokes–Einstein behavior explained. J Phys Chem B 119:7015–7029.  https://doi.org/10.1021/acs.jpcb.5b01093 PubMedGoogle Scholar
  4. Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B (2009) Ionic-liquid materials for the electrochemical challenges of the future. Nat Mater 8:621–629.  https://doi.org/10.1038/nmat2448 PubMedGoogle Scholar
  5. Attri P, Venkatesu P, Kumar A (2011) Activity and stability of [small alpha]-chymotrypsin in biocompatible ionic liquids: enzyme refolding by triethyl ammonium acetate. Phys Chem Chem Phys 13:2788–2796.  https://doi.org/10.1039/C0CP01291B PubMedGoogle Scholar
  6. Benedetto A, Ballone P (2016) Room temperature ionic liquids meet biomolecules: a microscopic view of structure and dynamics. ACS Sustain Chem Eng 4:392–412.  https://doi.org/10.1021/acssuschemeng.5b01385 Google Scholar
  7. Bihari M, Russell TP, Hoagland DA (2010) Dissolution and dissolved state of cytochrome c in a neat, hydrophilic ionic liquid. Biomacromolecules 11:2944–2948.  https://doi.org/10.1021/bm100735z PubMedGoogle Scholar
  8. Blesic M, Marques MH, Plechkova NV, Seddon KR, Rebelo LPN, Lopes A (2007) Self-aggregation of ionic liquids: micelle formation in aqueous solution. Green Chem 9:481–490.  https://doi.org/10.1039/B615406A Google Scholar
  9. Boersma AJ, Megens RP, Feringa BL, Roelfes G (2010) DNA-based asymmetric catalysis. Chem Soc Rev 39:2083–2092.  https://doi.org/10.1039/B811349C PubMedGoogle Scholar
  10. Borrell KL, Cancglin C, Stinger BL et al (2017) An experimental and molecular dynamics study of red fluorescent protein mCherry in novel aqueous amino acid ionic liquids. J Phys Chem B 121:4823–4832.  https://doi.org/10.1021/acs.jpcb.7b03582 PubMedGoogle Scholar
  11. Bowers J, Butts CP, Martin PJ, Vergara-Gutierrez MC, Heenan RK (2004) Aggregation behavior of aqueous solutions of ionic liquids. Langmuir 20:2191–2198.  https://doi.org/10.1021/la035940m PubMedGoogle Scholar
  12. Brogan APS, Hallett JP (2016) Solubilizing and stabilizing proteins in anhydrous ionic liquids through formation of protein–polymer surfactant nanoconstructs. J Am Chem Soc 138:4494–4501.  https://doi.org/10.1021/jacs.5b13425 PubMedGoogle Scholar
  13. Bruce DW, Cabry CP, Lopes JNC et al (2017) Nanosegregation and structuring in the bulk and at the surface of ionic-liquid mixtures. J Phys Chem B 121:6002–6020.  https://doi.org/10.1021/acs.jpcb.7b01654 PubMedGoogle Scholar
  14. Burd VN, Bantleon R, van Pee K-H (2001) Oxidation of indole and indole derivatives catalyzed by nonheme chloroperoxidases. Appl Biochem Microbiol 37:248–250.  https://doi.org/10.1023/a:1010220916145 Google Scholar
  15. Byrne N, Wang L-M, Belieres J-P, Angell CA (2007) Reversible folding-unfolding, aggregation protection, and multi-year stabilization, in high concentration protein solutions, using ionic liquids. Chem Commun:2714–2716.  https://doi.org/10.1039/B618943A
  16. Cammarata L, Kazarian SG, Salter PA, Welton T (2001) Molecular states of water in room temperature ionic liquids. Phys Chem Chem Phys 3:5192–5200.  https://doi.org/10.1039/B106900D Google Scholar
  17. Chandran A, Ghoshdastidar D, Senapati S (2012) Groove binding mechanism of ionic liquids: a key factor in long-term stability of DNA in hydrated ionic liquids? J Am Chem Soc 134:20330–20339.  https://doi.org/10.1021/ja304519d PubMedGoogle Scholar
  18. Chatel G, MacFarlane DR (2014) Ionic liquids and ultrasound in combination: synergies and challenges. Chem Soc Rev 43:8132–8149.  https://doi.org/10.1039/C4CS00193A PubMedGoogle Scholar
  19. Collins KD, Washabaugh MW (2009) The Hofmeister effect and the behaviour of water at interfaces. Q Rev Biophys 18:323–422.  https://doi.org/10.1017/S0033583500005369 Google Scholar
  20. Constantinescu D, Weingärtner H, Herrmann C (2007) Protein denaturation by ionic liquids and the Hofmeister Series: a case study of aqueous solutions of ribonuclease A. Angew Chem Int Ed 46:8887–8889.  https://doi.org/10.1002/anie.200702295 Google Scholar
  21. Constatinescu D, Herrmann C, Weingartner H (2010) Patterns of protein unfolding and protein aggregation in ionic liquids. Phys Chem Chem Phys 12:1756–1763.  https://doi.org/10.1039/B921037G PubMedGoogle Scholar
  22. Cull SG, Holbrey JD, Vargas-Mora V, Seddon KR, Lye GJ (2000) Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. Biotechnol Bioeng 69:227–233.  https://doi.org/10.1002/(SICI)1097-0290(20000720)69:2<227::AID-BIT12>3.0.CO;2-0 PubMedGoogle Scholar
  23. Dabirmanesh B, Daneshjou S, Sepahi AA et al (2011) Effect of ionic liquids on the structure, stability and activity of two related α-amylases. Int J Biol Macromol 48:93–97.  https://doi.org/10.1016/j.ijbiomac.2010.10.001 PubMedGoogle Scholar
  24. De Diego T, Lozano P, Gmouh S, Vaultier M, Iborra JL (2005) Understanding structure−stability relationships of Candida antartica lipase B in ionic liquids. Biomacromolecules 6:1457–1464.  https://doi.org/10.1021/bm049259q PubMedGoogle Scholar
  25. de Zoysa RSS, Jayawardhana DA, Zhao Q, Wang D, Armstrong DW, Guan X (2009) Slowing DNA translocation through nanopores using a solution containing organic salts. J Phys Chem B 113:13332–13336.  https://doi.org/10.1021/jp9040293 PubMedGoogle Scholar
  26. Diddens D, Lesch V, Heuer A, Smiatek J (2017) Aqueous ionic liquids and their influence on peptide conformations: denaturation and dehydration mechanisms. Phys Chem Chem Phys 19:20430–20440.  https://doi.org/10.1039/C7CP02897K PubMedGoogle Scholar
  27. Ding Y, Zhang L, Xie J, Guo R (2010) Binding characteristics and molecular mechanism of interaction between ionic liquid and DNA. J Phys Chem B 114:2033–2043.  https://doi.org/10.1021/jp9104757 PubMedGoogle Scholar
  28. Dominguez de Marıá P (ed) (2012) Ionic liquids in biotransformations and organocatalysis: solvents and beyond. John Wiley & Sons, Inc, HobokenGoogle Scholar
  29. Domínguez-Pérez M, Tomé LIN, Freire MG, Marrucho IM, Cabeza O, Coutinho JAP (2010) (Extraction of biomolecules using) aqueous biphasic systems formed by ionic liquids and aminoacids. Sep Purif Technol 72:85–91.  https://doi.org/10.1016/j.seppur.2010.01.008 Google Scholar
  30. Du Z, Yu Y-L, Wang J-H (2007) Extraction of proteins from biological fluids by use of an ionic liquid/aqueous two-phase system. Chem Eur J 13:2130–2137.  https://doi.org/10.1002/chem.200601234 PubMedGoogle Scholar
  31. Dupont J, Scholten JD (2010) On the structural and surface properties of transition-metal nanoparticles in ionic liquids. Chem Soc Rev 39:1780–1804.  https://doi.org/10.1039/B822551F PubMedGoogle Scholar
  32. Earle Martyn J, Seddon Kenneth R (2000) Ionic liquids. Green solvents for the future. Pure Appl Chem 72:1391.  https://doi.org/10.1351/pac200072071391 Google Scholar
  33. Eckstein M, Sesing M, Kragl U, Adlercreutz P (2002) At low water activity α-chymotrypsin is more active in an ionic liquid than in non-ionic organic solvents. Biotechnol Lett 24:867–872.  https://doi.org/10.1023/a:1015564608261 Google Scholar
  34. Egorova KS, Gordeev EG, Ananikov VP (2017) Biological activity of ionic liquids and their application in pharmaceutics and medicine. Chem Rev 117:7132–7189.  https://doi.org/10.1021/acs.chemrev.6b00562 PubMedGoogle Scholar
  35. Erbeldinger M, Mesiano AJ, Russell AJ (2000) Enzymatic catalysis of formation of Z-aspartame in ionic liquid—an alternative to enzymatic catalysis in organic solvents. Biotechnol Prog 16:1129–1131.  https://doi.org/10.1021/bp000094g PubMedGoogle Scholar
  36. Fedorov MV, Kornyshev AA (2008) Towards understanding the structure and capacitance of electrical double layer in ionic liquids. Electrochim Acta 53:6835–6840.  https://doi.org/10.1016/j.electacta.2008.02.065 Google Scholar
  37. Franklin RE, Gosling RG (1953) Molecular configuration in sodium thymonucleate. Nature 171:740–741.  https://doi.org/10.1038/171740a0 PubMedGoogle Scholar
  38. Freire MG, Neves CMSS, Marrucho IM, Canongia Lopes JN, Rebelo LPN, Coutinho JAP (2010) High-performance extraction of alkaloids using aqueous two-phase systems with ionic liquids. Green Chem 12:1715–1718.  https://doi.org/10.1039/C0GC00179A Google Scholar
  39. Fujita K, MacFarlane DR, Forsyth M (2005) Protein solubilising and stabilising ionic liquids. Chem Commun:4804–4806.  https://doi.org/10.1039/B508238B
  40. Fujita K, MacFarlane DR, Forsyth M et al (2007) Solubility and stability of cytochrome c in hydrated ionic liquids: effect of Oxo acid residues and kosmotropicity. Biomacromolecules 8:2080–2086.  https://doi.org/10.1021/bm070041o PubMedGoogle Scholar
  41. Fujita K, Ohno H (2012) Stable G-quadruplex structure in a hydrated ion pair: cholinium cation and dihydrogen phosphate anion. Chem Commun 48:5751–5753.  https://doi.org/10.1039/C2CC30554B Google Scholar
  42. Gao W-W, Zhang F-X, Zhang G-X, Zhou C-H (2015) Key factors affecting the activity and stability of enzymes in ionic liquids and novel applications in biocatalysis. Biochem Eng J 99:67–84.  https://doi.org/10.1016/j.bej.2015.03.005 Google Scholar
  43. Ghosh S, Parui S, Jana B, Bhattacharyya K (2015) Ionic liquid induced dehydration and domain closure in lysozyme: FCS and MD simulation. J Chem Phys 143:125103.  https://doi.org/10.1063/1.4931974 PubMedGoogle Scholar
  44. Hayes R, Warr GG, Atkin R (2015) Structure and nanostructure in ionic liquids. Chem Rev 115:6357–6426.  https://doi.org/10.1021/cr500411q PubMedGoogle Scholar
  45. He Y, Li Z, Simone P, Lodge TP (2006) Self-assembly of block copolymer micelles in an ionic liquid. J Am Chem Soc 128:2745–2750.  https://doi.org/10.1021/ja058091t PubMedGoogle Scholar
  46. Hofmeister F (1888) Zur Lehre von der Wirkung der Salze. Arch Exp Pathol Pharmakol 24:247–260Google Scholar
  47. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD (2001) Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem 3:156–164.  https://doi.org/10.1039/B103275P Google Scholar
  48. Itoh T (2017) Ionic liquids as tool to improve enzymatic organic synthesis. Chem Rev 117:10567–10607.  https://doi.org/10.1021/acs.chemrev.7b00158 PubMedGoogle Scholar
  49. Ivanov VI, Minchenkova LE, Minyat EE, Frank-Kamenetskii MD, Schyolkina AK (1974) The B̄ to Ā transition of DNA in solution. J Mol Biol 87:817–833.  https://doi.org/10.1016/0022-2836(74)90086-2 PubMedGoogle Scholar
  50. Jaeger VW, Pfaendtner J (2013) Structure, dynamics, and activity of xylanase solvated in binary mixtures of ionic liquid and water. ACS Chem Biol 8:1179–1186.  https://doi.org/10.1021/cb3006837 PubMedGoogle Scholar
  51. Jens S (2017) Aqueous ionic liquids and their effects on protein structures: an overview on recent theoretical and experimental results. J Phys Condens Matter 29:233001.  https://doi.org/10.1088/1361-648X/aa6c9d Google Scholar
  52. Jeong S, Ha SH, Han S-H et al (2012) Elucidation of molecular interactions between lipid membranes and ionic liquids using model cell membranes. Soft Matter 8:5501–5506.  https://doi.org/10.1039/C2SM25223F Google Scholar
  53. Jha I, Venkatesu P (2015) Endeavour to simplify the frustrated concept of protein-ammonium family ionic liquid interactions. Phys Chem Chem Phys 17:20466–20484.  https://doi.org/10.1039/C5CP01735A PubMedGoogle Scholar
  54. Jiang W, Wang Y, Voth GA (2007) Molecular dynamics simulation of nanostructural organization in ionic liquid/water mixtures. J Phys Chem B 111:4812–4818.  https://doi.org/10.1021/jp067142l PubMedGoogle Scholar
  55. Jordan A, Gathergood N (2015) Biodegradation of ionic liquids—a critical review. Chem Soc Rev 44:8200–8237.  https://doi.org/10.1039/C5CS00444F PubMedGoogle Scholar
  56. Jorgensen WL, Pranata J (1990) Importance of secondary interactions in triply hydrogen bonded complexes: guanine-cytosine vs uracil-2,6-diaminopyridine. J Am Chem Soc 112:2008–2010.  https://doi.org/10.1021/ja00161a061 Google Scholar
  57. Jumbri K, Abdul Rahman MB, Abdulmalek E, Ahmad H, Micaelo NM (2014) An insight into structure and stability of DNA in ionic liquids from molecular dynamics simulation and experimental studies. Phys Chem Chem Phys 16:14036–14046.  https://doi.org/10.1039/C4CP01159G PubMedGoogle Scholar
  58. Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ (2003) Impact of ionic liquid physical properties on lipase activity and stability. J Am Chem Soc 125:4125–4131.  https://doi.org/10.1021/ja028557x PubMedGoogle Scholar
  59. Kaintz A, Baker G, Benesi A, Maroncelli M (2013) Solute diffusion in ionic liquids, NMR measurements and comparisons to conventional solvents. J Phys Chem B 117:11697–11708.  https://doi.org/10.1021/jp405393d PubMedGoogle Scholar
  60. Kim K-W, Song B, Choi M-Y, Kim M-J (2001) Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. Org Lett 3:1507–1509.  https://doi.org/10.1021/ol015824f PubMedGoogle Scholar
  61. Kimizuka N, Nakashima T (2001) Spontaneous self-assembly of glycolipid bilayer membranes in sugar-philic ionic liquids and formation of ionogels. Langmuir 17:6759–6761.  https://doi.org/10.1021/la015523e Google Scholar
  62. Klahn M, Lim GS, Seduraman A, Wu P (2011) On the different roles of anions and cations in the solvation of enzymes in ionic liquids. Phys Chem Chem Phys 13:1649–1662.  https://doi.org/10.1039/C0CP01509A PubMedGoogle Scholar
  63. Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409:241–246.  https://doi.org/10.1038/35051719 PubMedGoogle Scholar
  64. Kohno Y, Ohno H (2012) Ionic liquid/water mixtures: from hostility to conciliation. Chem Commun 48:7119–7130.  https://doi.org/10.1039/C2CC31638B Google Scholar
  65. Kowsari MH, Alavi S, Ashrafizaadeh M, Najafi B (2008) Molecular dynamics simulation of imidazolium-based ionic liquids. I. Dynamics and diffusion coefficient. J Chem Phys 129:224508. doi:  https://doi.org/10.1063/1.3035978
  66. Kragl U, Eckstein M, Kaftzik N (2002) Enzyme catalysis in ionic liquids. Curr Opin Biotechnol 13:565–571.  https://doi.org/10.1016/S0958-1669(02)00353-1 PubMedGoogle Scholar
  67. Kulkarni M, Mukherjee A (2013) Sequence dependent free energy profiles of localized B- to A-form transition of DNA in water. J Chem Phys 139:155102.  https://doi.org/10.1063/1.4825175 PubMedGoogle Scholar
  68. Kulkarni M, Mukherjee A (2016) Ionic liquid prolongs DNA translocation through graphene nanopores. RSC Adv 6:46019–46029.  https://doi.org/10.1039/C6RA07017E Google Scholar
  69. Kunz W, Lo Nostro P, Ninham BW (2004) The present state of affairs with Hofmeister effects. Curr Opin Colloid Interface Sci 9:1–18.  https://doi.org/10.1016/j.cocis.2004.05.004 Google Scholar
  70. Kutzler MA, Weiner DB (2008) DNA vaccines: ready for prime time? Nat Rev Genet 9:776–788.  https://doi.org/10.1038/nrg2432 PubMedPubMedCentralGoogle Scholar
  71. Law G, Watson PR (2001) Surface tension measurements of N-Alkylimidazolium ionic liquids. Langmuir 17:6138–6141.  https://doi.org/10.1021/la010629v Google Scholar
  72. Lee SH, NgocDoan TT, HoHa S, Chang W-J, Koo Y-M (2007) Influence of ionic liquids as additives on sol−gel immobilized lipase. J Mol Catal B Enzym 47:129–134.  https://doi.org/10.1016/j.molcatb.2007.05.002 Google Scholar
  73. Lei Z, Dai C, Chen B (2014) Gas solubility in ionic liquids. Chem Rev 114:1289–1326.  https://doi.org/10.1021/cr300497a PubMedGoogle Scholar
  74. Lin Huang J, Noss ME, Schmidt KM, Murray L, Bunagan MR (2011) The effect of neat ionic liquid on the folding of short peptides. Chem Commun 47:8007–8009.  https://doi.org/10.1039/C1CC11527H Google Scholar
  75. Lindahl T, Nyberg B (1972) Rate of depurination of native deoxyribonucleic acid. Biochemistry 11:3610–3618.  https://doi.org/10.1021/bi00769a018 PubMedGoogle Scholar
  76. Liu X, Zhou G, He H, Zhang X, Wang J, Zhang S (2015) Rodlike micelle structure and formation of ionic liquid in aqueous solution by molecular simulation. Ind Eng Chem Res 54:1681–1688.  https://doi.org/10.1021/ie503109z Google Scholar
  77. Lou W-Y, Zong M-H (2006) Efficient kinetic resolution of (R,S)-1-trimethylsilylethanol via lipase-mediated enantioselective acylation in ionic liquids. Chirality 18:814–821.  https://doi.org/10.1002/chir.20307 PubMedGoogle Scholar
  78. Lozano P, Bernal JM, Garcia-Verdugo E et al (2015) Sponge-like ionic liquids: a new platform for green biocatalytic chemical processes. Green Chem 17:3706–3717.  https://doi.org/10.1039/C5GC00894H Google Scholar
  79. Machado MF, Queirós RP, Santos MD, Fidalgo LG, Delgadillo I, Saraiva JA (2014) Effect of ionic liquids alkyl chain length on horseradish peroxidase thermal inactivation kinetics and activity recovery after inactivation. World J Microbiol Biotechnol 30:487–494.  https://doi.org/10.1007/s11274-013-1466-2 PubMedGoogle Scholar
  80. Madeira Lau R, Sorgedrager MJ, Carrea G, van Rantwijk F, Secundo F, Sheldon RA (2004) Dissolution of Candida antarctica lipase B in ionic liquids: effects on structure and activity. Green Chem 6:483–487.  https://doi.org/10.1039/B405693K Google Scholar
  81. Madeira Lau R, Van Rantwijk F, Seddon KR, Sheldon RA (2000) Lipase-catalyzed reactions in ionic liquids. Org Lett 2:4189–4191.  https://doi.org/10.1021/ol006732d PubMedGoogle Scholar
  82. Méndez-Morales T, Carrete J, Cabeza Ó, Gallego LJ, Varela LM (2011) Molecular dynamics simulation of the structure and dynamics of water–1-Alkyl-3-methylimidazolium ionic liquid mixtures. J Phys Chem B 115:6995–7008.  https://doi.org/10.1021/jp202692g PubMedGoogle Scholar
  83. Micaêlo NM, Soares CM (2008) Protein structure and dynamics in ionic liquids. Insights from molecular dynamics simulation studies. J Phys Chem B 112:2566–2572.  https://doi.org/10.1021/jp0766050 PubMedGoogle Scholar
  84. Moon YH, Lee SM, Ha SH, Koo Y-M (2006) Enzyme-catalyzed reactions in ionic liquids. Korean J Chem Eng 23:247–263.  https://doi.org/10.1007/BF02705724 Google Scholar
  85. Nakano M, Tateishi-Karimata H, Tanaka S, Sugimoto N (2014) Choline ion interactions with DNA atoms explain unique stabilization of A–T Base pairs in DNA duplexes: a microscopic view. J Phys Chem B 118:379–389.  https://doi.org/10.1021/jp406647b PubMedGoogle Scholar
  86. Naushad M, Alothman ZA, Khan AB, Ali M (2012) Effect of ionic liquid on activity, stability, and structure of enzymes: a review. Int J Biol Macromol 51:555–560.  https://doi.org/10.1016/j.ijbiomac.2012.06.020 PubMedGoogle Scholar
  87. Noritomi H, Minamisawa K, Kamiya R, Kato S (2011) Thermal stability of proteins in the presence of aprotic ionic liquids. J Biomed Sci Eng 4:94–99.  https://doi.org/10.4236/jbise.2011.42013 Google Scholar
  88. Park S, Sugiyama H (2010) DNA-based hybrid catalysts for asymmetric organic synthesis. Angew Chem Int Ed 49:3870–3878.  https://doi.org/10.1002/anie.200905382 Google Scholar
  89. Parker TM, Hohenstein EG, Parrish RM, Hud NV, Sherrill CD (2013) Quantum-mechanical analysis of the energetic contributions to π stacking in nucleic acids versus rise, twist, and slide. J Am Chem Soc 135:1306–1316.  https://doi.org/10.1021/ja3063309 PubMedGoogle Scholar
  90. Pârvulescu VI, Hardacre C (2007) Catalysis in ionic liquids. Chem Rev 107:2615–2665.  https://doi.org/10.1021/cr050948h PubMedGoogle Scholar
  91. Persson M, Bornscheuer UT (2003) Increased stability of an esterase from Bacillus stearothermophilus in ionic liquids as compared to organic solvents. J Mol Catal B Enzym 22:21–27.  https://doi.org/10.1016/S1381-1177(02)00294-1 Google Scholar
  92. Plaquevent J-C, Levillain J, Guillen F, Malhiac C, Gaumont A-C (2008) Ionic liquids: new targets and media for α-amino acid and peptide chemistry. Chem Rev 108:5035–5060.  https://doi.org/10.1021/cr068218c PubMedGoogle Scholar
  93. Portella G, Germann MW, Hud NV, Orozco M (2014) MD and NMR analyses of choline and TMA binding to duplex DNA: on the origins of aberrant sequence-dependent stability by alkyl cations in aqueous and water-free solvents. J Am Chem Soc 136:3075–3086.  https://doi.org/10.1021/ja410698u PubMedGoogle Scholar
  94. Price DL, Borodin O, González MA et al (2017) Relaxation in a prototype ionic liquid: influence of water on the dynamics. J Phys Chem Lett 8:715–719.  https://doi.org/10.1021/acs.jpclett.6b02871 PubMedGoogle Scholar
  95. Rivera-Rubero S, Baldelli S (2004) Influence of water on the surface of hydrophilic and hydrophobic room-temperature ionic liquids. J Am Chem Soc 126:11788–11789.  https://doi.org/10.1021/ja0464894 PubMedGoogle Scholar
  96. Saha D, Kulkarni M, Mukherjee A (2016) Water modulates the ultraslow dynamics of hydrated ionic liquids near CG rich DNA: consequences for DNA stability. Phys Chem Chem Phys 18:32107–32115.  https://doi.org/10.1039/C6CP05959G PubMedGoogle Scholar
  97. Saha D, Supekar S, Mukherjee A (2015) Distribution of residence time of water around DNA base pairs: governing factors and the origin of heterogeneity. J Phys Chem B 119:11371–11381.  https://doi.org/10.1021/acs.jpcb.5b03553 PubMedGoogle Scholar
  98. Satpathi S, Kulkarni M, Mukherjee A, Hazra P (2016) Ionic liquid induced G-quadruplex formation and stabilization: spectroscopic and simulation studies. Phys Chem Chem Phys 18:29740–29746.  https://doi.org/10.1039/C6CP05732B PubMedGoogle Scholar
  99. Schröder C (2017) Proteins in ionic liquids: current status of experiments and simulations. Top Curr Chem 375:25.  https://doi.org/10.1007/s41061-017-0110-2 Google Scholar
  100. Shao Q (2013) On the influence of hydrated imidazolium-based ionic liquid on protein structure stability: a molecular dynamics simulation study. J Chem Phys 139:115102.  https://doi.org/10.1063/1.4821588 PubMedGoogle Scholar
  101. Sharma A, Ghorai PK (2016) Effect of water on structure and dynamics of [BMIM][PF6] ionic liquid: an all-atom molecular dynamics simulation investigation. J Chem Phys 144:114505.  https://doi.org/10.1063/1.4944083 PubMedGoogle Scholar
  102. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun:2399–2407.  https://doi.org/10.1039/B107270F
  103. Shimojo K, Kamiya N, Tani F, Naganawa H, Naruta Y, Goto M (2006) Extractive solubilization, structural change, and functional conversion of cytochrome c in ionic liquids via crown ether complexation. Anal Chem 78:7735–7742.  https://doi.org/10.1021/ac0612877 PubMedGoogle Scholar
  104. Singh UK, Kumari M, Khan SH, Bohidar HB, Patel R (2018) Mechanism and dynamics of long-term stability of cytochrome c conferred by long-chain imidazolium ionic liquids at low concentration. ACS Sustain Chem Eng 6:803–815.  https://doi.org/10.1021/acssuschemeng.7b03168 Google Scholar
  105. Sivapragasam M, Moniruzzaman M, Goto M (2016) Recent advances in exploiting ionic liquids for biomolecules: solubility, stability and applications. Biotechnol J 11:1000–1013.  https://doi.org/10.1002/biot.201500603 PubMedGoogle Scholar
  106. Socha AM, Parthasarathi R, Shi J et al (2014) Efficient biomass pretreatment using ionic liquids derived from lignin and hemicellulose. Proc Natl Acad Sci U S A 111:E3587–E3595.  https://doi.org/10.1073/pnas.1405685111 PubMedPubMedCentralGoogle Scholar
  107. Summers CA, Flowers RA (2000) Protein renaturation by the liquid organic salt ethylammonium nitrate. Protein Sci 9:2001–2008.  https://doi.org/10.1110/ps.9.10.2001 PubMedPubMedCentralGoogle Scholar
  108. Takekiyo T, Fukudome K, Yamazaki K, Abe H, Yoshimura Y (2014) Protein aggregation and partial globular state in aqueous 1-alkyl-3-methylimidazolium nitrate solutions. Chem Phys Lett 602:22–27.  https://doi.org/10.1016/j.cplett.2014.03.089 Google Scholar
  109. Tang S, Baker GA, Zhao H (2012) Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications. Chem Soc Rev 41:4030–4066.  https://doi.org/10.1039/C2CS15362A PubMedPubMedCentralGoogle Scholar
  110. Tao G-h, He L, Liu W-s et al (2006) Preparation, characterization and application of amino acid-based green ionic liquids. Green Chem 8:639–646.  https://doi.org/10.1039/B600813E Google Scholar
  111. Tarannum A, Muvva C, Mehta A, Raghava Rao J, Fathima NN (2016) Role of preferential ions of ammonium ionic liquid in destabilization of collagen. J Phys Chem B 120:6515–6524.  https://doi.org/10.1021/acs.jpcb.6b02723 PubMedGoogle Scholar
  112. Tateishi-Karimata H, Sugimoto N (2012) A–T base pairs are more stable than G–C base pairs in a hydrated ionic liquid. Angew Chem Int Ed 51:1416–1419.  https://doi.org/10.1002/anie.201106423 Google Scholar
  113. Tomé LIN, Catambas VR, Teles ARR, Freire MG, Marrucho IM, Coutinho JAP (2010) Tryptophan extraction using hydrophobic ionic liquids. Sep Purif Technol 72:167–173.  https://doi.org/10.1016/j.seppur.2010.02.002 Google Scholar
  114. Torriero AA (2015a) Electrochemistry in ionic liquids, vol 1: Fundamentals. Springer-Verlag, Berlin-HeidelbergGoogle Scholar
  115. Torriero AA (2015b) Electrochemistry in ionic liquids, vol 2: Applications. Springer-Verlag, Berlin-HeidelbergGoogle Scholar
  116. Triolo A, Russina O, Bleif H-J, Di Cola E (2007) Nanoscale segregation in room temperature ionic liquids. J Phys Chem B 111:4641–4644.  https://doi.org/10.1021/jp067705t PubMedGoogle Scholar
  117. van Rantwijk F, Sheldon RA (2007) Biocatalysis in ionic liquids. Chem Rev 107:2757–2785.  https://doi.org/10.1021/cr050946x PubMedGoogle Scholar
  118. Ventura SPM, e Silva FA, Quental MV, Mondal D, Freire MG, Coutinho JAP (2017) Ionic-liquid-mediated extraction and separation processes for bioactive compounds: past, present, and future trends. Chem Rev 117:6984–7052.  https://doi.org/10.1021/acs.chemrev.6b00550 PubMedPubMedCentralGoogle Scholar
  119. Ventura SPM, Sousa SG, Freire MG, Serafim LS, Lima ÁS, Coutinho JAP (2011) Design of ionic liquids for lipase purification. J Chromatogr B 879:2679–2687.  https://doi.org/10.1016/j.jchromb.2011.07.022 Google Scholar
  120. Vicent-Luna JM, Romero-Enrique JM, Calero S, Anta JA (2017) Micelle formation in aqueous solutions of room temperature ionic liquids: a molecular dynamics study. J Phys Chem B 121:8348–8358.  https://doi.org/10.1021/acs.jpcb.7b05552 PubMedGoogle Scholar
  121. Vijayaraghavan R, Izgorodin A, Ganesh V, Surianarayanan M, MacFarlane DR (2010) Long-term structural and chemical stability of DNA in hydrated ionic liquids. Angew Chem Int Ed 49:1631–1633.  https://doi.org/10.1002/anie.200906610 Google Scholar
  122. Wakai C, Oleinikova A, Ott M, Weingärtner H (2005) How polar are ionic liquids? Determination of the static dielectric constant of an imidazolium-based ionic liquid by microwave dielectric spectroscopy. J Phys Chem B 109:17028–17030.  https://doi.org/10.1021/jp053946+ PubMedGoogle Scholar
  123. Wasserscheid P, Keim W (2000) Ionic liquids—new “solutions” for transition metal catalysis. Angew Chem Int Ed 39:3772–3789.  https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5 Google Scholar
  124. Weingärtner H (2008) Understanding ionic liquids at the molecular level: facts, problems, and controversies. Angew Chem Int Ed 47:654–670.  https://doi.org/10.1002/anie.200604951 Google Scholar
  125. Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2084.  https://doi.org/10.1021/cr980032t PubMedGoogle Scholar
  126. Wilkes JS, Zaworotko MJ (1992) Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids. J Chem Soc Chem Commun :965–967. doi:  https://doi.org/10.1039/C39920000965
  127. Yang Z, Yue Y-J, Xing M (2008) Tyrosinase activity in ionic liquids. Biotechnol Lett 30:153–158.  https://doi.org/10.1007/s10529-007-9505-4 PubMedGoogle Scholar
  128. Yurke B, Turberfield AJ, Mills AP, Simmel FC, Neumann JL (2000) A DNA-fuelled molecular machine made of DNA. Nature 406:605–608.  https://doi.org/10.1038/35020524 PubMedGoogle Scholar
  129. Zein El Abedin S, Endres F (2006) Electrodeposition of metals and semiconductors in air- and water-stable ionic liquids. ChemPhysChem 7:58–61.  https://doi.org/10.1002/cphc.200500288 PubMedGoogle Scholar
  130. Zhao H (2005) Effect of ions and other compatible solutes on enzyme activity, and its implication for biocatalysis using ionic liquids. J Mol Catal B Enzym 37:16–25.  https://doi.org/10.1016/j.molcatb.2005.08.007 Google Scholar
  131. Zhao H, Xia S, Ma P (2005) Use of ionic liquids as ‘green’ solvents for extractions. J Chem Technol Biotechnol 80:1089–1096.  https://doi.org/10.1002/jctb.1333 Google Scholar

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© International Union for Pure and Applied Biophysics (IUPAB) and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Chemistry DepartmentIndian Institute of Science Education and ResearchPuneIndia

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