Applications of deep eutectic solvents in biotechnology and bioengineering—Promises and challenges

Biotechnology Advances

Volumn 35, Issue 2, 2017, Pages 105-134

  Mbous, Yves Paul ^a   Hayyan, Maan ^a   Hayyan, Adeeb ^a   Wong, Won Fen ^a   Hashim, Mohd Ali ^a   Looi, Chung Yeng ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Anti bacteria; Anti cancer agent; Biocatalysis; Biotransformation; Ionic liquid; Molecular biology; Nanomedicine; Nanoparticle; Therapeutic application; Toxicity profile

Indexed keywords

BIOTECHNOLOGY; CHEMICAL STABILITY; EUTECTICS; MEDICAL NANOTECHNOLOGY; MIXTURES; MOLECULAR BIOLOGY; NANOPARTICLES; TOXICITY;

ANTI-BACTERIA; ANTI-CANCER AGENTS; BIOCATALYSIS; BIOTRANSFORMATION; THERAPEUTIC APPLICATION;

IONIC LIQUIDS;

ANTIMICROBIAL ACTIVITY; BIOACTIVITY; BIOENGINEERING; BIOTECHNOLOGY; BIOTRANSFORMATION; CATALYSIS; ELECTROCHEMICAL METHOD; IONIC LIQUID; MEDICINE; NANOPARTICLE; SAFETY; SOLVENT; TOXICITY; VAPOR PRESSURE;

IONIC LIQUID; SOLVENT;

BIOENGINEERING; BIOTECHNOLOGY;

BIOENGINEERING; BIOTECHNOLOGY; IONIC LIQUIDS; SOLVENTS;

EID: 85010219824     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2016.11.006     Document Type: Review

References (122)

1. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., Tambyrajah, V., Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. 1 (2003), 70–71.
2. Abbott, A.P., Boothby, D., Capper, G., Davies, D.L., Rasheed, R.K., Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126:29 (2004), 9142–9147.
3. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., Ionic liquid analogues formed from hydrated metal salts. Chem. Eur. J. 10:15 (2004), 3769–3774.
4. Abbott, A.P., Barron, J.C., Ryder, K.S., Wilson, D., Eutectic-based ionic liquids with metal-containing anions and cations. Chem. Eur. J. 13:22 (2007), 6495–6501.
5. Agostini-Costa, T.D.S., Vieira, R.F., Bizzo, H.R., Silveira, D., Gimenes, M.A., Secondary metabolites. Dhanarasu, D.S., (eds.) Chromatography and Its Applications. Intech Janeza Trdine 9, 51000 Rijeka, Croatia, 2012.
6. Ardekani, M.R.S., Abdin, M.Z., Nasrullah, N., Samim, M., Calcium phosphate nanoparticles a novel non-viral gene delivery system for genetic transformation of Tobacco. Int J Pharm Pharm Sci 6:6 (2014), 605–609.
7. Azizi, N., Alipour, M., Eco-efficiency and scalable synthesis of bisamides in deep eutectic solvent. J. Mol. Liq. 206 (2015), 268–271.
8. Bardhan, R., Lal, S., Joshi, A., Halas, N.J., Theranostic nanoshells: from probe design to imaging and treatment of cancer. Acc. Chem. Res. 44:10 (2011), 936–946.
9. Bart, H.-J., Extraction of natural products from plants – an introduction. Industrial Scale Natural Products Extraction, 2011, Wiley-VCH Verlag GmbH & Co. KGaA, 1–25.
10. Bi, W., Tianb, M., Row, K.H., Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. J. Chromatogr. A 1285 (2013), 22–30.
11. Borse, B.N., Borude, V.S., Shukla, S.R., Synthesis of novel dihydropyrimidin-2(1H)-ones derivatives using lipase and their antimicrobial activity. Curr. Chem. Lett. 1 (2012), 59–68.
12. Broering, J.M., Bommarius, A.S., Evaluation of Hofmeister effects on the kinetic stability of proteins. J. Phys. Chem. B 109:43 (2005), 20612–20619.
13. Cardellini, F., Tiecco, M., Germani, R., Cardinali, G., Corte, L., Roscini, L., Spreti, N., Novel zwitterionic deep eutectic solvents from trimethylglycine and carboxylic acids: characterization of their properties and their toxicity. RSC Adv. 4:99 (2014), 55990–56002.
14. Cardellini, F., Germani, R., Cardinali, G., Corte, L., Roscini, L., Spreti, N., Tiecco, M., Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity. RSC Adv. 5:40 (2015), 31772–31786.
15. Carriazo, D., Serrano, M.C., Gutierrez, M.C., Ferrer, M.L., del Monte, F., Deep-eutectic solvents playing multiple roles in the synthesis of polymers and related materials. Chem. Soc. Rev. 41:14 (2012), 4996–5014.
16. Cho, K., Wang, X., Nie, S., Chen, Z., Shin, D.M., Therapeutic nanoparticles for drug delivery in cancer. Clin. Cancer Res. 14:5 (2008), 1310–1316.
17. Choi, Y.H., van Spronsen, J., Dai, Y., Verberne, M., Hollmann, F., Arends, I.W.C.E., Witkamp, G.-J., Verpoorte, R., Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology?. Plant Physiol. 156 (2011), 1701–1705.
18. Coleman, D., Gathergood, N., Biodegrability of ionic liquids. Chem. Soc. Rev. 39 (2010), 600–637.
19. Collins, K.D., Ions from the Hofmeister series and osmolytes: effects on proteins in solution and in the crystallization process. Methods 34:3 (2004), 300–311.
20. Craveiro, R., Aroso, I., Flammia, V., Carvalho, T., Viciosa, M.T., Dionísio, M., Barreiros, S., Reis, R.L., Duarte, A.R.C., Paiva, A., Properties and thermal behavior of natural deep eutectic solvents. J. Mol. Liq. 215 (2016), 534–540.
21. Dai, Y., van Spronsen, J., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Natural deep eutectic solvents as new potential media for green technology. Anal. Chim. Acta 766:0 (2013), 61–68.
22. Dai, Y., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L. Anal. Chem. 85:13 (2014), 6272–6278.
23. Dai, Y., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem. 187 (2015), 14–19.
24. Dako, E., Bernier, A.-M., Dadie, A.T., Jankowski, C.K., The problems associated with enzyme purification. Ekinci, P.D., (eds.) Chemical Biology, 2012, InTech, University Campus STeP Ri, Slavka Krautzeka 83/A, 51000 Rijeka, Croatia, Unit 405, Office Block, Hotel Equatorial Shanghai No.65, Yan An Road (West), Shanghai, 200040, China, 444.
25. Davey, R.J., Garside, J., Hilton, A.M., McEwan, D., Morrison, J.W., Purification of molecular mixtures below the eutectic by emulsion crystallization. Nature 375:6533 (1995), 664–666.
26. de Morais, P., Gonçalves, F., Coutinho, J.A.P., Ventura, S.P.M., Ecotoxicity of cholinium-based deep eutectic solvents. ACS Sustain. Chem. Eng. 3:12 (2015), 3398–3404.
27. Dominguez de Maria, P., Maugeri, Z., Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents. Curr. Opin. Chem. Biol. 15 (2011), 220–225.
28. Duan, X., Ma, J., Lian, J., Zheng, W., The art of using ionic liquids in the synthesis of inorganic nanomaterials. CrystEngComm 16:13 (2014), 2550–2559.
29. Duncan, T.V., Applications of nanotechnology in food packaging and food safety: barrier materials, antimicrobials and sensors. J. Colloid Interface Sci. 363 (2011), 1–24.
30. Durand, E., Lecomte, J., Baréa, B., Piombo, G., Dubreucq, E., Villeneuve, P., Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions. Process Biochem. 47 (2012), 2081–2089.
31. Durand, E., Lecomte, J., Baréa, B., Dubreucq, E., Lortiec, R., Villeneuve, P., Evaluation of deep eutectic solvent–water binary mixtures for lipase-catalyzed lipophilization of phenolic acids. Green Chem. 15 (2013), 2275–2282.
32. FDA, Guidance for industry Q3C—tables and list. (FDA), U.S.D.o.H.a.H.S.F.a.D.A., (CDER), C.f.D.E.a.R., (CBER), C.f.B.E.a.R, (eds.) U.S. Department of Health and Human Services Food and Drug Administration, 10903 New Hampshire Ave. Silver Spring, MD 20993, 2012.
33. Florindo, C., Oliveira, F.S., Rebelo, L.P.N., Fernandes, A.M., Marrucho, I.M., Insights into the synthesis and properties of deep eutectic solvents based on cholinium chloride and carboxylic acids. ACS Sustain. Chem. Eng. 2 (2014), 2416–2425.
34. Gal, N., Malferarri, D., Kolusheva, S., Galletti, P., Tagliavini, E., Jelinek, R., Membrane interactions of ionic liquids: possible determinants for biological activity and toxicity. Biochim. Biophys. Acta 1818:12 (2012), 2967–2974.
35. García-Argüelles, S., Serrano, M.C., Gutiérrez, M.C., Ferrer, M.L., Yuste, L., Rojo, F., del Monte, F., Deep eutectic solvent-assisted synthesis of biodegradable polyesters with antibacterial properties. Langmuir 29:30 (2013), 9525–9534.
36. Ghanemi, K., Navidi, M.-A., Fallah-Mehrjardi, M., Dadolahi-Sohrab, A., Ultra-fast microwave-assisted digestion in choline chloride–oxalic acid deep eutectic solvent for determining Cu, Fe, Ni and Zn in marine biological samples. Anal. Methods 6 (2014), 1774–1781.
37. Gill, I., Vulfson, E., Enzymatic catalysis in heterogeneous eutectic mixtures of substrates. Trends Biotechnol. 12:4 (1994), 118–122.
38. Goldsborough, A.S., Bates, M.R., Sample Fixation and Stabilisation. Publication No. WO2014131906 A1. 2014.
39. Gu, T., Zhang, M., Tan, T., Chen, J., Li, Z., Zhang, Q., Qiu, H., Deep eutectic solvents as novel extraction media for phenolic compounds from model oil. Chem. Commun. 50 (2014), 11749–11752.
40. Gutierrez, M.C., Ferrer, M.L., Yuste, L., Rojo, F., del Monte, F., Bacteria incorporation in deep-eutectic solvents through freeze-drying. Angew. Chem. Int. Ed. 49 (2010), 2158–2162.
41. Han, D., Tian, M., Row, K.H., Isolation of four compounds from Herba Artemisiae Scopariae by preparative column HPLC. J. Liq. Chromatogr. Relat. Technol. 32:16 (2009), 2407–2416.
42. Hayyan, M., Hashim, M.A., Al-Saadi, M.A., Hayyan, A., AlNashef, I.M., Mirghani, M.E.S., Assessment of cytotoxicity and toxicity for phosphonium-based deep eutectic solvents. Chemosphere 93 (2013), 455–459.
43. Hayyan, M., Hashim, M.A., Hayyan, A., Al-Saadi, M.A., AlNashef, I.M., Mirghani, M.E.S., Saheed, O.K., Are deep eutectic solvents benign or toxic?. Chemosphere 90 (2013), 2193–2195.
44. Hayyan, M., Looi, C.Y., Hayyan, A., Wong, W.F., Hashim, M.A., In vitro and in vivo toxicity profiling of ammonium-based deep eutectic solvents. PLoS One, 10(2), 2015, e0117934.
45. Hayyan, M., Mbous, Y.P., Looi, C.Y., Wong, W.F., Hayyan, A., Salleh, Z., Mohd-Ali, O., Natural deep eutectic solvents: cytotoxic profile. SpringerPlus, 5(1), 2016, 913.
46. Helalat-Nezhad, Z., Ghanemi, K., Fallah-Mehrjardi, M., Dissolution of biological samples in deep eutectic solvents: an approach for extraction of polycyclic aromatic hydrocarbons followed by liquid chromatography-fluorescence detection. J. Chromatogr. 1394 (2015), 46–53.
47. Hou, X.-D., Liu, Q.-P., Smith, T.J., Li, N., Zong, M.-H., Evaluation of toxicity and biodegradability of cholinium amino acids ionic liquids. PLoS One, 8(3), 2013, e59145.
48. Huang, X., El-Sayed, M.A., Gold nanoparticles: optical properties and implementations in cancer diagnosis and photothermal therapy. J. Adv. Res. 1:1 (2010), 13–28.
49. Huang, Z.-L., Wu, B.-P., Wen, Q., Yang, T.-X., Yang, Z., Deep eutectic solvents can be viable enzyme activators and stabilizers. J. Chem. Technol. Biotechnol. 89 (2014), 1975–1981.
50. Jain, P.K., El-Sayed, I.H., El-Sayed, M.A., Au nanoparticles target cancer. Nano Today 2:1 (2007), 18–29.
51. Jenkins, H.D.B., Marcus, Y., Viscosity B-coefficients of ions in solution. Chem. Rev. 95:8 (1995), 2695–2724.
52. Joana Gil-Chávez, G., Villa, J.A., Fernando Ayala-Zavala, J., Basilio Heredia, J., Sepulveda, D., Yahia, E.M., González-Aguilar, G.A., Technologies for extraction and production of bioactive compounds to be used as nutraceuticals and food ingredients: an overview. Compr. Rev. Food Sci. Food Saf. 12:1 (2013), 5–23.
53. Juneidi, I., Hayyan, M., Hashim, M.A., Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents. RSC Adv. 5:102 (2015), 83636–83647.
54. Juneidi, I., Hayyan, M., Mohd Ali, O., Toxicity profile of choline chloride-based deep eutectic solvents for fungi and Cyprinus carpio fish. Environ. Sci. Pollut. Res. 23:8 (2016), 7648–7659.
55. Juneidi, I., Hayyan, M., Hashim, M.A., Hayyan, A., Pure and aqueous deep eutectic solvents for a lipase-catalysed hydrolysis reaction. Biochem. Eng. J. 117:Part A (2017), 129–138.
56. Kang, X., Sun, X., Han, B., Synthesis of functional nanomaterials in ionic liquids. Adv. Mater. 28:6 (2016), 1011–1030.
57. Kleiner, B., Schörken, U., Native lipase dissolved in hydrophilic green solvents: a versatile 2-phase reaction system for high yield ester synthesis Eur. J. Lipid Sci. Technol. 117 (2014), 167–177.
58. Kurtoglu, M., Lampidis, T.J., From delocalized lipophilic cations to hypoxia: blocking tumor cell mitochondrial function leads to therapeutic gain with glycolytic inhibitors. Mol. Nutr. Food Res. 53:1 (2009), 68–75.
59. Li, Z., Jia, Z., Luan, Y., Mu, T., Ionic liquids for synthesis of inorganic nanomaterials. Curr. Opin. Solid State Mater. Sci. 12:1 (2008), 1–8.
60. Li, N., Wang, Y., Xu, K., Huang, Y., Wen, Q., Ding, X., Development of green betaine-based deep eutectic solvent aqueous two-phase system for the extraction of protein. Talanta 152 (2016), 23–32.
61. Lindberg, D., de la Fuente Revenga, M., Widersten, M., Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis. J. Biotechnol. 147 (2010), 169–171.
62. Liu, R., Lal, R., Synthetic apatite nanoparticles as a phosphorus fertilizer for soybean (Glycine max). Sci. Report., 4(5868), 2014.
63. Marrucho, I., Branco, L., Rebelo, L., Ionic liquids in pharmaceutical applications. Annu. Rev. Chem. Biomol. Eng. 5 (2014), 527–546.
64. Maugeri, Z., Dominguez de Maria, P., Whole-cell biocatalysis in deep-eutectic-solvents/aqueous mixtures. ChemCatChem 6:6 (2014), 1535–1537.
65. McDonnell, G., Russell, A.D., Antiseptics and disinfectants: activity, action, and resistance. Clin. Microbiol. Rev. 12:1 (1999), 147–179.
66. Modica-Napolitano, J.S., Aprille, J.R., Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells. Adv. Drug Deliv. Rev. 49:1–2 (2001), 63–70.
67. Mondal, D., Sharma, M., Mukesh, C., Gupta, V., Prasad, K., Improved solubility of DNA in recyclable and reusable bio-based deep eutectic solvents with long-term structural and chemical stability. Chem. Commun. 49:83 (2013), 9606–9608.
68. Mondal, D., Bhatt, J., Sharma, M.C., Shruti, Prasad, K., A facile approach to prepare a dual functionalized DNA based material in a bio-deep eutectic solvent. Chem. Commun. 50 (2014), 3989–3992.
69. Monhemi, H., Housaindokht, M.R., Moosavi-Movahedib, A.A., Bozorgmehr, M.R., How a protein can remain stable in a solvent with high content of urea: insights from molecular dynamics simulation of Candida antarctica lipase B in urea: choline chloride deep eutectic solvent. Phys. Chem. Chem. Phys. 16 (2014), 14882–14893.
70. Morrison, H.G., Sun, C.C., Neervannan, S., Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int. J. Pharm. 378 (2009), 136–139.
71. Mota-Morales, J.D., Gutierrez, M.C., Ferrer, M.L., Sanchez, I.C., Elizalde-Pena, E.A., Pojman, J.A., del Monte, F., Luna-Barcenas, G., Deep eutectic solvents as both active fillers and monomers for frontal polymerization. J. Polym. Sci. A Polym. Chem. 51 (2013), 1767–1773.
72. Nam, M.W., Zhao, J., Lee, M.S., Jeong, J.H., Lee, J., Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae. Green Chem. 17 (2014), 1718–1727.
73. OECD, OECD Guidelines for the Testing of Chemicals. Organization for Economic. 1994.
74. Oksman-Caldentey, K.-M., Inzé, D., Plant cell factories in the post-genomic era: new ways to produce designer secondary metabolites. Trends Plant Sci. 9:9 (2004), 433–440.
75. Paiva, A., Craveiro, R., Arosso, I., Martins, M., Reis, R.L., Duarte, A.R.C., Natural deep eutectic solvents - solvents for the 21st century. ACS Sustain. Chem. Eng. 2:5 (2014), 1063–1071.
76. Paiva, A., Craveiro, R., Martins, M., Rocha, Â., Aroso, I., Barreiros, S., Reis, R.L., Duarte, A.R.C., THEDES – therapeutic deep eutectic solvents: new solvents for the functionalization of natural-based polymers. Paiva, A., (eds.) 14th European Meeting on Supercritical Fluids, 2014, Marseille, France.
77. Palumbo, S.L., Ebbinghaus, S.W., Hurley, L.H., Formation of a unique end-to-end stacked pair of G-quadruplexes in the hTERT core promoter with implications for inhibition of telomerase by G-quadruplex-interactive ligands. J. Am. Chem. Soc. 131:31 (2009), 10878–10891.
78. Park, J.H., Oh, K.W., Choi, H.-M., Preparation and characterization of cotton fabrics with antibacterial properties treated by crosslinkable benzophenone derivative in choline chloride-based deep eutectic solvents. Cellulose 20 (2013), 2101–2114.
79. Park, H.E., Tang, B., Row, K.H., Application of deep eutectic solvents as additives in ultrasonic extraction of two phenolic acids from Herba Artemisiae Scopariae. Anal. Lett. 47:9 (2014), 1476–1484.
80. Patil, U.B., Singh, A.S., Nagarkar, J.M., Choline chloride based eutectic solvent: an efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles. RSC Adv. 4 (2014), 1102–1106.
81. Pedersen, E.B., Nielsen, J.T., Nielsen, C., Filichev, V.V., Enhanced anti-HIV-1 activity of G-quadruplexes comprising locked nucleic acids and intercalating nucleic acids. Nucleic Acids Res. 39:6 (2011), 2470–2481.
82. Pérez-Martínez, F.C., Carrión, B., Ceña, V., The use of nanoparticles for gene therapy in the nervous system. J. Alzheimers Dis. 31:4 (2012), 697–710.
83. Perkins, S.L., Painter, P., Colina, C.M., Experimental and computational studies of choline chloride-based deep eutectic solvents. J. Chem. Eng. Data 59:11 (2014), 3652–3662.
84. Qi, X.-L., Peng, X., Huang, Y.-Y., Li, L., Wei, Z.-F., Zu, Y.-G., Fu, Y.-J., Green and efficient extraction of bioactive flavonoids from Equisetum palustre L. by deep eutectic solvents-based negative pressurecavitation method combined with macroporous resin enrichment. Ind. Crop. Prod. 70 (2015), 142–148.
85. Radošević, K., Bubalo, M.C., GaurinaSrček, V., Grgas, D., Dragičević, T.L., Redovniković, I.R., Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol. Environ. Saf. 112 (2015), 46–53.
86. Radošević, K., Ćurko, N., Gaurina Srček, V., Cvjetko Bubalo, M., Tomašević, M., Kovačević Ganić, K., Radojčić Redovniković, I., Natural deep eutectic solvents as beneficial extractants for enhancement of plant extracts bioactivity. LWT Food Sci. Technol. 73 (2016), 45–51.
87. Raghuwanshi, V.S., Ochmann, M., Hoell, A., Polzer, F., Rademann, K., Deep eutectic solvents for the self-assembly of gold nanoparticles: a SAXS, UV–Vis, and TEM investigation. Langmuir 30 (2014), 6038–6046.
88. Ribeiro, B.D., Coelho, M.A.Z., Marrucho, I.M., Extraction of saponins from sisal (Agave sisalana) and juá (Ziziphus joazeiro) with cholinium-based ionic liquids and deep eutectic solvents. Eur. Food Res. Technol. 237:6 (2013), 965–975.
89. Sanchez-Leija, R.J.J., Pojman, A., Luna-Barcenas, G., Mota-Morales, J.D., Controlled release of lidocaine hydrochloride from polymerized drug-based deep-eutectic solvents. J. Mater. Chem. B 2 (2014), 7495–7501.
90. Sanvicens, N., Pastells, C., Pascual, N., Marco, M.-P., Nanoparticle-based biosensors for detection of pathogenic bacteria. Trends Anal. Chem. 28:11 (2009), 1243–1252.
91. Serrano, M.C., Carbajal, L., Ameer, G.A., Novel biodegradable shape-memory elastomers with drug-releasing capabilities. Adv. Mater. 23:19 (2011), 2211–2215.
92. Shahriari, S., Tome, L.C., Araujo, J.M.M., Rebelo, L.P.N., Coutinho, J.A.P., Marrucho, I.M., Freire, M.G., Aqueous biphasic systems: a benign route using cholinium-based ionic liquids. RSC Adv. 3:6 (2013), 1835–1843.
93. Singh, B.S., Lobo, H.R., Shankarling, G.S., Choline chloride based eutectic solvents: magical catalytic system for carbon–carbon bond formation in the rapid synthesis of β-hydroxy functionalized derivatives. Catal. Commun. 24 (2012), 70–74.
94. Smith, E.L., Abbott, A.P., Ryder, K.S., Deep eutectic solvents (DES) and their applications. Chem. Rev. 114:21 (2014), 11060–11082.
95. Song, M.C., Kim, E.J., Kim, E., Rathwell, K., Nam, S.-J., Yoon, Y.J., Microbial biosynthesis of medicinally important plant secondary metabolites. Nat. Prod. Rep. 31:11 (2014), 1497–1509.
96. Štěpánková, V., Haloalkane Dehydrogenase in Non-conventional Media. 2014, Department of Experimental Biology Masaryk University, Brno, 173.
97. Stepankova, V., Vanacek, P., Damborsky, J., Chaloupkova, R., Comparison of catalysis by haloalkane dehalogenases in aqueous solutions of deep eutectic and organic solvents. Green Chem. 16 (2014), 2754–2761.
98. Tang, B., Bi, W., Zhang, H., Row, K.H., Deep eutectic solvent-based HS-SME coupled with GC for the analysis of bioactive terpenoids in Chamaecyparis obtusa leaves. Chromatographia 77 (2014), 373–377.
99. Tateishi-Karimata, H., Sugimoto, N., Structure, stability and behaviour of nucleic acids in ionic liquids. Nucleic Acids Res. 42:14 (2014), 8831–8844.
100. Thomas, L.A., Dekker, L., Kallumadil, M., Southern, P., Wilson, M., Nair, S.P., Pankhurst, Q.A., Parkin, I.P., Carboxylic acid-stabilised iron oxide nanoparticles for use in magnetic hyperthermia. J. Mater. Chem. 19:36 (2009), 6529–6535.
101. Tuntarawongsa, S., Phaechamund, T., Polymeric eutectic drug delivery system. J. Met. Mater. Min. 22:2 (2012), 27–32.
102. Ventura, S.P.M., de Silva, F.A., Gonçalves, A.M.M., Pereira, J.L., Gonçalves, F., Coutinho, J.A.P., Ecotoxicity analysis of cholinium-based ionic liquids to Vibrio fischeri marine bacteria. Ecotoxicol. Environ. Saf. 102:0 (2014), 48–54.
103. Wagle, D.V., Zhao, H., Baker, G.A., Deep eutectic solvents: sustainable media for nanoscale and functional materials. Acc. Chem. Res. 47 (2014), 2299–2308.
104. Wang, L., Weller, C.L., Recent advances in extraction of nutraceuticals from plants. Trends Food Sci. Technol. 17 (2006), 300–312.
105. Wei, Z.-F., Wang, X.-Q., Peng, X., Wang, W., Zhao, C.-J., Zu, Y.-G., Fu, Y.-J., Fast and green extraction and separation of main bioactive flavonoids from Radix Scutellariae. Ind. Crop. Prod. 63 (2015), 175–181.
106. Wen, Q., Chen, J.-X., Tang, Y.-L., Wang, J., Yang, Z., Assessing the toxicity and biodegradability of deep eutectic solvents. Chemosphere 132 (2015), 63–69.
107. Wolfbeis, O.S., An overview of nanoparticles commonly used in fluorescent bioimaging. Chem. Soc. Rev. 44 (2015), 4743–4768.
108. Wu, B.-P., Wen, Q., Xu, H., Yang, Z., Insights into the impact of deep eutectic solvents on horseradish peroxidase: activity, stability and structure. J. Mol. Catal. B Enzym. 101 (2014), 101–107.
109. Xu, P., Cheng, J., Lou, W.-Y., Zong, M.-H., Using deep eutectic solvents to improve the resolution of racemic 1-(4-methoxyphenyl)ethanol through Acetobacter sp. CCTCC M209061 cell mediated asymmetric oxidation. RSC Adv. 5 (2014), 6357–6364.
110. Xu, P., Zheng, G.-W., Du, P.-X., Zong, M.-H., Lou, W.-Y., Whole-cell biocatalytic processes with ionic liquids. ACS Sustain. Chem. Eng. 4:2 (2016), 371–386.
111. Yang, J., Webb, A.R., Ameer, G.A., Novel citric acid-based biodegradable elastomers for tissue engineering. Adv. Mater. 16:6 (2004), 511–516.
112. Zeisel, S.H., da Costa, K.-A., Choline: an essential nutrient for public health. Nutr. Rev. 67:11 (2009), 615–623.
113. Zeng, Q., Wang, Y., Huang, Y., Ding, X., Chen, J., Xu, K., Deep eutectic solvents as novel extraction media for protein partitioning. Analyst 139 (2014), 2565–2573.
114. Zhang, Q., Vigier, K.D.O., Royer, S., Jerome, F., Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 41 (2012), 7108–7146.
115. Zhang, H., Tang, B., Row, K.H., A green deep eutectic solvent-based ultrasound-assisted method to extract astaxanthin from shrimp byproducts. Anal. Lett. 47:5 (2014), 742–749.
116. Zhang, Y., Lu, F., Cao, X., Zhao, J., Deep eutectic solvent supported TEMPO for oxidation of alcohols. RSC Adv. 4 (2014), 40161–40169.
117. Zhao, H., DNA stability in ionic liquids and deep eutectic solvents. J. Chem. Technol. Biotechnol. 90:1 (2015), 19–25.
118. Zhao, C., Qu, X., Recent progress in G-quadruplex DNA in deep eutectic solvent. Methods 64:1 (2013), 52–58.
119. Zhao, H., Baker, G.A., Holmes, S., New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel. Org. Biomol. Chem. 9:6 (2011), 1908–1916.
120. Zhao, H., Baker, G.A., Holmes, S., Protease activation in glycerol-based deep eutectic solvents. J. Mol. Catal. B Enzym. 72 (2011), 163–167.
121. Zhao, C., Ren, J., Qu, X., G-quadruplexes form ultrastable parallel structures in deep eutectic solvent. Langmuir 29:4 (2013), 1183–1191.
122. Zhao, B.-Y., Xu, P., Yang, F.-X., Wu, H., Zong, M.-H., Lou, W.-Y., Biocompatible deep eutectic solvents based on choline chloride: characterization and application to the extraction of rutin from Sophora japonica. ACS Sustain. Chem. Eng. 3:11 (2015), 2746–2755.