Long‐Term Structural and Chemical Stability of DNA in Hydrated Ionic Liquids

Vijayaraghavan, R.; Izgorodin, Aleksey; Venkatraman, Ganesh; Surianarayanan, M.; MacFarlane, Douglas R.

doi:10.1002/anie.200906610

Cited by 219 publications

(228 citation statements)

References 26 publications

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“…MacFarlane et al. measured the CD spectrum of the long DNA duplex obtained from salmon testes in hydrated choline dhp (47). In choline dhp, these long DNA duplexes have the same B-form conformation structure as that in aqueous solution.…”

Section: Dna Structure In Ilsmentioning

confidence: 99%

Structure, stability and behaviour of nucleic acids in ionic liquids

Tateishi‐Karimata

2014

Nucleic Acids Res

116

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Nucleic acids have become a powerful tool in nanotechnology because of their conformational polymorphism. However, lack of a medium in which nucleic acid structures exhibit long-term stability has been a bottleneck. Ionic liquids (ILs) are potential solvents in the nanotechnology field. Hydrated ILs, such as choline dihydrogen phosphate (choline dhp) and deep eutectic solvent (DES) prepared from choline chloride and urea, are ‘green’ solvents that ensure long-term stability of biomolecules. An understanding of the behaviour of nucleic acids in hydrated ILs is necessary for developing DNA materials. We here review current knowledge about the structures and stabilities of nucleic acids in choline dhp and DES. Interestingly, in choline dhp, A–T base pairs are more stable than G–C base pairs, the reverse of the situation in buffered NaCl solution. Moreover, DNA triplex formation is markedly stabilized in hydrated ILs compared with aqueous solution. In choline dhp, the stability of Hoogsteen base pairs is comparable to that of Watson–Crick base pairs. Moreover, the parallel form of the G-quadruplex is stabilized in DES compared with aqueous solution. The behaviours of various DNA molecules in ILs detailed here should be useful for designing oligonucleotides for the development of nanomaterials and nanodevices.

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Section: Dna Structure In Ilsmentioning

confidence: 99%

Structure, stability and behaviour of nucleic acids in ionic liquids

Tateishi‐Karimata

2014

Nucleic Acids Res

116

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“…In particular, a large number of studies of the combined use of DNA, the molecular memory of living things, and ionic liquids have been reported [6]. The design of ionic liquids as solvent media for DNA is underway [13] to determine the important IL structural features for this purpose [6,8]. DNA has also attracted interest as a novel functional material and research on electroconductive [14] and ion conductive DNA [15,16], amphiphilic DNA films [17] and electrochemical sensors is of great interest [18].…”

Section: Introductionmentioning

confidence: 99%

Nucleic acid bases in 1-alkyl-3-methylimidazolium acetate ionic liquids: A thermophysical and ionic conductivity analysis

Araújo¹,

Pereiro²,

Alves³

et al. 2013

The Journal of Chemical Thermodynamics

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“…DNA maintains B-form structures and a long-term stability (up to 6 months) in the first IL but is denatured by the second one. The MacFarlane group 43 observed the long-term (up to 6 months) stability of salmon testes DNA in choline lactate, choline dihydrogenphosphate (containing 20–50 wt% water) and choline nitrate (containing 20% water), as suggested by the circular dichroism (CD) and fluorescence spectra as well as gel electrophoresis. The Hud group 41 investigated the secondary structures of DNA and RNA in a neat DES known as choline chloride/urea (1:2) using CD spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

DNA-based asymmetric catalysis: role of ionic solvents and glymes

Zhao

Shen

2014

RSC Adv.

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Recently, DNA has been evaluated as a chiral scaffold for metal complexes to construct so called ‘DNA-based hybrid catalysts’, a robust and inexpensive alternative to enzymes. The unique chiral structure of DNA allows the hybrid catalysts to catalyze various asymmetric synthesis reactions. However, most current studies used aqueous buffers as solvents for these asymmetric reactions, where substrates/products are typically suspended in the solutions. The mass transfer limitation usually requires a long reaction time. To overcome this hurdle and to advance DNA-based asymmetric catalysis, we evaluated a series of ionic liquids (ILs), inorganic salts, deep eutectic solvents (DES), glymes, glycols, acetonitrile and methanol as co-solvents/additives for the DNA-based asymmetric Michael addition. In general, these additives induce indistinguishable changes to the DNA B-form duplex conformation as suggested by circular dichroism (CD) spectroscopy, but impose a significant influence on the catalytic efficiency of the DNA-based hybrid catalyst. Conventional organic solvents (e.g. acetonitrile and methanol) led to poor product yields and/or low enantioselectivities. Most ILs and inorganic salts cause the deactivation of the hybrid catalyst except 0.2 M [BMIM][CF3COO] (95.4% ee and 93% yield) and 0.2 M [BMIM]Cl (93.7% ee and 89% yield). Several other additives have also been found to improve the catalytic efficiency of the DNA-based hybrid catalyst (control reaction without additive gives >99% ee and 87% yield): 0.4 M glycerol (>99% ee and 96% yield at 5 °C or 96.2% ee and 83% yield at room temperature), 0.2 M choline chloride/glycerol (1:2) (92.4% ee and 90% yield at 5 °C or 94.0% ee and 88% yield at room temperature), and 0.5 M dipropylene glycol dimethyl ether (>99% ee and 87% yield at room temperature). The use of some co-solvents/additives allows the Michael addition to be performed at a higher temperature (e.g. room temperature vs 5 °C) and a shorter reaction time (24 h vs 3 days). In addition, we found that a brief pre-sonication (5 min) of DNA in MOPS buffer prior to the reaction could improve the performance of the DNA-based hybrid catalyst. We have also shown that this DNA-based catalysis method is suitable for a variety of different substrates and relatively large-scale reactions. In conclusion, a judicious selection of benign co-solvents/additives could improve the catalytic efficiency of DNA-based hybrid catalyst.

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Long‐Term Structural and Chemical Stability of DNA in Hydrated Ionic Liquids

Abstract: Storage solutions: DNA is shown to be soluble in a variety of choline‐based, hydrated ionic liquids (ILs; see picture). The IL‐stored DNA molecules have exceptional long‐term stability, in excess of one year.

Cited by 219 publications

References 26 publications

Structure, stability and behaviour of nucleic acids in ionic liquids

Structure, stability and behaviour of nucleic acids in ionic liquids

Nucleic acid bases in 1-alkyl-3-methylimidazolium acetate ionic liquids: A thermophysical and ionic conductivity analysis

DNA-based asymmetric catalysis: role of ionic solvents and glymes

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