Why is dmso a good solvent

Why are dimethyl sulfoxide and dimethyl sulfone such good solvents?. J Mol Model 14, — Download citation. Received : 16 November Accepted : 24 January Published : 06 May Issue Date : August Anyone you share the following link with will be able to read this content:. Sorry, a shareable link is not currently available for this article.

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Because DMSO serves not only as a vehicle for various hydrophobic compounds but also as a cryoprotectant for cell storage, most researchers and engineers in life sciences hundreds of thousands to millions of people use DMSO and it has been recognised as an irreplaceable solvent 3 , 4 , 5 , 6 , 7.

On the other hand, DMSO is somewhat toxic and affects cell behaviours in a range of ways. Mechanistically, DMSO is a cell-permeable reagent known to bind to various proteins in the cytoplasm or nucleus 8 , which directly chemically and physically interrupts their functions 9.

These intracellular modifications can also indirectly epigenetically alter cell behaviours 6 , 10 and, worse, cause apoptosis Therefore, DMSO is indispensable but not a be-all end-all solvent in the life sciences. Recently, we reported a solvent that has a zwitterionic structure zwitterionic liquid—zwitterion-type ionic liquid; ZIL , whose modules are similar to histidine shown in Fig.

ZIL exists as a liquid at ambient temperature, while almost all zwitterions, including amino acids, are solids. Notably, ZIL dissolves cellulose and related materials that exhibit very low solubility in water and DMSO, indicating strong potential as a nonaqueous solvent. However, ZIL does not have any positive effect for the culture of E. We here discover the further biocompatibility of ZIL based on the molecular mechanisms and suggest ZIL as a functionalised solution superior to DMSO, serving as a cryoprotectant and a vehicle for hydrophobic drugs, for instance.

Animal cells and tissues are used in this research to suggest practical feasible applications. Furthermore, ZIL enabled preparation of stock solutions of platinating agents, whose anticancer effects are completely abolished by dissolution in DMSO. The ZIL-containing freezing media cryopreserved animal cells with high efficiency. Lipid molecules sticks of the final structure are displayed, and water molecules are omitted for clarity.

The embryos were stained with o -dianisidine to check erythropoiesis. All error bars indicate standard error. It is here noted that the ZIL solutions were prepared based on weight per volume, although the DMSO solutions were based on volume per volume, the most general method in the life sciences. The reason is that we wanted to prepare solutions with precise concentrations—ZIL is too viscous to measure its precise volume at small scales. We found that structurally similar ions scissored at one or two points Supplementary Fig.

Consistent with these results, molecular dynamics MD simulations clearly showed that no ZIL molecules passed through the cell membrane Fig. Because most polar solvents, such as N,N -dimethylacetamide and triethylene glycol, are also reported to cause differentiation of some cells 16 , our results suggest that ZIL possesses high potential for application in stem cell research. These results indicate that ZIL is less toxic even in embryogenesis. Taken together, these results strongly suggest that ZIL possesses higher biocompatibility than DMSO and has great potential for application in the life sciences.

The high biocompatibility of ZIL motivated us to examine whether it can also serve as a vehicle for various compounds, as DMSO serves as a good solvent for hydrophobic drugs. We tested 12 hydrophobic compounds the structures are shown in Supplementary Fig. Interestingly, ZIL aq. DMSO is a polar organic solvent and dissolves a wide range of drugs from relatively polar drugs to relatively non-polar drugs.

ZIL is also a polar solvent and seems to dissolve polar drugs. The difference in dissolution abilities of water and ZIL may be based on hydrogen bond acidity and basicity: water and ZIL have high hydrogen bond acidity and basicity, respectively 12 , Importantly, the anticancer effects of platinating agents especially cisplatin are almost completely abolished by solvolysis in DMSO 5 , Therefore, these drugs cannot be stocked at high concentrations and must be prepared as low-scale working solutions when needed.

Here, we suggest ZIL aq. DMSO is also used as a universal cryoprotectant, which strongly interacts with water molecules and prevents ice crystal formation On the other hand, because DMSO is a cell-permeable cryoprotectant and considered to exert its cryoprotective effect both intra- and extracellularly, non-cell-permeable ZIL theoretically cannot completely replace DMSO. Therefore, ZIL may adequately dehydrate the cells to prevent intracellular ice formation like other non-cell-permeable cryoprotectants 20 , 21 , It is also reported that non-cell-permeable cryoprotectants can exert their efficacy by stabilising the plasma membranes 23 , 24 ; however, it is totally unclear at this stage whether ZIL has similar effect as these non-cell-permeable cryoprotectants.

In addition, a tiny glass transition signal was also observed in the DSC chart, indicating that the solution contains unfrozen compartment Fig.

It is unclear at this stage whether the glass transition of the unfrozen part is involved with the cryoprotecting effect. In addition, Matsumura and co-workers 25 have reported that polyampholytes which possess strong affinity to plasma membranes act as good cryoprotectans.

ZIL might cryopreserve cells through a similar mechanism to the polyampholyte-type cryoprotectants but further investigation should be needed. The unique cryoprotectant further inspired us to apply ZIL aq. Given that the cells were stocked in an extremely simple aqueous solution, there is apparently room for improvement in ZIL aq. In this context, ZIL aq. Furthermore, ZIL aq. We expect that these advantages should especially contribute to and accelerate tissue engineering and regenerative medicine, where only defined chemicals are preferred for large-scale use.

Here, we propose ZIL as a potent, multifunctional and biocompatible solvent for use in the life sciences, which we also confirmed to be applicable to general plastic tools in biological and biochemical laboratories Supplementary Fig. Notably, ZIL aq. In addition, a better alternative to DMSO is needed in metabolomics 27 , epigenetics 6 , 10 and embryology 17 , Moreover, the development of ZIL aq.

In a wide range of basic science research, alternatives or equivalents to DMSO have long been desired. Erik Sahai. PC9 human lung cancer cells and Mardin-Darby canine kidney cells are kind gifts from Prof. Etsuko Kiyokawa Kanazawa Medical University , respectively. Mouse primary astrocytes were established from euthanized neonatal C57BL6 mice P, male and female as reported previously The cells were sub-cultured every 4—6 days using trypsin solution 0.

ZIL was synthesised as reported The volume of the cells was calculated by measuring the radii of the cells under microscopic observation by an IX83 inverted microscope Olympus Corporation.

ZIL analogue 1 was synthesised as reported The solvents were added to each medium at indicated concentrations. The cell membrane in the simulation system was composed of dioleoylphosphatidylethanolamine DOPE —dioleoylphosphatidylglycerol DOPG lipids with a ratio 90 and 30 molecules, respectively.

The atoms used for the calculations are shown in Supplementary Fig. The cell line was grown and maintained by culturing with feeder cells SL10, Reprocell Inc. CTK solution 0. The removed cells were treated with 0. The supernatant was removed before use. Feeder cells were seeded with 1. Gapdh was used as an internal control. All animal experiments were performed in accordance with a protocol approved by the committee on animal experimentation of Kanazawa university.

Embryos were then washed twice with E3 medium and were treated with 1-phenylthiourea Fujifilm Wako Pure Chemical Corporation to prevent pigmentation.