Dataset for "Interactions of Choline and Geranate (CAGE) and Choline Octanoate (CAOT) Deep Eutectic Solvents with Lipid Bilayers"

Deep eutectic solvents (DES) and ionic liquids (ILs) are often amphiphilic and interact with phospholipid membranes. Mixtures between choline and gernanic acid, coined 'CAGE', have been found to facilitate the transdermal delivery of larger pharmaceuticals, such as insulin. However, little is known about its mechanism of activity. The purpose for obtaining this data was to characterise aqueous suspensions of choline and germanic acid (CAGE) and choline and octanoic acid (CAOT) and compare their interactions with solid-supported lipid bilayers and vesicle layers. Particularly, dynamic light scattering (DLS) and quartz crystal microbalance with dissipation (QCM-D) measurements were used alongside neutron reflectivity (NR) to evaluate any structure-function relationships contributing to the DES behaviour, aiming towards the rational design of neoteric solvents for transdermal delivery.

Keywords:
deep eutectic solvents, ionic liquids, lipid bilayers, neutron reflectivity, neutron scattering, transdermal delivery
Subjects:
Biomolecules and biochemistry
Materials sciences

Cite this dataset as:
Neville, G., Dobre, A., Smith, G., Micciulla, S., Brooks, N., Arnold, T., Welton, T., Edler, K., 2023. Dataset for "Interactions of Choline and Geranate (CAGE) and Choline Octanoate (CAOT) Deep Eutectic Solvents with Lipid Bilayers". Bath: University of Bath Research Data Archive. Available from: https://doi.org/10.15125/BATH-01289.

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Data

DataRepository CAGE.zip
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Dataset for "Interactions of Choline and Geranate (CAGE) and Choline Octanoate (CAOT) Deep Eutectic Solvents with Lipid Bilayers"

Creators

George Neville
University of Bath

Ana-Maria Dobre
Imperial College London

Gavin Smith
Imperial College London

Samantha Micciulla
Institut Laue–Langevin

Nick Brooks
Imperial College London

Thomas Arnold
European Spallation Source; Diamond Light Source Ltd; European Spallation Source ERIC; University of Bath; Rutherford Appleton Laboratory; ISIS Neutron and Muon Source

Tom Welton
Imperial College London

Karen Edler
University of Bath

Contributors

University of Bath
Rights Holder

Documentation

Data collection method:

Both 1:1 (IL) and 1:2 (DES) mixtures between choline (Ch) and geranic acid (GA) or octanoic acid (OA) were synthesised using hydrogenated and deuterated species for neutron reflectivity (NR) experiments. The structure of the mixtures were first characterised by dynamic light scattering (DLS), before their behaviour with lipidic phases was assessed by quartz-crystal microbalance with dissipation (QCM-D) measurements alongside NR. IL/DES preparation: Briefly, either geranic acid or octanoic acid were dissolved in ethanol and added dropwise to a solution of d9-choline hydroxide or choline bicarbonate in water, as appropriate. This was stirred for 2 h before excess solvent was removed under reduced pressure. Resultant viscous liquids were dried under vacuum for 24 h before use. SUV preparation: SUVs were prepared from a thin-film technique where DMPC was initial dissolved in chloroform (1 mg ml-1) and rotary dried under N2 (g). The resulting film was swelled with 2 ml of water heated to 35 oC and vortexed to create a suspension. Whilst the mixture was still warm, suspensions were bath sonicated to clarity indicating the formation of SUVs (~20-100 nm) that do not scatter light. Supported Vesicle Layer (SVL) preparation: DMPC SUVs were incubated with Au-coated substrates for 30 minutes before rinsing with clean solvent. Supported Lipid Bilayer (SLB) preparation: SLBs were prepared by SUV collapse. Prior to use, SUV suspensions were centrifuged for 15 mins (16,000 x g) to remove any multi-lamellar vesicles. Separately, an aqueous CaCl2 solution (1 mM) was prepared and used to dilute the vesicles to 0.3 mg ml-1. This solution was then injected over SiO2-coated substrates (0.5 ml min-1, 30 mins), before rinsing with clean solvent.

Data processing and preparation activities:

Beamline data from the FIGARO specular NR instrument is available separately from Institut Laue-Langevin. 1H NMR: Spectra were analysed using Mestrelab MNova 11.0 software where spectra were baseline corrected to allow integration of peak area. QCM-D: Before the relevant injection point, a stable baseline was chosen as the zero reference and the frequency and dissipation data relativised accordingly. Mass deposition was calculated using the Sauerbrey equation. A sensitivity of 17.7 ng Hz-1 cm-2 was used for 5 MHz chips (SiO2-coated) and 4.4 ng Hz-1 cm-2 for 10 MHz (Au-coated) was used.

Technical details and requirements:

DFT Calculations: To estimate molecular volume, DFT calculations of 1:2 CAGE, 1:2 CAOT and their constituent parts were performed using Gaussian 16. All structures were visualised and checked using frequency analysis. DLS: DLS was conducted using a Malvern Zetasizer Nanoseries and plastic cuvettes. Measurements were taken using backscattering and a wavelength of 663 nm. For each sample five sets of measurements were taken, consisting of at least 12 runs each. QCM-D: Measurements were conducted using an OpenQCM Q-1 sensor module with either SiO2-coated (5 MHz) or Au-coated (10 MHz) quartz chips (13.9 mm diameter). Chips were rinsed with ethanol, acetone and water before cleaning under UV/ozone for 15 mins. These were then sealed in flow cells and calibrated in air before incubation with clean solvents. Once a stable baseline occurred, experimental protocols were commenced. NR: Experiments were conducted at the Institut Laue-Langevin (ILL), France, on the FIGARO specular neutron reflectivity beamline. Before use, Si blocks (8 x 5 cm; 3 Å roughness) were cleaned under UV/ozone for 15 mins, rinsed with ultrafiltered water and then sealed into flow cells flanked by steel plates for temperature control. Resulting multidimensional time-of-flight data were reduced using the COSMOS software available at ILL. Models were fit using the Markov-Chain-Monte-Carlo (MCMC) algorithm within Refnx.

Additional information:

Details of the data and labelling is available in the README.txt file.

Documentation Files

README.txt
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Creative Commons: Attribution 4.0

Index for the the dataset.

Funders

Engineering and Physical Sciences Research Council (EPSRC)
https://doi.org/10.13039/501100000266

EPSRC Doctoral Training Centre in Sustainable Chemical Technologies
EP/L016354/1

GlaxoSmithKline Biologicals (GSK)
https://doi.org/10.13039/100020955

National Institute for Health Research (NIHR)
https://doi.org/10.13039/501100000272

Health Protection Research Unit in Chemical and Radiation Threats and Hazards
NIHR-INF-1654

Publication details

Publication date: 2 October 2023
by: University of Bath

Version: 1

DOI: https://doi.org/10.15125/BATH-01289

URL for this record: https://researchdata.bath.ac.uk/id/eprint/1289

Related papers and books

Neville, G. M., Dobre, A.‐M., Smith, G. J., Micciulla, S., Brooks, N. J., Arnold, T., Welton, T., and Edler, K. J., 2023. Interactions of Choline and Geranate (CAGE) and Choline Octanoate (CAOT) Deep Eutectic Solvents with Lipid Bilayers. Advanced Functional Materials, 34(2). Available from: https://doi.org/10.1002/adfm.202306644.

Related datasets and code

Karen J Edler, BROOKS Nick, CES OSCAR, DOBRE Ana, MICCIULLA Samantha, NEVILLE George, and WELTON Tom, 2021. Interactions of the Choline And GEranate (CAGE) Deep Eutectic Solvent with Lipid Bilayers. Institut Laue-Langevin (ILL). Available from: https://doi.org/10.5291/ILL-DATA.9-13-927.

Contact information

Please contact the Research Data Service in the first instance for all matters concerning this item.

Contact person: George Neville

Departments:

Faculty of Science
Chemistry

Research Centres & Institutes
Centre for Sustainable and Circular Technologies (CSCT)