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Aggregation and Morphological Aptitude of Drug-Based Ionic Liquids in Aqueous Solution.

ABSTRACT: Here, we present how replacing the usual inorganic counter ion with a pharmaceutically active aromatic one can greatly affect the interfacial as well as bulk properties of ionic liquids (ILs). We have synthesized a series of novel drug-based ILs, namely, 1-alkyl-3-methylimidazolium diclofenate ([C _n mim][DF]; n = 6, 8, 10, 12, and 14) abbreviated as DF-ILs, wherein DF^- is a well-recognized analgesic and nonsteroidal anti-inflammatory drug. We show strong synergistic interactions between C _n mim⁺ and aromatic DF^- attributed to reduced electrostatic repulsions and increased hydrophobicity from their incorporation, reflecting a 300-fold smaller critical aggregation concentration than that of their Cl^- analogue [C _n mim][Cl]. Interfacial properties for such strongly associating systems are discussed and clearly established to have remarkably improved properties than those of their Cl^- analogues. The decreasing polarity of the cybotactic region of pyrene with increase in the chain length "n" indicates an increased extent of packing of cationic head groups in the Stern layer. DF^- ion seems to play a vital role in the formation of the resulting aggregates, as probed by small angle neutron scattering and transmission electron microscopy. The thermodynamical insights of the aggregation process have been studied using isothermal titration calorimetry and temperature-dependent conductivity experiments. Unilamellar vesicles are formed at extremely low concentration, and also it is the first report that puts into picture the formation of vesicles for [C₆mim][DF] with such a short chain.

SUBMITTER: Singh O

PROVIDER: S-EPMC6641264 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Aggregation and Morphological Aptitude of Drug-Based Ionic Liquids in Aqueous Solution.

Singh Onkar O Singla Pankaj P Aswal Vinod Kumar VK Mahajan Rakesh Kumar RK

ACS omega 20170707 7

Here, we present how replacing the usual inorganic counter ion with a pharmaceutically active aromatic one can greatly affect the interfacial as well as bulk properties of ionic liquids (ILs). We have synthesized a series of novel drug-based ILs, namely, 1-alkyl-3-methylimidazolium diclofenate ([C n mim][DF]; n = 6, 8, 10, 12, and 14) abbreviated as DF-ILs, wherein DF- is a well-recognized analgesic and nonsteroidal anti-inflammatory drug. We show strong syner ...[more]

PMID: 31457654

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Project description:Deoxyribonucleic acid (DNA) carries the genetic information essential for the growth and functioning of living organisms, playing a significant role in life sciences research. However, the long-term storage and preservation of DNA, while ensuring its bioactivity, are still current challenges to overcome. In this work, aqueous solutions of ionic liquids (ILs) were investigated as potential preservation media for double stranded (dsDNA). A screening of several ILs, by combining the cholinium, tetrabutylammonium, tetrabutylphosphonium, and 1-ethyl-3-methylimidazolium, cations with the anions bromide, chloride, dihydrogen phosphate, acetate, and glycolate, was carried out in order to gather fundamental knowledge on the molecular features of ILs that improve the dsDNA stability. Different IL concentrations and the pH effect were also addressed. Circular dichroism (CD) spectroscopy was used to evaluate the conformational structure and stability of dsDNA. IL-DNA interactions were appraised by UV-Vis absorption spectrophotometry and 31P nuclear magnetic resonance (NMR) spectroscopy. The results obtained demonstrate that pH has a significant effect towards the dsDNA stability. Amongst the ILs investigated, cholinium-based ILs are the most promising class of ILs to preserve the dsDNA structure, in which electrostatic interactions between the cholinium cation and the DNA phosphate groups play a significant role as demonstrated by the 31P NMR data, being more relevant at higher IL concentrations. On the other hand, the denaturation of dsDNA mainly occurs with ILs composed of more hydrophobic cations and able to establish dispersive interactions with the nucleobases environment. Furthermore, the IL anion has a weaker impact when compared to the IL cation effect to interact with DNA molecules. The experimental data of this work provide relevant fundamental knowledge for the application of ILs in the preservation of nucleic acids, being of high relevance in the biotechnology field.

Dataset Information

Aggregation and Morphological Aptitude of Drug-Based Ionic Liquids in Aqueous Solution.

Publications

Aggregation and Morphological Aptitude of Drug-Based Ionic Liquids in Aqueous Solution.

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