Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: Experimental and modelling approaches

Ahmad, N.A. and Jumbri, K. and Ramli, A. and Ghani, N.A. and Ahmad, H. and Kassim, M.A. (2019) Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: Experimental and modelling approaches. Journal of Molecular Liquids, 278 . pp. 309-319.

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Active pharmaceutical ingredients (APIs) in the form of crystalline solid are commonly produced in drug manufacturing industries. However, crystalline solid APIs have a low solubility and the ability to cause polymorphism transformation. In order to overcome these problems, a modification of APIs in the form of protic ionic liquids (PILs) has been proposed. In the present study, a series of five ferulate-based PILs were successfully synthesised and characterised by appropriate spectral analysis. The antioxidant activity of synthesised PILs was determined through the 2,2�diphenyl�1�picrylhydrazyl (DPPH) free radical scavenging assays. The spectroscopy analysis confirmed the formation of PILs supported by the Density Function Theory (DFT) calculation. The synthesised ferulate-based PILs exhibited low EC 50 ranging from 12.93 ± 0.05 to 17.40 ± 0.04 μM indicating a strong antioxidant activity compared to parent acid (EC 50 of 21.40 ± 0.05 μM). Prediction of antioxidant activity of the PILs and their ionic interactions at the molecular level were studied by applying DFT calculation at B3-LYP/6-311G*** level and COSMO-RS. Based on the optimised geometry, the ion-pair of PILs formed a strong directional intermolecular hydrogen bond between the �NH group of the cation with the �COOH group of the anion with interaction energy of �111 to �120 kcal mol �1 . Predicted antioxidant activity indicated that the PILs's cation has a weak interaction with an anion as observed from the �-potential analysis. © 2019 Elsevier B.V.

Item Type:Article
Impact Factor:cited By 0
Uncontrolled Keywords:Crystalline materials; Density functional theory; Free radicals; Hydrogen bonds; Ionic liquids; Positive ions; Probability density function; Spectrum analysis, Active pharmaceutical ingredients; COSMO-RS; Density function theory calculations; DFT calculation; Dpph radicals; Free radical scavenging; Intermolecular hydrogen bonds; Protic ionic liquids, Antioxidants
ID Code:22112
Deposited By: Ahmad Suhairi
Deposited On:28 Feb 2019 08:02
Last Modified:28 Feb 2019 08:02

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