Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches
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...
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| Format: | Article |
| Language: | English |
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Elsevier
2019
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| Online Access: | http://psasir.upm.edu.my/id/eprint/82352/ http://psasir.upm.edu.my/id/eprint/82352/1/Synthesis%2C%20characterisation%20and%20antioxidant%20properties%20of%20ferulate-based%20protic%20ionic%20liquids.pdf |
| _version_ | 1848859277795524608 |
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| author | Ahmad, Nur Afiqah Jumbri, Khairulazhar Ramli, Anita Abd Ghani, Noraini Ahmad, Haslina Kassim, Mohd Azlan |
| author_facet | Ahmad, Nur Afiqah Jumbri, Khairulazhar Ramli, Anita Abd Ghani, Noraini Ahmad, Haslina Kassim, Mohd Azlan |
| author_sort | Ahmad, Nur Afiqah |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | 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 EC₅₀ ranging from 12.93 ± 0.05 to 17.40 ± 0.04 μM indicating a strong antioxidant activity compared to parent acid (EC₅₀ 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 σ-potential analysis. |
| first_indexed | 2025-11-15T12:26:47Z |
| format | Article |
| id | upm-82352 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T12:26:47Z |
| publishDate | 2019 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-823522021-08-07T23:58:49Z http://psasir.upm.edu.my/id/eprint/82352/ Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches Ahmad, Nur Afiqah Jumbri, Khairulazhar Ramli, Anita Abd Ghani, Noraini Ahmad, Haslina Kassim, Mohd Azlan 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 EC₅₀ ranging from 12.93 ± 0.05 to 17.40 ± 0.04 μM indicating a strong antioxidant activity compared to parent acid (EC₅₀ 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 σ-potential analysis. Elsevier 2019-03 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/82352/1/Synthesis%2C%20characterisation%20and%20antioxidant%20properties%20of%20ferulate-based%20protic%20ionic%20liquids.pdf Ahmad, Nur Afiqah and Jumbri, Khairulazhar and Ramli, Anita and Abd Ghani, Noraini and Ahmad, Haslina and Kassim, Mohd Azlan (2019) Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches. Journal of Molecular Liquids, 278. pp. 309-319. ISSN 0167-7322; ESSN: 1873-3166 https://www.sciencedirect.com/science/article/abs/pii/S0167732218348062 10.1016/j.molliq.2019.01.048 |
| spellingShingle | Ahmad, Nur Afiqah Jumbri, Khairulazhar Ramli, Anita Abd Ghani, Noraini Ahmad, Haslina Kassim, Mohd Azlan Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title | Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title_full | Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title_fullStr | Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title_full_unstemmed | Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title_short | Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| title_sort | synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches |
| url | http://psasir.upm.edu.my/id/eprint/82352/ http://psasir.upm.edu.my/id/eprint/82352/ http://psasir.upm.edu.my/id/eprint/82352/ http://psasir.upm.edu.my/id/eprint/82352/1/Synthesis%2C%20characterisation%20and%20antioxidant%20properties%20of%20ferulate-based%20protic%20ionic%20liquids.pdf |