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...

Full description

Main Authors: Ahmad, N.A., Jumbri, K., Ramli, A., Ghani, N.A., Ahmad, H., Kassim, M.A.
Format: Article
Institution: Universiti Teknologi Petronas
Record Id / ISBN-0: utp-eprints.22112 /
Published: 2019
Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85060105123&doi=10.1016%2fj.molliq.2019.01.048&partnerID=40&md5=622db65f63683cc4be89bfa0367b1d8c
http://eprints.utp.edu.my/22112/
Tags: Add Tag
No Tags, Be the first to tag this record!
id utp-eprints.22112
recordtype eprints
spelling utp-eprints.221122019-02-28T08:02:09Z Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: Experimental and modelling approaches Ahmad, N.A. Jumbri, K. Ramli, A. Ghani, N.A. Ahmad, H. Kassim, M.A. 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. 2019 Article NonPeerReviewed https://www.scopus.com/inward/record.uri?eid=2-s2.0-85060105123&doi=10.1016%2fj.molliq.2019.01.048&partnerID=40&md5=622db65f63683cc4be89bfa0367b1d8c 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. http://eprints.utp.edu.my/22112/
institution Universiti Teknologi Petronas
collection UTP Institutional Repository
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 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.
format Article
author Ahmad, N.A.
Jumbri, K.
Ramli, A.
Ghani, N.A.
Ahmad, H.
Kassim, M.A.
spellingShingle Ahmad, N.A.
Jumbri, K.
Ramli, A.
Ghani, N.A.
Ahmad, H.
Kassim, M.A.
Synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: Experimental and modelling approaches
author_sort Ahmad, N.A.
title 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_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_sort synthesis, characterisation and antioxidant properties of ferulate-based protic ionic liquids: experimental and modelling approaches
publishDate 2019
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85060105123&doi=10.1016%2fj.molliq.2019.01.048&partnerID=40&md5=622db65f63683cc4be89bfa0367b1d8c
http://eprints.utp.edu.my/22112/
_version_ 1741196570141917184
score 11.62408

Similar Items