Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid‐liquid extraction

Chen, Xing; Ding, Qi; Shan, Ruo-Ni; He, Chao‐Hong; Wu, Ke‐Jun

doi:10.1002/chir.23071

Cited by 26 publications

(18 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, requirements for complicated operations or expensive equipment might limit some of these techniques. Among these possibilities, the importance of the liquid medium is the most conspicuous in liquid–liquid extraction, where an additive or the solvent itself acts as selector, resulting in an efficient and low-cost process that is easy to scale up. Furthermore, asymmetric synthesis can be directed by a chiral solvent. , Even more interestingly, significant solvent effects on enantioselectivity have been observed also in nonchiral solvents .…”

mentioning

confidence: 99%

Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!

et al. 2021

View full text Add to dashboard Cite

By simulating butan-2-ol dissolved in the chiral ionic liquid 1-ethyl-3-methylimidazolium (S)-alaninate, we investigate the chiral recognition of butan-2-ol in the ionic liquid. The hydrogen bonding between the chiral anion and both enantiomers of butan-2-ol is similar; however, both chiral molecules (anion and alcohol) induce an asymmetry in the achiral cation which leads to a more favorable environment for the alcohol in the heterochiral system as compared to the homochiral system and hence provides an energetic stabilization of the former.

show abstract

mentioning

confidence: 99%

Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!

et al. 2021

View full text Add to dashboard Cite

show abstract

“…In addition, flurbiprofen, NSAID available for OA, is also chiral. [ 220 ] Its S‐enantiomer is used to treat OA and rheumatoid arthritis with high pharmacological activity and low side effects, but its R‐enantiomer has limited therapeutic effect and high toxicity. [ 220 ] It has also been studied to compare the transdermal penetration of flurbiprofen S‐and R‐enantiomers.…”

Section: Nanomaterials Properties and Responsive Systems For Treating Oamentioning

confidence: 99%

“…[ 220 ] Its S‐enantiomer is used to treat OA and rheumatoid arthritis with high pharmacological activity and low side effects, but its R‐enantiomer has limited therapeutic effect and high toxicity. [ 220 ] It has also been studied to compare the transdermal penetration of flurbiprofen S‐and R‐enantiomers. However, in vitro studies on rat abdominal skin at different pH and chemical penetration promoters showed that there appeared to be no difference in the penetration ability of S‐flurbiprofen and flurbiprofen racemate (R‐flurbiprofen).…”

Section: Nanomaterials Properties and Responsive Systems For Treating Oamentioning

confidence: 99%

Analysis of Nanomedicine Efficacy for Osteoarthritis

Wang

Liu

et al. 2022

Advanced NanoBiomed Research

View full text Add to dashboard Cite

Osteoarthritis (OA) is a chronic disease and it causes considerable medical and socioeconomic burden. Currently, OA can be classified into different stages depending on its severity, from mild to severe, but there is no treatment focusing on a particular stage. In addition, conventional treatments suffer from drawbacks such as the poor effectiveness of physiotherapy, short‐term efficacy of medication, and invasiveness of surgery. Nanomedicine is a promising approach to improve OA treatments such as by prolonging the residence time of drugs in the joint and on‐demand drug release. Herein, the pathological development of OA and the cellular involvement in this process is reviewed and classified into three stages: early, intermediate, and advanced, according to its pathology and severity. Subsequently, nanomaterials that have been used to deliver drug cargo relevant to different stages of OA are reviewed. The impact of nanomaterial physicochemical properties, on therapeutic efficacy, is discussed. This is concluded by discussing the significance of minimum information reporting to standardize the use of nanomedicine for OA treatment and the potential of emerging methods including microneedles and DNA barcoding technology to improve the understanding of OA biology and improve clinical translation.

show abstract

“…In the following work [166], chiral ionic liquids, tryptophan derivatives were used, in an extraction system with an organic solvent. The maximum enantioselectivity (1.2) towards flurbiprofen enantiomers was obtained at pH 2.0 at 25 • C using 1,2-dichloroethane as an organic solvent and 1-butyl-3-methylimidazolium L-tryptophan (BMIM)(L-trp) as a chiral selector.…”

Section: The Liquid-liquid Extraction By Hydrophilic Cilsmentioning

confidence: 99%

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

View full text Add to dashboard Cite

Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.

show abstract

Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid‐liquid extraction

Abstract: This is a repository copy of Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid liquid extraction- .

Cited by 26 publications

References 45 publications

Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!

Recognition in Chiral Ionic Liquids: The Achiral Cation Makes the Difference!

Analysis of Nanomedicine Efficacy for Osteoarthritis

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Contact Info

Product

Resources

About