Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid-liquid extraction.

Abstract:

:Flurbiprofen is a kind of nonsteroidal anti-inflammatory drug, which has been widely used in clinic for treatment of rheumatoid arthritis and osteoarthritis. It has been reported that S-flurbiprofen shows good performance on clinic anti-inflammatory treatment, while R-enantiomer almost has no pharmacological activities. It has important practical values to obtain optically pure S-flurbiprofen. In this work, chiral ionic liquids, which have good structural designability and chiral recognize ability, were selected as the extraction selector by the assistance of quantum chemistry calculations. The distribution behaviors of flurbiprofen enantiomers were investigated in the extraction system, which was composed of organic solvent and aqueous phase containing chiral ionic liquid. The results show that maximum enantioselectivity up to 1.20 was attained at pH 2.0, 25°C using 1,2-dichloroethane as organic solvent, 1-butyl-3-methylimidazole L-tryptophan ([Bmim][L-trp]) as chiral selector. The racemic flurbiprofen initial concentration was 0.2 mmol L-1 , and [Bmim][L-trp] concentration was 0.02 mol L-1 . Furthermore, the recycle of chiral ionic liquids has been achieved by reverse extraction process of the aqueous phase with chiral selector, which is significant for industrial application of chiral ionic liquids and scale-up of the extraction process.

journal_name

Chirality

journal_title

Chirality

authors

Cui X,Ding Q,Shan RN,He CH,Wu KJ

doi

10.1002/chir.23071

subject

Has Abstract

pub_date

2019-06-01 00:00:00

pages

457-467

issue

6

eissn

0899-0042

issn

1520-636X

journal_volume

31

pub_type

杂志文章
  • Synthesis and circular dichroism studies of N,N-bis(2-quinolylmethyl)amino acid Cu(II) complexes: determination of absolute configuration and enantiomeric excess by the exciton coupling method.

    abstract::We report a method to determine the absolute configuration of alpha-amino acids by exciton coupled circular dichroism (ECCD). Naturally occurring amino acids were successfully derivatized with 2-bromomethylquinoline. Complexation of these conformationally flexible ligands with Cu(II) salts yielded defined propeller-li...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10079

    authors: Holmes AE,Zahn S,Canary JW

    更新日期:2002-06-01 00:00:00

  • Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.

    abstract::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10124

    authors: Gonçalves PV,Matthes Ado C,Da Cunha SP,Lanchote VL

    更新日期:2002-08-01 00:00:00

  • Conformation change of hornet silk proteins in the solid phase in response to external stimulation.

    abstract::Hornet silks adopt a variety of morphology such as fibers, sponge, films, and gels depending on the preparation methods. We have studied the conformation change of hornet silk proteins (Vespa mandarina) as regenerated films, using chiroptical spectrophotometer universal chiroptical spectrophotometer 1, which can measu...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22824

    authors: Kuroda R,Kameda T

    更新日期:2018-05-01 00:00:00

  • Theoretical and Molecular Docking Study of Ketoconazole on Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as Chiral Selector.

    abstract::A molecular docking study, using molecular mechanics calculations with AutoDock and semi-empirical PM3 calculations, was used to predict the enantiodiscrimination of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and ketoconazole (KTZ) enantiomers. A Density Functional Theory (DFT) single-point calculation at the...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22554

    authors: Arsad SR,Maarof H,Wan Ibrahim WA,Aboul-Enein HY

    更新日期:2016-03-01 00:00:00

  • Enantioseparation of chiral perfluorooctane sulfonate (PFOS) by supercritical fluid chromatography (SFC): Effects of the chromatographic conditions and separation mechanism.

    abstract::Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23120

    authors: Zhao L,Chen F,Guo F,Liu W,Liu K

    更新日期:2019-10-01 00:00:00

  • Unequivocal Enantiomeric Identification and Analysis of 10 Chiral Pesticides in Fruit and Vegetables by QuEChERS Method Combined With Liquid Chromatography-Quadruple/Linear Ion Trap Mass Spectrometry Determination.

    abstract::In this research, 10 chiral pesticides in fruits and vegetables were simultaneously determined using chiral liquid chromatography triple quadrupole-linear ion trap hybrid mass spectrometry (LC-QqLIT). The QuEChERS method was applied for sample preparation, and an enhanced product ion (EPI) scan was used to acquire tan...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22531

    authors: He Z,Peng Y,Wang L,Luo M,Liu X

    更新日期:2015-12-01 00:00:00

  • Short step enantioselective synthesis of (-)-swainsonine.

    abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2

    authors: Punniyamurthy T,Irie R,Katsuki T

    更新日期:2000-06-01 00:00:00

  • Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.

    abstract::A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated elec...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22322

    authors: Frelek J,Karchier M,Madej D,Michalak K,Różański P,Wicha J

    更新日期:2014-06-01 00:00:00

  • Circular dichroism and the interactions of water soluble porphyrins with DNA.

    abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.10206

    authors: Pasternack RF

    更新日期:2003-05-05 00:00:00

  • Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector.

    abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22508

    authors: Caminati G,Cicchi S,Lascialfari L,Brandi A

    更新日期:2015-11-01 00:00:00

  • Polymer-Supported Optically Active fac(S)-Tris(thiotato)rhodium(III) Complex for Sulfur-Bridging Reaction With Precious Metal Ions.

    abstract::The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22546

    authors: Aizawa S,Tsubosaka S

    更新日期:2016-01-01 00:00:00

  • High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase.

    abstract::The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, wit...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20968

    authors: Aranyi A,Ilisz I,Pataj Z,Szatmári I,Fülöp F,Armstrong DW,Péter A

    更新日期:2011-08-01 00:00:00

  • Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

    abstract::2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10068

    authors: Sato I,Yanagi T,Soai K

    更新日期:2002-02-01 00:00:00

  • Enantioselective separation and degradation of the herbicide dichlorprop methyl in sediment.

    abstract::Chiral pesticides currently constitute about 50% of all pesticides dosage used in China, and this ratio is increasing as more complex structures are introduced. Dichlorprop methyl (DCPPM) is a chiral herbicide consisting of a pair of enantiomers. In this study, the enantiomeric separation of DCPPM was investigated by ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20624

    authors: Ma Y,Xu C,Wen Y,Liu W

    更新日期:2009-04-01 00:00:00

  • Chiral memory: induction, amplification, and switching in porphyrin assemblies.

    abstract::The interaction between the tetra-anionic porphyrin H2TPPS and its copper derivative, CuTPPS, with the tetra-cationic porphyrin H2T4 and its copper derivative, CuT4, leads, in aqueous solution, to the formation of remarkably stable and kinetically inert heteroaggregates. The aggregation process is under hierarchic con...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20464

    authors: Rosaria L,D'urso A,Mammana A,Purrello R

    更新日期:2008-03-01 00:00:00

  • Viewing and inducing symmetry breaking at the single-molecule limit.

    abstract::Symmetry breaking by photons, electrons, and molecular interactions lies at the heart of many important problems as varied as the origin of homochiral life to enantioselective drug production. Herein we report a system in which symmetry breaking can be induced and measured in situ at the single-molecule level using sc...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22096

    authors: Tierney HL,Jewell AD,Baber AE,Iski EV,Sykes EC

    更新日期:2012-12-01 00:00:00

  • Chiral discrimination by albumin: a mechanistic study of liquid chromatographic optical resolution of nonaromatic carboxylic acids.

    abstract::In order to get further insight into the mechanism by which bovine serum albumin (BSA) discriminates between enantiomers of organic acids, some radioisotopically labeled, nonaromatic carboxylic acids were studied under varying mobile phase conditions. It was found for a series of N-alkanoyl-DL-[3H]leucines that the D-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050503

    authors: Allenmark S

    更新日期:1993-01-01 00:00:00

  • Novel P,N-bidentate phosphite ligands in asymmetric catalysis.

    abstract::Results achieved by the authors in the synthesis of chiral P,N-phosphite ligands are summarized. Three groups of new chiral P,N-phosphites are discussed, namely, ligands derived from 1,1'-bi-2-naphthol, ligands possessing an acyclic phosphorus center, and P*-chiral ligands derived from (S)-2-anilinomethylpyrrolidine. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10258

    authors: Gavrilov KN,Bondarev OG,Korostylev AV,Polosukhin AI,Tsarev VN,Kadilnikov NE,Lyubimov SE,Shiryaev AA,Zheglov SV,Gais HJ,Davankov VA

    更新日期:2003-01-01 00:00:00

  • Variable stereochemistry in highly branched isoprenoids from diatoms.

    abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1053

    authors: Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

    更新日期:2001-08-01 00:00:00

  • Programmed assembly of rigid-rod beta-barrel pores: thermal inversion of chirality.

    abstract::The programmed assembly of p-octiphenyl rods carrying six complementary tripeptide strands was studied in the presence of bilayer membranes using circular dichroism (CD) spectroscopy. Thermal CD experiments demonstrated programmed assembly of anionic and cationic rods into supramolecules at low temperature that irreve...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20034

    authors: Sakai N,Matile S

    更新日期:2004-01-01 00:00:00

  • Stereoselective sulfation of terbutaline by the rat liver cytosol: evaluation of experimental approaches.

    abstract::Little is known about the stereochemistry of sulfation of chiral phenolic drugs. In this study we examined several in vitro approaches to this question, using (+)-, (-)-, or (+/-)-terbutaline as the substrate and the rat liver cytosol as the phenolsulfotransferase enzyme source. The cosubstrate PAPS was either generat...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530010205

    authors: Walle UK,Walle T

    更新日期:1989-01-01 00:00:00

  • Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy.

    abstract::Metoprolol is available for clinical use as a racemic mixture. The S-(-)-metoprolol enantiomer is the one expressing higher activity in the blockade of the β(1)-adrenergic receptor. The α-hydroxymetoprolol metabolite also has activity in the blockade of the β(1)-adrenergic receptor. The present study describes the dev...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22102

    authors: Antunes Nde J,Cavalli RC,Marques MP,Lanchote VL

    更新日期:2013-01-01 00:00:00

  • Chiroptical studies on supramolecular chirality of molecular aggregates.

    abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22482

    authors: Sato H,Yajima T,Yamagishi A

    更新日期:2015-10-01 00:00:00

  • Efficient resolution of venlafaxine and mechanism study via X-ray crystallography.

    abstract::Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O'-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of 'Dutch resolution' from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22790

    authors: Liu ZJ,Liu H,Chen XW,Lin M,Hu Y,Tuo X,Yuan ZY,Sun XX

    更新日期:2018-03-01 00:00:00

  • Highly diastereoselective addition of silyldihalomethyllithiums to chiral alkyl esters.

    abstract::Treatment of benzoate, formate, or trifluoroacetate esters with silyldibromomethyllithiums provides alkyl silyl mixed acetals via the 1,3-rearrangement of a silyl group from carbon to oxygen. A high level of asymmetric induction onto the acetal carbon is observed when chiral alkyl esters are employed. The stereochemic...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10152

    authors: Shinokubo H,Kondo J,Inoue A,Oshima K

    更新日期:2003-01-01 00:00:00

  • Chiral bioanalytical methods in bioequivalence studies of intravenous vs. oral formulations of ibuprofen.

    abstract::According to the Ibuprofen Product-Specific Bioequivalence Guidance of the European Medicines Agency, achiral bioanalytical methods are considered acceptable for demonstration of bioequivalence of ibuprofen-containing products. The aim of this investigation is to compare the bioequivalence outcomes obtained with indiv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23258

    authors: González-Rojano E,Marcotegui J,Laredo L,Gwaza L,Gordon J,Portolés A,Vargas E,Morales-Alcelay S,García-Arieta A

    更新日期:2020-09-01 00:00:00

  • Stereoselective disposition of fenoprofen in plasma and synovial fluid of patients with rheumatoid arthritis.

    abstract::The simultaneous disposition of fenoprofen enantiomers in synovial fluid and plasma was studied in 11 patients with arthritis and chronic knee effusions treated with a single oral dose of 600 mg rac-fenoprofen. A plasma sample and a synovial fluid sample were collected simultaneously from each patient up to 16 h after...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20374

    authors: De Miranda Silva C,Marques MP,Barissa GR,Donadi EA,Da Silva LM,Lanchote VL

    更新日期:2007-05-05 00:00:00

  • Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.

    abstract::The pharmacokinetics of (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) and its enantiomer (L-enantiomer) was studied in Goto-Kakizaki (GK) rats after intravenous administration of nateglinide or L-enantiomer at a dose of 40 micromol/kg body weight. Nateglinide, its L-enantiomer and their me...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20711

    authors: Tamura M,Shiba S,Kudo N,Kawashima Y

    更新日期:2010-01-01 00:00:00

  • Stereoselective effect of warfarin and bilirubin on the binding of 5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2- one enantiomers to human serum albumin.

    abstract::The binding of the title benzodiazepine enantiomers and its modulation by warfarin and bilirubin were studied by chromatography on human serum albumin (HSA) immobilized on Sepharose 4B, and also by a combination of ultrafiltration and circular dichroism (UF-CD) methods. In the absence of warfarin and bilirubin the bin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020307

    authors: Fitos I,Visy J,Magyar A,Kajtár J,Simonyi M

    更新日期:1990-01-01 00:00:00

  • Optically active α-phenylethylamine as efficient organocatalyst in the solvent-free reactions between 2,3-butanedione and conjugated nitroolefins.

    abstract::(R)-(+) and (S)-(-)-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2,3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3-nitrocyclopentanone derivatives. The reactions ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22088

    authors: Felluga F,Forzato C,Nitti P,Pitacco G,Prati F,Valentin E,Zangrando E

    更新日期:2012-12-01 00:00:00