New data on the sorption properties of ?1-acid glycoprotein chiral stationary phase

Gyimesi‐Forrás, Krisztina; Szabó, György; Budvári‐Bárány, Zsuzsa; Gergely, András

doi:10.1002/(sici)1520-636x(1999)11:3<212::aid-chir7>3.0.co;2-p

Cited by 8 publications

(2 citation statements)

References 17 publications

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“…Among these, columns based on a-1-acid glycoprotein (CHIRAL AGP) and ovomucoid protein (ULTRON ES-OVM) have shown a wide range of applicability. 11,12 Due to the highly complex structure of the protein, the chiral discrimination mechanism is only incompletely known. It has been suggested that retention and enantioselectivity in protein-based chiral stationary phases depend on hydrophobic interactions, hydrogen bonding, ionic bonding and ion-pairing interactions.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Bonato¹,

Bortocan²,

Gaitani³

et al. 2002

J. Braz. Chem. Soc.

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Várias fases estacionárias baseadas em derivados de polissacarídeos e proteínas foram avaliadas para a resolução de alguns fármacos quirais e seus metabólitos. As fases estacionárias baseadas em polissacarídeos CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD e CHIRALPAK AS foram avaliadas em condições de fase normal, usando hexano:2-propanol como fase móvel. Dietilamina ou ácido trifluoracético foram adicionados para melhorar a simetria dos picos. As colunas CHIRALCEL OJ-R, CHIRALCEL OD-R e CHIRALCEL OD-H foram avaliadas em condições de fase reversa, usando acetonitrila:água ou acetonitrila: NaClO 4 . As fases estacionárias baseadas em proteínas CHIRAL AGP e ULTRON ES-OVM foram usadas com fases móveis consistindo de soluções tampão adicionadas de modificadores orgânicos. Entre as fases estacionárias baseadas em derivados de polissacarídeos, a CHIRALPAK AD mostrou melhor resolução de quase todos os fármacos e metabólitos estudados. A coluna ULTRON ES-OVM foi particularmente útil para a resolução dos quatro estereoisômeros da tioridazina-2-sulfóxido.Several chiral stationary phases based on polysaccharide derivatives and proteins were evaluated for the resolution of some chiral drugs and their metabolites. The polysaccharide-based stationary phases CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD and CHIRALPAK AS were evaluated under normal phase conditions, using hexane:2-propanol or hexane:ethanol as mobile phase. Diethylamine and trifluoracetic acid were also added to improve peak shape. The CHIRALCEL OJ-R, CHIRALCEL OD-R and CHIRALCEL OD-H columns were evaluated under reversed-phase conditions, using acetonitrile:H 2 O or acetonitrile:NaClO 4 solution. The protein-based stationary phases, CHIRAL AGP and ULTRON ES-OVM columns were used with mobile phases consisting of a buffer solution supplemented with an organic modifier. Among the polysaccharide-based stationary phases, CHIRALPAK AD provided better resolution for almost all drugs and metabolites studied. The ULTRON ES-OVM column was particularly suitable for the resolution of the four enantiomers of thioridazine-2-sulfoxide.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Bonato¹,

Bortocan²,

Gaitani³

et al. 2002

J. Braz. Chem. Soc.

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“…Esses eluentes orgânicos são extremamente úteis para separações em escala preparativa por apresentarem elevada solubilidade para analitos polares e simplicidade relativa na evaporação (Tachibana;Ohnish, 2001 (Haginaka, 2001, Millot, 2003 (Gyimesi-Forrás et al, 1999;Haginaka, 2001).…”

Section: Fases Estacionárias Quirais Derivadas De Polissacarídeosunclassified

Análise enantiosseletiva da mirtazapina em plasma: comparação de métodos de preparação das amostras

Santana¹

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Figura 25. Efeito do pH da fase doadora na recuperação de 250 ng mL -1 de cada enantiômero da mirtazapina. Condições de extração: 25 ºC; 30 min; 7 cm de fibra; 700 µL de plasma e 3,1 mL de água MILLI-Q-PLUS ® ou tampão fosfato (Fase doadora); 22 µL de tolueno (Fase aceptora). As condições cromatográficas são apresentadas na seção 3.2.2. (n = 3 para cada experimento). 72Figura 26. Efeito da adição de diferentes volumes de NaOH 10 mol L -1 na recuperação de 250 ng mL -1 de cada enantiômero da mirtazapina. Condições de extração: 25 ºC; 30 min; 7 cm de fibra; 700 µL de plasma e 3,1 mL de água MILLI-Q-PLUS ® (Fase doadora); 22 µL de tolueno (Fase aceptora). As condições cromatográficas são apresentadas na seção 3.2.2. (n = 3 para cada experimento). 72Figura 27. Efeito da adição de cloreto de sódio na recuperação de 250 ng mL -1 de cada enantiômero da mirtazapina. Condições de extração: 25 ºC; 30 min; 7 cm de membrana; 700 µL de plasma, 150 µL de NaOH 10 mol L -1 e 3,1 mL de água MILLI-Q-PLUS ® (Fase doadora); 22 µL de tolueno (Fase aceptora). As condições cromatográficas são apresentadas na seção 3.2.2.. (n = 3 para cada experimento)._____________________________________________________ 74Figura 28. Perfil de múltiplas extrações na recuperação de 250 ng mL -1 de cada enantiômero da mirtazapina. Condições de extração: 25 ºC; 7 cm de membrana; 700 µL de plasma, 150 µL de NaOH 10 mol L -1 e 3,1 mL de água MILLI-Q-PLUS ® (Fase doadora); 22 µL de tolueno (Fase aceptora). As condições cromatográficas são apresentadas na seção 3.2.2.. (n = para cada experimento)._____________________________________________________ 75Figura 29. Efeito da temperatura na recuperação de 250 ng mL -1 de cada enantiômero da mirtazapina. Condições de extração: 30 min; 7 cm de membrana; 700 µL de plasma, 150 µL de NaOH 10 mol L -1 e 3,1 mL de água MILLI-Q-PLUS A A B B S S T T R R A A C C T T $EVWUDFW A AB BS ST TR RA AC CT TThe increased interest in enantioselective pharmacokinetic and pharmacodynamic properties of chiral drugs, aiming to establish the advantages in the production of estereochemically pure drugs, has led to the development of methods of analysis with low limits of quantification, selectivity and reproducibility, which are suitable to be used in kinetic disposition studies.On this basis, mirtazapine, a new antidepressant with estereoselective pharmacokinetic and pharmacodynamic properties but with few suitable methodologies for the separation and quantification of its enantiomers, was selected to evaluate two techniques of sample preparation.The procedure involved a classic liquid-liquid extraction and a new technique of liquid-phase microextraction using microporous polypropylene hollow fiber, both using toluene as extraction solvent. The analyses were carried out by high-performance liquid chromatography using chiral stationary phase and UV detection, at 292 nm. The chromatographic separation of (+)-(S)-e (-)-(R)-mirtazapine was performed on a Chiralpak AD column protected by a CN guard column, using hexane:ethanol (98:2, v/v) ...

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Resolution of enantiomers of bupropion and its metabolites by liquid chromatography

Batra

Bhushan

2015

Biomedical Chromatography

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Bupropion, a tricyclic aminoketone, is used primarily in the treatment of depression, the management of patients with bipolar and schizo-affective disorder, and the treatment of Parkinson's disease. Bupropion is marketed as a racemate, but the racemic mixture is known to have several disadvantages while the two isomers of bupropion and its metabolite differ significantly in their pharmacological activities. Therefore, the stereoselective determination of the drug enantiomers in pharamaceutical dosages, plasma or urine is of potential clinical and analytical importance. Different chromatographic methods have been employed for the separation of the two enantiomers. This is the first attempt to review the methods of enantiosepartion of bupropion using both direct and indirect approaches in both HPLC and TLC. The review presents a detailed discussion on the use of chiral stationary phase (based on polysaccharide, α1 acid glycoprotein and ovomucoid column) and chiral derivatizing reagents (based on isothiocyanate and cyanuric chloride) along with TLC separation of bupropion enantiomers using ligand exchange and impregnation methods. The focus is also on the separation mechanism for enantioresolution using the various methods described herein.

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New data on the sorption properties of ?1-acid glycoprotein chiral stationary phase

Cited by 8 publications

References 17 publications

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Análise enantiosseletiva da mirtazapina em plasma: comparação de métodos de preparação das amostras

Resolution of enantiomers of bupropion and its metabolites by liquid chromatography

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