Use of cyclodextrins in capillary electrophoresis for the chiral resolution of some 2-arylpropionic acid non-steroidal anti-inflammatory drugs

Fanali, Salvatore; Aturki, Zeineb

doi:10.1016/0021-9673(94)00945-6

Cited by 113 publications

(66 citation statements)

References 28 publications

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“…Hence, the production of active profens in enantiomerically pure forms, their optical purity control and stereoselective pharmacokinetic studies have become important tasks in the chiral drug development [4][5][6][7][8]. These tasks could be more effectively conducted in high-throughput analysis mode by simultaneous enantioseparation of multiple profens in a single run [9][10][11][12] rather than in more commonly employed individual profen analysis mode [13][14][15][16][17][18][19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 98%

Simultaneous chiral discrimination of multiple profens by cyclodextrin‐modified capillary electrophoresis in normal and reversed polarity modes

Kim

et al. 2003

Electrophoresis

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Simultaneous enantioseparations of nine profens for their accurate chiral discrimination were achieved by capillary electrophoresis (CE) in the normal polarity (NP) mode with a single cyclodextrin (CD) system and in the reversed polarity (RP) mode with a dual CD system. The single CD system in the NP mode employed heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TMbetaCD) added at 75 mM-100 mM 2-(N-morpholino)ethanesulfonic acid buffer (pH 6.0) as the optimum run buffer. The dual CD system operated in the RP mode used 30 mM TMbetaCD and 1.0% anionic carboxymethyl-beta-cyclodextrin dissolved in pH 3.0, 100 mM phosphoric acid-triethanolamine buffer containing 0.01% hexadimethrine bromide added to reverse the electroosmotic flow. Fairly good enantiomeric resolutions and the opposite enantiomer migration orders were achieved in the two modes. Relative migration times to internal standard under respective optimum conditions were characteristic of each enantiomer with good precision (< 2% relative standard deviation, RSD), thereby enabling to crosscheck the chemical identification of profens and also their accurate chiralities. The method linearity in the two modes was found to be adequate (r > or = 0.9991) for the chiral assay of the profens investigated. Simultaneous enantiomeric purity test of ibuprofen, ketoprofen and flurbiprofen in a mixture was feasible in a single analysis by the present method.

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Section: Introductionmentioning

confidence: 98%

Simultaneous chiral discrimination of multiple profens by cyclodextrin‐modified capillary electrophoresis in normal and reversed polarity modes

Kim

et al. 2003

Electrophoresis

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“…Moreover, charged CDs are expected to offer better resolutions when the analytes are oppositely charged, because the interactions between charged CDs and analytes are based not only on inclusion complexation but also on strong electrostatic interactions [6]. The present commercialized cationic CD, quaternary ammonium hydroxypropyl-b-CD (QA-b-CD), is a randomly functionalized CD with a substitution degree of 3-5.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of single-isomer 6-mono(alkylimidazolium)-β-cyclodextrins as chiral selectors in chiral capillary electrophoresis

et al. 2005

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Novel single isomers of positively charged beta-CDs were prepared via nucleophilic substitution of 6-monotosyl-beta-CD with alkylimidazoles to afford 6-mono(alkylimidazolium)-beta-CD tosylates and then 6-mono(alkylimidazolium)-beta-CD chlorides by anion exchange. The chiral resolution abilities of these cationic CDs were studied by CE using dansyl (Dns)-amino acids as model analytes. From the experimental results, it was found that both resolution and selectivity of these cationic CDs were dependent on the following parameters: concentration of chiral selectors, pH of the running buffer, counteranions of the CDs, side chain length of the n-alkyl-imidazolium cation, temperature of the capillary column, and organic modifier used. The concentration of chiral selectors required for enantioseparation varied from 3 to 30 mM. The BGE pH played an important role in the resolution of Dns-amino acids. For acidic BGEs, chiral resolution increased with pH (4.0-6.0) and reached a local maximum at pH 6.0. However, better resolutions were obtained with basic phosphate buffer at pH 9.6. Methanol was found to be an effective organic modifier for the resolution of Dns-amino acids by CE.

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“…Cyclodextrins have been used to increase the resolution in capillary electrophoresis of anti-inflamatory drugs of the profen family [187] of propanolol [188] and other important drugs such as opiates and fenfluramine enantiomers [176,189,190]. They have also been successfully employed as chiral stationary phases in HPLC for trimetoquinol, denopamine and timepidium [191,192] or profens [193].…”

Section: Micelles and Cyclodextrins In Separation Science Using Fluormentioning

confidence: 99%

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Lerner¹,

Martín²

2000

Analusis

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Introduction Molecular luminescence of analytes in organized media or in supramolecular complexes of cyclodextrinsThe photophysical and photochemical behaviour of molecules complexed to cyclodextrins (CD) is generally different from their behaviour in solution. The first observations in the field were qualitative and were related to the increased stabilisation of labile molecules, mostly drugs, against photodegradation when complexed to natural cyclodextrins [1]. Complexation by CD's was then the preferred subject for those involved in supramolecular chemistry and drug vectorisation techniques [2] as well as in separation techniques [3][4][5]. Stabilization of a molecule against photochemical degradation is still very important in the field of pharmaceutical sciences. A recent example is the stabilisation of promazine as an inclusion complex with β-cyclodextrin [6]. Other photochemists were attracted quite early to this field of research and initiated studies, which were mostly photophysical in nature [7,8]. The key observation was that the formation of supramolecular complexes of analytes with cyclodextrins (CDs) resulted in an increase of their fluorescence quantum yield or even in the appearance of room temperature phosphorescence (RTP) [9][10][11][12]. This enhancement has been used to increase the sensitivity and the selectivity in both luminescence and chromatographic techniques [13-15].We will not say more about RTP with CDs as the subject will be developed in another contribution in the same issue of this Journal. However RTP is also observed in the solubilization of analytes in micellar colloïdal solutions and this field will be reviewed hereunder.These properties have been used to develop analytical techniques, which combine the selectivity of complexation with an enhanced emission [16][17][18][19]. In this way an improvement in the detection limits is obtained in many separation techniques such as HPLC, capillary electrophoresis (CE) or planar chromatography. Furthermore these molecular interactions allow to reveal or to stabilize new molecular forms or to turn species which are normally non-emitting into luminescent ones. All these aspects are reviewed hereunder after a short summary on the nature of the intermolecular interactions, which lie at the heart of these effects. Nature of the interactions between an analyte and a CD or a micelleWithout going into a thorough analysis of the origin of the interactions which exist between molecules in dense media which concern us here, it seems useful to recall the most important factors which should be taken into account when any type of luminescence, fluorescence or phosphorescence is involved.

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Use of cyclodextrins in capillary electrophoresis for the chiral resolution of some 2-arylpropionic acid non-steroidal anti-inflammatory drugs

Cited by 113 publications

References 28 publications

Simultaneous chiral discrimination of multiple profens by cyclodextrin‐modified capillary electrophoresis in normal and reversed polarity modes

Simultaneous chiral discrimination of multiple profens by cyclodextrin‐modified capillary electrophoresis in normal and reversed polarity modes

Synthesis and application of single-isomer 6-mono(alkylimidazolium)-β-cyclodextrins as chiral selectors in chiral capillary electrophoresis

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

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