Article (Scientific journals)
Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems
Abushoffa, Adel M.; Fillet, Marianne; Hubert, Philippe et al.
2002In Journal of Chromatography. A, 948 (1-2), p. 321-9
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Keywords :
Anti-Inflammatory Agents, Non-Steroidal/chemistry/isolation & purification; enantiomer separation; pharmaceutical analysis; Buffers; selectivity; Cyclodextrins/chemistry; mathematical modelling; Electrophoresis, Capillary; cyclodextrins; Hydrogen-Ion Concentration; profens; Indicators and Reagents; nonsteroidal anti-inflammatory drugs; Models, Statistical; Spectrophotometry, Ultraviolet; Stereoisomerism; beta-Cyclodextrins
Abstract :
[en] The single-isomer polyanionic cyclodextrin (CD) derivative heptakis-6-sulfato-beta-cyclodextrin (HSbetaCD) has been tested as chiral additive for the enantioseparation of non-steroidal anti-inflammatory drugs, such as fenoprofen, flurbiprofen, ibuprofen and ketoprofen, in capillary electrophoresis, using a pH 2.5 phosphoric acid-triethanolamine buffer in the reversed polarity mode. In most cases, the enantiomers of these acidic compounds, present in uncharged form at that pH, were only poorly resolved with HSbetaCD alone. However, the use of HSbetaCD in combination with the neutral CD derivative, heptakis-(2,3,6-tri-O-methyl)-beta-cyclodextrin (TMbetaCD), which has a particularly high enantioselectivity towards these compounds, has led to complete enantioresolution in reasonably low migration times in most cases. Affinity constants for the enantiomers with the two cyclodextrins were determined, using linear regression in a two-step approach. Affinity constants with the charged HSbetaCD were first calculated in single systems while those with the neutral TMbetaCD were determined in dual systems. Selectivity for the enantiomeric separation of these compounds in dual CD systems could be predicted using recently developed mathematical models.
Disciplines :
Biochemistry, biophysics & molecular biology
Chemistry
Pharmacy, pharmacology & toxicology
Author, co-author :
Abushoffa, Adel M.;  Université de Liège - ULiège > Analyse des médicaments
Fillet, Marianne  ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Hubert, Philippe  ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Crommen, Jacques ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Language :
English
Title :
Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems
Publication date :
2002
Journal title :
Journal of Chromatography. A
ISSN :
0021-9673
eISSN :
1873-3778
Publisher :
Elsevier Science, Amsterdam, Netherlands
Volume :
948
Issue :
1-2
Pages :
321-9
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Available on ORBi :
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