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- Title
Chiral Selectivities of Permethylated α-, β-, and γ-Cyclodextrins Containing Gas Chromatographic Stationary Phases towards Ibuprofen and Its Derivatives.
- Authors
Juvancz, Zoltan; Bodane-Kendrovics, Rita; Agoston, Csaba; Czegledi, Balazs; Kaleta, Zoltan; Jicsinszky, Laszlo; Riszter, Gergo
- Abstract
Ibuprofen is a well-known and broadly used, nonsteroidal anti-inflammatory and painkiller medicine. Ibuprofen is a chiral compound, and its two isomers have different biological effects, therefore, their chiral separation is necessary. Ibuprofen and its derivatives were used as model compounds to establish transportable structure chiral selectivity relationships. Chiral selectors were permethylated α-, β-, and γ-cyclodextrins containing gas chromatographic stationary phases. The chiral selectivity of ibuprofen as a free acid and its various alkyl esters (methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and isoamyl esters) derivatives were tested at different temperatures. Every tested stationary phase was capable of the chiral separations of ibuprofen in its free acid form. The less strong included S optical isomers eluted before R optical isomers in every separate case. The results offer to draw transportable guidelines for the chiral selectivity vs. analyte structures. It was recognized that the S isomers of free ibuprofen acid showed an overloading phenomenon, but the R isomer did not. The results were supported by molecular modeling studies.
- Subjects
IBUPROFEN; CHIRAL stationary phases; OPTICAL isomers; CYCLODEXTRINS; ENANTIOMERS; ISOMERS; GASES; ANALGESICS
- Publication
International Journal of Molecular Sciences, 2024, Vol 25, Issue 14, p7802
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms25147802