Rejtő Sándor Faculty of Light Industry and Environmental Engineering, Institute of Environmental Engineering and Natural Science, Óbuda University, Doberdó út 6, H-1034 Budapest, Hungary.
Department of Organic Chemistry, Semmelweis University, Hőgyes Endre Street 7, H-1092 Budapest, Hungary.
Int J Mol Sci. 2024 Jul 16;25(14):7802. doi: 10.3390/ijms25147802.
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 optical isomers eluted before 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 isomers of free ibuprofen acid showed an overloading phenomenon, but the isomer did not. The results were supported by molecular modeling studies.
布洛芬是一种众所周知且广泛使用的非甾体抗炎药和止痛药。布洛芬是一种手性化合物，其两个对映异构体具有不同的生物学效应，因此需要对其进行手性分离。布洛芬及其衍生物被用作模型化合物，以建立可传输的结构手性选择性关系。手性选择剂是含有气相色谱固定相的全甲基化α-、β-和γ-环糊精。在不同温度下测试了布洛芬作为游离酸及其各种烷基酯（甲酯、乙酯、丙酯、异丙酯、丁酯、异丁酯和异戊酯）衍生物的手性选择性。每种测试的固定相都能够对手性分离布洛芬的游离酸形式。在每种单独的情况下，较弱的包含光学异构体在光学异构体之前洗脱。结果提供了针对手性选择性与分析物结构的可传输指南。结果表明，游离布洛芬酸的对映异构体表现出过载现象，但对映异构体没有。分子建模研究支持了这一结果。
