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Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti‐inflammatory drugs incapillary liquid chromatography
Author(s) -
Kafková Boz̆ena,
Bosáková Zuzana,
Tesar̆ová Eva,
Coufal Pavel,
Messina Antonella,
Sinibaldi Massimo
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20284
Subject(s) - chemistry , enantioselective synthesis , nonsteroidal , chromatography , vancomycin , anti inflammatory , chiral stationary phase , high performance liquid chromatography , pharmacology , organic chemistry , catalysis , staphylococcus aureus , bacteria , medicine , biology , genetics
Abstract The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti‐inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin‐bonded chiral stationary phase, it was difficult to get enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism. Chirality 18:531–538, 2006. © 2005 Wiley‐Liss, Inc.