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Enantioselective recognition of sutezolid by cyclodextrin modified non-aqueous capillary electrophoresis and explanation of complex formation by means of infrared spectroscopy, NMR and molecular modelling

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cris.lastimport.scopus2024-02-12T19:59:29Z
dc.abstract.enA method for the enantioseparation of sutezolid, the next analogue after linezolid and tedizolid, belonging to the truly new class of antibacterial agents, the oxazolidinones, was developed based on non-aqueous capillary electrophoresis (NACE), using a single isomer of cyclodextrins as a chiral pseudophase. During the experiment, the enantioseparation of sutezolid together with its predecessor, linezolid, both weak base antibacterial agents, was evaluated using anionic single-isomers of cyclodextrins from hydrophilic, up to hydrophobic: heptakis-(2,3-dihydroxy-6-sulfo)-β-cyclodextrin, heptakis-(2,3-diacetyl-6-sulfo)-β-cyclodextrin (HDAS-β-CD), as well as heptakis-(2,3-dimethyl-6-sulfo)-β-cyclodextrin (HDMS-β-CD), respectively. Based on the observed results, the cyclodextrins, HDAS-β-CD and HDMS-β-CD which carry the acetyl and methyl groups at the C2 and C3 positions, respectively, provided the baseline separation of sutezolid enantiomers. However, HDMS-β-CD led to a reversal of enantiomer migration order (EMO) in comparison to HDAS-β-CD. Instead, enantiomers of linezolid were separated only by HDMS-β-CD. During the experiments, different organic solvents and their mixtures in various ratios were tested. The selectivity and separation efficiency were critically affected by the nature of the buffer system, the type of organic solvent, and the concentrations of trifluoroacetic acid (TFA) in the NACE buffer system. Focusing on the desired EMO in which the eutomers (S)-sutezolid and (S)-linezolid migrated last, the highest enantioresolution using the NACE method was achieved at normal polarity mode with 45  mM HDMS-β-CD dissolved in MeOH/ACN (85:15, v/v) containing 200  mM TFA/20  mM ammonium formate. Moreover, infrared spectroscopy, NMR and molecular modelling were investigated to provide information about complex formation.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCielecka-Piontek, Judyta
dc.contributor.authorMichalska, Katarzyna
dc.contributor.authorBocian, Wojciech
dc.contributor.authorBednarek, Elżbieta
dc.contributor.authorPałys, Barbara
dc.date.accessioned2024-01-24T22:47:29Z
dc.date.available2024-01-24T22:47:29Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.volume169
dc.identifier.doi10.1016/J.JPBA.2019.02.033
dc.identifier.issn0731-7085
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106157
dc.identifier.weblinkhttps://www.sciencedirect.com/science/article/pii/S0731708518326803
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Pharmaceutical and Biomedical Analysis
dc.relation.pages49-59
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enCD-NACE
dc.subject.enEnantioseparation
dc.subject.enMolecular modelling
dc.subject.enSpectroscopic approach
dc.subject.enSutezolid
dc.titleEnantioselective recognition of sutezolid by cyclodextrin modified non-aqueous capillary electrophoresis and explanation of complex formation by means of infrared spectroscopy, NMR and molecular modelling
dc.typeJournalArticle
dspace.entity.typePublication