Enantioseparation of warfarin derivatives on molecularly imprinted polymers for (S)- and (R)-chlorowarfarin.

Arisa Kubo, Tetsutaro Kimachi, Jun Haginaka

Journal of chromatography. A 2021 Mar 29

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Monodisperse molecularly imprinted polymers (MIPs) for warfarin (WF), 4'-chlorowarfarin (CWF), (S)-CWF and (R)-CWF (MIPWF, MIPCWF, MIP(S)-CWF and MIP(R)-CWF, respectively) were prepared using 4-vinylpyridine (4-VPY) and ethylene glycol dimethacrylate (EDMA) as a functional monomer and a crosslinker, respectively, by multi-step swelling and polymerization. The molar ratio of a template molecule, 4-VPY to EDMA was 6:18:25 or 4:18:25. The retention and molecular recognition properties of MIPWF and MIPCWF were evaluated using a mixture of sodium phosphate buffer or ammonium formate and acetonitrile in reversed-phase LC. WF and CWF on these MIPs gave the maximal retentions at mobile phase pH 7, and those retentions were decreased with an increase of acetonitrile content. The retention and imprinting factors were in the order of WF < CWF < 4'-bromowarfarin (BWF) on MIPWF and MIPCWF in neutral mobile phases. On the other hands, in acidic mobile phases the retention factors were in the same order with those in neutral mobile phases, while the imprinting factors of WF and CWF were higher on the respective MIPs. These results suggest that ionic or hydrogen bonding interactions, hydrophobic interactions and π-π interactions could work for the retention and molecular recognition of WF, CWF and BWF on these MIPs in a reversed-phase mode. Furthermore, MIP(S)-CWF and MIP(R)-CWF could separate WF, CWF and BWF enantiomers in acidic mobile phases. Copyright © 2021. Published by Elsevier B.V.

Citation

Arisa Kubo, Tetsutaro Kimachi, Jun Haginaka. Enantioseparation of warfarin derivatives on molecularly imprinted polymers for (S)- and (R)-chlorowarfarin. Journal of chromatography. A. 2021 Mar 29;1641:461995