Chiral discrimination by HPLC and CE and antifungal activity of racemic fenticonazole and its enantiomers

Fenticonazole is a chiral antifungal agent, used in therapy as the racemic mixture. The investigation on the chirality fenticonazole is reported in this study. Rac-fenticonazole was resolved by HPLC and by capillary electrophoresis (CE). The chiral stationary phase (CSP) used in HPLC, was Daicel OD-H, a commercial phase, which allowed the separate collection of the two enantiomers. The analysis time required from CE was about the half of that of HPLC enantioseparation time. The biological activity of the rac- mixture and each individual enantiomer was tested against Cryptococcus neoformans and two Aspergillus nidulans strains. the minimum inhibitory concentration (MIC) evaluation showed that the eutomer was the enantiomer chromatographically more retained and had a longer migration time in the electrophoretic enantiomer separation. The CD spectrum of the eutomer showed a positive cotton effect.