Fenticonazole is a chiral antifungal agent, used in therapy as the racemic mixture. The investigation on the chirality of fenticonazole is reported in this study. rae-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 chiral selectors used for CE were some cyclodextrin derivatives. The analysis time required from CE was about the half the 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 enantioseparation. The CD spectrum of the eutomer showed a positive Cotton effect. (C) 2002 Wiley-Liss, Inc.

Chiral discrimination by HPLC and CE and antifungal activity of racemic fenticonazole and its enantiomers / Quaglia, Maria Giovanna; E., Donati; Desideri, Nicoletta; S., Fanali; F. D., D'Auria; M., Tecca. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 14:5(2002), pp. 449-454. [10.1002/chir.10112]

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

QUAGLIA, Maria Giovanna;DESIDERI, Nicoletta;F. D. D'Auria;
2002

Abstract

Fenticonazole is a chiral antifungal agent, used in therapy as the racemic mixture. The investigation on the chirality of fenticonazole is reported in this study. rae-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 chiral selectors used for CE were some cyclodextrin derivatives. The analysis time required from CE was about the half the 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 enantioseparation. The CD spectrum of the eutomer showed a positive Cotton effect. (C) 2002 Wiley-Liss, Inc.
capillary electrophoresis; chiral hplc; cyclodextrin derivatives; enantiomeric separation; fenticonazole
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Chiral discrimination by HPLC and CE and antifungal activity of racemic fenticonazole and its enantiomers / Quaglia, Maria Giovanna; E., Donati; Desideri, Nicoletta; S., Fanali; F. D., D'Auria; M., Tecca. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 14:5(2002), pp. 449-454. [10.1002/chir.10112]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/252234
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