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 of 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...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2002, Vol.14 (5), p.449-454 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Quaglia, M.G. Donati, E. Desideri, N. Fanali, S. D'auria, F.D. Tecca, M. |
| description | 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. 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 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. Chirality 14:449–454, 2002. © 2002 Wiley‐Liss, Inc. |
| doi_str_mv | 10.1002/chir.10112 |
| format | Article |
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The investigation on the chirality of 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 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. 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The investigation on the chirality of 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 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. 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The investigation on the chirality of 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 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. Chirality 14:449–454, 2002. © 2002 Wiley‐Liss, Inc.</abstract><cop>New York</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>11984761</pmid><doi>10.1002/chir.10112</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Aspergillus nidulans - drug effects capillary electrophoresis chiral HPLC Chromatography, High Pressure Liquid Cryptococcus neoformans - drug effects cyclodextrin derivatives Electrophoresis, Capillary enantiomeric separation fenticonazole Imidazoles - chemistry Imidazoles - isolation & purification Imidazoles - pharmacology Microbial Sensitivity Tests Stereoisomerism |
| title | Chiral discrimination by HPLC and CE and antifungal activity of racemic fenticonazole and its enantiomers |
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