Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test
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Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test. / Casas, Mònica Escolà; Kretschmann, Andreas Christopher; Andernach, Lars; Opatz, Till; Bester, Kai.
In: Journal of Chromatography A, Vol. 1452, 24.06.2016, p. 116-20.Research output: Contribution to journal › Journal article › Communication
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TY - JOUR
T1 - Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test
AU - Casas, Mònica Escolà
AU - Kretschmann, Andreas Christopher
AU - Andernach, Lars
AU - Opatz, Till
AU - Bester, Kai
N1 - Copyright © 2016 Elsevier B.V. All rights reserved.
PY - 2016/6/24
Y1 - 2016/6/24
N2 - A simple method for the separation of the enantiomers of the fungicide imazalil was developed. Racemic imazalil was separated into its enantiomers with an enantiomeric purity of 99% using HPLC-UV with an enantioselective column (permethylated cyclodextrin) operated in reversed phase mode (water with 0.2% trimethylamine and 0.08% acetic acid and methanol). The absolute configuration of the separated enantiomers was assigned and unequivocally confirmed by optical rotation as well as by vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) combined with ab-initio calculations. The same enantioselective column was also used to develop an HPLC-MS/MS method for the quantification of imazalil enantiomers. The HPLC-MS/MS method reached limits of quantification (LOQs) of 0.025mg/mL with 5μL injections. This method was used to verify imazalil concentrations and enantiomeric fractions in samples from an in vitro test on effects on human steroidogenesis (H295R steroidogenesis assay). The quantification verified the stability of the enantiomers of imazalil during the in vitro tests.
AB - A simple method for the separation of the enantiomers of the fungicide imazalil was developed. Racemic imazalil was separated into its enantiomers with an enantiomeric purity of 99% using HPLC-UV with an enantioselective column (permethylated cyclodextrin) operated in reversed phase mode (water with 0.2% trimethylamine and 0.08% acetic acid and methanol). The absolute configuration of the separated enantiomers was assigned and unequivocally confirmed by optical rotation as well as by vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) combined with ab-initio calculations. The same enantioselective column was also used to develop an HPLC-MS/MS method for the quantification of imazalil enantiomers. The HPLC-MS/MS method reached limits of quantification (LOQs) of 0.025mg/mL with 5μL injections. This method was used to verify imazalil concentrations and enantiomeric fractions in samples from an in vitro test on effects on human steroidogenesis (H295R steroidogenesis assay). The quantification verified the stability of the enantiomers of imazalil during the in vitro tests.
KW - Journal Article
U2 - 10.1016/j.chroma.2016.05.008
DO - 10.1016/j.chroma.2016.05.008
M3 - Journal article
C2 - 27234843
VL - 1452
SP - 116
EP - 120
JO - Journal of Chromatography
JF - Journal of Chromatography
SN - 0301-4770
ER -
ID: 169380555