Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Monica Escola Casas
  • Andreas Christopher Kretschmann
  • Lars Andernach
  • Till Opatz
  • Kai Bester
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000377732800013&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1016/j.chroma.2016.05.008
eISSN
1873-3778
Externe Identifier
  • Clarivate Analytics Document Solution ID: DO4DU
  • PubMed Identifier: 27234843
ISSN
0021-9673
Zeitschrift
JOURNAL OF CHROMATOGRAPHY A
Schlüsselwörter
  • Imazalil
  • Enantiomers
  • HPLC-UV
  • Isolation
  • Vibrational circular dichroism
  • HPLC-MS/MS
Paginierung
116 - 120
Datum der Veröffentlichung
2016
Status
Published
Titel
Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an <i>in vitro</i> toxicity test
Sub types
  • Article
Ausgabe der Zeitschrift
1452

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Autoren
  • Mònica Escolà Casas
  • Andreas Christopher Kretschmann
  • Lars Andernach
  • Till Opatz
  • Kai Bester
DOI
10.1016/j.chroma.2016.05.008
ISSN
0021-9673
Zeitschrift
Journal of Chromatography A
Sprache
en
Paginierung
116 - 120
Datum der Veröffentlichung
2016
Status
Published
Herausgeber
Elsevier BV
Herausgeber URL
http://dx.doi.org/10.1016/j.chroma.2016.05.008
Datum der Datenerfassung
2018
Titel
Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test
Ausgabe der Zeitschrift
1452

Datenquelle: Crossref

Abstract
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.
Addresses
  • Environmental Science, Aarhus University, Frederiksborgvej 399, 4000 Roskilde, Denmark.
Autoren
  • Mònica Escolà Casas
  • Andreas Christopher Kretschmann
  • Lars Andernach
  • Till Opatz
  • Kai Bester
DOI
10.1016/j.chroma.2016.05.008
eISSN
1873-3778
Externe Identifier
  • PubMed Identifier: 27234843
Open access
false
ISSN
0021-9673
Zeitschrift
Journal of chromatography. A
Schlüsselwörter
  • Humans
  • Imidazoles
  • Steroids
  • Fungicides, Industrial
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Toxicity Tests
  • Stereoisomerism
  • Vibration
  • Optical Rotation
  • Tandem Mass Spectrometry
  • In Vitro Techniques
Sprache
eng
Medium
Print-Electronic
Online publication date
2016
Paginierung
116 - 120
Datum der Veröffentlichung
2016
Status
Published
Datum der Datenerfassung
2016
Titel
Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
1452

Datenquelle: Europe PubMed Central

Abstract
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.
Date of acceptance
2016
Autoren
  • Mònica Escolà Casas
  • Andreas Christopher Kretschmann
  • Lars Andernach
  • Till Opatz
  • Kai Bester
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/27234843
DOI
10.1016/j.chroma.2016.05.008
eISSN
1873-3778
Zeitschrift
J Chromatogr A
Schlüsselwörter
  • Enantiomers
  • HPLC-UV
  • HPLC–MS/MS
  • Imazalil
  • Isolation
  • Vibrational circular dichroism
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Fungicides, Industrial
  • Humans
  • Imidazoles
  • In Vitro Techniques
  • Optical Rotation
  • Stereoisomerism
  • Steroids
  • Tandem Mass Spectrometry
  • Toxicity Tests
  • Vibration
Sprache
eng
Country
Netherlands
Paginierung
116 - 120
PII
S0021-9673(16)30563-5
Datum der Veröffentlichung
2016
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2016
Titel
Separation, isolation and stereochemical assignment of imazalil enantiomers and their quantitation in an in vitro toxicity test.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
1452

Datenquelle: PubMed

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