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Hexabromocyclododecane enantiomers: microsomal degradation and patterns of hydroxylated metabolites

  • The degradation of the enantiomers of α-, β-, and γ-hexabromocyclododecane (HBCD) by phase I metabolism was investigated using induced rat liver microsomes. HBCD isomers were quantified using HPLC-MS/MS (ESI-) after separation on a combination of a reversed phase and a chiral analytical column. The degradation of all six isomers followed first-order kinetics and the estimated half-lives ranged from 6.3 min for both β-HBCD enantiomers to 32.3 min in case of (+)-γ-HBCD. (+)-α- and (–)-γ-HBCD displayed significantly shorter half-lives than their corresponding antipodes. It could be shown that this degradation led to a significant enrichment of the first eluting enantiomers (–)-α- and (+)-γ-HBCD. Individual patterns of mono- and dihydroxylated derivatives obtained from each α- and γ-HBCD enantiomer were seen to be distinctly characteristic. The patterns of monohydroxylated HBCD derivatives detected in liver and muscle tissues of pollack, mackerel and in herring gull eggs were largelyThe degradation of the enantiomers of α-, β-, and γ-hexabromocyclododecane (HBCD) by phase I metabolism was investigated using induced rat liver microsomes. HBCD isomers were quantified using HPLC-MS/MS (ESI-) after separation on a combination of a reversed phase and a chiral analytical column. The degradation of all six isomers followed first-order kinetics and the estimated half-lives ranged from 6.3 min for both β-HBCD enantiomers to 32.3 min in case of (+)-γ-HBCD. (+)-α- and (–)-γ-HBCD displayed significantly shorter half-lives than their corresponding antipodes. It could be shown that this degradation led to a significant enrichment of the first eluting enantiomers (–)-α- and (+)-γ-HBCD. Individual patterns of mono- and dihydroxylated derivatives obtained from each α- and γ-HBCD enantiomer were seen to be distinctly characteristic. The patterns of monohydroxylated HBCD derivatives detected in liver and muscle tissues of pollack, mackerel and in herring gull eggs were largely similar to those observed in the in vitro experiments with rat liver microsomes. This enabled individual hydroxy-HBCDs to be assigned to their respective parent HBCD enantiomers.zeige mehrzeige weniger

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Metadaten
Autoren/innen:Susanne Esslinger, Roland Becker, Ronald Maul, Irene Nehls
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Environmental science & technology
Jahr der Erstveröffentlichung:2011
Herausgeber (Institution):American Chemical Society
Verlag:ACS Publ.
Verlagsort:Washington, DC
Jahrgang/Band:45
Ausgabe/Heft:9
Erste Seite:3938
Letzte Seite:3944
Freie Schlagwörter:Brominated flame retardant; Cytochromes; HPLC-MS/MS; Hydroxylation; Phase I metabolism
DOI:https://doi.org/10.1021/es1039584
ISSN:0013-936X
ISSN:1520-5851
Verfügbarkeit des Volltexts:Volltext-PDF im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:19.02.2016
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:16.06.2011