Identification of hydroxylated metabolites in 2,2',4,4'-tetrabromodiphenyl ether exposed rats

Chemosphere. 2006 Apr;63(4):690-7. doi: 10.1016/j.chemosphere.2005.07.072. Epub 2005 Oct 5.

Abstract

Faeces from day 1-5 of orally administered 2,2',4,4'-tetrabromodiphenyl ether (BDE-47) in rat have been analysed for hydroxylated metabolites. Six hydroxylated tetrabrominated diphenyl ethers, as well as three hydroxylated tribrominated diphenyl ethers found, were structurally identified. They were 2'-hydroxy-2,4,4'-tribromodiphenyl ether, 3'-hydroxy-2,4,4'-tribromodiphenyl ether, 4'-hydroxy-2,2',4-tribromodiphenyl ether, 6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether, 2'-hydroxy-2,3',4,4'-tetrabromodiphenyl ether, 3-hydroxy-2,2',4,4'-tetrabromodiphenyl ether, 5-hydroxy-2,2',4,4'-tetrabromodiphenyl ether, 4'-hydroxy-2,2',4,5'-tetrabromodiphenyl ether and 4-hydroxy-2,2',3,4'-tetrabromodiphenyl ether. The analysis was performed using gas chromatography-mass spectrometry (GC-MS). The identification of the hydroxylated polybrominated diphenyl ether (OH-PBDE) metabolites in the rat faeces was supported by similar relative retention times (RRTs) versus 2,2',3,4,4',5-hexabromodiphenyl ether (BDE-138) on two columns of different polarities compared to the authentic references. The identification of the OH-PBDE metabolites was also supported by full scan electron ionisation mass spectra. Two of the identified OH-PBDE metabolites have identical structures as natural products, which previously have been isolated from marine sponges and an ascidian.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Feces
  • Gas Chromatography-Mass Spectrometry / methods
  • Halogenated Diphenyl Ethers
  • Hydrocarbons, Brominated / analysis*
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / metabolism*
  • Hydroxylation
  • Phenyl Ethers / analysis*
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / metabolism*
  • Polybrominated Biphenyls
  • Rats

Substances

  • Halogenated Diphenyl Ethers
  • Hydrocarbons, Brominated
  • Phenyl Ethers
  • Polybrominated Biphenyls
  • 2,2',4,4'-tetrabromodiphenyl ether