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Titre du document / Document title

Metabolic degradation, inducing potency, and metabolites of fluorinated and chlorinated-fluorinated dibenzodioxins and dibenzofurans

Auteur(s) / Author(s)

WEBER R. (1) ; SCHMITZ H.-J. (2) ; SCHRENK D. (2) ; HAGENMAIER H. (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Institute of Organic Chemistry, University of Tübingen, 72076 Tübingen, ALLEMAGNE
(2) Institute of Toxicology, University of Tübingen, 72076 Tübingen, ALLEMAGNE

Résumé / Abstract

The metabolic degradation of fluorinated, chlorinated-fluorinated and chlorinated congeners was measured in liver homogenate of NMRI mice. While in the time period between 0 and 240 min no degradation of the 2,3,7,8-TCDD/TCDF could be detected, for all fluorinated congeners a perceptible degradation was found, even for the 2,3,7,8-TFDD. Stepwise chlorination of the 2,3,7,8-fluorinated congeners leads to a decrease of the degradation rate. In the EROD test, the exchange of chloro- with fluorosubstituents in the 2,3,7,8-TCDF leads to a decrease of induction potency. 3,7-Dichloro-2,8-difluorodibenzofuran was about 1/1000th as potent as 2,3,7,8-TCDF, while 2,3,7,8-TFDF was complete inactive. Comparison of the metabolic rates of different TCDD with those of the analogous TFDD demonstrates that the order of enzymatic degradation of different TCDD and the analogous TFDD is identical. The TFDD are degraded slightly faster than the corresponding TCDD. Surprisingly 1,4,6,9-TXDD showed the second slowest metabolic rate of the fluorinated and chlorinated TXDD after 2,3,7,8-TXDD although none ofthe 2,3,7,8-positions were substituted. Judging from 2,3,7,8-TFDD and 1,7-dichloro-2,8-difluorodibenzofuran the metabolic pathway of fluorinated and chlorinated-fluorinated congeners seem to be comparable to the chlorinated congeners.

Revue / Journal Title

Chemosphere    ISSN  0045-6535   CODEN CMSHAF 

Source / Source

1997, vol. 34, no1, pp. 29-40 (31 ref.)

Langue / Language

Anglais

Editeur / Publisher

Elsevier, Kidlington, ROYAUME-UNI  (1972) (Revue)

Mots-clés anglais / English Keywords

Toxicokinetics

;

Kinetics

;

Pollutant

;

Polycyclic aromatic compound

;

Oxygen heterocycle

;

Chlorine Organic compounds

;

Fluorine Organic compounds

;

Metabolism

;

Mechanism of action

;

Cytochrome P450

;

Isozyme

;

Animal

;

Mouse

;

Rodentia

;

Mammalia

;

Vertebrata

;

Mots-clés français / French Keywords

Toxicocinétique

;

Cinétique

;

Polluant

;

Composé aromatique polycyclique

;

Hétérocycle oxygène

;

Chlore Composé organique

;

Fluor Composé organique

;

Dibenzofurane

;

Métabolisme

;

Mécanisme action

;

Cytochrome P450

;

Isozyme

;

Animal

;

Souris

;

Dibenzo-p-dioxine(dichloro difluoro)

;

Dibenzo-p-dioxine(2,3,7,8-tétrafluoro)

;

Dibenzofurane(3,7-dichloro-2,8-difluoro)

;

Dibenzo-p-dioxine(2,3,7,8-tétrachloro)

;

Cytochrome CYP1A

;

Rodentia

;

Mammalia

;

Vertebrata

;

Mots-clés espagnols / Spanish Keywords

Toxicocinética

;

Cinética

;

Contaminante

;

Compuesto aromático policíclico

;

Heterociclo oxígeno

;

Cloro Compuesto orgánico

;

Fluor Compuesto orgánico

;

Metabolismo

;

Mecanismo acción

;

Citocromo P450

;

Isozima

;

Animal

;

Ratón

;

Rodentia

;

Mammalia

;

Vertebrata

;

Localisation / Location

INIST-CNRS, Cote INIST : 15565, 35400006142039.0030

Nº notice refdoc (ud4) : 2545048



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