Enhancement of toxicity and enzyme-repressing activity of p-dioxane by chlorination: Stereoselective effects

The acute toxicity of p-dioxane may be enhanced up to 1000-fold by chlorination of the compound. The effect was stereoselective. Of the stereoisomers tested, tetrachloro- p-dioxane, isomer I (2r, 3t, 5t, 6c) was over 80 times more toxic than isomer II (2r, 3c, 5t, 6t). The latter compound was also a...

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Veröffentlicht in:	Toxicology letters 1980, Vol.5 (1), p.69-75
Hauptverfasser:	Woo, Y.-T., Neuburger, B.J., Arcos, J.C., Argus, M.F., Nishiyama, K., Griffin, G.W.
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors Carcinogens, Environmental - metabolism Chemical Phenomena Chemistry Chlorine - toxicity Dimethylnitrosamine - metabolism Dioxanes - toxicity Dioxins - toxicity Enzyme Induction Male Oxidoreductases, N-Demethylating - antagonists & inhibitors Polychlorinated Dibenzodioxins - pharmacology Rats Stereoisomerism Structure-Activity Relationship
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Zusammenfassung:	The acute toxicity of p-dioxane may be enhanced up to 1000-fold by chlorination of the compound. The effect was stereoselective. Of the stereoisomers tested, tetrachloro- p-dioxane, isomer I (2r, 3t, 5t, 6c) was over 80 times more toxic than isomer II (2r, 3c, 5t, 6t). The latter compound was also a potent repressor of hepatic dimethylnitrosamine-demethylase I (DMN-d) and aryl hydrocarbon hydroxylase (AHH).
ISSN:	0378-4274 1879-3169
DOI:	10.1016/0378-4274(80)90150-2