title: Identification of NIH-shifted metabolites of 1,3,7,8-tetrachlorodibenzo-p-dioxin in the rat by NMR comparison with synthesized isomers.
abstract: In the rat, 1,3,7,8-tetrachlorodibenzo-p-dioxin was oxidatively metabolized to the NIH-shifted products 2-hydroxy-1,4,7,8-tetrachlorodibenzo-p-dioxin and 3-hydroxy-1, 2,7,8-tetrachlorodibenzo-p-dioxin. The chlorine substitution patterns were determined by comparison with 1H NMR spectra of six synthesized isomers in CDCl3, CD3OD, and acetone-d6. Glucuronide and glucuronide-sulfate conjugates of the monohydroxy dioxins were identified in the bile by FAB-MS. The dominance of the NIH-shift products in the metabolism of tetrachlorodibenzo-p-dioxins indicates that the same isomers may be produced from differently substituted chlorinated dioxins.
authors.affiliation: Biosciences Research Laboratory, U.S. Department of Agriculture, Fargo, North Dakota 58105, USA.
authors.forename: E
authors.initials: E
authors.lastname: Petroske
authors.forename: J K
authors.initials: JK
authors.lastname: Huwe
authors.forename: V J
authors.initials: VJ
authors.lastname: Feil
authors.forename: G L
authors.initials: GL
authors.lastname: Larsen
mesh_terms: D000818:Animals; D002404:Catheterization; D003135:Common Bile Duct; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008297:Male; D009316:National Institutes of Health (U.S.); D000072317:Polychlorinated Dibenzodioxins / Q000138:chemical synthesis / Q000378:metabolism*; D011522:Protons; D051381:Rats; D017207:Rats, Sprague-Dawley; D013237:Stereoisomerism; D014481:United States
chemical_list: D000072317:Polychlorinated Dibenzodioxins; D011522:Protons