Fate of thianthrene in biological systems

• Published in: Xenobiotica Vol. 47; no. 8; pp. 731 - 740
• Main Authors: Mitchell, Steve C., Waring, Rosemary H.
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 03.08.2017
• Subjects: Animals; Anthracene; Fishes - metabolism; Heterocyclic Compounds - metabolism; microorganism; organosulfur; Oxidation-Reduction; Rats; sulfoxide; thianthrene; thioxanthene; microorganism; thioxanthene; organosulfur; thianthrene; Anthracene; sulfoxide
• ISSN: 0049-8254; 1366-5928
• DOI: 10.1080/00498254.2016.1222107

1. Thianthrene is a sulfur-containing tricyclic molecule distributed widely within the macrostructure of hydrocarbon fossil fuels. Identified nearly 150 years ago, its chemistry has been widely explored leading to insights into reaction mechanisms and radical ion formation. 2. It has been claimed to have therapeutic application in the treatment of dermal infections and to interfere with enzyme and nucleic acid function, but appears to have little toxicity. 3. Following its oral administration to the rat, the majority remained within the gastrointestinal tract. After three days, about 88% was detected in the combined excreta with the remainder still within the animal. It is readily taken up into fish from the surrounding aqueous environment and has been placed within the "bioaccumulative category" to be regarded with concern. 4. Mammalian metabolism appeared to be restricted to ring carbon oxidation and subsequent glucuronic acid conjugation. Small amounts of sulfoxide and disulfoxide were also formed. No ring degradation was evident. Microorganisms similarly undertook aromatic ring hydroxylation but were able also to rupture the ring system by attacking the carbon-sulfur linkages and thereby degrading the molecule.