The metabolic sulfonation and side-chain oxidation of 3'-hydroxyisosafrole in the mouse and its inactivity as a hepatocarcinogen relative to 1'-hydroxysafrole

Chemico-biological Interactions
E W BobergJ A Miller

Abstract

The chemically synthesized sulfuric acid esters of 1'-hydroxysafrole and 3'-hydroxyisosafrole, 1'-sulfooxysafrole and 3'-sulfooxyisosafrole, respectively, are both strong electrophiles. Each ester reacted with deoxyguanosine (dGuo) in aqueous solution to form both safrol-1'-yl- and isosafrol-3'-yl-deoxyguanosine adducts. Both 1'-hydroxysafrole and 3'-hydroxyisosafrole were also formed from each ester in the presence of water. When either 1'-[3H]hydroxysafrole or 3'-[3H]hydroxyisosafrole was incubated with mouse liver cytosols fortified with 3'-phosphoadenosine-5'-phosphosulfate (PAPS) and RNA, similar levels of RNA- and protein-bound adducts were formed; thus, the hepatic sulfotransferase activities for these two substrates appear to be similar. In contrast, the levels of hepatic nucleic acid and protein adducts formed after administration of 3'-[3H]hydroxyisosafrole to mice were only 2-4% and 8-14%, respectively, of those obtained after an equimolar dose of 1'-[3H]hydroxysafrole. Likewise, when 3'-hydroxyisosafrole was injected into 12-day-old male B6C3F1 mice at a level of 0.1 or 2.5 mumol/g body wt., the average numbers of hepatomas per mouse (0.2 and 0.4, respectively) were not significantly increased over the average numbe...Continue Reading

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