Metabolism of polycyclic compounds. 15. The conversion of naphthalene into a derivative of glutathione by rat-liver slices

Abstract

S-(1-Naphthyl) glutathione, S-(l-naphthyl) -L-cysteine and 1-naphthylmercapturic acid have been synthesized. Livers slices of male rats convert naphthalene into a compound which is almost certainly S-(l,2-dihydro-2-hydroxy-l-naphthyl) glutathione and which yields S-(l-naphthyl) glutathione when treated with acid at room temperature. Rat-kidney homogenates convert S-(l,2-dihydro-2-hydroxy-l-naphthyl) glutathione into a compound believed to be S-(l,2-dihydro-2-hydroxy-l-naphthyl) -l-cysteine and which forms S-(l-naphthyl) -L-cysteine on treatment with acid at room temperature. Kidney homogenates also hydrolyse S-(l-naphthyl) glutathione to S-(l-naphthyl) -L-cysteine. S-(l,2-Dihydro-2-hydroxy-l-naphthyl)-L-cysteine is acetylated by liver slices or kidney homogenate and boiled liver extract to N-acetyl-S-(l,2-dihydro-2-hydroxy-1-naphthyl) -L-cysteine.