9-Sulfooxymethylanthracene is an ultimate electrophilic and carcinogenic form of 9-hydroxymethylanthracene.

J W Flesher, J Horn, A F Lehner

Index: Biochem. Biophys. Res. Commun. 251(1) , 239-43, (1998)

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Abstract

The role of electrophilic hydroxymethyl sulfate esters in the metabolic activation, DNA-damage, mutagenicity, and complete carcinogenicity of polycyclic aromatic hydrocarbons has been elucidated considerably in recent years. The observations are in agreement with a unified hypothesis which predicts that electrophilic hydroxymethyl sulfate esters and closely related aralkylating agents are major ultimate carcinogenic forms of most, if not all, carcinogenic alkyl-substituted and even unsubstituted carcinogenic polycyclic aromatic hydrocarbons. The common final step in a chain of enzymatic substitution reactions is the formation of an aralkylating agent bearing a good leaving group. Activation of hydroxymethyl derivatives, including 9-hydroxymethylanthracene, to electrophilic mutagens has been shown to be catalyzed by 3'-phosphoadenosine-5'-phosphosulfate-dependent sulfotransferase activity. Recent studies, in a complete carcinogenic model, demonstrate that a number of sulfuric acid ester derivatives are more potent than their hydroxymethyl precursors by repeated subcutaneous injection in female Sprague-Dawley rats. In this paper, these observations have been extended to include 9-sulfooxymethylanthracene as an ultimate electrophilic and carcinogenic form of 9-hydroxymethylanthracene.Copyright 1998 Academic Press.