Alkylation of Inorganic Oxo Compounds and Insights on Preventing DNA Damage

Metabolism of food- and tobacco-borne procarcinogens results in the exposure of DNA to toxic
alkylating agents. These assaults can bring about DNA alkylation damage, mutations, and cancer. Dietary
inorganic compounds such as selenium and vanadium are known to prevent cancer, possibly by reacting
directly with alkylating agents, thereby preventing DNA damage. To understand potential interactions
between oxo species and alkylating toxins, we reacted a series of alkylating agents with varied classes of
oxo compounds (i.e., vanadates, selenate, phosphate, sulfate, acetate, nitrate, and nitrite). A new organic-soluble selenate, [(C6H5)4P]3(O3SeOCH2OSeO3)(HSeO4), was synthesized and characterized for these
studies. Vanadates were found to convert ethylating agents into ethanol, whereas other anions formed
esters upon alkylation. General trends show that oxo anions of the greatest charge density were the most
reactive. These studies suggest that the design of new compounds for cancer prevention should incorporate
reactive oxo groups with high anionic charge density.