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Correlations between Oncogenic and Chemical Properties of Several Derivatives of 3-Hydroxyxanthine and 3-Hydroxyguanine¹

Divisions of Biological Chemistry [G. B. B., N. J. M. B., T.-C. L., J. C. P., G. S.] and Experimental Chemotherapy [M. N. T., I. S.], Sloan-Kettering Institute for Cancer Research, New York, New York 10021

Comparative assays of the oncogenicities of a series of N-methyl and other derivatives of 3-hydroxyxanthine and 3-hydroxyguanine have been carried out. The oncogenicities are directly correlated with the chemical reactivities of esters of those derivatives in water at temperatures and pH's approaching physiological. The oncogenic 3-hydroxypurine derivatives yield anions, which subsequently undergo either a reaction with nucleophilic groups via an ionic substitution mechanism or one via a reduction that appears to result from a free radical mechanism. Serious consideration should be given to each highly reactive intermediate, the free radical and the ionic, as candidate for the agent responsible for inducing the oncogenic process.

¹ This investigation was supported in part by the National Cancer Institute (Grant CA 08748), the American Cancer Society (Grant BC-32), and the Atomic Energy Commission [Contract AT(11-1)-3521]. Portions were presented at the Annual Meetings of the American Association for Cancer Research (9, 10). This is Contribution 50 in a series on "Purine N-Oxides."

Received 12/ 8/72. Accepted 2/15/73.