Collect. Czech. Chem. Commun. 1994, 59, 1691-1698

Polarographic Reduction and Potential Carcinogenity of Synthetic 1,3,5-Triazine Bases and Nucleosides

Ladislav Novotnýa, Anna Vachálkováa and Alois Pískalab

a Cancer Research Institute, Slovak Academy of Sciences, 812 32 Bratislava, Slovak Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


DC polarographic parameters were measured for a series of 15 synthetic 5-aza compounds derived from cytosine, cytidine, uracil and uridine in nonaqueous (dimethylformamide) solutions. The substances in aprotic media are reduced in a single two-electron step at the mercury drop electrode, except for 5,6-dihydro derivatives of 5-azauracil and 5-azauridine which are reduced in two steps. α-Lipoic acid was added to the solutions of the substances, and the slopes tg α of the plots of diffusion current of the substances versus a-lipoic acid concentration, which can serve as an index of potential carcinogenic activity of the substances measured, were determined. The tg α values of all the compounds studied are low as compared to related substances whose carcinogenic activity has been proved. 5-Azacytidine and 5-azauracil are exceptions exhibiting tg a values of 0.295 and 0.400, respectively. For the former compound, this is consistent with the WHO classification as "probably carcinogenic to humans".