Polarographic properties and potential carcinogenicity of some natural nucleosides and their synthetic analogues

The polarographic reduction and the index of potential carcinogenicity tg c t determined polarographically in aprotic conditions and in the presence of ol-lipoic acid of nine naturally occurring and synthetic pyrimidine and si x synthetic 1,3,5-triazine (5-aza) nucleosides was compared to the reductio n of eight synthetic 1,3,6-triazine (6-aza) nucleosides. Nucleosides are of interest because of their key role in the nucleic acid structure and becau se of the antimetabolite and cytotoxic/antileukemia properties of their syn thetic analogues. It was shown that polarographic reduction of the studied compounds is achieved at gradually increased potentials in the order of 6-a za < 5-aza < pyrimidine nucleosides. On other hand, the potential carcinoge nicity of studied compounds increases usually in the order of pyrimidine < 6-aza <<5-aza nucleoside. The only compounds with remarkable potential carc inogenicity identified at this study were those ones from the 5-aza (1,3,5- triazine) antimetabolite series - arabinosyl-5-azacytosine (0.275), 5-aza-c ytidine (0.295) and 5-aza-uracil (0.400) - and 2,2'-anhydrouridine (0.260). The relation of the data obtained to biological activity of nucleosides in cluded in the study is discussed. (C) 1999 Elsevier Science S.A. All rights reserved.