Polarographic properties and potential carcinogenicity of some natural nucleosides and their synthetic analogues.
The polarographic reduction and the index of potential carcinogenicity tg alpha determined polarographically in aprotic conditions and in the presence of alpha-lipoic acid of nine naturally occurring and synthetic pyrimidine and six synthetic 1,3,5-triazine (5-aza) nucleosides was compared to the reduction 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 because of the antimetabolite and cytotoxic/antileukemia properties of their synthetic analogues. It was shown that polarographic reduction of the studied compounds is achieved at gradually increased potentials in the order of 6-aza < 5-aza < pyrimidine nucleosides. On other hand, the potential carcinogenicity of studied compounds increases usually in the order of pyrimidine < 6-aza << 5-aza nucleoside. The only compounds with remarkable potential carcinogenicity identified at this study were those ones from the 5-aza (1,3,5-triazine) antimetabolite series-arabinosyl-5-azacytosine (0.275), 5-aza-cytidine (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 included in the study is discussed.
Novotny
L
L
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kuwait University, Kuwait.
Vachalkova
A
A
Piskala
A
A
D002273:Carcinogens / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011048:Polarography; D011743:Pyrimidines / Q000737:chemistry; D013329:Structure-Activity Relationship; D008063:Thioctic Acid / Q000737:chemistry; D014227:Triazines / Q000737:chemistry
D002273:Carcinogens; D009705:Nucleosides; D011743:Pyrimidines; D014227:Triazines; D008063:Thioctic Acid