Redoks-svojstva ferocenom supstituiranih nukleobaza / Mateja Toma, Valerije Vrček.
Sažetak

Pripravljena je serija ferocenom supstituiranih purinskih nukleobaza 1-10 te su izmjereni njihovi redoks-potencijali metodom cikličke voltametrije. Svi ispitani spojevi pokazali su reverzibilnu jednoelektronsku oksidaciju u rasponu potencijala od 330 do 470 mV. Također je uočena razlika redoks-potencijala od 100 mV između N7 i N9 regioizomera ispitivanih nukleobaza. Ispitana je i acelularna aktivnost stvaranja reaktivnih kisikovih vrsta (ROS) kolorimetrijskom metodom s DCFH2-DA te je utvrđeno da konjugati generiraju ROS, dok su ferocen i nukleobaze neaktivni. Različiti supstituenti na purinskom prstenu utječu na stvaranje ROS-a, što omogućuje dizajn biološki aktivnih konjugata ferocena i prikladnih nukleobaza.; A series of ferrocene-substituted purine-nucleobase derivatives 1-10 were synthesized and their redox potential was measured by cyclic voltammetry. Measured compounds showed a reversible one-electron oxidation in the range of 330–470 mV. A difference of 100 mV between N7 and N9 regioisomers was observed. In order to examine the tendency of ferrocene-nucleobase conjugates to produce reactive oxygen species (ROS), an acellular screening with DCFH2-DA assay was carried out. The nucleobases coupled with ferrocene generated ROS, while neither ferrocene itself nor the nucleobases were active. Changing the substituents on the purine ring can significantly influence the ROS generation of ferrocene-substituted nucleobases, which support design of biologically active ferrocene-nucleobase conjugates.