https://doi.org/10.15255/KUI.2020.025
Published: Kem. Ind. 69 (13) (2020) P21–P29
Paper reference number: KUI-25/2020
Paper type: Original scientific paper
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Redox Properties of Ferrocene-substituted Nucleobases

M. Toma and V. Vrček

Abstract

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.

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Keywords

ferrocene-substituted purine-nucleobase, redox potential, reactive oxygen species (ROS)