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FERROCENYL-NUCLEOBASE CONJUGATES: SYNTHESIS AND APPLICATIONS

Organometallic derivatives (those with a metal– carbon bond) of nucleic acids and nucleobases have attracted substantial attention. The incorporation of metals into nucleic acids or their components is currently considered to be a topic of great interest across the chemical sciences. The combination of the redox-active, unnatural ferrocenyl group with biogenic nucleobases leads to conjugates that retain their electrochemical and self-pairing properties. These properties make ferrocenyl- nucleobases attractive objects for further studies and for applications across the entire spectrum of physico-chemical and engineering sciences. The main reasons behind the synthesis of ferrocenyl-nucleobase conjugates are to obtain new electrochemically active biomarkers or anticancer active agents or to investigate their self-assembly and supramolecular arrangement in the solid state.[1] In contrast to the well established classical medicinal chemistry of purely organic nucleobase derivatives, the bioorganometallic chemistry of ferrocenyl-nucleobase conjugates is still an undeveloped area, as shown by the limited literature on the subject. A series of ferrocene-substituted nucleobases has been described incorporating a different set of linkers [1] but no carbonyl group has been used as a chemical spacer. Carbonyl spacers enable extended conjugation involving ferrocenyl and nucleobase aromatic moieties, and the electron delocalization can be tuned by inserting substituents at the ferrocene ring system. Our research group have developed a one-step synthetic route to prepare ferocenoyl derivatives of nucleobases, the Fc–C=O fragment has been linked to “standard” pyrimidine or purine bases. The ferrocenoyl units introduced into different N-positions of the purine and pyrimidine ring systems and the regioselective of substitution in products has been confirmed by NMR spectroscopic analysis and quantum chemical calculations. [2]

Ferrocene, Bioconjugates, Nucleobase, Synthesis

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