Electrochemical investigation of interactions between quinone derivatives and single stranded DNA

The interactions of 5-hydroxy-1,4-naphthoquinone with three nucleobases (thymine, cytosine, adenine) and one nucleoside (guanosine), investigated by cyclic voltammetry in aprotic solvent, showed significant change in the redox behavior of the quinone group. Then, the interactions between 5-hydroxy-1,4-naphthoquinone and single-stranded oligonucleotides were studied in phosphate buffer saline solution using a random sequence and homo-oligonucleotides (polyA20, polyT20, polyC20 and polyG20). Finally, the interactions of 1,4-benzoquinone and 1,4-naphthoquinone were studied to compare with 5-hydroxy-1,4-naphthoquinone and to propose different interaction modes. The results help to elucidate the transduction mechanism involved in label-free quinone-based electrochemical DNA sensors.

► Redox indicator for electrochemical DNA sensors. ► Interactions of juglone with nucleobases, investigated by cyclic voltammetry. ► Nucleobases induce significant changes in the redox behavior of the quinone group. ► Homo-oligonucleotides (polyA20, polyT20, polyG20, polyC20) give similar changes. ► Random oligonucleotides induce similar changes.