In recent years, DNA has attracted much attention as a conductive biopolymer. Recent efforts to elucidate the mechanism of long-range hole transport in DNA has encouraged us in the view that DNA can be a good mediator for hole transport by the selection of an appropriate sequence. However, when natural DNA is used as a molecular wire, serious unavoidable oxidative degradation of G bases occurs. In addition, the hole transport in natural DNA is strongly influenced by the sequence and the transport distance. Of great importance in the realization of a real DNA wire is the molecular design of an artificial nucleobase that can effectively mediate hole transport and, at the same time, is not oxidatively decomposed. We now report on a protocol for designing an artifi-cial nucleobase that can act as an effective mediator for long-range hole transport without subsequent decomposition. Additionally, we also describe the applications of the artificial hole-transporting DNA to (i) combinational logic gates, (ii) drug-releasing systems, and (iii) genotyping biofilms on a gold electrode.