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Paper | Regular issue | Vol 63, No. 1, 2004, pp.29-39
Published online, 14th November, 2003
DOI: 10.3987/COM-03-9890
Bipyrrole Derivatives as New DNA-Minor Groove Binders

Mikimasa Tanada, Yoshihiro Shibata, Minoru Maeda, and Shigeki Sasaki*

*Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

Small molecules with capability of binding with DNA or RNA would have broad application as probes in genomic studies, and also as potential candidates for new therapeutic agents. In this study, we synthesized dithioamido-bipyrrole derivatives as new binding molecules to the duplex DNA. It has been revealed from the competitive binding experiments with the known intercalater, ethidum bromide, and the minor groove binder Hoechst 33258 that the dithioamido-bipyrrole derivatives with alkyl chains with medium length bind the duplex DNA in a similar manner with the minor groove binder. As ionic interactions are not included in the binding with the duplex DNA, the new dithioamido-bipyrrole skeleton may provide an interesting motif for DNA binding.