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Nucleic Acids Symposium Series 2007 51(1):35-36; doi:10.1093/nass/nrm018
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© 2007 Oxford University Press

Synthesis and biological properties of pyrrole-imidazole polyamide conjugates

Masafumi Minoshima, Shunta Sasaki, Jun Fujimoto, Ken-ichi Shinohara, Toshikazu Bando and Hiroshi Sugiyama

Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-oiwakecho, Sakyo, Kyoto 606-8502, Japan

Abstract

We have developed a series of conjugates between pyrrole (Py)-imidazole (Im) polyamides and 1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H benz[e]indole (seco-CBI) with an indole linker. High resolution polyacrylamide gel electrophoresis revealed that these conjugates alkylated DNA at predetermined sequences. Then, we demonstrated that conjugates 1 and 2 have DNA alkylation activities at double stranded human telomere sequence and potent cytotoxicities in cancer cell lines. In addition, we showed that conjugate 3 alkylates DNA with ten-base-pair recognition sequence in the presence of partner polyamide 4, which suggested alkylation through 3-4 heterodimer formation.


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