Effects of structural modification on the DNA binding properties and photo-induced cleavage reactivity of propargylic sulfones conjugated with an anthraquinone structure |
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Authors: | Haruna Ken-ichi Kanezaki Hiroshi Tanabe Kazuhito Dai Wei-Min Nishimoto Sei-ichi |
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Institution: | Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Japan. |
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Abstract: | Propargylic sulfones are known as pH-dependent DNA cleaving agents. We have designed a novel propargylic sulfone conjugated with an anthraquinone structure and evaluated its DNA binding and cleavage characteristics. The propargylic sulfone 3 showed high intercalating ability attributable to anthraquinone chromophore, leading to the efficient alkylation of DNA. The anthraquinone chromophore in 3 also acted as a photosensitizer, and photoirradiation of 3 with DNA induced one-electron oxidation, resulting in the further DNA cleavage. Evaluation of the effect of 3 against EMT6/KU cells revealed that 3 exhibited potent cytotoxicity, even without photoirradiation. |
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