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タイトル: | Synthesis and photooxidation of oligodeoxynucleotides containing 5-dimethylaminocytosine as an efficient hole-trapping site in the positive-charge transfer through DNA duplexes. |
著者: | Yamada, Hisatsugu Kurata, Masayuki Tanabe, Kazuhito Ito, Takeo Nishimoto, Sei-ichi |
著者名の別形: | 山田, 久嗣 |
発行日: | 12-Dec-2012 |
出版者: | Royal Society of Chemistry |
誌名: | Organic & biomolecular chemistry |
巻: | 10 |
号: | 10 |
開始ページ: | 2035 |
終了ページ: | 2043 |
抄録: | We have designed and synthesized DNA duplexes containing 5-dimethylaminocytosine ((DMA)C) to investigate the effects of C(5)-substituted cytosine bases on the transfer and trapping of positive charge (holes) in DNA duplexes. Fluorescence quenching experiments revealed that a (DMA)C base is more readily one-electron oxidized into a radical cation intermediate as compared with other natural nucleobases. Upon photoirradiation of the duplexes containing (DMA)C, the photosensitizer-injected hole migrated through the DNA bases and was trapped efficiently at the (DMA)C sites, where an enhanced oxidative strand cleavage occurred by hot piperidine treatment. The (DMA)C radical cation formed by hole transfer may undergo specific hydration and subsequent addition of molecular oxygen, thereby leading to its decomposition followed by a predominant strand cleavage at the (DMA)C site. This remarkable property suggests that the modified cytosine (DMA)C can function as an efficient hole-trapping site in the positive-charge transfer in DNA duplexes. |
著作権等: | © The Royal Society of Chemistry 2012. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/166076 |
DOI(出版社版): | 10.1039/c2ob06642d |
PubMed ID: | 22273807 |
出現コレクション: | 学術雑誌掲載論文等 |
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