title: Efficient photooxidative strand cleavage at 5-methylcytosine in DNA by sensitization with 9,10-anthraquinone-tethered oligonucleotides.
abstract: Photoirradiation and subsequent hot piperidine treatment of the duplex consisting of 5-methylcytosine ((m)C)-containing DNA and 9,10-anthraquinone (AQ)-tethered complementary oligodeoxynucleotide led to selective oxidative strand cleavage at the target (m)C site, whereas no strand cleavage was observed for the duplex containing normal cytosine instead of (m)C. Incorporation of an AQ sensitizer into the interior of a strand induced an enhanced one-electron photooxidation, presumably because of a much larger intersystem crossing efficiency, leading to an efficient strand cleavage at the target (m)C site in DNA. Optimization of the photosensitizer could afford more strand cleavage at (m)C in DNA, thereby allowing for the more sensitive detection of the target (m)C on a sequencing gel.
authors.affiliation: Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. hisatsugu@t03.mbox.media.kyoto-u.ac.jp
authors.forename: Hisatsugu
authors.initials: H
authors.lastname: Yamada
authors.forename: Yuya
authors.initials: Y
authors.lastname: Kitauchi
authors.forename: Kazuhito
authors.initials: K
authors.lastname: Tanabe
authors.forename: Takeo
authors.initials: T
authors.lastname: Ito
authors.forename: Sei-ichi
authors.initials: S
authors.lastname: Nishimoto
mesh_terms: D000880:Anthraquinones / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D053837:DNA Cleavage; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D009841:Oligonucleotides; D017319:Photosensitizing Agents; C042834:9,10-anthraquinone; D004247:DNA