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 (mC)-containing DNA and 9,10-anthraquinone (AQ)-tethered complementary oligodeoxynucleotide led to selective oxidative strand cleavage at the target mC site, whereas no strand cleavage was...

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Bibliographic Details
Published inNucleic Acids Symposium Series Vol. 53; no. 1; pp. 209 - 210
Main Authors Yamada, Hisatsugu, Kitauchi, Yuya, Tanabe, Kazuhito, Ito, Takeo, Nishimoto, Sei-ichi
Format Journal Article
LanguageEnglish
Published England Oxford University Press 2009
Subjects
Anthraquinones - chemistry
DNA - chemistry
DNA Cleavage
Oligonucleotides - chemistry
Oxidation-Reduction
Photochemical Processes
Photosensitizing Agents - chemistry
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Summary:Abstract Photoirradiation and subsequent hot piperidine treatment of the duplex consisting of 5-methylcytosine (mC)-containing DNA and 9,10-anthraquinone (AQ)-tethered complementary oligodeoxynucleotide led to selective oxidative strand cleavage at the target mC site, whereas no strand cleavage was observed for the duplex containing normal cytosine instead of mC. 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 mC site in DNA. Optimization of the photosensitizer could afford more strand cleavage at mC in DNA, thereby allowing for the more sensitive detection of the target mC on a sequencing gel.
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ISSN:0261-3166
1746-8272
DOI:10.1093/nass/nrp105