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Mechanistic Studies on the Photooxidation of Methylated Cytosine in DNA and Its Application to Novel DNA Methylation Analysis

Research Project

Project/Area Number 21710228
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Living organism molecular science
Research InstitutionKyoto University

Principal Investigator

YAMADA Hisatsugu  Kyoto University, 先端医工学研究ユニット, 助教 (80512764)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords機能性核酸 / 光増感反応 / DNA内電荷移動反応 / 5-メチルシトシン / 同位体効果 / DNA内電荷移動 / DNAメチル化 / 修飾シトシン塩基 / 重水素同位体効果
Research Abstract

Our interest focuses on the potential application of remarkable photooxidative reactivity of 5-methylcytosine (^mC) to methylation-mapping system and on further understanding the mechanism of photooxidation at ^mC in DNA. In the project, we revealed that (1) incorporation of an anthraquinone (AQ) sensitizer into a DNA strand enhanced one-electron photooxidation, leading to efficient strand cleavage at the ^mC site, (2) deprotonation at the C5-methyl group of an intermediate ^mC radical cation may occur as a key elementary reaction in the AQ-photooxidative strand cleavage at the ^mC, and (3) DNA strand cleavage at multiple ^mC residues was induced by AQ-photoinjected positive charge (hole) transfer through DNA duplex. The results obtained may provide a guide for the molecular design of highly sensitive and selective photochemical methods for the identification and analysis of ^mC in DNA.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (29 results)

All 2011 2010 2009 Other

All Journal Article (11 results) (of which Peer Reviewed: 6 results) Presentation (18 results)

  • [Journal Article] Preparation of Functionalized Oligodeoxynucleotides and Photochemical One-Electron Oxidation of 5-Methylcytosine in DNA2011

    • Author(s)
      Tanabe, K., Yamada, H., Nishimoto S.
    • Journal Title

      J.Synth.Org.Chem. in press

    • NAID

      10029438334

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anthraquinone-Sensitized Photooxidation of 5-Methylcytosine in DNA Leading to Piperidine-Induced Efficient StrandCleavage2011

    • Author(s)
      Yamada, H., Kitauchi, Y., Tanabe, K., Ito, T., Nishimoto, S.
    • Journal Title

      Chem.Eur.J. 17

      Pages: 2225-2235

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Electron Injection into DNA by N-Cyclopropyl-1-aminonaphthalene2011

    • Author(s)
      Ito, T., Uchida, T., Tanabe, K., Nishimoto, S.
    • Journal Title

      J.Photochem.Photobiol.A Chem. 219

      Pages: 115-121

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anthraquinone-Sensitized Photooxidation of 5-Methylcytosine in DNA Leading to Piperidine-Induced Efficient Strand Cleavage2011

    • Author(s)
      Yamada, H.; Kitauchi, Y.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Journal Title

      Chem.Eur.J.

      Volume: 17 Pages: 2225-2235

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Electron Injection into DNA by N-Cyclopropyl-1-aminonaphthalene2011

    • Author(s)
      Ito, T.; Uchida, T.; Tanabe, K.; Yamada, H.; Nishimoto, S.
    • Journal Title

      J.Photochem.Photobiol.A Chem.

      Volume: 219 Pages: 115-121

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photo-Induced Electron Transfer Reaction in Diaminostilbene-Tethered DNA Duplexes2009

    • Author(s)
      Ito, T., Hayashi, A., Uchida, T., Tanabe, K., Yamada, H., Nishimoto, S.
    • Journal Title

      Nucleic Acids Symp.Ser. 53

      Pages: 201-202

    • Related Report
      2010 Final Research Report
  • [Journal Article] Efficient Photooxidative Strand Cleavage at 5-Methylcytosine in DNA by Sensitization with 9,10-Anthraquinone-Tethered Oligonucleotides2009

    • Author(s)
      Yamada, H., Kitauchi, Y., Tanabe, K., Ito, T., Nishimoto, S.
    • Journal Title

      Nucleic Acids Symp.Ser. 53

      Pages: 209-210

    • Related Report
      2010 Final Research Report
  • [Journal Article] Photoelectrochemical Identification of 5-Methylcytosine Modification in DNA : Combination of Photosensitization and Enzymatic Cleavage2009

    • Author(s)
      Tanabe, K., Yamada, H., Ito, T.; Nishimoto, S.
    • Journal Title

      Nucleic Acids Symp.Ser. 53

      Pages: 205-206

    • Related Report
      2010 Final Research Report
  • [Journal Article] Efficient Photooxidative Strand Cleavage at 5-Methylcytosine in DNA by Sensitization with 9,10-Anthraquinone-Tethered Oligonucleotides2009

    • Author(s)
      Yamada, H, ; Kitauchi, Y.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Journal Title

      Nucleic Acids Symp.Ser. 53

      Pages: 209-210

    • Related Report
      2009 Annual Research Report
  • [Journal Article] Photoelectrochemical Identification of 5-Methylcytosine Modification in DNA : Combination of Photosensitization and Enzymatic Cleavage2009

    • Author(s)
      Tanabe, K.; Yamada, H.; Ito, T.; Nishimoto, S.
    • Journal Title

      Nucleic Acids Symp.Ser. 53

      Pages: 205-206

    • Related Report
      2009 Annual Research Report
  • [Journal Article] Preparation of Functionalized Oligodeoxynucleotides and Photochemical One-Electron Oxidation of 5-Methylcytosine in DNA

    • Author(s)
      Tanabe, K.; Yamada, H.; Nishimoto S.
    • Journal Title

      J.Synth.Org.Chem.

      Volume: (In press)

    • NAID

      10029438334

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Efficient one-electron photooxidation and site-selective strand cleavage at 5-methylcytosine in DNA by oligonucleotide bearing 9,10-anthraquinone sensitizer2010

    • Author(s)
      Kitauchi, Y., Yamada, H., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Selective trapping at cytosine derivatives of photosensitizer-injected and migrated hole in DNA2010

    • Author(s)
      Kurata, M., Yamada, H., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Efficient one-electron photooxidation and site-selective strand cleavage at 5-methylcytosine in DNA by oligonucleotide bearing 9, 10-anthraquinone sensitizer2010

    • Author(s)
      Kitauchi, Y.; Yamada, H.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Selective trapping at cytosine derivatives of photosensitizerinjected and migrated hole in DNA2010

    • Author(s)
      Kurata, M.; Yamada, H.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Efficient Hole Trapping at C(5)-Substituted Cytosine in the Photosensitizer-Injected Positive Charge Transfer through DNA Duplex2010

    • Author(s)
      Kurata, M., Yamada, H., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      7thInternational Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      2010-11-11
    • Related Report
      2010 Final Research Report
  • [Presentation] One-Electron Oxidation at 5-Methylcytosine Induced by thePhotosensitizer-Injected Positive ChargeTransfer through DNA2010

    • Author(s)
      Kitauch, Y., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      7th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      2010-11-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Efficient Hole Trapping at C(5)-Substituted Cytosine in the Photosensitizer-Injected Positive Charge Transfer through DNA Duplex2010

    • Author(s)
      Kurata, M.; Yamada, H.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Organizer
      7th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      2010-11-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] One-Electron Oxidation at 5-Methylcytosine Induced by the Photosensitizer-Injected Positive Charge Transfer through DNA2010

    • Author(s)
      Kitauchi, Y.; Yamada.H.; Tanabe, K.; Ito, T.; Nishimoto, S.
    • Organizer
      7th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      2010-11-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] メチル化DNAの光増感酸化反応に及ぼす重水素同位体効果2010

    • Author(s)
      山田久嗣、北内佑哉、田邉一仁、伊藤健雄、西本清一
    • Organizer
      第90回日本化学会春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] メチル化DNAの光増感酸化反応に及ぼす重水素同位体効果2010

    • Author(s)
      山田久嗣、北内佑哉、田邉一仁、伊藤健雄、西本清一
    • Organizer
      第90回日本化学会春季年会
    • Place of Presentation
      東大阪市
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光化学反応を利用したDNAメチル化検出法の開発2010

    • Author(s)
      山田久嗣
    • Organizer
      バイオ計測・試薬研究会「バイオ計測・試薬分野における若手科学者・技術者のシーズ・構想発表会」
    • Place of Presentation
      京都
    • Year and Date
      2010-03-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Efficient Photooxidative Strand Cleavage at 5-Methylcytosine in DNA by Sensitization with 9,10-Anthraquinone-Tethered Oligonucleotides2009

    • Author(s)
      山田久嗣、北内佑哉、田邉一仁、伊藤健雄、西本清一
    • Organizer
      6th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Takayama, Japan
    • Year and Date
      2009-09-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] アントラキノン光増感剤を導入したオリゴDNA : 5-メチルシトシン塩基部位での選択的DNA切断2009

    • Author(s)
      北内佑哉、山田久嗣、田邉一仁、伊藤健雄、西本清一
    • Organizer
      第24回生体機能関連化学シンポジウム
    • Place of Presentation
      福岡市
    • Year and Date
      2009-09-14
    • Related Report
      2009 Annual Research Report
  • [Presentation] C(5)位に置換基を導入した修飾シトシン含有DNAオリゴマーの合成と四重鎖形成特性2009

    • Author(s)
      藏田真之、山田久嗣、田邉一仁、伊藤健雄、山田久嗣、西本清一
    • Organizer
      第24回生体機能関連化学シンポジウム若手フォーラム
    • Place of Presentation
      福岡
    • Related Report
      2010 Final Research Report
  • [Presentation] アントラキノン光増感剤を導入したオリゴDNA:5-メチルシトシン塩基部位での選択的DNA切断2009

    • Author(s)
      北内佑哉、田邉一仁、伊藤健雄、西本清一
    • Organizer
      第24回生体機能関連化学シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2010 Final Research Report
  • [Presentation] Efficient Photooxidative Strand Cleavage at 5-Methylcytosine in DNA by Sensitization with9,10-Anthraquinone-Tethered Oligonucleotides2009

    • Author(s)
      Yamada, H., Kitauchi, Y., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      6th Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Takayama, Japan
    • Related Report
      2010 Final Research Report
  • [Presentation] Photoelectrochemical Identification of 5-Methylcytosine Modification in DNA : Combination of Photosensitization and Enzymatic Cleavage2009

    • Author(s)
      Tanabe, K., Yamada, H., Ito, T., Nishimoto,S.
    • Organizer
      6th International Symposium on Nucleic Acids Chemistry
    • Place of Presentation
      Takayama, Japan
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Photochemical Approach to Discrimination of Methylated Cytosine in DNA : pH Effect on theNaphthoquinone-Sensitized One-Electron Photooxidation of 5-Methylcytosine2009

    • Author(s)
      Yamada, H., Kitauchi, Y., Tanabe, K., Ito, T., Nishimoto, S.
    • Organizer
      XXIV International Conference on Photochemistry
    • Place of Presentation
      Toledo, Spain
    • Related Report
      2010 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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