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著作: [山田 久嗣]/Kitauchi Yuya/Tanabe Kazuhito/Ito Takeo/Nishimoto Sei-Ichi/Anthraquinone-sensitized photooxidation of 5-methylcytosine in DNA leading to piperidine-induced efficient strand cleavage./[Chemistry - A European Journal]

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EID
291046
EOID
768086
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LastModified
2015年3月3日(火) 21:04:02
Operator
山田 久嗣
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山田 久嗣
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種別 必須 学術論文(審査論文)
言語 必須 英語
招待 推奨
審査 推奨
カテゴリ 推奨
共著種別 推奨
学究種別 推奨
組織 推奨
著者 必須
  1. 山田 久嗣([徳島大学.大学院社会産業理工学研究部.生物資源産業学域.応用生命系.応用生物資源学分野]/[徳島大学.生物資源産業学部.生物資源産業学科.応用生命講座])
    役割 任意
    貢献度 任意
    学籍番号 推奨
  2. (英) Kitauchi Yuya
    役割 任意
    貢献度 任意
    学籍番号 推奨
  3. (英) Tanabe Kazuhito
    役割 任意
    貢献度 任意
    学籍番号 推奨
  4. (英) Ito Takeo
    役割 任意
    貢献度 任意
    学籍番号 推奨
  5. (英) Nishimoto Sei-Ichi
    役割 任意
    貢献度 任意
    学籍番号 推奨
題名 必須

(英) Anthraquinone-sensitized photooxidation of 5-methylcytosine in DNA leading to piperidine-induced efficient strand cleavage.

副題 任意
要約 任意

(英) One-electron photooxidations of 5-methyl-2'-deoxycytidine (d(m)C) and 5-trideuteriomethyl-2'-deoxycytidine ([D(3)]d(m)C) by sensitization with anthraquinone (AQ) derivatives were investigated. Photoirradiation of an aerated aqueous solution containing d(m)C and anthraquinone 2-sulfonate (AQS) afforded 5-formyl-2'-deoxycytidine (d(f)C) and 5-hydroxymethyl-2'-deoxycytidine (d(hm)C) in good yield through an initial one-electron oxidation process. The deuterium isotope effect on the AQS-sensitized photooxidation of d(m)C suggests that the rate-determining step in the photosensitized oxidation of d(m)C involves internal transfer of the C5-hydrogen atom of a d(m)C-tetroxide intermediate to produce d(f)C and d(hm)C. In the case of a 5-methylcytosine ((m)C)-containing duplex DNA with an AQ chromophore that is incorporated into the backbone of the DNA strand so as to be immobilized at a specific position, (m)C underwent efficient direct one-electron oxidation by the photoexcited AQ, which resulted in an exclusive DNA strand cleavage at the target (m)C site upon hot piperidine treatment. In accordance with the suppression of the strand cleavage at 5-trideuterio-methylcytosine observed in a similar AQ photosensitization, it is suggested that deprotonation at the C5-methyl group of an intermediate (m)C radical cation may occur as a key elementary reaction in the photooxidative strand cleavage at the (m)C site. Incorporation of an AQ sensitizer into the interior of a strand of the duplex enhanced the one-electron photooxidation of (m)C, presumably because of an increased intersystem crossing efficiency that may lead to efficient piperidine-induced strand cleavage at an (m)C site in a DNA duplex.

キーワード 推奨
  1. (英) Anthraquinones
  2. (英) DNA
  3. (英) DNA Cleavage
  4. (英) DNA Methylation
  5. (英) Deoxycytidine
  6. (英) Electrons
  7. (英) Molecular Structure
  8. (英) Oxidation-Reduction
  9. (英) Photochemistry
  10. (英) Piperidines
  11. (英) Solutions
  12. (英) Water
発行所 推奨
誌名 必須 Chemistry - A European Journal([Wiley-VCH])
(pISSN: 0947-6539, eISSN: 1521-3765)
ISSN 任意 1521-3765
ISSN: 0947-6539 (pISSN: 0947-6539, eISSN: 1521-3765)
Title: Chemistry (Weinheim an der Bergstrasse, Germany)
Title(ISO): Chemistry
Supplier: Chemistry Europe
Publisher: Wiley
 (NLM Catalog  (Wiley  (Scopus  (CrossRef (Scopus information is found. [need login])
必須 17
必須 7
必須 2225 2235
都市 任意
年月日 必須 2011年 1月 14日
URL 任意
DOI 任意 10.1002/chem.201001884    (→Scopusで検索)
PMID 任意 21294186    (→Scopusで検索)
NAID 任意
WOS 任意
Scopus 任意
評価値 任意
被引用数 任意
指導教員 推奨
備考 任意
  1. (英) PublicationType: Journal Article

  2. (英) PublicationType: Research Support, Non-U.S. Gov't