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著作: Tanabe Kazuhito/[山田 久嗣]/Nishimoto Sei-ichi/One-electron photooxidation and site-selective strand cleavage at 5-methylcytosine in DNA by sensitization with 2-methyl-1,4-naphthoquinone-tethered oligonucleotides./[Journal of the American Chemical Society]

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EID
291060
EOID
768136
Map
0
LastModified
2015年3月3日(火) 22:08:06
Operator
山田 久嗣
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Owner
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. (英) Tanabe Kazuhito
    役割 任意
    貢献度 任意
    学籍番号 推奨
  2. 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
  3. (英) Nishimoto Sei-ichi
    役割 任意
    貢献度 任意
    学籍番号 推奨
題名 必須

(英) One-electron photooxidation and site-selective strand cleavage at 5-methylcytosine in DNA by sensitization with 2-methyl-1,4-naphthoquinone-tethered oligonucleotides.

副題 任意
要約 任意

(英) Photosensitized one-electron oxidation was applied to discriminate a specific base site of 5-methylcytosine (mC) generated in DNA possessing a partial sequence of naturally occurring p53 gene, using a sensitizing 2-methyl-1,4-naphthoquinone (NQ) chromophore tethered to an interior of oligodeoxynucleotide (ODN) strands. Photoirradiation and subsequent hot piperidine treatment of the duplex consisting of mC-containing DNA and NQ-tethered complementary ODN led to oxidative strand cleavage selectively at the mC site, when the NQ chromophore was arranged so as to be in close contact with the target mC. The target mC is most likely to be one-electron oxidized into the radical cation intermediate by the sensitization of NQ. The resulting mC radical cation may undergo rapid deprotonation and subsequent addition of molecular oxygen, thereby leading to its degradation followed by strand cleavage at the target mC site. In contrast to mC-containing ODN, ODN analogs with replacement of normal cytosine, thymine, adenine, or guanine at the mC site underwent less amount of such an oxidative strand cleavage at the target base site, presumably due to occurrence of charge transfer and charge recombination processes between the base radical cation and the NQ radical anion. Furthermore, well designed incorporation of the NQ chromophore into an interior of ODN could suppress a competitive strand cleavage at consecutive guanines, which occurred as a result of positive charge transfer. Thus, photosensitization by an NQ-tethered ODN led to one-electron oxidative strand cleavage exclusively at the target mC site, providing a convenient method of discriminating mC in naturally occurring DNA such as human p53 gene as a positive band on a sequencing gel.

キーワード 推奨
  1. (英) DNA
  2. (英) Electrons
  3. (英) Nucleic Acid Conformation
  4. (英) Oligonucleotides
  5. (英) Oxidation-Reduction
  6. (英) Photochemistry
  7. (英) Vitamin K 3
発行所 推奨
誌名 必須 Journal of the American Chemical Society([アメリカ化学会])
(pISSN: 0002-7863, eISSN: 1520-5126)
ISSN 任意 0002-7863
ISSN: 0002-7863 (pISSN: 0002-7863, eISSN: 1520-5126)
Title: Journal of the American Chemical Society
Title(ISO): J Am Chem Soc
Publisher: American Chemical Society
 (NLM Catalog  (Scopus  (CrossRef (Scopus information is found. [need login])
必須 129
必須 25
必須 8034 8040
都市 任意
年月日 必須 2007年 6月 5日
URL 任意
DOI 任意 10.1021/ja071369s    (→Scopusで検索)
PMID 任意 17547405    (→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