The Relationship between the Chemical Structures of Dihydropyrazine Derivatives and DNA Strand-Breakage Activity

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Dihydropyrazine, a compound derived from sugars, possesses DNA strand-breakage activity. The relationship between the activity as assayed using pBR 322 ccc-DNA and the chemical structures of derivatives of dihydropyrazine (DHPs) has been investigated. The addition of Cu2+ enhanced the activity remarkably. The introduction of a methyl or phenyl group onto the DHP ring or a cyclohexyl group fused onto the DHP ring also increased the activity. These properties indicated that the activity was due to the facility of electron release from the DHP ring, followed by radical generation. The determination of ionization potential and electrostatic potential values, and bond dissociation energy via semi-empirical MO calculations suggested strongly that the activity is induced by a DHP ring structure that contains a configuration suitable for hyperconjugation.

収録刊行物

  • Chemical & pharmaceutical bulletin

    Chemical & pharmaceutical bulletin 55(4), 532-536, 2007-04-01

    公益社団法人日本薬学会

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被引用文献:  4件中 1-4件 を表示

各種コード

  • NII論文ID(NAID)
    110006241811
  • NII書誌ID(NCID)
    AA00602100
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092363
  • NDL 記事登録ID
    8691125
  • NDL 雑誌分類
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-D167
  • データ提供元
    CJP書誌  CJP引用  NDL  NII-ELS  J-STAGE 
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