N²-methyl-8-oxoguanine | 98141-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N²-methyl-8-oxoguanine
• 英文别名: N(2)-Methyl-8-oxoguanine；2-(methylamino)-7,9-dihydro-1H-purine-6,8-dione
• CAS: 98141-17-4
• 化学式: C₆H₇N₅O₂
• 分子量: 181.154
• InChiKey: CVOMRGUGVVOEDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.6
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N2-甲基鸟苷 在 甲酸 、 溴 作用下， 以 水 为溶剂， 反应 16.33h， 生成 N²-methyl-8-oxoguanine
  参考文献：
  名称：

  Quantitation of 8-Oxoguanine and Strand Breaks Produced by Four Oxidizing Agents

  摘要：

  Reactive oxygen species, produced endogenously or by exposure to environmental chemicals and ionizing radiation, induce a wide range of DNA lesions. The variety of chemistries associated with different oxidants suggests that each will produce a unique spectrum of DNA damage products. To extend our efforts to relate genotoxin chemistry to DNA damage, we measured both strand breaks and 8-oxoguanine (8-oxoG) in DNA after exposure to gamma-radiation, Fe(II)-EDTA/H2O2, Cu(II)H2O2, and peroxynitrite at concentrations approaching physiological relevance. We found that the ratio of 8-oxoG to strand breaks varied more than 10-fold depending on the oxidizing agent: similar to 0.4 for Cu(II)H2O2 and peroxynitrite and similar to 0.03 for Fe(II)-EDTA/H2O2 and gamma-radiation. In the case of Cu(II)H2O2, the relative proportion of 8-oxoG and strand breaks was found to vary more than 2-fold (0.14-0.37) for different Cu(II) concentrations, consistent with other studies. We were able to detect 8-oxoG formation by peroxynitrite by using low peroxynitrite concentrations in conjunction with a sensitive immunoaffinity/KPLC-ECD methodology. The level of 8-oxoG relative to strand breaks produced by peroxynitrite was higher than that produced by Fe(II)-EDTA/H2O2 and gamma-radiation, which is consistent with the altered reactivity or accessibility of a non-hydroxyl radical species produced by peroxynitrite.

  DOI：

  10.1021/tx960102w