8-(2-oxobutyl)-3,N4-etheno-dC | 1207187-88-9

• 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: 8-(2-oxobutyl)-3,N4-etheno-dC
• 英文别名: 4-OHE-dC
• CAS: 1207187-88-9
• 化学式: C₁₅H₁₉N₃O₅
• 分子量: 321.333
• InChiKey: VOAJOYAMDODQSI-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  106.06
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-oxo-2-hexenal 、 2'-脱氧胞苷盐酸盐 以 乙醇 为溶剂， 反应 120.0h， 以32%的产率得到8-(2-oxobutyl)-3,N4-etheno-dC
  参考文献：
  名称：

  DNA Modifications by the ω-3 Lipid Peroxidation-Derived Mutagen 4-Oxo-2-hexenal in Vitro and Their Analysis in Mouse and Human DNA

  摘要：

  4-Oxo-2-hexenal (4-OHE), which forms a 2'-deoxyguanosine (dG) adduct in a model lipid peroxidation system, is mutagenic in the Ames test. It is generated by the oxidation of omega-3 fatty acids and is commonly found in dietary fats, such as fish oil, perilla oil, rapeseed oil, and soybean oil. 4-OHE also forms adducts with 2'-deoxyadenosine (dA), 2'-deoxycytidine (dC), and 5-methyl-2'-deoxycytidine (5-Me-dC) in DNA. In this study, we characterized the structures of these adducts in detail. We measured the amounts of 4-OHE-DNA adducts in mouse organs by LC/MS/MS, after 4-OHE was orally administered to mice. The 4-OHE-dA, 4-OHE-dC, 4-OHE-dG, and 4-OHE-5-Me-dC adducts were detected in stomach and intestinal DNA in the range of 0.25-43.71/10(8) bases. After the 4-OHE administration, the amounts of these DNA adducts decreased gradually over 7 days. We also detected 4-OHE-dC in human lung DNA, in the range of 2.6-5.9/10(9) bases. No difference in the 4-OHE adduct levels was detected between smokers and nonsmokers. Our results suggest that 4-OHE-DNA adducts are formed by endogenous as well as environmental lipid peroxides.

  DOI：

  10.1021/tx9003819