ES-3'-C8-dG | 1282040-43-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: ES-3'-C8-dG
• CAS: 1282040-43-0
• 化学式: C₂₀H₂₃N₅O₅
• 分子量: 413.433
• InChiKey: QYLSMFKPGUSFPI-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  148.51
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 ES-3'-N2-dG 、 ES-3'-C8-dG
  参考文献：
  名称：

  Detection and Quantification of Specific DNA Adducts by Liquid Chromatography−Tandem Mass Spectrometry in the Livers of Rats Given Estragole at the Carcinogenic Dose

  摘要：

  Estragole (ES) is a natural constituent of several herbs and spices that acts as a carcinogen in the livers of rodents. Given that the proximal electrophilic form of ES with a reactive carbocation is generated by cytochrome P450 and a sulfotransferase metabolizing pathway, there is a possibility that the resultant covalent adducts with DNA bases may play a key role in carcinogenesis. The existence of ES-specific deoxyguanosine reported with the precise chemical structures of the dG adducts (dG) and deoxyadenosine (dA) adducts has already been being confirmed. In the present study, we examined ES-specific dA adduct formation using LC-ESI/MS after the reaction of dA with 1'-acetoxy-ES produced by a sulfotransferase metabolic pathway mimic. Although two peaks were observed in the LC-ESI/MS chromatogram, the identification of ES-3'-N-6-dA as the measurable peak was determined by NMR analysis. To confirm ES-specific dG and dA adduct formation in vivo, an isotope dilution LC-ESI/MS/MS method applicable to in vivo samples for ES-3'-N-6-dA together with the two major dG adducts, that is, ES-3'-C8-dG and ES-3'-N-2-dG, was developed using selected ion recording. The limit of quantification was 0.2 fmol on column for ES-3'-C8-dG and ES-3'-N-2-dG and 0.06 fmol on column for ES-3'-N6-dA, respectively. Using the developing analytical method, we attempted to measure adduct levels in the livers of rats treated with ES at a possible carcinogenic dose (600 mg/kg bw) for 4 weeks. ES-3'-C8-dG, ES-N-2-dG, and ES-3'-N-6-dA were detected at levels of 3.5 +/- 0.4, 4.8 +/- 0.8, and 20.5 +/- 1.6/10(6) dG or dA in the livers of ES-treated rats. This quantitative data and newly developed technique for adduct observation in vivo might be helpful for ES hepatocarcinogenesis investigations.

  DOI：

  10.1021/tx100410y