[(15)N5]7-carboxymethylguanine | 1227782-49-1

• 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: [(15)N5]7-carboxymethylguanine
• CAS: 1227782-49-1
• 化学式: C₇H₇N₅O₃
• 分子量: 214.131
• InChiKey: DUXOREVYDYHYSJ-XHUNWAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  126.89
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  碘乙酸 、 ¹⁵N₅-2′-deoxyguanosine 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 1.17h， 生成 [(15)N5]7-carboxymethylguanine
  参考文献：
  名称：

  Detection of 7-(2′-Carboxyethyl)guanine but Not 7-Carboxymethylguanine in Human Liver DNA

  摘要：

  7-Carboxymethylguanine (7-CMGua) and 7-(2'-carboxyethyl)guanine (7-CEGua) are DNA adducts that potentially could be formed upon the metabolism of the carcinogenic nitrosamines N-nitrososarcosine (NSAR) and 3-(methylnitrosamino)propionic acid (MNPA), respectively, or from other sources such as nitrosation of glycine (7-CMGua) or reaction of DNA with acrylic acid (7-CEGua). Since both NSAR and MNPA have been detected in human urine and there are plausible sources of exposure to other precursors to these adducts, we analyzed human liver DNA for 7-CMGua and 7-CEGua, using liquid chromatography-electrospray ionization-tandem mass spectrometry-selected reaction monitoring (LC-ESI-MS/MS-SRM). Human hepatic DNA was mixed with [N-15(5)]7-CMGua and [N-15(5)]7-CEGua as internal standards and enzymatically hydrolyzed. The hydrolysate was partially purified by solid-phase extraction, and the resulting fraction was treated with acetyl chloride in methanol to convert 7-CMGua and 7-CEGua to their methyl esters. After a second solid-phase extraction, LC-ESI-MS/MS-SRM analysis was carried out using the transitions m/z 224 [M + H](+) -> m/z 164 [(M + H) - HCOOCH3](+) and m/z 238 [M + H](+) -> m/z 152 [BH](+) for the methyl esters of 7-CMGua and 7-CEGua, respectively. The method was sensitive, accurate, precise, and apparently free from artifact formation. 7-CEGua, as its methyl ester, was detected in all 24 human liver samples analyzed, mean +/- SD, 373 +/- 320 fmol/mu mol Gua (74.6 adducts per 10(9) nucleotides), range 17-1189 fmol/mu mol Gua, but the methyl ester of 7-CMGua was not detected in any sample. These results demonstrate the ubiquitous presence of 7-CEGua in human liver DNA. Acrylic acid may be a likely endogenous precursor to 7-CEGua.

  DOI：

  10.1021/tx100062v