N7-(2-羟乙基)黄嘌呤 | 106827-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: N7-(2-羟乙基)黄嘌呤
• 英文名称: N7-(2-hydroxyethyl)xanthine
• 英文别名: 3,7-Dihydro-7-(2-hydroxyethyl)-1H-purine-2,6-dione；7-(2-hydroxyethyl)-3H-purine-2,6-dione
• CAS: 106827-32-1
• 化学式: C₇H₈N₄O₃
• 分子量: 196.166
• InChiKey: WBLBWQSLGKOLTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103.77
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N7-(2-羟乙基)黄嘌呤 在 氢氧化钾 、 二氯甲烷 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  A Gas Chromatography/Electron Capture/Negative Chemical Ionization High-Resolution Mass Spectrometry Method for Analysis of Endogenous and Exogenous N7-(2-Hydroxyethyl)guanine in Rodents and Its Potential for Human Biological Monitoring

  摘要：

  A gas chromatography/electron capture/negative chemical ionization high-resolution mass spectrometry (GC/EC/NCI-HRMS) method was developed for quantitating N7-(2-hydroxyethyl)guanine (N7-HEG) with excellent sensitivity and specificity. [4,5,6,8-C-13(4)]-N7-HEG was synthesized, characterized and quantitated using HPLC/electrospray ionization mass spectrometry (HPLC/ESI-MS) so it could serve as an internal standard. After being converted to its corresponding xanthine and derivatized with pentafluorobenzyl (PFB) bromide twice, the PFB derivative of N7-HEG was characterized using GC/EC/NCI-HRMS carried out at full scan mode. The most abundant fragment was at m/z 555, with a molecular formula of C21H9N4O3F10, resulting from the loss of one PFB group. By monitoring m/z 555.0515 (analyte) and m/z 559.0649 (internal standard), this assay demonstrated a linear relationship over a range of I fmol to 1 pmol of N7-HEG versus 20 fmol of [C-13(4)]-N7-HEG on column. The limit of detection (LOD) for the complete assay was 600 amol (S/N = 5) injected on column. The variation of this assay was within 15% from 1 to 20 fmol of N7-HEG versus 2 fmol of [C-13(4)]-N7-HEG; with four replications for each calibration standard. Two hundred to three hundred micrograms of spleen DNA of control rats and mice and 100 mu g of spleen DNA of rats and mice exposed to 3000 ppm ethylene far 6 h/day for 5 days were analyzed using GC/EC/NCI-HRMS. The amounts of N7-HEG varied from 0.2 to 0.3 pmol/mu mol of guanine in tissues of control rats. Ethylene-exposed animals had 5-15-fold higher N7-HEG levels than controls. This assay was able to quantitate N7-HEG in 25-30 mu g of DNA from human lymphocytes with excellent specificity. This was due in part to human tissues having 10-15-fold higher amounts of endogenous N7-HEG than rodents. These results show that this GC/EC/NCI-HRMS method is highly sensitive and specific and can be used in biological monitoring and molecular dosimetry and molecular epidemiology studies.

  DOI：

  10.1021/tx990059n
• 作为产物：
  描述：

  N(7)-羟基乙基鸟嘌呤 在 盐酸 、 亚硝酸特丁酯 作用下， 反应 4.0h， 生成 N7-(2-羟乙基)黄嘌呤
  参考文献：
  名称：

  A Gas Chromatography/Electron Capture/Negative Chemical Ionization High-Resolution Mass Spectrometry Method for Analysis of Endogenous and Exogenous N7-(2-Hydroxyethyl)guanine in Rodents and Its Potential for Human Biological Monitoring

  摘要：

  A gas chromatography/electron capture/negative chemical ionization high-resolution mass spectrometry (GC/EC/NCI-HRMS) method was developed for quantitating N7-(2-hydroxyethyl)guanine (N7-HEG) with excellent sensitivity and specificity. [4,5,6,8-C-13(4)]-N7-HEG was synthesized, characterized and quantitated using HPLC/electrospray ionization mass spectrometry (HPLC/ESI-MS) so it could serve as an internal standard. After being converted to its corresponding xanthine and derivatized with pentafluorobenzyl (PFB) bromide twice, the PFB derivative of N7-HEG was characterized using GC/EC/NCI-HRMS carried out at full scan mode. The most abundant fragment was at m/z 555, with a molecular formula of C21H9N4O3F10, resulting from the loss of one PFB group. By monitoring m/z 555.0515 (analyte) and m/z 559.0649 (internal standard), this assay demonstrated a linear relationship over a range of I fmol to 1 pmol of N7-HEG versus 20 fmol of [C-13(4)]-N7-HEG on column. The limit of detection (LOD) for the complete assay was 600 amol (S/N = 5) injected on column. The variation of this assay was within 15% from 1 to 20 fmol of N7-HEG versus 2 fmol of [C-13(4)]-N7-HEG; with four replications for each calibration standard. Two hundred to three hundred micrograms of spleen DNA of control rats and mice and 100 mu g of spleen DNA of rats and mice exposed to 3000 ppm ethylene far 6 h/day for 5 days were analyzed using GC/EC/NCI-HRMS. The amounts of N7-HEG varied from 0.2 to 0.3 pmol/mu mol of guanine in tissues of control rats. Ethylene-exposed animals had 5-15-fold higher N7-HEG levels than controls. This assay was able to quantitate N7-HEG in 25-30 mu g of DNA from human lymphocytes with excellent specificity. This was due in part to human tissues having 10-15-fold higher amounts of endogenous N7-HEG than rodents. These results show that this GC/EC/NCI-HRMS method is highly sensitive and specific and can be used in biological monitoring and molecular dosimetry and molecular epidemiology studies.

  DOI：

  10.1021/tx990059n

文献信息

• A Gas Chromatography/Electron Capture/Negative Chemical Ionization High-Resolution Mass Spectrometry Method for Analysis of Endogenous and Exogenous <i>N</i>7-(2-Hydroxyethyl)guanine in Rodents and Its Potential for Human Biological Monitoring
  作者：Kuen-Yuh Wu、Nova Scheller、Asoka Ranasinghe、Ten-Yang Yen、Ramiah Sangaiah、Roger Giese、James A. Swenberg

  DOI：10.1021/tx990059n

  日期：1999.8.1

  A gas chromatography/electron capture/negative chemical ionization high-resolution mass spectrometry (GC/EC/NCI-HRMS) method was developed for quantitating N7-(2-hydroxyethyl)guanine (N7-HEG) with excellent sensitivity and specificity. [4,5,6,8-C-13(4)]-N7-HEG was synthesized, characterized and quantitated using HPLC/electrospray ionization mass spectrometry (HPLC/ESI-MS) so it could serve as an internal standard. After being converted to its corresponding xanthine and derivatized with pentafluorobenzyl (PFB) bromide twice, the PFB derivative of N7-HEG was characterized using GC/EC/NCI-HRMS carried out at full scan mode. The most abundant fragment was at m/z 555, with a molecular formula of C21H9N4O3F10, resulting from the loss of one PFB group. By monitoring m/z 555.0515 (analyte) and m/z 559.0649 (internal standard), this assay demonstrated a linear relationship over a range of I fmol to 1 pmol of N7-HEG versus 20 fmol of [C-13(4)]-N7-HEG on column. The limit of detection (LOD) for the complete assay was 600 amol (S/N = 5) injected on column. The variation of this assay was within 15% from 1 to 20 fmol of N7-HEG versus 2 fmol of [C-13(4)]-N7-HEG; with four replications for each calibration standard. Two hundred to three hundred micrograms of spleen DNA of control rats and mice and 100 mu g of spleen DNA of rats and mice exposed to 3000 ppm ethylene far 6 h/day for 5 days were analyzed using GC/EC/NCI-HRMS. The amounts of N7-HEG varied from 0.2 to 0.3 pmol/mu mol of guanine in tissues of control rats. Ethylene-exposed animals had 5-15-fold higher N7-HEG levels than controls. This assay was able to quantitate N7-HEG in 25-30 mu g of DNA from human lymphocytes with excellent specificity. This was due in part to human tissues having 10-15-fold higher amounts of endogenous N7-HEG than rodents. These results show that this GC/EC/NCI-HRMS method is highly sensitive and specific and can be used in biological monitoring and molecular dosimetry and molecular epidemiology studies.