6-bromo-9-[14C]methylpurine | 1194667-37-2

• 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: 6-bromo-9-[14C]methylpurine
• 英文别名: 6-bromo-7-(114C)methylpurine
• CAS: 1194667-37-2
• 化学式: C₆H₅BrN₄
• 分子量: 215.025
• InChiKey: PGSOWMMUOJWDST-NJFSPNSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 6-bromo-9-[14C]methylpurine 生成 S-[6-(7-[14C]methylpurinyl)]glutathione
  参考文献：
  名称：

  Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1

  摘要：

  6-Bromo-7-[C-11]methylpurine is reported to react with glutathione via glutathione S-transferases in the brain and to be converted into a substrate for multidrug resistance-associated protein 1 (MRP1), an efflux pump. The compound with a rapid conversion rate allows quantitative assessment of MRP1 function, but this rate is probably susceptible to interspecies differences. Hence, for application to different species, including humans, it is necessary to adjust the conversion rate by modifying the chemical structure. We therefore designed 6-Halo-9-(or 7)-[C-14]methylpurine (halogen: F, Cl, Br, or I), and evaluated them in vitro with respect to enzymatic reactivity with glutathione using brain homogenates from the mouse, rat, or monkey. There was a marked difference in reactivity between these species. Changes in the position of the methyl group and halogen on N-methyl-6-halopurine provided various compounds possessing wide-ranging reactivity with glutathione. In conclusion, the adjustment of reactivity of 6-bromo-7-[C-11]methylpurine may allow assessment of MRP1 function in the brain in various species.

  DOI：

  10.1021/jm901332c
• 作为产物：
  描述：

  碘化甲烷-14C 、 6-溴嘌呤 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 6-bromo-9-[14C]methylpurine 、 6-bromo-9-[14C]methylpurine
  参考文献：
  名称：

  Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1

  摘要：

  6-Bromo-7-[C-11]methylpurine is reported to react with glutathione via glutathione S-transferases in the brain and to be converted into a substrate for multidrug resistance-associated protein 1 (MRP1), an efflux pump. The compound with a rapid conversion rate allows quantitative assessment of MRP1 function, but this rate is probably susceptible to interspecies differences. Hence, for application to different species, including humans, it is necessary to adjust the conversion rate by modifying the chemical structure. We therefore designed 6-Halo-9-(or 7)-[C-14]methylpurine (halogen: F, Cl, Br, or I), and evaluated them in vitro with respect to enzymatic reactivity with glutathione using brain homogenates from the mouse, rat, or monkey. There was a marked difference in reactivity between these species. Changes in the position of the methyl group and halogen on N-methyl-6-halopurine provided various compounds possessing wide-ranging reactivity with glutathione. In conclusion, the adjustment of reactivity of 6-bromo-7-[C-11]methylpurine may allow assessment of MRP1 function in the brain in various species.

  DOI：

  10.1021/jm901332c

文献信息

• Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1
  作者：Toshimitsu Okamura、Tatsuya Kikuchi、Kiyoshi Fukushi、Toshiaki Irie

  DOI：10.1021/jm901332c

  日期：2009.11.26

  6-Bromo-7-[C-11]methylpurine is reported to react with glutathione via glutathione S-transferases in the brain and to be converted into a substrate for multidrug resistance-associated protein 1 (MRP1), an efflux pump. The compound with a rapid conversion rate allows quantitative assessment of MRP1 function, but this rate is probably susceptible to interspecies differences. Hence, for application to different species, including humans, it is necessary to adjust the conversion rate by modifying the chemical structure. We therefore designed 6-Halo-9-(or 7)-[C-14]methylpurine (halogen: F, Cl, Br, or I), and evaluated them in vitro with respect to enzymatic reactivity with glutathione using brain homogenates from the mouse, rat, or monkey. There was a marked difference in reactivity between these species. Changes in the position of the methyl group and halogen on N-methyl-6-halopurine provided various compounds possessing wide-ranging reactivity with glutathione. In conclusion, the adjustment of reactivity of 6-bromo-7-[C-11]methylpurine may allow assessment of MRP1 function in the brain in various species.