9-<<2-<(3-carboxypropionyl)oxy>ethoxy>methyl>guanine sodium salt | 84499-67-2

• 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: 9-<<2-<(3-carboxypropionyl)oxy>ethoxy>methyl>guanine sodium salt
• 英文别名: sodium 4-{2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethoxy}-4-oxobutanoate；sodium;4-[2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethoxy]-4-oxobutanoate
• CAS: 84499-67-2
• 化学式: C₁₂H₁₄N₅O₆*Na
• 分子量: 347.263
• InChiKey: XPEHGEOTNUXTHO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.25
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-<<2-<(3-carboxypropionyl)oxy>ethoxy>methyl>guanine sodium salt 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以45%的产率得到
  参考文献：
  名称：

  Synthesis and physico-chemical characterization of a β-cyclodextrin conjugate for sustained release of Acyclovir

  摘要：

  We report the synthesis of an oligomeric prodrug of the antiviral agent Acyclovir (Acy) conjugated to beta-cyclodextrin (beta-CyD). The drug was selectively linked through a succinic spacer to one of the primary hydroxyl groups of beta-CyD by ester linkage in a 1:1 molar ratio. The conjugate was purified by semipreparative reverse-phase chromatography and characterized by FAB mass spectrometry and NMR experiments. The release of Acy from the conjugate was evaluated both in acidic and in neutral conditions and in the presence of porcine liver esterase. In all cases we observed the release of both free Acy and Acy succinate (AcySucc) at differing rates as a function of the hydrolysis conditions. In the presence of esterase the release of free Acy was favoured over AcySucc, showing a release rate of 100% of Acy within 7 days. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2015.05.071

文献信息

• Synthesis and physico-chemical characterization of a β-cyclodextrin conjugate for sustained release of Acyclovir
  作者：Sonia Pedotti、Venerando Pistarà、Carmela Cannavà、Claudia Carbone、Felisa Cilurzo、Antonino Corsaro、Giovanni Puglisi、Cinzia Anna Ventura

  DOI：10.1016/j.carbpol.2015.05.071

  日期：2015.10

  We report the synthesis of an oligomeric prodrug of the antiviral agent Acyclovir (Acy) conjugated to beta-cyclodextrin (beta-CyD). The drug was selectively linked through a succinic spacer to one of the primary hydroxyl groups of beta-CyD by ester linkage in a 1:1 molar ratio. The conjugate was purified by semipreparative reverse-phase chromatography and characterized by FAB mass spectrometry and NMR experiments. The release of Acy from the conjugate was evaluated both in acidic and in neutral conditions and in the presence of porcine liver esterase. In all cases we observed the release of both free Acy and Acy succinate (AcySucc) at differing rates as a function of the hydrolysis conditions. In the presence of esterase the release of free Acy was favoured over AcySucc, showing a release rate of 100% of Acy within 7 days. (C) 2015 Elsevier Ltd. All rights reserved.