3'-azido-3'-deoxythymidine 5'-(choline phosphate)

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3'-azido-3'-deoxythymidine 5'-(choline phosphate)
• 英文别名: 2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₁₅H₂₅N₆O₇P
• 分子量: 432.373
• InChiKey: KBSXNKNEMXEZOR-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxythymidine 5'-(choline phosphate) 在 phosphate buffer 作用下， 生成 齐多夫定
  参考文献：
  名称：

  AZT 5′-Cholinephosphate as an Anti-HIV Agent: The Study of Biochemical Properties and Metabolic Transformations Using Its³²P-Labelled Counterpart

  摘要：

  Biochemical and metabolic transformations of 3'-azido-3'-deoxythymidine 5'-choline phosphate (1) were studied using its 32P-labelled counterpart for the evaluation of possible reasons for its enhanced anti-HIV activity. An effective synthesis of 32P-labelled 1 with a specific activity >1,000 Ci/mmol was developed by esterification of 32P-phosphoric acid with choline in the presence of BrCN followed by the coupling of the resulting choline phosphate with 3'-azido-3'-deoxythymidine (AZT). Chemical and enzymatic stabilities of 1 as well as the dynamics of penetration through HL-60 cell membranes were studied at the concentrations comparable to its antiviral concentrations. The products of intracellular transformations of the studied nucleotide were identified.

  DOI：

  10.1080/15257770601052257

文献信息

• AZT 5′-Cholinephosphate as an Anti-HIV Agent: The Study of Biochemical Properties and Metabolic Transformations Using Its³²P-Labelled Counterpart
  作者：Dmitry V. Yanvarev、Elena A. Shirokova、Maria V. Astapova、Yury S. Skoblov

  DOI：10.1080/15257770601052257

  日期：2007.1

  Biochemical and metabolic transformations of 3'-azido-3'-deoxythymidine 5'-choline phosphate (1) were studied using its 32P-labelled counterpart for the evaluation of possible reasons for its enhanced anti-HIV activity. An effective synthesis of 32P-labelled 1 with a specific activity >1,000 Ci/mmol was developed by esterification of 32P-phosphoric acid with choline in the presence of BrCN followed by the coupling of the resulting choline phosphate with 3'-azido-3'-deoxythymidine (AZT). Chemical and enzymatic stabilities of 1 as well as the dynamics of penetration through HL-60 cell membranes were studied at the concentrations comparable to its antiviral concentrations. The products of intracellular transformations of the studied nucleotide were identified.