N(4)-[B-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)methyl]-2'-deoxycytidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N(4)-[B-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)methyl]-2'-deoxycytidine
• 英文别名: N(4)-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)methyl]-2′-deoxycytidine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylamino]pyrimidin-2-one
• 化学式: C₁₆H₂₆BN₃O₆
• 分子量: 367.21
• InChiKey: DMPHACJQGITGPI-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘甲基硼酸频哪醇酯 、 2'-脱氧胞嘧啶核苷 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 71.0h， 以84%的产率得到N(4)-[B-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)methyl]-2'-deoxycytidine
  参考文献：
  名称：

  Biological activity of N(4)-boronated derivatives of 2′-deoxycytidine, potential agents for boron-neutron capture therapy

  摘要：

  Boron-neutron capture therapy (BNCT) is a binary anticancer therapy that requires boron compound for nuclear reaction during which high energy alpha particles and lithium nuclei are formed. Unnatural, boron-containing nucleoside with hydrophobic pinacol moiety was investigated as a potential BNCT boron delivery agent. Biological properties of this compound are presented for the first time and prove that boron nucleoside has low cytotoxicity and that observed apoptotic effects suggest alteration of important functions of cancer cells. Mass spectrometry analysis of DNA from cancer cells proved that boron nucleoside is inserted into nucleic acids as a functional nucleotide derivative. NMR studies present very high degree of similarity of natural dG-dC base pair with dG-boron nucleoside system. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.026

文献信息

• Biological activity of N(4)-boronated derivatives of 2′-deoxycytidine, potential agents for boron-neutron capture therapy
  作者：Joanna Nizioł、Łukasz Uram、Magdalena Szuster、Justyna Sekuła、Tomasz Ruman

  DOI：10.1016/j.bmc.2015.08.026

  日期：2015.10

  Boron-neutron capture therapy (BNCT) is a binary anticancer therapy that requires boron compound for nuclear reaction during which high energy alpha particles and lithium nuclei are formed. Unnatural, boron-containing nucleoside with hydrophobic pinacol moiety was investigated as a potential BNCT boron delivery agent. Biological properties of this compound are presented for the first time and prove that boron nucleoside has low cytotoxicity and that observed apoptotic effects suggest alteration of important functions of cancer cells. Mass spectrometry analysis of DNA from cancer cells proved that boron nucleoside is inserted into nucleic acids as a functional nucleotide derivative. NMR studies present very high degree of similarity of natural dG-dC base pair with dG-boron nucleoside system. (C) 2015 Elsevier Ltd. All rights reserved.