| 1311934-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• CAS: 1311934-38-9
• 化学式: C₃₆H₅₈N₃O₈PSi₃
• 分子量: 776.102
• InChiKey: SJLXIXVCPYMMAP-NNEHKIPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  113.48
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  beta-胸苷 在 咪唑 、 4,5-二氰基咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Solid-Phase Synthesis, Thermal Denaturation Studies, Nuclease Resistance, and Cellular Uptake of (Oligodeoxyribonucleoside)methylborane Phosphine–DNA Chimeras

  摘要：

  The major hurdle associated with utilizing oligo-deoxyribonucleotides for therapeutic purposes is their poor delivery into cells coupled with high nuclease susceptibility. In an attempt to combine the nonionic nature and high nuclease stability of the P-C bond of methylphosphonates with the high membrane permeability, low toxicity, and improved gene silencing ability of borane phosphonates, we have focused our research on the relatively unexplored methylborane phosphine (Me-P-BH3) modification. This Article describes the automated solid-phase synthesis of mixed-backbone oligodeoxynu-cleotides (ODNs) consisting of methylborane phosphine and phosphate or thiophosphate linkages (16-mers). Nuclease stability assays show that methylborane phosphine ODNs are highly resistant to 5' and 3' exonucleases. When hybridized to a complementary strand, the ODN:RNA duplex was more stable than its corresponding ODN:DNA duplex. The binding affinity of ODNANA duplex increased at lower salt concentration and approached that of a native DNA:RNA duplex under conditions close to physiological saline, indicating that the Me-P-BH3 linkage is positively charged. Cellular uptake measurements indicate that these ODNs are efficiently taken up by cells even when the strand is 13% modified. Treatment of HeLa cells and WM-239A cells with fluorescently labeled ODNs shows significant cytoplasmic fluorescence when viewed under a microscope. Our results suggest that methylborane phosphine ODNs may prove very valuable as potential candidates in antisense research and RNAi.

  DOI：

  10.1021/ja201314q