3',5'-diisobutyryl-N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine | 1263758-22-0

• 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: 3',5'-diisobutyryl-N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine
• CAS: 1263758-22-0
• 化学式: C₂₆H₄₃N₄O₇
• 分子量: 523.65
• InChiKey: OPXFBXOLKNQFNY-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  131.89
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3',5'-diisobutyryl-N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine
  参考文献：
  名称：

  Electron Paramagnetic Resonance (EPR) Study of Spin-Labeled Camptothecin Derivatives: A Different Look of the Ternary Complex

  摘要：

  Camptothecin (CPT) derivatives are clinically effective poisons of DNA topoisomerase I (Top 1) able to form a ternary complex with the Top1 DNA complex. The aim of this investigation was to examine the dynamic aspects of the ternary complex formation by means of site-directed spin labeling electron paramagnetic resonance (SDSL-EPR). Two semisynthetic CPT derivatives bearing the paramagnetic moiety were synthesized, and their biological activity was tested. A 22-mer DNA oligonucleotide sequence with high affinity cleavage site for Top1 was also synthesized. EPR experiments were carried out on modified CPT in the presence of DNA, of Top1, or of both. In the last case, a slow motion component in the EPR signal appeared, indicating the formation of the ternary complex. Deconvolution of the EPR spectrum allowed to obtain the relative drug amounts in the complex. It was also possible to demonstrate that the residence time of CPT "trapped" in the ternary complex is longer than hundreds of microseconds.

  DOI：

  10.1021/jm101232t
• 作为产物：
  描述：

  4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate 在 sodium tungstate 、 双氧水 、 ethylene diamine tetraacetic acid tetrasodium salt 、 sodium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 52.0h， 生成 3',5'-diisobutyryl-N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine
  参考文献：
  名称：

  Electron Paramagnetic Resonance (EPR) Study of Spin-Labeled Camptothecin Derivatives: A Different Look of the Ternary Complex

  摘要：

  Camptothecin (CPT) derivatives are clinically effective poisons of DNA topoisomerase I (Top 1) able to form a ternary complex with the Top1 DNA complex. The aim of this investigation was to examine the dynamic aspects of the ternary complex formation by means of site-directed spin labeling electron paramagnetic resonance (SDSL-EPR). Two semisynthetic CPT derivatives bearing the paramagnetic moiety were synthesized, and their biological activity was tested. A 22-mer DNA oligonucleotide sequence with high affinity cleavage site for Top1 was also synthesized. EPR experiments were carried out on modified CPT in the presence of DNA, of Top1, or of both. In the last case, a slow motion component in the EPR signal appeared, indicating the formation of the ternary complex. Deconvolution of the EPR spectrum allowed to obtain the relative drug amounts in the complex. It was also possible to demonstrate that the residence time of CPT "trapped" in the ternary complex is longer than hundreds of microseconds.

  DOI：

  10.1021/jm101232t