7-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-aminyl)iminomethyl camptothecin | 1263701-15-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: 7-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-aminyl)iminomethyl camptothecin
• CAS: 1263701-15-0
• 化学式: C₃₀H₃₅N₄O₅
• 分子量: 531.632
• InChiKey: DDAMHYIMJXOLPS-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基-4-哌啶酮肟 在 sodium tungstate 、 lithium aluminium tetrahydride 、 双氧水 、 ethylene diamine tetraacetic acid tetrasodium salt 、 sodium carbonate 、 potassium hydroxide 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 7-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-aminyl)iminomethyl camptothecin
  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