N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine | 159550-18-2

• 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: N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine
• 英文别名: 4-N-TEMPO-2'-deoxycytidine
• CAS: 159550-18-2
• 化学式: C₁₈H₃₁N₄O₅
• 分子量: 383.468
• InChiKey: HBQNOSJHYPWNJT-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  119.75
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以81%的产率得到5'-dimethoxytrityl-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：

  tempamine 在 ammonium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 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

文献信息

• Identification of Single-Base Mismatches in Duplex DNA by EPR Spectroscopy
  作者：Pavol Cekan、Snorri Th. Sigurdsson

  DOI：10.1021/ja905623k

  日期：2009.12.23

  The spin-labeled nucleoside C-T, containing 2,2,6,6-tetramethyipiperidine-l-oxyL (TEMPO) conjugated to the exocyclic amino group of C, was used to detect single-base mismatches in duplex DNA for the first time by electron paramagnetic resonance (EPR) spectroscopy. Furthermore, the EPR spectra of the fully base-paired duplex (TC-G) and the mismatches (C-T-A, C-T-C, and C-T-T) were significantly different, showing that the probe can identify its base-pairing partner in DNA. At lower pH, the mobility of C-T-A, TC.C, and C-T-T became higher, consistent with increased protonation of the mismatched pairs. Although the duplexes for each of the three flanking sequences tested gave distinguishable EPR signals, the best discrimination between base pairs was achieved for sequences containing a flanking A-T base pair, in particular 5'-d(G(T)CA) and 5'-d(IICA). This study shows that minor structural variations in nucleic acids can be detected with carefully chosen spin [abets in conjunction with EPR spectroscopy.