1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-4-nitroimidazole | 52290-63-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-4-nitroimidazole
• 英文别名: (1S)-O²,O³-isopropylidene-1-(4-nitro-imidazol-1-yl)-D-1,4-anhydro-ribitol；[(3aR,4S,6R,6aR)-2,2-dimethyl-4-(4-nitroimidazol-1-yl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 52290-63-8
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: KOXSMZWKTLPOHI-QQRDMOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-4-nitroimidazole 在 4-二甲氨基吡啶 、 水 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 1-(2,3-dioleyl-5-trimethylammonium-α-D-ribofuranosyl)-4-nitroimidazole tosylate
  参考文献：
  名称：

  Cationic Nucleoside Lipids Derived from Universal Bases: A Rational Approach for siRNA Transfection

  摘要：

  Cationic nucleoside lipids (CNLs) derived from 5-nitroindole and 4-nitroimidazole bases were prepared from D-ribose by using a straightforward chemical synthesis. TEM experiments indicate that these amphiphilic molecules self-assemble to form supramolecular organizations in aqueous solutions. Electrophoresis and standard ethidium bromide (EB) fluorescence displacement assay shows that CNLs are able to bind siRNA. We demonstrated that both the nature of the universal bases and the stereochemistry of the anomeric position (alpha, beta) have an impact on the CNLs-siRNA complex formation. Correlations among chemical structure, stereochemistry, siRNA knockdown effect, and binding affinities for all the compounds were shown and analyzed with a simple molecular modeling study. The best binding affinities for siRNA were found for the beta anomer of the 5-nitroindole CNL which exhibits protein knockdown activity similar to the standard siPORT NeoFX positive control. It is noteworthy that no significant cytotoxicity at the tested concentration was observed for the novel CNLs.

  DOI：

  10.1021/bc100005k
• 作为产物：
  描述：

  5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 在 四氯化碳 、 六甲基磷酰三胺 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 40.5h， 生成 1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-4-nitroimidazole
  参考文献：
  名称：

  Cationic Nucleoside Lipids Derived from Universal Bases: A Rational Approach for siRNA Transfection

  摘要：

  Cationic nucleoside lipids (CNLs) derived from 5-nitroindole and 4-nitroimidazole bases were prepared from D-ribose by using a straightforward chemical synthesis. TEM experiments indicate that these amphiphilic molecules self-assemble to form supramolecular organizations in aqueous solutions. Electrophoresis and standard ethidium bromide (EB) fluorescence displacement assay shows that CNLs are able to bind siRNA. We demonstrated that both the nature of the universal bases and the stereochemistry of the anomeric position (alpha, beta) have an impact on the CNLs-siRNA complex formation. Correlations among chemical structure, stereochemistry, siRNA knockdown effect, and binding affinities for all the compounds were shown and analyzed with a simple molecular modeling study. The best binding affinities for siRNA were found for the beta anomer of the 5-nitroindole CNL which exhibits protein knockdown activity similar to the standard siPORT NeoFX positive control. It is noteworthy that no significant cytotoxicity at the tested concentration was observed for the novel CNLs.

  DOI：

  10.1021/bc100005k

文献信息

• Cationic Nucleoside Lipids Derived from Universal Bases: A Rational Approach for siRNA Transfection
  作者：Claire Ceballos、Salim Khiati、Carla A. H. Prata、Xiao-Xiang Zhang、Suzanne Giorgio、Philippe Marsal、Mark W. Grinstaff、Philippe Barthélémy、Michel Camplo

  DOI：10.1021/bc100005k

  日期：2010.6.16

  Cationic nucleoside lipids (CNLs) derived from 5-nitroindole and 4-nitroimidazole bases were prepared from D-ribose by using a straightforward chemical synthesis. TEM experiments indicate that these amphiphilic molecules self-assemble to form supramolecular organizations in aqueous solutions. Electrophoresis and standard ethidium bromide (EB) fluorescence displacement assay shows that CNLs are able to bind siRNA. We demonstrated that both the nature of the universal bases and the stereochemistry of the anomeric position (alpha, beta) have an impact on the CNLs-siRNA complex formation. Correlations among chemical structure, stereochemistry, siRNA knockdown effect, and binding affinities for all the compounds were shown and analyzed with a simple molecular modeling study. The best binding affinities for siRNA were found for the beta anomer of the 5-nitroindole CNL which exhibits protein knockdown activity similar to the standard siPORT NeoFX positive control. It is noteworthy that no significant cytotoxicity at the tested concentration was observed for the novel CNLs.