N-(cholesteryloxycarbonyl)aza-15-crown-5 | 108694-78-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-(cholesteryloxycarbonyl)aza-15-crown-5
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 1,4,7,10-tetraoxa-13-azacyclopentadecane-13-carboxylate
• CAS: 108694-78-6
• 化学式: C₃₈H₆₅NO₆
• 分子量: 631.937
• InChiKey: QVFILOWCPWOTEM-HMVYLTCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  胆固醇甲酰氯 、 氮杂-15-冠醚-5 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到N-(cholesteryloxycarbonyl)aza-15-crown-5
  参考文献：
  名称：

  Enhancement of transfection activity in HEK293 cells by lipoplexes containing cholesteryl nitrogen-pivoted aza-crown ethers

  摘要：

  Two nitrogen-pivoted aza-crown ethers (aza-CEs) linked to the cholesteryl-fused ring system N-(cholesteryloxycarbonyl)aza-15-crown-5 and N-(cholesteryloxycarbonyl)aza-18-crown-6 have been incorporated into cationic liposomes containing the cytofectin 3 beta[N-(N',N'-dimethylaminopropane) carbamoyl] cholesterol (Chol-T) and the neutral co-lipid dioleoylphosphatidylethanolamine. These novel liposomes form stable complexes with plasmid DNA and afford it good protection from serum nuclease digestion. Ethidium displacement studies suggest that the DNA is more loosely packed in aza-CE containing lipoplexes, a finding which is supported by band shift assays that reveal N/P end point ratios of 2:1, 3:1 and 3.5:1 for Chol-T control liposomes, aza-15-crown-5 and aza-18-crown-6 containing liposomes, respectively. The transfection activities of crown ether-containing lipoplex formulations in the human embryonic kidney cell line HEK293 are twofold greater than those achieved by Chol-T lipoplexes not containing the aza-CEs. This observation may be attributable to the more loosely packed DNA, which facilitates disassembly, and to endosomal perturbations caused by macrocycle entrapped cations.

  DOI：

  10.1007/s00044-012-0252-2

文献信息

• GOKEL, GEORGE W.
  作者：GOKEL, GEORGE W.

  DOI：——

  日期：——