4-N,N-dihexadecylamino-4'-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}chalcone | 497165-74-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-N,N-dihexadecylamino-4'-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}chalcone
• 英文别名: (E)-3-[4-(dihexadecylamino)phenyl]-1-[4-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]phenyl]prop-2-en-1-one
• CAS: 497165-74-9
• 化学式: C₅₃H₈₉NO₅
• 分子量: 820.293
• InChiKey: XVPXYPJISGWWRI-BZDUDJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.3
• 重原子数：
  59
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-N,N-dihexadecylamino-4'-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}chalcone 在 咪唑 、 四氯化碳 、 三苯基膦 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 51.0h， 生成 4-N,N-dihexadecylamino-4'-{2-[2-(2-iodoethoxy)ethoxy]ethoxy}chalcone
  参考文献：
  名称：

  Micelles of Lipid−Oligonucleotide Conjugates:  Implications for Membrane Anchoring and Base Pairing

  摘要：

  This report examines the organization properties of new fluorescent DNA-lipids, either alone in water or in interaction with 1-otyl-beta-D-glucopyranoside micelles or egg phosphatidylcholine vesicles. We first describe the design and the syntheses of the conjugates. Then, we use UV-Vis absorption, steady-state fluorescence emission, electron microscopy, and fluorescence correlation spectroscopy after two-photon excitation to show that these DNA-lipids form spherical micelles in aqueous solution and incorporate much better in micelles than in vesicles. We also investigate the significance of the lipophilic chains of these DNA-lipids on the melting behavior of the double-stranded hybrids: in water melting curves are broadened whereas in amphiphilic assemblies duplexes melt as the unconjugated controls. This work is expected to be useful for improving the rational design of antisense medicines.

  DOI：

  10.1021/jp031188m
• 作为产物：
  描述：

  N,N-dihexadecylphenylamine 在 氢氧化钾 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 4-N,N-dihexadecylamino-4'-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}chalcone
  参考文献：
  名称：

  Micelles of Lipid−Oligonucleotide Conjugates:  Implications for Membrane Anchoring and Base Pairing

  摘要：

  This report examines the organization properties of new fluorescent DNA-lipids, either alone in water or in interaction with 1-otyl-beta-D-glucopyranoside micelles or egg phosphatidylcholine vesicles. We first describe the design and the syntheses of the conjugates. Then, we use UV-Vis absorption, steady-state fluorescence emission, electron microscopy, and fluorescence correlation spectroscopy after two-photon excitation to show that these DNA-lipids form spherical micelles in aqueous solution and incorporate much better in micelles than in vesicles. We also investigate the significance of the lipophilic chains of these DNA-lipids on the melting behavior of the double-stranded hybrids: in water melting curves are broadened whereas in amphiphilic assemblies duplexes melt as the unconjugated controls. This work is expected to be useful for improving the rational design of antisense medicines.

  DOI：

  10.1021/jp031188m

文献信息

• Micelles of Lipid−Oligonucleotide Conjugates:  Implications for Membrane Anchoring and Base Pairing
  作者：C. Gosse、A. Boutorine、I. Aujard、M. Chami、A. Kononov、E. Cogné-Laage、J.-F. Allemand、J. Li、L. Jullien

  DOI：10.1021/jp031188m

  日期：2004.5.1

  This report examines the organization properties of new fluorescent DNA-lipids, either alone in water or in interaction with 1-otyl-beta-D-glucopyranoside micelles or egg phosphatidylcholine vesicles. We first describe the design and the syntheses of the conjugates. Then, we use UV-Vis absorption, steady-state fluorescence emission, electron microscopy, and fluorescence correlation spectroscopy after two-photon excitation to show that these DNA-lipids form spherical micelles in aqueous solution and incorporate much better in micelles than in vesicles. We also investigate the significance of the lipophilic chains of these DNA-lipids on the melting behavior of the double-stranded hybrids: in water melting curves are broadened whereas in amphiphilic assemblies duplexes melt as the unconjugated controls. This work is expected to be useful for improving the rational design of antisense medicines.