uridine acetonide phosphatidylcholine | 725693-25-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: uridine acetonide phosphatidylcholine
• CAS: 725693-25-4
• 化学式: C₁₇H₂₈N₃O₉P
• 分子量: 449.398
• InChiKey: IXOUFTGGOMLGFB-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  141.14
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  uridine acetonide phosphatidylcholine 在 盐酸 、 4-二甲氨基吡啶 、 甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 1,2-dioleyl-uridino-phosphocholine
  参考文献：
  名称：

  Supramolecular Assemblies of Nucleoside Phosphocholine Amphiphiles

  摘要：

  A family of new uridine phosphocholine amphiphiles that were prepared using a convenient four-step synthetic route is described. Physicochemical studies (differential scanning calorimetry, small-angle X-ray scattering, UV-vis and circular dichroism spectroscopies, light microscopy, transmission electronic microscopy, and scanning electron microscopy) show that these amphiphiles spontaneously assemble into supramolecular structures including vesicles, fibers, hydrogels, and organogels. In aqueous solution, the amphiphiles possessing saturated alkyl chains self-assemble into DNA-like helical fibers in the crystalline state below T-m and compact bilayers above the melting temperature (T-m). The transition from bilayers to fibers is thermally reversible. Above a threshold concentration (>6% w/w), a hydrogel is formed due to an entangled network of the fibers. A therapeutic agent such as DNA can be entrapped within the hydrogel structure. In addition to forming bilayer vesicles and hydrogels in aqueous solution, these nucleoside amphiphiles also form organogels in cyclohexane above T, Scanning electron microscopy shows a continuous multilamellar phase in the organogels.

  DOI：

  10.1021/ja039597j
• 作为产物：
  描述：

  2’,3’邻异亚丙基尿苷 在 TEA 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 63.0h， 生成 uridine acetonide phosphatidylcholine
  参考文献：
  名称：

  Supramolecular Assemblies of Nucleoside Phosphocholine Amphiphiles

  摘要：

  A family of new uridine phosphocholine amphiphiles that were prepared using a convenient four-step synthetic route is described. Physicochemical studies (differential scanning calorimetry, small-angle X-ray scattering, UV-vis and circular dichroism spectroscopies, light microscopy, transmission electronic microscopy, and scanning electron microscopy) show that these amphiphiles spontaneously assemble into supramolecular structures including vesicles, fibers, hydrogels, and organogels. In aqueous solution, the amphiphiles possessing saturated alkyl chains self-assemble into DNA-like helical fibers in the crystalline state below T-m and compact bilayers above the melting temperature (T-m). The transition from bilayers to fibers is thermally reversible. Above a threshold concentration (>6% w/w), a hydrogel is formed due to an entangled network of the fibers. A therapeutic agent such as DNA can be entrapped within the hydrogel structure. In addition to forming bilayer vesicles and hydrogels in aqueous solution, these nucleoside amphiphiles also form organogels in cyclohexane above T, Scanning electron microscopy shows a continuous multilamellar phase in the organogels.

  DOI：

  10.1021/ja039597j

文献信息

• Functional synthetic molecules and macromolecules for gene delivery
  申请人：Grinstaff W. Mark

  公开号：US20060241071A1

  公开（公告）日：2006-10-26

  The present invention describes a synthetic non-viral vector composition for gene therapy and the use of such compositions for in vitro, ex vivo and/or in vivo transfer of genetic material. The invention proposes a pharmaceutical composition containing 1) a non-cationic amphiphilic molecule or macromolecule and its use for delivery of nucleic acids or 2) a cationic amphiphilic molecule or macromolecule that transforms from a cationic entity to an anionic, neutral, or zwitterionic entity by a chemical, photochemical, or biological reaction and its use for delivery of nucleic acids. Moreover this invention describes the use of these non-viral vector compositions in conjunction with a surface to mediate the delivery of nucleic acids. An additional embodiment is the formation of a hydrogel with these compositions and the use of this hydrogel for the delivery of genetic material. A further embodiment of this invention is the use of a change in ionic strength for the delivery of genetic material.

  本发明描述了一种用于基因治疗的合成非病毒载体组合，以及这种组合在体外、体内和/或体外转移遗传物质中的应用。该发明提出了一种包含1）非阳离子性两性分子或大分子的药物组合物及其用于传递核酸或2）由化学、光化学或生物反应从阳离子实体转变为阴离子、中性或带电离子实体的两性阳离子分子或大分子的药物组合物，以及其用于核酸传递。此外，本发明描述了这些非病毒载体组合物与表面结合以介导核酸传递的应用。另一实施例是使用这些组合物形成水凝胶，并利用该水凝胶传递遗传物质。本发明的另一实施例是利用离子强度变化传递遗传物质。
• Supramolecularly engineered phospholipids constructed by nucleobase molecular recognition: upgraded generation of phospholipids for drug delivery
  作者：Dali Wang、Chunlai Tu、Yue Su、Chuan Zhang、Udo Greiser、Xinyuan Zhu、Deyue Yan、Wenxin Wang

  DOI：10.1039/c5sc01188d

  日期：——

  Supramolecularly engineered phospholipids and liposomes based on complementary hydrogen bonding of nucleosides have been developed.

  基于互补的核苷酸氢键的超分子工程磷脂和脂质体已经被开发出来。