3,6,9,12,15,18,21,24,27,30,33,36-Dodecaoxaoctatetracontan-1-ol, hydrogen sulfate, sodium salt | 66161-57-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 3,6,9,12,15,18,21,24,27,30,33,36-Dodecaoxaoctatetracontan-1-ol, hydrogen sulfate, sodium salt
• 英文别名: sodium;2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl sulfate
• CAS: 66161-57-7
• 化学式: C₃₆H₇₃O₁₆S*Na
• 分子量: 817.022
• InChiKey: AGMRJQXCAJZJNK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  54
• 可旋转键数：
  48
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  四聚乙二醇单月桂醚 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 生成 3,6,9,12,15,18,21,24,27,30,33,36-Dodecaoxaoctatetracontan-1-ol, hydrogen sulfate, sodium salt
  参考文献：
  名称：

  Application of Monodisperse PEGs in Pharmaceutics: Monodisperse Polidocanols

  摘要：

  Polydisperse PEGs are ubiquitously used in pharmaceutical industry and biomedical research. However, the monodispersity in PEGs may play a role in the development of safe and effective PEGylated small molecular drugs. Here, to avoid the polydispersity in polidocanol, the active ingredient in a clinically used drug, a macro cyclic sulfate-based strategy for the efficient and scalable synthesis of monodisperse polidocanols, their sulfates, and their methylated derivatives, was developed. TLC and HPLC analysis indicated a complex mixture in regular polidocanol and high purifies in monodisperse polidocanols and their derivatives. Assay on HUVEC, L929, and HePG2. cells showed-that monodisperse polidocanols have much higher cytotoxicity and safety than that of regular polidocanol. It was found that the monodispersity of PEGs in polidocanols is crucial for achieving the optimal therapeutic results. Therefore, based on this case study, it would be beneficial to optimize PEGylated small molecular drugs with monodisperse PEGs in pharmaceutical research and development.

  DOI：

  10.1021/acs.molpharmaceut.7b00496

文献信息

• Application of Monodisperse PEGs in Pharmaceutics: Monodisperse Polidocanols
  作者：Zeqiong Yu、Shaowei Bo、Huiyuan Wang、Yu Li、Zhigang Yang、Yongzhuo Huang、Zhong-Xing Jiang

  DOI：10.1021/acs.molpharmaceut.7b00496

  日期：2017.10.2

  Polydisperse PEGs are ubiquitously used in pharmaceutical industry and biomedical research. However, the monodispersity in PEGs may play a role in the development of safe and effective PEGylated small molecular drugs. Here, to avoid the polydispersity in polidocanol, the active ingredient in a clinically used drug, a macro cyclic sulfate-based strategy for the efficient and scalable synthesis of monodisperse polidocanols, their sulfates, and their methylated derivatives, was developed. TLC and HPLC analysis indicated a complex mixture in regular polidocanol and high purifies in monodisperse polidocanols and their derivatives. Assay on HUVEC, L929, and HePG2. cells showed-that monodisperse polidocanols have much higher cytotoxicity and safety than that of regular polidocanol. It was found that the monodispersity of PEGs in polidocanols is crucial for achieving the optimal therapeutic results. Therefore, based on this case study, it would be beneficial to optimize PEGylated small molecular drugs with monodisperse PEGs in pharmaceutical research and development.