| 1142172-97-1

• 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
• CAS: 1142172-97-1
• 化学式: C₃₅H₅₅NO₄
• 分子量: 553.826
• InChiKey: LUYSVLMCADGARR-VOXPRPGQSA-N

物化性质

• 沸点：
  667.0±55.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 palladium dihydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、310.27 kPa 条件下， 反应 8.0h， 生成 7α-(7-aminoheptyl)-17β-estradiol 、
  参考文献：
  名称：

  Chemical synthesis and biochemical characterization of a biotinylated derivative of 17β-estradiol with a long side chain covalently attached to its C-7α position

  摘要：

  High-affinity biotinylated derivatives of 17 beta-estradiol (E(2)) are of value for isolation of various estrogen-binding proteins (including estrogen receptors) and also for studying protein-protein interactions involving these proteins. In this study, we developed a simplified route for the chemical synthesis of a biotinylated derivative of E2 (compound 7) with a side chain attached to its C-7 alpha position. Compound 7, i.e., 7 alpha-{7-[8-(biotinamido)-octanamido]-heptyl}-estradiol, could be readily synthesized from 6-keto-estradiol-3,17 beta-di-tetrahydropyranyl ether (compound 2, which can be prepared from E2), With a final yield of 36%. In vitro receptor-binding assay confirmed that the synthesized affinity ligand has a high binding affinity for both human estrogen receptor alpha and beta. When the affinity ligand (compound 7) was immobilized with avidin on an affinity column, it effectively bound human estrogen receptor, and the receptor protein could be selectively eluted with a biotin-containing buffer. Using the same affinity ligand, prolyl 4-hydroxylase beta-subunit (also known as protein disulfide isomerase) was identified as one of the high-affinity E(2)-binding proteins in the whole cytosolic protein mixture prepared from MCF-7 human breast cancer cells. Computational molecular modeling analysis showed that compound 7 can bind to human estrogen receptor alpha in a similar manner as ICI-182,780 and raloxifene, and their binding energy values are also similar. (C) 2008 Elsevier Inc. All fights reserved.

  DOI：

  10.1016/j.steroids.2008.06.004