2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol | 57434-13-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol
• CAS: 57434-13-6
• 化学式: C₃₀H₆₂O₆
• 分子量: 518.819
• InChiKey: CZJFAXLNLWNETL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  36.0
• 可旋转键数：
  21.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 tris(benzyltriazolylmethyl)amine 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 24.25h， 生成 N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-4-[1-[6-[14-[6-[4-[4-[[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]amino]-4-oxobutyl]triazol-1-yl]hexoxy]-7,11,18,22-tetrahydroxy-2,6,10,15,19,23-hexamethyltetracosan-3-yl]oxyhexyl]triazol-4-yl]butanamide
  参考文献：
  名称：

  角鲨烯衍生的生物活性肽柔性接头。

  摘要：

  从角鲨烯的两个步骤合成了带有末端叠氮化物功能的柔性接头的区域化学和立体化学混合物，并用于连接两个高亲和力NDP-alpha-MSH配体或两个低亲和力MSH（4）配体。所述配体使用N-羟基琥珀酰亚胺基5-己酸酯在N-末端酰化，随后通过铜催化的叠氮化物和炔烃部分的“点击” 3 + 2环化连接至连接体。体外生物学评估表明，相对于相应的亲本配体，大多数接头-配体组合对人黑皮质素4受体的结合亲和力并未降低。包含低亲和力配体MSH（4）的二聚体构建体观察到统计和合作结合效果，但对于二聚体NDP-alpha-MSH构建体则没有观察到，

  DOI：

  10.1016/j.bmcl.2007.04.001
• 作为产物：
  描述：

  角鲨烯 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 以67%的产率得到2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol
  参考文献：
  名称：

  角鲨烯衍生的生物活性肽柔性接头。

  摘要：

  从角鲨烯的两个步骤合成了带有末端叠氮化物功能的柔性接头的区域化学和立体化学混合物，并用于连接两个高亲和力NDP-alpha-MSH配体或两个低亲和力MSH（4）配体。所述配体使用N-羟基琥珀酰亚胺基5-己酸酯在N-末端酰化，随后通过铜催化的叠氮化物和炔烃部分的“点击” 3 + 2环化连接至连接体。体外生物学评估表明，相对于相应的亲本配体，大多数接头-配体组合对人黑皮质素4受体的结合亲和力并未降低。包含低亲和力配体MSH（4）的二聚体构建体观察到统计和合作结合效果，但对于二聚体NDP-alpha-MSH构建体则没有观察到，

  DOI：

  10.1016/j.bmcl.2007.04.001

文献信息

• Synthesis and Characterization of Time-resolved Fluorescence Probes for Evaluation of Competitive Binding to Melanocortin Receptors
  作者：Ramesh Alleti、Josef Vagner、Dilani Chathurika Dehigaspitiya、Valerie E. Moberg、N.G.R.D. Elshan、Narges K. Tafreshi、Nabila Brabez、Craig S. Weber、Ronald M. Lynch、Victor J. Hruby、Robert J. Gillies、David L. Morse、Eugene A. Mash

  DOI：10.1016/j.bmc.2013.06.052

  日期：2013.9

  Probes for use in time-resolved fluorescence competitive binding assays at melanocortin receptors based on the parental ligands MSH(4), MSH(7), and NDP-alpha-MSH were prepared by solid phase synthesis methods, purified, and characterized. The saturation binding of these probes was studied using HEK-293 cells engineered to overexpress the human melanocortin 4 receptor (hMC4R) as well as the human cholecystokinin 2 receptor (hCCK2R). The ratios of non-specific binding to total binding approached unity at high concentrations for each probe. At low probe concentrations, receptor-mediated binding and uptake was discernable, and so probe concentrations were kept as low as possible in determining K-d values. The Eu-DTPA-PEGO-MSH(4) probe exhibited low specific binding relative to non-specific binding, even at low nanomolar concentrations, and was deemed unsuitable for use in competition binding assays. The Eu-DTPA-PEGO probes based on MSH(7) and NDP-alpha-MSH exhibited K-d values of 27 +/- 3.9 nM and 4.2 +/- 0.48 nM, respectively, for binding with hMC4R. These probes were employed in competitive binding assays to characterize the interactions of hMC4R with monovalent and divalent MSH(4), MSH(7), and NDP-alpha-MSH constructs derived from squalene. Results from assays with both probes reflected only statistical enhancements, suggesting improper ligand spacing on the squalene scaffold for the divalent constructs. The K-i values from competitive binding assays that employed the MSH(7)-based probe were generally lower than the K-i values obtained when the probe based on NDP-alpha-MSH was employed, which is consistent with the greater potency of the latter probe. The probe based on MSH(7) was also competed with monovalent, divalent, and trivalent MSH(4) constructs that previously demonstrated multivalent binding in competitive binding assays against a variant of the probe based on NDP-alpha-MSH. Results from these assays confirm multivalent binding, but suggest a more modest increase in avidity for these MSH(4) constructs than was previously reported. (C) 2013 Elsevier Ltd. All rights reserved.