11-(triisopropylsilyl)undec-10-ynoic acid | 1449370-27-7

• 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: 11-(triisopropylsilyl)undec-10-ynoic acid
• CAS: 1449370-27-7
• 化学式: C₂₀H₃₈O₂Si
• 分子量: 338.606
• InChiKey: DEZPVPMKDFWPLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  11-(triisopropylsilyl)undec-10-ynoic acid 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 11-(triisopropylsilyl)undec-10-yn-1-amine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Polyyne-Containing Sphingoid Base Probe as a Chemical Tool

  摘要：

  The sphingolipid metabolites have emerged as a starting point for the development of novel therapeutics for many diseases. However, details of the functions and mechanisms of sphingolipids remain unknown. To better understand the roles of sphingolipids, chemical tools with unique biological and physicochemical properties are needed. In this regard, we previously reported the synthesis of sphingoid base analogues in which the carbon chains are restricted by triple bonds. Here, we have conjugated a fluorescent dye to the polyyne analogues of the sphingoid bases to generate optical probes. Like the parent polyyne-containing sphingoid base, the 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)-labeled triyne-sphingosine inhibited cancer cell growth far more effectively than did the corresponding sphingosine. NBD-triyne-sphingosine was rapidly incorporated into the cells and displayed broad cytoplasmic distribution. According to the results of a flow cytometric analysis, cancer cells fed with NBD-triyne-sphingosine showed significantly increased fluorescence intensity compared with the NBD-sphingosine treated cells. The metabolism of NBD-triyne-sphingosine was somewhat different from that of NBD-sphingosine. These results indicated that the incorporated rigid polyyne moiety in the sphingoid base altered the physicochemical properties of the sphingolipid, thereby affecting its biological behavior. The higher antiproliferative activity in the SRB assay and the significantly higher fluorescence intensity observed in the flow cytometric analysis are some of the interesting and distinct aspects of NBD-triyne-sphingosine compared to standard NBD-sphingosine probes. Thus, it is believed that the fluorescently labeled polyyne-containing sphingoid base developed in this study will be a useful chemical tool in sphingolipid research.

  DOI：

  10.1021/bc300684q
• 作为产物：
  描述：

  10-十一碳炔酸 、 三异丙基氯硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以40%的产率得到11-(triisopropylsilyl)undec-10-ynoic acid
  参考文献：
  名称：

  First access to a mycolic acid-based bioorthogonal reporter for the study of the mycomembrane and mycoloyltransferases in Corynebacteria

  摘要：

  在这项研究中，我们描述了一种基于炔基的海藻糖单酰酰基探针的合成，紧密模拟了肉豆蔻酸的复杂模式，并且它在研究肉桂酸酰基转移酶和肉豆蔻酸膜中的应用。该研究针对科林氏菌。

  DOI：

  10.1039/c9cc05754d