(2S,3R)-2-amino-18-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)octadeca-4,6,8-triyne-1,3-diol | 1449370-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: (2S,3R)-2-amino-18-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)octadeca-4,6,8-triyne-1,3-diol
• 英文别名: (2S,3R)-2-amino-18-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]octadeca-4,6,8-triyne-1,3-diol
• CAS: 1449370-24-4
• 化学式: C₂₄H₂₉N₅O₅
• 分子量: 467.525
• InChiKey: SJBZSWAXOJJTNS-SIKLNZKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl 4-((R)-1-acetoxy-16-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)hexadeca-2,4,6-triynyl)-2,2-dimethyloxazolidine-3-carboxylate 在 甲醇 、 potassium carbonate 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以69%的产率得到(2S,3R)-2-amino-18-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)octadeca-4,6,8-triyne-1,3-diol
  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

文献信息

• Synthesis and Biological Evaluation of a Polyyne-Containing Sphingoid Base Probe as a Chemical Tool
  作者：Yun Mi Lee、Chaemin Lim、Hun Seok Lee、Young Kee Shin、Kyong-Oh Shin、Yong-Moon Lee、Sanghee Kim

  DOI：10.1021/bc300684q

  日期：2013.8.21

  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.