24-O-biotinylbullatacin

• 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: 24-O-biotinylbullatacin
• 英文别名: [(1S)-1-[(2R,5R)-5-[(2R,5R)-5-[(1R,12R)-1,12-dihydroxy-13-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tridecyl]oxolan-2-yl]oxolan-2-yl]undecyl] 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate
• 化学式: C₄₇H₈₀N₂O₉S
• 分子量: 849.226
• InChiKey: WAHXSZQNTRVZEB-SPUFHOSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  59
• 可旋转键数：
  32
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (5S)-3-[(2R,13R)-2,13-二羟基-13-{(2R,2'R,5'R)-5'-[(1S)-1-羟基十一烷基]八氢-2,2'-联呋喃-5-基}十三烷基]-5-甲基呋喃-2(5H)-酮 、 D-生物素 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以8.4%的产率得到4-O-biotinylbullatacin
  参考文献：
  名称：

  Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins

  摘要：

  Nineteen biotinylated squamocin/bullatacin derivatives have been synthesized for targeted delivery to biotin receptor overexpressed tumor cells. Most biotinylated squamocin and bullatacin derivatives show similar in vitro cytotoxicity against the biotin receptor non-overexpressed L1210 cells as squamocin and bullatacin, respectively, while against biotin receptor overexpressed 4T1 and P815 tumor cells, several derivatives show significantly higher potency and better selectivity. Among all the synthesized compounds, 15,28-di-O-(6-biotinylamidohexanoyl)squamocin (16) is the most potent, which is 10 and 26 times more active than squamocin against 4T1 and P815 cells, respectively. Compound 16 also appears to be six and fifteen times more selective than squamocin towards 4T1 and P815 cells, respectively, against L1210 cells. The structure activity relationship analysis has revealed that the preferred site for bio-tinylation is different for squamocin and bullatacin, and it also depends on whether a linking spacer is present. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.012

文献信息

• Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins
  作者：Jing-Fang Shi、Ping Wu、Zi-Hua Jiang、Xiao-Yi Wei

  DOI：10.1016/j.ejmech.2013.11.012

  日期：2014.1

  Nineteen biotinylated squamocin/bullatacin derivatives have been synthesized for targeted delivery to biotin receptor overexpressed tumor cells. Most biotinylated squamocin and bullatacin derivatives show similar in vitro cytotoxicity against the biotin receptor non-overexpressed L1210 cells as squamocin and bullatacin, respectively, while against biotin receptor overexpressed 4T1 and P815 tumor cells, several derivatives show significantly higher potency and better selectivity. Among all the synthesized compounds, 15,28-di-O-(6-biotinylamidohexanoyl)squamocin (16) is the most potent, which is 10 and 26 times more active than squamocin against 4T1 and P815 cells, respectively. Compound 16 also appears to be six and fifteen times more selective than squamocin towards 4T1 and P815 cells, respectively, against L1210 cells. The structure activity relationship analysis has revealed that the preferred site for bio-tinylation is different for squamocin and bullatacin, and it also depends on whether a linking spacer is present. (C) 2013 Elsevier Masson SAS. All rights reserved.