alpha-生育胺 | 7666-00-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: alpha-生育胺
• 英文名称: α-tocopheramine
• 英文别名: all-rac-tocopheramine；2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ylamine；(+/-)-6-Amino-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-tridecyl)-chroman; α-Tocopherylamin；α-Tocopheramin；3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-amine；2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-amine
• CAS: 7666-00-4
• 化学式: C₂₉H₅₁NO
• 分子量: 429.73
• InChiKey: VHDHAAWAAIWBBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氟琥珀酸酐 、 alpha-生育胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,3,3-tetrafluoro-4-oxo-4-((2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-yl)amino)butanoic acid
  参考文献：
  名称：

  维生素C衍生化合物在小鼠C6胶质瘤细胞中的抗癌活性

  摘要：

  合成了一个小型维生素E类似物文库，该文库具有一个通过酰胺，醚或酯键与苯并二氢吡喃核连接的游离酸基，并评估了它们对C6鼠神经胶质瘤细胞的抗癌能力。几种化合物显示出比替莫唑胺更好的抗肿瘤活性，替莫唑胺是治疗神经胶质瘤最常用的药物。

  DOI：

  10.1002/cmdc.200900492

文献信息

• Tocopheramine succinate and tocopheryl succinate: Mechanism of mitochondrial inhibition and superoxide radical production
  作者：Julia Gruber、Katrin Staniek、Christopher Krewenka、Rudolf Moldzio、Anjan Patel、Stefan Böhmdorfer、Thomas Rosenau、Lars Gille

  DOI：10.1016/j.bmc.2013.12.036

  日期：2014.1

  Tocopherols (TOH) are lipophilic antioxidants which require the phenolic OH group for their redox activity. In contrast, non-redox active esters of alpha-TOH with succinate (alpha-TOS) were shown to possess proapoptotic activity in cancer cells. It was suggested that this activity is mediated via mitochondrial inhibition with subsequent O-2(center dot-) production triggering apoptosis and that the modification of the linker between the succinate and the lipophilic chroman may modulate this activity. However, the specific mechanism and the influence of the linker are not clear yet on the level of the mitochondrial respiratory chain. Therefore, this study systematically compared the effects of alpha-TOH acetate (alpha-TOA), alpha-TOS and alpha-tocopheramine succinate (alpha-TNS) in cells and submitochondrial particles (SMP). The results showed that not all cancer cell lines are highly sensitive to alpha-TOS and alpha-TNS. In HeLa cells alpha-TNS did more effectively reduce cell viability than alpha-TOS. The complex I activity of SMP was little affected by alpha-TNS and alpha-TOS while the complex II activity was much more inhibited (IC50 = 42 +/- 8 mu M alpha-TOS, 106 +/- 8 mu M alpha-TNS, respectively) than by alpha-TOA (IC50 > 1000 mu M). Also the complex III activity was inhibited by alpha-TNS (IC50 = 137 +/- 6 lM) and alpha-TOS (IC50 = 315 +/- 23 lM). Oxygen consumption of NADH-or succinate-respiring SMP, involving the whole electron transfer machinery, was dose-dependently decreased by alpha-TOS and alpha-TNS, but only marginal effects were observed in the presence of alpha-TOA. In contrast to the similar inhibition pattern of alpha-TOS and alpha-TNS, only alpha-TOS triggered O-2 center dot- 2 formation in succinate- and NADH-respiring SMP. Inhibitor studies excluded complex I as O-2(center dot-) 2 source and suggested an involvement of complex III in O-2(center dot-) 2 production. In cancer cells only alpha-TOS was reproducibly able to increase O-2(center dot-) 2 levels above the background level but neither alpha-TNS nor alpha-TOA. Furthermore, the stability of alpha-TNS in liver homogenates was significantly lower than that of alpha-TOS. In conclusion, this suggests that alpha-TNS although it has a structure similar to alpha-TOS is not acting via the same mechanism and that for alpha-TOS not only complex II but also complex III interactions are involved. (C) 2013 Elsevier Ltd. All rights reserved.