[10-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)decyl] triphenylphosphonium bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [10-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)decyl] triphenylphosphonium bromide
• 英文别名: 10-(3-Methyl-1,4-dioxonaphthalen-2-yl)decyl-triphenylphosphanium;bromide；10-(3-methyl-1,4-dioxonaphthalen-2-yl)decyl-triphenylphosphanium;bromide
• 化学式: Br*C₃₉H₄₂O₂P
• 分子量: 653.639
• InChiKey: FLAZMZZMUDGOBC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  11-溴十一酸 在 ammonium peroxydisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 [10-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)decyl] triphenylphosphonium bromide
  参考文献：
  名称：

  Phosphonium lipocations as antiparasitic agents

  摘要：

  Phosphonium lipocations were synthesized and evaluated for inhibition of the development of Plasmodium falciparum and Trypanosoma cruzi, etiological agents of malaria and Chagas disease, respectively. Optimal phthalimides and 1,4-naphthoquinone-based lipocations were active in vitro at mid-high nM concentrations against P. falciparum and low mu M concentrations against T. cruzi. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.02.045

文献信息

• Mitochondria-targeted 1,4-naphthoquinone (SkQN) is a powerful prooxidant and cytotoxic agent
  作者：Tatyana N. Goleva、Konstantin G. Lyamzaev、Anton G. Rogov、Ljudmila S. Khailova、Khoren K. Epremyan、Galina P. Shumakovich、Lidia V. Domnina、Olga Yu. Ivanova、Natalia V. Marmiy、Tatiana V. Zinevich、Dmitry S. Esipov、Renata A. Zvyagilskaya、Vladimir P. Skulachev、Boris V. Chernyak

  DOI：10.1016/j.bbabio.2020.148210

  日期：2020.8

  membrane potential, and blocked ATP synthesis, being more efficient uncoupler of oxidative phosphorylation than MitoK3. In yeast cells, SkQN decreased cell viability and induced oxidative stress and mitochondrial fragmentation. SkQN killed various tumor cells much more efficiently than MitoK3. Since many tumors are characterized by increased oxidative stress, the use of new mitochondria-targeted prooxidants

  由于氧化还原活性化合物的靶向递送，线粒体中活性氧物质（ROS）的产量增加可能在研究线粒体ROS对细胞功能的调节中有用。最近，合成了甲萘醌的线粒体靶向衍生物（MitoK3）。但是，MitoK3在发挥明显的细胞毒性作用时，并未诱导线粒体ROS的产生和脂质过氧化。在这里，我们合成了与烷基三苯基phosph（SkQN）共轭的1，4-萘醌作为线粒体靶向的氧化剂的原型，并研究了其氧化还原特性，与分离的线粒体，酵母细胞和各种人类细胞系的相互作用。根据电化学测量，SkQN是更具活性的氧化还原剂，由于萘醌环中不存在甲基，作为亲电子试剂的反应性比MitoK3高。SkQN（而非MitoK3）刺激了孤立的线粒体中过氧化氢的产生。在低浓度下，SkQN刺激线粒体的状态4呼吸，降低膜电位并阻止ATP合成，是比MitoK3更有效的氧化磷酸化解偶联剂。在酵母细胞中，SkQN降低细胞活力并诱导氧化应激和线粒体片段化。SkQN
• Phosphonium lipocations as antiparasitic agents
  作者：Timothy E. Long、Xiao Lu、Melina Galizzi、Roberto Docampo、Jiri Gut、Philip J. Rosenthal

  DOI：10.1016/j.bmcl.2012.02.045

  日期：2012.4

  Phosphonium lipocations were synthesized and evaluated for inhibition of the development of Plasmodium falciparum and Trypanosoma cruzi, etiological agents of malaria and Chagas disease, respectively. Optimal phthalimides and 1,4-naphthoquinone-based lipocations were active in vitro at mid-high nM concentrations against P. falciparum and low mu M concentrations against T. cruzi. Published by Elsevier Ltd.
• Synthesis of mitochondria-targeted menadione cation derivatives: Inhibiting mitochondrial thioredoxin reductase (TrxR2) and inducing apoptosis in MGC-803 cells
  作者：Qun Tang、Yu Xie、Yongpeng Liu、Lifang Zheng

  DOI：10.1016/j.bmcl.2022.128586

  日期：2022.3