(4-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenoxy]butyl)triphenylphosphonium iodide | 656826-74-3

• 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: (4-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenoxy]butyl)triphenylphosphonium iodide
• 英文别名: MitoPeroxidase 1；2-[4-(4-triphenylphosphoniobutoxy)phenyl]-1,2-benzisoselenazol-3(2H)-one iodide；4-[4-(3-Oxo-1,2-benzoselenazol-2-yl)phenoxy]butyl-triphenylphosphanium;iodide
• CAS: 656826-74-3
• 化学式: C₃₅H₃₁NO₂PSe*I
• 分子量: 734.475
• InChiKey: ZMCHCDQNJOWFSN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid 在 (2-[[2-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenyl]acetyl]amino]ethyl)triphenylphosphonium chloride 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (4-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenoxy]butyl)triphenylphosphonium iodide
  参考文献：
  名称：

  Design and Synthesis of a Mitochondria-Targeted Mimic of Glutathione Peroxidase, MitoEbselen-2, as a Radiation Mitigator

  摘要：

  Ionizing radiation (IR) triggers mitochondrial overproduction of H2O2 and accumulation of lipid hydroperoxides leading to the induction of apoptotic and necroptotic cell death pathways. Given the high catalytic efficiency of the seleno-enzyme glutathione peroxidase (Gpx) toward reduction of lipid hydroperoxides and H2O2, we tested the potential of mitochondria-targeted derivatives of ebselen to mitigate the deleterious effects of IR. We report that 2-[[2-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenyl]acetyl]amino]ethyl-triphenyl-phosphonium chloride (MitoPeroxidase 2) was effective in reducing lipid hydroperoxides, preventing apoptotic cell death, and, when administered 24 h postirradiation, increased the survival of mice exposed to whole body gamma-irradiation.

  DOI：

  10.1021/ml5003635

文献信息

• Mitochondrially targeted antioxidants
  申请人：Medical Research Council

  公开号：US20040029851A1

  公开（公告）日：2004-02-12

  The invention provides mitochondrially targeted antioxidant compounds comprising a lipophilic cation moiety covalently coupled to an antioxidant moiety which is either a superoxide dismutase (SOD) mimetic or a glutathione peroxidase mimetic. These compounds can be used to treat patients who would benefit from the reduction of oxidative stress.

  本发明提供了线粒体定向抗氧化化合物，包括一个脂溶性阳离子基团与一个抗氧化基团共价耦合，该抗氧化基团可以是超氧化物歧化酶（SOD）类似物或谷胱甘肽过氧化物酶（GPx）类似物。这些化合物可用于治疗需要减少氧化应激的患者。
• Design and Synthesis of a Mitochondria-Targeted Mimic of Glutathione Peroxidase, MitoEbselen-2, as a Radiation Mitigator
  作者：Detcho A. Stoyanovsky、Jianfei Jiang、Michael P. Murphy、Michael Epperly、Xiaolan Zhang、Song Li、Joel Greenberger、Valerian Kagan、Hülya Bayır

  DOI：10.1021/ml5003635

  日期：2014.12.11

  Ionizing radiation (IR) triggers mitochondrial overproduction of H2O2 and accumulation of lipid hydroperoxides leading to the induction of apoptotic and necroptotic cell death pathways. Given the high catalytic efficiency of the seleno-enzyme glutathione peroxidase (Gpx) toward reduction of lipid hydroperoxides and H2O2, we tested the potential of mitochondria-targeted derivatives of ebselen to mitigate the deleterious effects of IR. We report that 2-[[2-[4-(3-oxo-1,2-benzoselenazol-2-yl)phenyl]acetyl]amino]ethyl-triphenyl-phosphonium chloride (MitoPeroxidase 2) was effective in reducing lipid hydroperoxides, preventing apoptotic cell death, and, when administered 24 h postirradiation, increased the survival of mice exposed to whole body gamma-irradiation.