4-(2-(6,8-dimercaptooctanamido)ethylamino)-3-methyl-4-oxobut-2-enoic acid | 1187531-36-7

• 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: 4-(2-(6,8-dimercaptooctanamido)ethylamino)-3-methyl-4-oxobut-2-enoic acid
• 英文别名: 4-[2-[6,8-bis(sulfanyl)octanoylamino]ethylamino]-2-methyl-4-oxobut-2-enoic acid
• CAS: 1187531-36-7
• 化学式: C₁₅H₂₆N₂O₄S₂
• 分子量: 362.514
• InChiKey: MKXPSDIHSKJESE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  23.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.5
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-2-methyl-4-oxobut-2-enoic acid 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 0.5h， 生成 4-(2-(6,8-dimercaptooctanamido)ethylamino)-3-methyl-4-oxobut-2-enoic acid
  参考文献：
  名称：

  pH-Induced Aggregation of Gold Nanoparticles for Photothermal Cancer Therapy

  摘要：

  We report a "smart" gold nanoparticle that is designed to aggregate in mild acidic intracellular environments by its hydrolysis-susceptible citraconic amide surface, With a relatively small size of 10 nm, the "smart" gold nanoparticles can be efficiently internalized into cancerous cells. Triggered by pH change, the nanoparticle surfaces are engineered to have both positive and negative charges. Electrostatic attractions between the nanoparticles can rapidly form aggregates inside the cells, and the aggregates accumulate as the exocytosis is blocked by the increased size. Endocytosis of gold nanoparticles and the aggregation are monitored real-time by dark field optical microscopy. The pH-induced formation of aggregates shifts the absorption to far-red and near-infrared. The absorption shift to longer wavelength is used for photothermal cancer therapy as it guarantees maximal tissue penetration for potential therapeutic applications. The gold nanoparticles show selective and efficient destruction of cancerous cells with an intensity threshold of 5 W/cm(2) to induce the thermal destruction. In the intensity range 5-13 W/cm(2), the circular area of damaged cells increases linearly with the irradiation power density. This shows a new proof-of-concept for photothermal cancer therapy that exploits collective plasmon modes of metal nanoparticles.

  DOI：

  10.1021/ja902062j

文献信息

• EP2559429
  申请人：——

  公开号：——

  公开（公告）日：——