2-((5-(1,2-dithiolan-3-yl)pentanoyl)amino)-N,N,N-trimethylethanaminium chloride | 85344-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-((5-(1,2-dithiolan-3-yl)pentanoyl)amino)-N,N,N-trimethylethanaminium chloride
• 英文别名: 2-(5-(1,2-dithiolan-3-yl)pentanamido)-N,N,N-trimethylethanaminium chloride
• CAS: 85344-63-4
• 化学式: C₁₃H₂₇N₂OS₂*Cl
• 分子量: 326.955
• InChiKey: WEDUKLHOPNIPPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-((5-(1,2-dithiolan-3-yl)pentanoyl)amino)-N,N,N-trimethylethanaminium chloride 在 sodium tetrahydroborate 作用下， 生成 2-(6,8-dimercaptooctanamido)-N,N,N-trimethylethan-1-aminium chloride
  参考文献：
  名称：

  Strong polyelectrolyte quantum dot surface for stable bioconjugation and layer-by-layer assembly applications

  摘要：

  报告了一系列量子点（QD）配体，这些配体可以使得具有磺酸盐或季铵盐的强聚电解质QD表面，从而赋予QD优异的胶体稳定性，这种稳定性独立于pH值和离子强度，具有最小的流体动力学尺寸，并可以用于实现稳定灵活的生物偶联和逐层组装。

  DOI：

  10.1039/c0cc04524a
• 作为产物：
  描述：

  Thioctic acid 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 29.0h， 生成 2-((5-(1,2-dithiolan-3-yl)pentanoyl)amino)-N,N,N-trimethylethanaminium chloride
  参考文献：
  名称：

  Strong polyelectrolyte quantum dot surface for stable bioconjugation and layer-by-layer assembly applications

  摘要：

  报告了一系列量子点（QD）配体，这些配体可以使得具有磺酸盐或季铵盐的强聚电解质QD表面，从而赋予QD优异的胶体稳定性，这种稳定性独立于pH值和离子强度，具有最小的流体动力学尺寸，并可以用于实现稳定灵活的生物偶联和逐层组装。

  DOI：

  10.1039/c0cc04524a

文献信息

• pH-Induced Aggregation of Gold Nanoparticles for Photothermal Cancer Therapy
  作者：Jutaek Nam、Nayoun Won、Ho Jin、Hyokyun Chung、Sungjee Kim

  DOI：10.1021/ja902062j

  日期：2009.9.30

  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.