N-[2-(1-piperazinyl)ethyl]-5-(1,2-dithiolan-3-yl)pentanamide | 1309825-93-1

• 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: N-[2-(1-piperazinyl)ethyl]-5-(1,2-dithiolan-3-yl)pentanamide
• 英文别名: 5-(dithiolan-3-yl)-N-(2-piperazin-1-ylethyl)pentanamide
• CAS: 1309825-93-1
• 化学式: C₁₄H₂₇N₃OS₂
• 分子量: 317.52
• InChiKey: IPHFWTNVTIADAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(1-piperazinyl)ethyl]-5-(1,2-dithiolan-3-yl)pentanamide 在 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  [EN] COMPACT MULTIFUNCTIONAL LIGAND TO ENHANCE COLLOIDAL STABILITY OF NANOPARTICLES
  [FR] LIGAND MULTIFONCTIONNEL COMPACT PERMETTANT D'AMPLIFIER LA STABILITÉ COLLOÏDALE DE NANOPARTICULES

  摘要：

  配体设计允许紧凑的纳米颗粒材料，如量子点（QDs），在广泛的pH范围和高盐浓度下具有良好的胶体稳定性。可以获得与QDs稳定在生物环境中的自组装生物分子共轭物。通过将直接附加到配体或组装在其表面上的给体/受体与QDs/纳米颗粒之间的距离最小化，最大化这些配体的能量转移。

  公开号：

  WO2013025347A1
• 作为产物：
  描述：

  Thioctic acid 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 N-[2-(1-piperazinyl)ethyl]-5-(1,2-dithiolan-3-yl)pentanamide
  参考文献：
  名称：

  [EN] COMPACT MULTIFUNCTIONAL LIGAND TO ENHANCE COLLOIDAL STABILITY OF NANOPARTICLES
  [FR] LIGAND MULTIFONCTIONNEL COMPACT PERMETTANT D'AMPLIFIER LA STABILITÉ COLLOÏDALE DE NANOPARTICULES

  摘要：

  配体设计允许紧凑的纳米颗粒材料，如量子点（QDs），在广泛的pH范围和高盐浓度下具有良好的胶体稳定性。可以获得与QDs稳定在生物环境中的自组装生物分子共轭物。通过将直接附加到配体或组装在其表面上的给体/受体与QDs/纳米颗粒之间的距离最小化，最大化这些配体的能量转移。

  公开号：

  WO2013025347A1

文献信息

• Multifunctional Compact Zwitterionic Ligands for Preparing Robust Biocompatible Semiconductor Quantum Dots and Gold Nanoparticles
  作者：Kimihiro Susumu、Eunkeu Oh、James B. Delehanty、Juan B. Blanco-Canosa、Brandy J. Johnson、Vaibhav Jain、William Judson Hervey、W. Russ Algar、Kelly Boeneman、Philip E. Dawson、Igor L. Medintz

  DOI：10.1021/ja201919s

  日期：2011.6.22

  We describe the synthesis of a series of four different ligands which are used to prepare hydrophilic, biocompatible luminescent quantum dots (QDs) and gold nanoparticles (AuNPs). Overall, the ligands are designed to be compact while still imparting a zwitterionic character to the NPs. Ligands are synthesized appended to a bidentate dihydrolipoic acid- (DHLA) anchor group, allowing for high-affinity NP attachment, and simultaneously incorporate tertiary amines along with carboxyl and/or hydroxyl groups. These are placed in close proximity within the ligand structure and their capacity for joint ionization imparts the requisite zwitterionic nature to the nanocrystal. QDs functionalized with the four different compact ligands were subjected to extensive physical characterization including surface charge, wettability, hydrodynamic size, and tolerance to a wide pH range or high salt concentration over time. The utility of the compact ligand coated QDs was further examined by testing of direct conjugation to polyhistidine-appended protein and peptides, aqueous covalent-coupling chemistry, and the ability to engage in Forster resonance energy transfer (FRET). Conjugating cell penetrating peptides to the compact ligand coated QD series facilitated their rapid and efficient cellular uptake, while subsequent cytotoxicity tests showed no apparent decreases in cell viability. In vivo biocompatibility was also demonstrated by microinjecting the compact ligand coated QDs into cells and monitoring their stability over time. Inherent benefits of the ligand design could be extended beyond QDs as AuNPs functionalized with the same compact ligand series showed similar colloidal properties. The strong potential of these ligands to expand NP capabilities in many biological applications is highlighted.
• Compact Multifunctional Ligand to Enhance Colloidal Stability of Nanoparticles
  申请人：Medintz Igor L.

  公开号：US20130045499A1

  公开（公告）日：2013-02-21

  A ligand design allows compact nanoparticle materials, such as quantum dots (QDs), with excellent colloidal stability over a wide range of pH and under high salt concentrations. Self-assembled biomolecular conjugates with QDs can be obtained which are stable in biological environments. Energy transfer with these ligands is maximized by minimizing distances between QDs/nanoparticles and donors/acceptors directly attached to the ligands or assembled on their surfaces.
• US8512755B2
  申请人：——

  公开号：US8512755B2

  公开（公告）日：2013-08-20
• US9304124B2
  申请人：——

  公开号：US9304124B2

  公开（公告）日：2016-04-05
• [EN] COMPACT MULTIFUNCTIONAL LIGAND TO ENHANCE COLLOIDAL STABILITY OF NANOPARTICLES<br/>[FR] LIGAND MULTIFONCTIONNEL COMPACT PERMETTANT D'AMPLIFIER LA STABILITÉ COLLOÏDALE DE NANOPARTICULES
  申请人：US GOV SEC NAVY

  公开号：WO2013025347A1

  公开（公告）日：2013-02-21

  A ligand design allows compact nanoparticle materials, such as quantum dots (QDs), with excellent colloidal stability over a wide range of pH and under high salt concentrations. Self- assembled biomolecular conjugates with QDs can be obtained which are stable in biological environments. Energy transfer with these ligands is maximized by minimizing distances between QDs/nanoparticles and donors/acceptors directly attached to the ligands or assembled on their surfaces.

  配体设计允许紧凑的纳米颗粒材料，如量子点（QDs），在广泛的pH范围和高盐浓度下具有良好的胶体稳定性。可以获得与QDs稳定在生物环境中的自组装生物分子共轭物。通过将直接附加到配体或组装在其表面上的给体/受体与QDs/纳米颗粒之间的距离最小化，最大化这些配体的能量转移。