2-((2-decyltetradecyl)oxy)-1,3,5-triethynylbenzene | 1609380-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((2-decyltetradecyl)oxy)-1,3,5-triethynylbenzene
• CAS: 1609380-35-9
• 化学式: C₃₆H₅₄O
• 分子量: 502.824
• InChiKey: ZKVXFLGMRUXACR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  37.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-((2-decyltetradecyl)oxy)-1,3,5-triethynylbenzene 、 [Gd(HPN3DO3A)] 在 甲醇 、 copper(l) iodide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到5-(2,4,6-tris(1-(2-hydroxy-3-(1H-1,2,3-triazol-1-yl)-propyl)-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecylgadolinium(III))phenoxy)-2-decyltetradecyl
  参考文献：
  名称：

  Cell Labeling via Membrane-Anchored Lipophilic MR Contrast Agents

  摘要：

  Cell tracking in vivo with MR imaging requires the development of contrast agents with increased sensitivity that effectively label and are retained by cells. Most clinically approved Gd(III)-based contrast agents require high incubation concentrations and prolonged incubation times for cellular internalization. Strategies to increase contrast agent permeability have included conjugating Gd(III) complexes to cell penetrating peptides, nanoparticles, and small molecules which have greatly improved cell labeling but have not resulted in improved cellular retention. To overcome these challenges, we have synthesized a series of lipophilic Gd(III)-based MR contrast agents that label cell membranes in vitro. Two of the agents were synthesized with a multiplexing strategy to contain three Gd(III) chelates (1 and 2) while the third contains a single Gd(III) chelate (3). These new agents exhibit significantly enhanced labeling and retention in HeLa and MDA-MB-231-mcherry cells compared to agents that are internalized by cells (4 and Prohance).

  DOI：

  10.1021/bc500083t
• 作为产物：
  描述：

  ((2-((2-decyltetradecyl)oxy)benzene-1,3,5-triyl)-tris(ethyne-2,1-diyl))tris(trimethylsilane) 在 甲醇 、 potassium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以77%的产率得到2-((2-decyltetradecyl)oxy)-1,3,5-triethynylbenzene
  参考文献：
  名称：

  Cell Labeling via Membrane-Anchored Lipophilic MR Contrast Agents

  摘要：

  Cell tracking in vivo with MR imaging requires the development of contrast agents with increased sensitivity that effectively label and are retained by cells. Most clinically approved Gd(III)-based contrast agents require high incubation concentrations and prolonged incubation times for cellular internalization. Strategies to increase contrast agent permeability have included conjugating Gd(III) complexes to cell penetrating peptides, nanoparticles, and small molecules which have greatly improved cell labeling but have not resulted in improved cellular retention. To overcome these challenges, we have synthesized a series of lipophilic Gd(III)-based MR contrast agents that label cell membranes in vitro. Two of the agents were synthesized with a multiplexing strategy to contain three Gd(III) chelates (1 and 2) while the third contains a single Gd(III) chelate (3). These new agents exhibit significantly enhanced labeling and retention in HeLa and MDA-MB-231-mcherry cells compared to agents that are internalized by cells (4 and Prohance).

  DOI：

  10.1021/bc500083t