1,3-bis-[4-(1,5,9-triazacyclododec-1-ylmethyl)-1,2,3-triazol-1-yl]-2-(1-naphthylmeth-yl)propane | 1359848-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis-[4-(1,5,9-triazacyclododec-1-ylmethyl)-1,2,3-triazol-1-yl]-2-(1-naphthylmeth-yl)propane
• 英文别名: 1-[[1-[2-(Naphthalen-1-ylmethyl)-3-[4-(1,5,9-triazacyclododec-1-ylmethyl)triazol-1-yl]propyl]triazol-4-yl]methyl]-1,5,9-triazacyclododecane
• CAS: 1359848-44-4
• 化学式: C₃₈H₆₀N₁₂
• 分子量: 684.975
• InChiKey: YJUHTCAMVQTNDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,3-dihydroxy-2-(1-naphthylmethyl)propane 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 4.0h， 生成 1,3-bis-[4-(1,5,9-triazacyclododec-1-ylmethyl)-1,2,3-triazol-1-yl]-2-(1-naphthylmeth-yl)propane
  参考文献：
  名称：

  Effective and reversible DNA condensation induced by bifunctional molecules containing macrocyclic polyamines and naphthyl moieties

  摘要：

  A series of bifunctional molecules containing macrocyclic polyamines [12]aneN(3) and naphthyl moieties 1-3(a, b) have been designed and synthesized through efficient N-alkylation and copper-mediated alkyne-azide click reactions. Experiments on gel electrophoresis, dynamic light scattering and atomic force microscopy confirmed that 2b and 3b with two [12]aneN(3) units efficiently induced the DNA condensation at the concentration of 120 mu M in less than 5 min. The condensation mechanism was studied by EB displacement fluorescence spectra, viscosity titration, and ionic strength effects. The condensation process was found to be reversible, and the presence of both naphthyl and [12]aneN(3) units in the molecules was proved to be necessary for the effective DNA condensation inductions. Cytotoxicity assay showed that the presence of triazole moieties can result in lower toxicity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.069

文献信息

• Effective and reversible DNA condensation induced by bifunctional molecules containing macrocyclic polyamines and naphthyl moieties
  作者：Hao Yan、Zhi-Fen Li、Zhi-Fo Guo、Zhong-Lin Lu、Feng Wang、Li-Zhu Wu

  DOI：10.1016/j.bmc.2011.11.069

  日期：2012.1

  A series of bifunctional molecules containing macrocyclic polyamines [12]aneN(3) and naphthyl moieties 1-3(a, b) have been designed and synthesized through efficient N-alkylation and copper-mediated alkyne-azide click reactions. Experiments on gel electrophoresis, dynamic light scattering and atomic force microscopy confirmed that 2b and 3b with two [12]aneN(3) units efficiently induced the DNA condensation at the concentration of 120 mu M in less than 5 min. The condensation mechanism was studied by EB displacement fluorescence spectra, viscosity titration, and ionic strength effects. The condensation process was found to be reversible, and the presence of both naphthyl and [12]aneN(3) units in the molecules was proved to be necessary for the effective DNA condensation inductions. Cytotoxicity assay showed that the presence of triazole moieties can result in lower toxicity. (C) 2011 Elsevier Ltd. All rights reserved.