1-(propargyl)-1,5,9-triazacyclododecane | 1359848-47-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(propargyl)-1,5,9-triazacyclododecane
• 英文别名: 1-Prop-2-ynyl-1,5,9-triazacyclododecane
• CAS: 1359848-47-7
• 化学式: C₁₂H₂₃N₃
• 分子量: 209.335
• InChiKey: KHCZNKJWBRYOGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bisazido-2-(1-naphthylmethyl)propane 、 1-(propargyl)-1,5,9-triazacyclododecane 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以96%的产率得到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
• 作为产物：
  描述：

  在 盐酸 、 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以2.27 g的产率得到1-(propargyl)-1,5,9-triazacyclododecane
  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

• Macrocyclic polyamine [12]aneN₃ modified triphenylamine-pyrazine derivatives as efficient non-viral gene vectors with AIE and two-photon imaging properties
  作者：Le-Le Ma、Ming-Xuan Liu、Xu-Ying Liu、Wan Sun、Zhong-Lin Lu、Yong-Guang Gao、Lan He

  DOI：10.1039/d0tb00321b

  日期：——

  With the aim to develop a novel multifunctional gene delivery system that may overcome the common barriers of gene transfection, near-infrared fluorescent triphenylamine-pyrazine was modified with a DNA condensing triazole-[12]aneN3 moiety through different length alkyl ester linkages to afford three new non-viral gene vectors, TDM-A/B/C. All compounds showed prominent solvatochromic fluorescence (Stokes

  为了开发一种可以克服基因转染常见障碍的新型多功能基因递送系统，将近红外荧光三苯胺-吡嗪通过DNA缩合三唑-[12] aneN3部分的DNA通过不同长度的烷基酯键进行修饰，得到三个新的非病毒基因载体TDM-A / B / C。所有化合物均显示出显着的溶剂变色荧光（斯托克斯位移最大383 nm）和双光子吸收特性（σ2P至101 GM），并表现出强聚集诱导发射（AIE）。凝胶电泳显示质粒DNA在10μM（TDM-A），14μM（TDM-B）和16μM（TDM-C）的浓度下完全浓缩，并在酯酶和酸性环境中释放。SEM显示这三种化合物能够自组装并与DNA共聚集形成规则的纳米粒子。实验表明，TDM-A / B / C能够通过静电相互作用和超分子堆积与DNA整合，而短烷基键有利于与DNA的强相互作用。在这三种化合物中，在DOPE存在下，TDM-B表现出最好的荧光素酶和GFP转染活性，分别比Lipo2000
• 基于绿色荧光蛋白生色团BI的大环多胺类两 亲化合物及其制备方法和用途
  申请人：北京师范大学

  公开号：CN110003185B

  公开（公告）日：2020-05-19

  本发明提供一种基于绿色荧光蛋白生色团BI的大环多胺类两亲化合物及其制备方法与用途。本发明公开的化合物主要由羰氨缩合、1，3偶极环加成、酯化反应以及Click反应合成制备。本发明所提供的化合物具有良好的双光子荧光的性质，有发射波长，3D分辨率高以及低自发光等优点；本发明人工模拟了绿色荧光蛋白的生色机理；本发明提供的化合物可以与二油酰磷脂酰乙醇胺(DOPE)形成pH响应的小分子非病毒基因载体，从而促进DNA的释放，具有极高的转染效率并且可以靶向细胞核。