(Boc)2-[12]aneN3-CH2COOH | 1367281-19-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Boc)2-[12]aneN3-CH2COOH
• 英文别名: 2-[5,9-Bis[(2-methylpropan-2-yl)oxycarbonyl]-1,5,9-triazacyclododec-1-yl]acetic acid
• CAS: 1367281-19-3
• 化学式: C₂₁H₃₉N₃O₆
• 分子量: 429.557
• InChiKey: ACISQEPLEOULQH-UHFFFAOYSA-N

物化性质

• 沸点：
  540.1±50.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Boc)2-[12]aneN3-CH2COOH 在 盐酸 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [12]aneN3-CH2CO-Gly-Gly-OCH3*3HCl
  参考文献：
  名称：

  Synthesis of [12]aneN3–dipeptide conjugates as metal-free DNA nucleases

  摘要：

  In this Letter, a series of macrocyclic polyamine [12]aneN(3)-dipeptide conjugates as a new type of metal-free nucleases were synthesized and fully characterized with H-1 NMR, C-13 NMR, IR, and HR-MS. Results indicate that these conjugates can bind to calf thymus DNA mainly through electrostatic interaction and can cleave the plasmid DNA at 200 mu M ( pH 7.2, 37 degrees C), with an acceleration of 10(6)-fold via hydrolytic pathway. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.075
• 作为产物：
  描述：

  1,5,9-triazatricyclo[7.3.1.05,13 ]tridecane 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.17h， 生成 (Boc)2-[12]aneN3-CH2COOH
  参考文献：
  名称：

  Synthesis of [12]aneN3–dipeptide conjugates as metal-free DNA nucleases

  摘要：

  In this Letter, a series of macrocyclic polyamine [12]aneN(3)-dipeptide conjugates as a new type of metal-free nucleases were synthesized and fully characterized with H-1 NMR, C-13 NMR, IR, and HR-MS. Results indicate that these conjugates can bind to calf thymus DNA mainly through electrostatic interaction and can cleave the plasmid DNA at 200 mu M ( pH 7.2, 37 degrees C), with an acceleration of 10(6)-fold via hydrolytic pathway. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.075

文献信息

• 基于TPA-BI的大环多胺[12]aneN3化合物及 其制备方法和用途
  申请人：北京师范大学

  公开号：CN109369621B

  公开（公告）日：2020-07-17

  本发明提供一种基于TPA‑BI的大环多胺[12]aneN 3 化合物及其制备方法与用途。本发明公开的化合物主要由Suzuki偶联、酯化反应以及Click反应制备合成。本发明所提供的化合物具有大Stock位移以及双光子荧光的性质，具有长波激发，低自发光，高3D分辨率的优点；该化合物具有聚集诱导效应(AIE)；本发明提供的化合物可以与二油酰磷脂酰乙醇胺(DOPE)形成对pH刺激响应的阳离子脂质体，促进DNA在细胞内的释放，并且该阳离子脂质体可以高效地进入细胞核从而提高细胞的转染效率。
• Synthesis of Glutathione (GSH)‐Responsive Amphiphilic Duplexes and their Application in Gene Delivery
  作者：Yong‐Qiang Li、Wan Sun、Xu‐Ying Liu、Li‐Qing Chen、Wei Huang、Zhong‐Lin Lu、Lan He

  DOI：10.1002/cplu.201900295

  日期：2019.8

  retard the DNA mobiliy at concentrations of 30, 30, 10, and 20 μM, respectively. Reversible DNA release in O-1 and O-2 complexes can be achieved in the presence of heparin sodium, whereas the presence of GSH greatly improved DNA release in D-1 and D-2 complexes. The particles formed were in a size range of 50-170 nm with positively charged surfaces. D-1 and D-2 transfected pEGFP-N1 into HeLa cells successfully

  具有氢键键序列DADDAD和胍（O-1）或1,5,9-三氮杂环十二烷（[12] aneN3; O-2）侧链的寡酰胺分子链和具有氢键键序列ADAADA和辛基部分（O- 3），合成。通过序列特异性的氢键缔合和交联的二硫键将亲水性O-1或O-2和疏水性O-3偶联，制备了两个双链体（D-1和D-2）。电泳测量表明，O-1，O-2，D-1和D-2能够分别分别以30、30、10和20μM的浓度完全延迟DNA的迁移。在肝素钠存在下，可实现O-1和O-2复合物中DNA的可逆释放，而GSH的存在可大大改善D-1和D-2复合物中DNA的释放。所形成的颗粒的尺寸范围为50-170 nm，表面带正电。D-1和D-2成功地将pEGFP-N1转染到HeLa细胞中。
• Syntheses of [12]aneN3–oligopeptide conjugates as effective DNA condensation agents
  作者：Zhi-Fen Li、Zhi-Fo Guo、Hao Yan、Zhong-Lin Lu、Da-Yong Wu

  DOI：10.1016/j.bmc.2012.03.022

  日期：2012.5

  With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h center dot 3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 mu M, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors. (C) 2012 Elsevier Ltd. All rights reserved.