2-amino-3,3'-propane-1,3-dioxybis(1,10-phenanthroline) | 321595-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-amino-3,3'-propane-1,3-dioxybis(1,10-phenanthroline)
• 英文别名: 1-(1,10-phenanthrolin-3-yloxy)-3-(1,10-phenanthrolin-8-yloxy)propan-2-amine；3,3'-propane-2-amino-1,3-dioxybis(1,10-phenanthroline)；1,3-bis(1,10-phenanthrolin-3-yloxy)propan-2-amine
• CAS: 321595-65-7
• 化学式: C₂₇H₂₁N₅O₂
• 分子量: 447.496
• InChiKey: HPYPDGBOACEIRW-UHFFFAOYSA-N

物化性质

• 沸点：
  743.3±60.0 °C(predicted)
• 密度：
  1.363±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-3,3'-propane-1,3-dioxybis(1,10-phenanthroline) 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N¹-{6-[1-(1,10-phenanthrolin-3-yloxy)-3-(1,10-phenanthrolin-8-yloxy)propan-2-amine]-hexyl}-ethane-1,2-diamine
  参考文献：
  名称：

  New Approach for the Preparation of Efficient DNA Cleaving Agents:  Ditopic Copper−Platinum Complexes Based on 3-Clip-Phen and Cisplatin

  摘要：

  The design and synthesis of new heterodinuclear DNA-targeting agents are described. The abilities of cisplatin and Cu(3-Clip-Phen) [Cu(1-(1,10-phenanthrolin-3-yloxy)-3-(1,10-phenanthrolin-8-yloxy)propan-2-amine)Cl-2], an artificial DNA-cleaving agent, have been combined through their "covalent coupling". This strategy has led to bifunctional complexes that are able to cleave the DNA in a double-stranded fashion in contrast to Cu(3-Clip-Phen) alone and have promising cytotoxicities compared to cisplatin in several cell lines.

  DOI：

  10.1021/jm0614331
• 作为产物：
  描述：

  3-溴-1,10-菲罗啉 、 丝氨醇 在 sodium hydride 作用下， 生成 2-amino-3,3'-propane-1,3-dioxybis(1,10-phenanthroline)
  参考文献：
  名称：

  通过一种新型的Phen铜共轭物与含有N-甲基咪唑环的聚酰胺的复合物对位点选择性DNA进行切割。

  摘要：

  合成了一种新型的3-Clip-Phen和含有三个N-甲基咪唑（Im）环的聚酰胺共轭物，用于靶向5'-TTAGGG-3'的人端粒重复序列，并具有DNA切割活性和该复合物的序列选择性。通过电喷雾电离质谱法确认了共轭铜。

  DOI：

  10.1016/j.bmcl.2006.07.049

文献信息

• Site-Selective DNA cleavage by a novel complex of copper-conjugate of Phen and polyamide containing N-methylimidazole rings
  作者：Dan Liu、Jiang Zhou、Huihui Li、Bo Zheng、Gu Yuan

  DOI：10.1016/j.bmcl.2006.07.049

  日期：2006.10

  A novel conjugate of 3-Clip-Phen and polyamide containing three N-methylimidazole (Im) rings was synthesized for the targeting human telomeric repeat of 5'-TTAGGG-3', and the DNA cleaving activity and the sequence selectivity of the complex of copper-conjugate were confirmed by electrospray ionization mass spectrometry.

  合成了一种新型的3-Clip-Phen和含有三个N-甲基咪唑（Im）环的聚酰胺共轭物，用于靶向5'-TTAGGG-3'的人端粒重复序列，并具有DNA切割活性和该复合物的序列选择性。通过电喷雾电离质谱法确认了共轭铜。
• Dramatic increase of the DNA cleavage activity of Cu(Clip-phen) by fixing the bridging linker on the C3 position of the phenanthroline units
  作者：Marguerite Pitié、Brigitte Sudres、Bernard Meunier

  DOI：10.1039/a807807f

  日期：——

  The synthesis of a new ligand with two phenanthrolines bridged on their C3 carbon by a serinol is reported; Cu(3-Clip-phen) cleaves DNA more efficiently than the parent Cu(2-Clip-phen) bridged on the C2 carbon.

  报告了一种新配体的合成过程，该配体的 C3 碳上有丝氨醇桥接的两个菲罗啉；与 C2 碳上桥接的母体 Cu（2-Clip-phen）相比，Cu（3-Clip-phen）能更有效地裂解 DNA。
• DNA Cleavage by Copper Complexes of 2‐ and 3‐Clip‐Phen Derivatives
  作者：Marguerite Pitié、Christophe Boldron、Heinz Gornitzka、Catherine Hemmert、Bruno Donnadieu、Bernard Meunier

  DOI：10.1002/ejic.200390075

  日期：2003.2

  active as DNA cleavage agents than complexes with the bridge at the C-3 positions. Copper complexes with a bridge containing three methylene units appear to give the best results in DNA cleavage experiments. This activity is increased in the case of 3-Clip-Phen·CuCl2 by the presence of the primary amine function of the serinol bridge. This amine function is probably coordinated to the copper atom in

  通过使用含有两个由丝氨醇桥连接的菲咯啉实体的“2-Clip-Phen”和“3-Clip-Phen”配体，菲咯啉的铜复合物的 DNA 切割活性增加。为了优化 DNA 切割活性，合成了两个系列的新 Clip-Phen 配体 (L)，其中两个菲咯啉残基通过不同的桥通过其 C-2 或 C-3 碳原子连接。在还原剂和空气存在下研究了相应的 (Clip-Phen) 铜复合物的理化性质和 DNA 切割活性。单晶的 X 射线分析表明，Clip-Phen 的铜配合物能够采用二聚体双螺旋几何形状，固态时具有 L2Cu2 化学计量。这些配合物在溶液中采用不同的几何形状和化学计量，以单体 LCu 物种为主。与在 C-3 位置连接桥的复合物相比，在 C-2 上连接桥的化合物作为 DNA 切割剂的活性较低。带有包含三个亚甲基单元的桥的铜配合物似乎在 DNA 切割实验中给出了最好的结果。在 3-Clip-Phen·CuCl2
• MÉTHODE DE DÉCONTAMINATION D'UNE SOLUTION DES ACIDES NUCLÉIQUES INDÉSIRABLES
  申请人：BIOMERIEUX SA

  公开号：EP2129804B1

  公开（公告）日：2015-03-18
• METHOD FOR DECONTAMINATING A SOLUTION WITH RESPECT TO UNWANTED NUCLEIC ACIDS
  申请人：Paranhos-Baccala Glaucia

  公开号：US20100086976A1

  公开（公告）日：2010-04-08

  The present invention concerns a method for decontaminating a solution of any nucleic acid present in said solution, comprising the following steps: for a sufficient period, subjecting the solution to the action of at least one type of molecule having the property of degrading the nucleic acids by fragmentation, termed a fragmentation molecule, until said nucleic acids, termed contaminating nucleic acids, have been completely degraded; and stopping the activity of the fragmentation molecule. The invention also concerns the use of said treated solution. The preferred application of the invention is in the field of diagnostics.