N,N'-bis[2-(methylamino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide | 113447-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis[2-(methylamino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide
• CAS: 113447-62-4
• 化学式: C₃₀H₂₄N₄O₄
• 分子量: 504.545
• InChiKey: JKTKVERACUDMTC-UHFFFAOYSA-N

物化性质

• 沸点：
  765.2±50.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.82
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis[2-(methylamino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide 、 异硫氰酸甲酯 以 氯仿 为溶剂， 反应 6.0h， 以74%的产率得到N,N'-bis[1,3-dimethylthioureaethyl]-3,4,9,10-perylenetetracarboxylic diimide
  参考文献：
  名称：

  Interactions of a Platinum-Modified Perylene Derivative with the Human Telomeric G-Quadruplex

  摘要：

  The interactions of a newly synthesized platinum-modified perylene derivative, compound 7 ([{Pt(dien)}(2)-(mu-4-S,S')](NO(3))(4) (then = diethylenetriamine, 4 = N,N'-bis-(1-(2-aminoethyl)-1,3-dimethylthiourea)-3,4,9,10-perylenete-tracarboxylic acid diimide), with the human telomeric repeat were studied using various model oligo(deoxy)ribonucleotides to mimic the polymorphic nature of the telomeric G-quadruplex. UV/visible spectroscopy, CD spectropolarimetry, electrospray mass spectrometry (ES-MS), and isothermal titration calorimetry (ITC) were used to demonstrate that compound 7 selectively recognizes the antiparallel form of the unimolecular telomeric G-quadruplex formed by the sequence d(TTAGGG)(4) (dG-24), to which it binds with a 2:1 stoichiometry and nanomolar affinity. Compared with telomeric DNA, the first binding event of compound 7 in titrations with the RNA quadruplex formed by r(UUAGGG)(4) (rG-24) is 1 order of magnitude weaker. Compound 7 does not induce the antiparallel G-quadruplex RNA, which invariably exists in a parallel form and dimerizes in solution. On the basis of the cumulative experimental data, two distinct mechanisms are proposed for the recognition of G-quadruplex DNA and RNA by compound 7. Potential biomedical and biochemical applications of the platinum-perylene technology are discussed.

  DOI：

  10.1021/jp207265s
• 作为产物：
  描述：

  N,N'-bis[2-(tert-butoxycarbonylmethylamino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide 在 盐酸 、 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 96.0h， 以82%的产率得到N,N'-bis[2-(methylamino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide
  参考文献：
  名称：

  Interactions of a Platinum-Modified Perylene Derivative with the Human Telomeric G-Quadruplex

  摘要：

  The interactions of a newly synthesized platinum-modified perylene derivative, compound 7 ([{Pt(dien)}(2)-(mu-4-S,S')](NO(3))(4) (then = diethylenetriamine, 4 = N,N'-bis-(1-(2-aminoethyl)-1,3-dimethylthiourea)-3,4,9,10-perylenete-tracarboxylic acid diimide), with the human telomeric repeat were studied using various model oligo(deoxy)ribonucleotides to mimic the polymorphic nature of the telomeric G-quadruplex. UV/visible spectroscopy, CD spectropolarimetry, electrospray mass spectrometry (ES-MS), and isothermal titration calorimetry (ITC) were used to demonstrate that compound 7 selectively recognizes the antiparallel form of the unimolecular telomeric G-quadruplex formed by the sequence d(TTAGGG)(4) (dG-24), to which it binds with a 2:1 stoichiometry and nanomolar affinity. Compared with telomeric DNA, the first binding event of compound 7 in titrations with the RNA quadruplex formed by r(UUAGGG)(4) (rG-24) is 1 order of magnitude weaker. Compound 7 does not induce the antiparallel G-quadruplex RNA, which invariably exists in a parallel form and dimerizes in solution. On the basis of the cumulative experimental data, two distinct mechanisms are proposed for the recognition of G-quadruplex DNA and RNA by compound 7. Potential biomedical and biochemical applications of the platinum-perylene technology are discussed.

  DOI：

  10.1021/jp207265s