N,N'-bis[1,3-dimethylthioureaethyl]-3,4,9,10-perylenetetracarboxylic diimide | 1346253-96-0

• 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[1,3-dimethylthioureaethyl]-3,4,9,10-perylenetetracarboxylic diimide
• 英文别名: 1,3-Dimethyl-1-[2-[18-[2-[methyl(methylcarbamothioyl)amino]ethyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-7-yl]ethyl]thiourea；1,3-dimethyl-1-[2-[18-[2-[methyl(methylcarbamothioyl)amino]ethyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-7-yl]ethyl]thiourea
• CAS: 1346253-96-0
• 化学式: C₃₄H₃₀N₆O₄S₂
• 分子量: 650.782
• InChiKey: AFSNTLRIZVVHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {Pt(diethylenetriamine)NO3}NO3 、 N,N'-bis[1,3-dimethylthioureaethyl]-3,4,9,10-perylenetetracarboxylic diimide 、 水 在 activated carbon 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到[[Pt(dietylenetriamine)]2(N,N'-bis[1,3-dimethylthioureaethyl]-3,4,9,10-perylenetetracarboxylic diimide](NO3)4*2H2O
  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 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 102.0h， 生成 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

文献信息

• Interactions of a Platinum-Modified Perylene Derivative with the Human Telomeric G-Quadruplex
  作者：Lu Rao、Joshua D. Dworkin、William E. Nell、Ulrich Bierbach

  DOI：10.1021/jp207265s

  日期：2011.11.24

  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.