1,7-dimethyl-5-(4-succinimidocarboxyphenyl)-6H-indolo[3,2-b]quinoline | 881662-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 1,7-dimethyl-5-(4-succinimidocarboxyphenyl)-6H-indolo[3,2-b]quinoline
• CAS: 881662-18-6
• 化学式: C₂₈H₂₁N₃O₄
• 分子量: 463.492
• InChiKey: LIZFDJUNPQVVCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92.36
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,7-dimethyl-5-(4-succinimidocarboxyphenyl)-6H-indolo[3,2-b]quinoline 、 N,N-二甲基乙二胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以62%的产率得到C₂₈H₂₈N₄O
  参考文献：
  名称：

  In vitro anticancer activity and evaluation of DNA duplex binding affinity of phenyl-substituted indoloquinolines

  摘要：

  Phenyl-substituted indoloquinolines were studied for their biological activity and their DNA binding affinity. Water-soluble aminoalkyl derivatives were prepared and have shown significant in vitro anticancer activity. Unlike previous reports on the potential role of duplex DNA as target for various indoloquinoline based drugs, duplex UV melting experiments and fluorescence titrations suggest only weak and moderately strong binding of the phenyl-substituted indoloquinolines at 120 mM and 20 mM Na+ concentrations, respectively. Binding is suggested by ethidium displacement and circular dichroism experiments to be associated with drug intercalation between base pairs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.088
• 作为产物：
  描述：

  1,7-dimethyl-5-(4-methyloxycarbonylphenyl)-6H-indolino[3,2-b]quinoline 在 甲醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 1,7-dimethyl-5-(4-succinimidocarboxyphenyl)-6H-indolo[3,2-b]quinoline
  参考文献：
  名称：

  In vitro anticancer activity and evaluation of DNA duplex binding affinity of phenyl-substituted indoloquinolines

  摘要：

  Phenyl-substituted indoloquinolines were studied for their biological activity and their DNA binding affinity. Water-soluble aminoalkyl derivatives were prepared and have shown significant in vitro anticancer activity. Unlike previous reports on the potential role of duplex DNA as target for various indoloquinoline based drugs, duplex UV melting experiments and fluorescence titrations suggest only weak and moderately strong binding of the phenyl-substituted indoloquinolines at 120 mM and 20 mM Na+ concentrations, respectively. Binding is suggested by ethidium displacement and circular dichroism experiments to be associated with drug intercalation between base pairs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.088

文献信息

• DNA triplex stabilization by a δ-carboline derivative tethered to third strand oligonucleotides
  作者：Nina Todorović、Nguyen Thi Bich Phuong、Peter Langer、Klaus Weisz

  DOI：10.1016/j.bmcl.2005.12.014

  日期：2006.3

  covalently coupled to a 7 mer oligonucleotide at its 5'- or 3'-end. The stability of triplexes formed from the conjugates and a double-helical target was studied by UV melting experiments. Compared to the unmodified control triple helices, triplexes with the conjugate exhibit a significantly higher stability. However, the degree of stabilization depends on the particular triplex structure formed.

  将δ-咔啉衍生物在其5'-或3'-末端共价偶联至7聚体寡核苷酸。通过紫外熔融实验研究了由共轭物和双螺旋靶形成的三链体的稳定性。与未修饰的对照三重螺旋相比，具有缀合物的三重螺旋显示出明显更高的稳定性。但是，稳定程度取决于所形成的特定三重结构。
• Spectroscopic studies on the formation and thermal stability of DNA triplexes with a benzoannulated δ-carboline–oligonucleotide conjugate
  作者：Andrea Eick、Zhou Xiao、Peter Langer、Klaus Weisz

  DOI：10.1016/j.bmc.2008.09.026

  日期：2008.10

  A benzoannulated delta-carboline with a phenyl substituent has been covalently tethered to the 3 '-end of a triplex-forming oligonucleotide and its ability to bind and stabilize DNA triple helices has been examined by various spectroscopic methods. UV thermal melting experiments were conducted with different hairpin duplexes and with a complementary single-stranded oligonucleotide as targets for the conjugate. The delta-carboline ligand preferentially binds triplexes over duplexes and leads to a temperature increase of the triplex-to-duplex transition by up to 23 degrees C. The results obtained from UV, CD and. fluorescence measurements suggest that the delta-carboline ligand exhibits specific interactions with a triplex and favors binding by intercalation at the triplex-duplex junction. (C) 2008 Elsevier Ltd. All rights reserved.