2'-(4-hydroxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3'H-2,5'-bibenzoimidazoyl-4-carboxylic acid | 874301-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2'-(4-hydroxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3'H-2,5'-bibenzoimidazoyl-4-carboxylic acid
• 英文别名: Hoechst33258；2-[2-(4-hydroxyphenyl)-3H-benzimidazol-5-yl]-6-(4-methylpiperazin-1-yl)-1H-benzimidazole-4-carboxylic acid
• CAS: 874301-24-3
• 化学式: C₂₆H₂₄N₆O₃
• 分子量: 468.515
• InChiKey: RIQIXSIKZNYIAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-(4-hydroxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3'H-2,5'-bibenzoimidazoyl-4-carboxylic acid 在 DL-dithiothreitol 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Equilibrium shift by target DNA substrates for determination of DNA binding ligands

  摘要：

  An equilibrium containing the thiol derivative of Hoechst33258 (Ht-SH), glutathione (G-SH), and the corresponding homo and hetero disulfides was shifted by the addition of the duplex DNA. It was shown from the analysis of the components that the hetero disulfide Ht-SS-G increased by binding with the DNA (CA14) with an A(3)T(3) binding motif for the structure of Hoechst33258, and that the different equilibrium shift was observed in the presence of CT14 with no A(3)T(3) binding motif. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.089
• 作为产物：
  描述：

  3-amino-5-chloro-2-nitrobenzoic acid methyl ester 在 sodium hydroxide 、 sodium disulfite 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 2'-(4-hydroxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3'H-2,5'-bibenzoimidazoyl-4-carboxylic acid
  参考文献：
  名称：

  Design of New Bidentate Ligands Constructed of Two Hoechst 33258 Units for Discrimination of the Length of Two A₃T₃ Binding Motifs

  摘要：

  The aim of this study is to develop bidentate minor-groove binders that bind the double binding motifs cooperatively. The new bidentate ligands (1) have been designed by connecting two Hoechst 33258 units with a polyether linker for cooperative binding with two remote A(3)T(3) sites of DNA. The linker is introduced to the benzimidazole ring so that it is located at the convex side of the Hoechst unit. DNA binding affinity of the ligands was evaluated by measuring surface plasmon resonance (SPR), circular dichroism, and fluorescence spectra. Interestingly, the bidentate ligands (1) did not show affinity to DNA1 with a single A(3)T(3) motif but showed selective affinity to DNA2 with two A(3)T(3) motifs. The Long Bis-H (1L) having a long polyether linker showed specific binding to DNA2(6) with two A3T3 motifs separated by six nonbinding base pairs. The Long Bis-H (1L) has also shown specific binding to the three-way junction DNA4 with two A(3)T(3) motifs. This study has demonstrated that DNA with double binding motifs can be selectively recognized by the newly designed bidentate ligands.

  DOI：

  10.1021/jo051836t

文献信息

• Cu²⁺-Mediated Assembly of the Minor Groove Binders on the DNA Template with Sequence Selectivity
  作者：Mikimasa Tanada、Saori Tsujita、Tomonobu Kataoka、Shigeki Sasaki

  DOI：10.1021/ol060632b

  日期：2006.6.1

  Hoechst33258 skeleton for DNA binding and 2,2'-bipyridine for Cu(2+) complexation. It has been revealed that the new Hoechst ligand long Bpy-H (5L) having a long linker exhibits Cu(2+)-mediated assembly on the DNA template having two A(3)T(3) sites in a selective manner depending on the length of the linker of the ligand as well as on the distance between the two A(3)T(3) sites of DNA. [reaction: see text]

  配体（Bpy-H，5）已设计为连接用于DNA结合的Hoechst33258骨架和用于Cu（2+）络合的2,2'-联吡啶。已经发现具有长连接子的新的Hoechst配体长Bpy-H（5L）在具有两个A（3）T（3）位点的DNA模板上以选择性方式显示Cu（2+）介导的组装，具体取决于配体连接体的长度，以及DNA的两个A（3）T（3）位点之间的距离。[反应：看文字]
• Strong positive cooperativity in binding to the A3T3 repeat by Hoechst 33258 derivatives attaching the quinoline units at the end of a branched linker
  作者：Hironori Koda、John Alan Brazier、Ippei Onishi、Shigeki Sasaki

  DOI：10.1016/j.bmc.2015.05.056

  日期：2015.8

  Hoechst 33258 derivatives with additional interacting moieties attached at the ends of branched linkers were synthesized, and their DNA binding properties were investigated with regard to the A3T3 repeat by measuring fluorescence spectra. The binding property of the ligand was investigated by fluorescence titration, and the titration data were analyzed using the McGhee-von Hippel method. Ligand 6Q with the quinolin-6-yloxyacetyl group and Ligand IQ with isoquinolin-6-yloxyacetyl group at the ends of the branched linkers exhibit highly positive cooperativity for the DNA having 5 A3T3 sites with 3 base-insertions between them with sequence selectivity. The strategy developed in this study may be generally applicable for designing ligands for repetitive DNA sequences. (C) 2015 Elsevier Ltd. All rights reserved.