Hoechst acid | 682809-60-5

• 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: Hoechst acid
• 英文别名: Hoechst 33258 acid；4-[4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]phenoxy]butanoic acid
• CAS: 682809-60-5
• 化学式: C₂₉H₃₀N₆O₃
• 分子量: 510.596
• InChiKey: ZRCXXQWDSLKBMP-UHFFFAOYSA-N

物化性质

• 沸点：
  837.0±75.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Hoechst acid 、 [3-(吖啶-9-基氨基)-5-氨基苯基]甲醇 在 2-吡啶基硫醚 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以72%的产率得到2'-[4-[3-(9-acridinylamino)-5-hydroxymethylanilino]carbonylpropoxyphenyl]-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole
  参考文献：
  名称：

  Antitumor AHMA Linked to DNA Minor Groove Binding Agents:  Synthesis and Biological Evaluation

  摘要：

  DNA minor groove binder hybrid molecules, netropsin derivatives such as N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide (MePy) or its derivatives containing two units of N-methylpyrrolecarboxamide (diMePy) and bisbenzimidazole (Ho33258), were linked to the NH2 function of AHMA or to the CH2OH group of AHMA-ethylcarbamate to form AHMA-N-netropsins (13-16) and AHMA-ethylcarbamate-O-netropsins (19-22), and AHMA-bis-benzimidazole (AHMA-Ho33258, 25), respectively. These conjugates' in vitro antitumor activity, inhibition of a variety of human tumor cell growth, revealed that AHMA-ethylcarbamate-O-netropsin derivatives were more cytotoxic than AHMA-N-netropsin compounds. In the same studies, all compounds bearing MePy were more potent than those compounds linked with diMePy. Moreover, AHMA-netropsin derivatives bearing a succinyl chain as the linking spacer were more potent than those compounds having a glutaryl bridge. Among these hybrid molecules, AHMA-ethylcarbamate-O-succinyl-MePy (19) was 2- to 6-fold more cytotoxic than the parent compound AHMA (5) in various cell lines, whereas compound 25 had very poor solubility and was inactive. Studies on the inhibitory effect against topoisomerase II (Topo II) and DNA interaction of these conjugates showed no correlation between the potency of DNA binding and inhibitory activity against Topo II.

  DOI：

  10.1021/jm0200714
• 作为产物：
  描述：

  4-{4-[5-(4-Methyl-piperazin-1-yl)-1H,3'H-[2,5']bibenzoimidazolyl-2'-yl]-phenoxy}-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以100%的产率得到Hoechst acid
  参考文献：
  名称：

  带正电的脱氧核胍 (DNG) 的固相合成束缚 Hoechst 33258 类似物：通过同时小槽结合的三链和双链稳定

  摘要：

  脱氧核胍 (DNG) 是一种 DNA 类似物，其中带正电荷的胍取代了磷酸二酯键，通过不同长度与 Hoechst 33258 荧光团相连。在固相上以 3' --> 5' 方向合成了五聚体胸苷 DNG，允许使用 PyBOP/HOBt 化学在 5'-末端逐步掺入直链氨基酸接头和双苯并咪唑 (Hoechst 33258) 配体. (DNA)(2).DNG-H 三链体和 DNA.DNG-H 双链体的稳定性由 DNG 和 DNG-Hoechst 33258 (DNG-H) 偶联物​​与 30 聚体双链 (ds) DNA、d(CGCCGCGCGCGCGAAAAACCCGGCGCGCGC) 形成)/d(GCGGCGCGCGCGCTTTTTGGGCCGCGCGCG) 和单链 (ss) DNA，5'-CGCCGCGCGCGCGAAAAACCCGGCGCGCGC-3'，分别通过热熔解和荧光发射实验进行了评估。在

  DOI：

  10.1021/ja031557s

文献信息

• 用于抑制EB病毒相关肿瘤的化合物及其制备 方法和用途
  申请人：深圳先进技术研究院

  公开号：CN109912577B

  公开（公告）日：2021-10-22

  本发明涉及一种用于抑制EB病毒相关肿瘤的化合物及其制备方法和用途，具体公开了一种用于抑制EB病毒相关肿瘤和其他疾病的化合物及其药学上可接受的盐，其具有式I所示的结构。还公开了式I所示化合物或者其药学上可接受盐在制备抑制EB病毒、EB病毒介导的肿瘤以及EB病毒介导的其他疾病的药物中的用途。本发明的化合物能够高效特异性结合在病毒DNA的复制起点上，特异性强，能够干扰EBNA1与复制起点的结合，影响EBNA1的功能，抑制病毒基因的表达。同时引入Ht‑1，能够增强聚酰胺分子穿透生物膜的能力和结合目标DNA的能力，从而抑制病毒复制，导致宿主细胞死亡。
• Tracking the Oxygen Status in the Cell Nucleus with a Hoechst-Tagged Phosphorescent Ruthenium Complex
  作者：Daiki Hara、Yui Umehara、Aoi Son、Wataru Asahi、Sotaro Misu、Ryohsuke Kurihara、Teruyuki Kondo、Kazuhito Tanabe

  DOI：10.1002/cbic.201700685

  日期：2018.5.4

  An oxygen‐sensing probe for use in the cell nucleus was designed. We prepared “Ru‐Hoechsts”, each consisting of a phosphorescent ruthenium complex linked to a Hoechst 33258 moiety, and characterized their properties as oxygen sensors. The Ru‐Hoechsts accumulated in the cell nucleus and showed oxygen‐dependent signals allowing visualization of oxygen fluctuations in the nucleus.

  设计了用于细胞核的氧气感应探针。我们制备了“ Ru-Hoechsts”，每种由与Hoechst 33258部分相连的磷光钌配合物组成，并表征了其作为氧传感器的特性。Ru-Hoechsts积累在细胞核中，并显示出氧依赖性信号，从而可以观察到氧在核中的波动。
• 能够提高寡核苷酸链Tm值的标记化合物及其 应用
  申请人：浙江大学

  公开号：CN107573331B

  公开（公告）日：2019-11-15

  本发明涉及能够提高寡核苷酸链Tm值的标记化合物(I)及其应用。本发明的有益效果主要体现在：本发明提供了一种能够提高寡核苷酸链Tm值的标记化合物(HT琥珀酸酯)及其应用，采用HT标记的探针能够有效的甄别DPYD*9A位点野生型和突变型模板，可用于检测消化系统肿瘤，具有重要应用前景。
• DNA sequence recognition in the minor groove by hairpin pyrrole polyamide–Hoechst 33258 analogue conjugate
  作者：Putta Mallikarjuna Reddy、Rachel Dexter、Thomas C Bruice

  DOI：10.1016/j.bmcl.2004.04.089

  日期：2004.7

  hairpin pyrrole polyamide conjugated to a Hoechst 33258 (Ht) analogue, PyPyPy-gamma-PyPyPy-gamma-Ht, was synthesized on solid-phase by adaptation of an Fmoc technique using a series of PyBOP/HOBt mediated coupling reactions. Sequence selectivity and complex stabilities were characterized by spectrofluorometric titrations and thermal melting studies. The polyamide of the conjugate was observed to bind in

  通过使用一系列PyBOP / HOBt介导的偶联反应通过Fmoc技术在固相上合成与Hoechst 33258（Ht）类似物PyPyPy-γ-PyPyPy-γ-Ht共轭的发夹吡咯聚酰胺。序列选择性和复杂的稳定性通过荧光荧光滴定和热熔研究进行了表征。观察到结合物的聚酰胺结合在发夹基序中，形成1：1的结合物：dsDNA复合物。该缀合物能够识别九个连续的A / T bps，区别于包含少于九个连续的A / T bps的序列。
• Synthetic Self-Localizing Ligands That Control the Spatial Location of Proteins in Living Cells
  作者：Manabu Ishida、Hideaki Watanabe、Kazumasa Takigawa、Yasutaka Kurishita、Choji Oki、Akinobu Nakamura、Itaru Hamachi、Shinya Tsukiji

  DOI：10.1021/ja4046907

  日期：2013.8.28

  Small-molecule ligands that control the spatial location of proteins in living cells would be valuable tools for regulating biological systems. However, the creation of such molecules remains almost unexplored because of the lack of a design methodology. Here we introduce a conceptually new type of synthetic ligands, self-localizing ligands (SLLs), which spontaneously localize to specific subcellular regions in mammalian cells. We show that SLLs bind their target proteins and relocate (tether) them rapidly from the cytoplasm to their targeting sites, thus serving as synthetic protein translocators. SLL-induced protein translocation enables us to manipulate diverse synthetic/endogenous signaling pathways. The method is also applicable to reversible protein translocation and allows control of multiple proteins at different times and locations in the same cell. These results demonstrate the usefulness of SLLs in the spatial (and temporal) control of intracellular protein distribution and biological processes, opening a new direction in the design of small-molecule tools or drugs for cell regulation.