N,N'-bis(5-bromopentyl)quinacridone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N'-bis(5-bromopentyl)quinacridone
• 英文别名: 5,12-Bis(5-bromopentyl)quinolino[2,3-b]acridine-7,14-dione
• 化学式: C₃₀H₃₀Br₂N₂O₂
• 分子量: 610.388
• InChiKey: FCZKVSYPCNDRRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 N,N'-bis(5-bromopentyl)quinacridone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到N,N'-bis(5-(4-methylpiperazin-1-yl)pentyl)quinacridone
  参考文献：
  名称：

  DNA interaction, cellular localization and cytotoxicity of quinacridone derivatives

  摘要：

  Quinacridone derivatives (QAs) are widely used in industrial colorant, chemical sensors and organic optoelectronic devices; however their biological applications are rarely reported. Here we describe the interaction of QAs with different DNA forms and cancer cells. Quinacridone and N,N'-bis(5-bromopentyl) quinacridone (QAB) selectively bind parallel G-quadruplex DNA through end-stacking. N,N'-bis(methylpiperazinylpentyl) quinacridone (QAP) and N,N'-bis(dimethyl-aminopentyl) quinacridone (QAT) strongly bind all DNA forms through hydrogen bonding and electrostatic interaction of the alkylamine side chains and DNA. Quinacridone does not enter living cells; QAB enters living cells and mainly locates in lysosome; QAP and QAT enter living cells and locate in whole cells, especially in nuclei through binding DNA. However, these QAs do not show significant cytotoxicity. These results suggest that side chains greatly affect the DNA interaction, cellular permeability and localization of QAs, and provide useful information for the design of DNA-binding drugs and fluorescent probes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.035
• 作为产物：
  描述：

  1,5-二溴戊烷 、 喹吖啶酮 在 四乙基溴化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 N,N'-bis(5-bromopentyl)quinacridone
  参考文献：
  名称：

  A fluorescent metal sensor based on macrocyclic chelation

  摘要：

  功能化的乙二胺奎纳克酮衍生物 3a–c 显示出橙色荧光 (λem(max) = 558 nm)，当添加络合金属离子时，荧光会被猝灭，因而形成了一个大环螯合物，使金属离子与荧光团彼此靠近。

  DOI：

  10.1039/b100535i

文献信息

• A fluorescent metal sensor based on macrocyclic chelation
  作者：Gérard Klein、Daniel Kaufmann、Stefan Schürch、Jean-Louis Reymond

  DOI：10.1039/b100535i

  日期：——

  The ethylenediamine functionalized quinacridone derivatives 3a–c display an orange fluorescence (λem(max) = 558 nm) which is quenched upon addition of coordinating metal ions by formation of a macrocyclic chelate bringing metal ion and fluorophore in close proximity to one another.

  功能化的乙二胺奎纳克酮衍生物 3a–c 显示出橙色荧光 (λem(max) = 558 nm)，当添加络合金属离子时，荧光会被猝灭，因而形成了一个大环螯合物，使金属离子与荧光团彼此靠近。
• N,N-二戊烷取代的喹吖啶酮类化合物及其制 备方法与应用
  申请人：中国科学院化学研究所

  公开号：CN104650080B

  公开（公告）日：2017-04-05

  本发明提供一种特异性地结合核酸的N,N‑二戊烷取代的喹吖啶酮类化合物及其制备方法与其在抗肿瘤中的应用。其结构式如式I所示。利用式I所示N,N‑二戊烷取代的喹吖啶酮类化合物通过荧光光谱可快速判断待测样品是否为核酸。在光照条件下所述式I所示N,N‑二戊烷取代的喹吖啶酮类化合物有较高的杀死肿瘤细胞或导致肿瘤细胞凋亡的活性，有作为光化学抗肿瘤治疗剂的潜力。式I所示化合物容易合成，并且十分稳定，便于储存。
• DNA interaction, cellular localization and cytotoxicity of quinacridone derivatives
  作者：Ying Liu、Linlin Wang、Jin Zhou、Shangrong Wu、Yongbiao Wei、Ang Chang、Xiangjun Liu、Dihua Shangguan

  DOI：10.1016/j.dyepig.2015.05.035

  日期：2015.10

  Quinacridone derivatives (QAs) are widely used in industrial colorant, chemical sensors and organic optoelectronic devices; however their biological applications are rarely reported. Here we describe the interaction of QAs with different DNA forms and cancer cells. Quinacridone and N,N'-bis(5-bromopentyl) quinacridone (QAB) selectively bind parallel G-quadruplex DNA through end-stacking. N,N'-bis(methylpiperazinylpentyl) quinacridone (QAP) and N,N'-bis(dimethyl-aminopentyl) quinacridone (QAT) strongly bind all DNA forms through hydrogen bonding and electrostatic interaction of the alkylamine side chains and DNA. Quinacridone does not enter living cells; QAB enters living cells and mainly locates in lysosome; QAP and QAT enter living cells and locate in whole cells, especially in nuclei through binding DNA. However, these QAs do not show significant cytotoxicity. These results suggest that side chains greatly affect the DNA interaction, cellular permeability and localization of QAs, and provide useful information for the design of DNA-binding drugs and fluorescent probes. (C) 2015 Elsevier Ltd. All rights reserved.