pyrazino[2,3-h]dipyrido[3,2-a:2',3'-c]phenazine | 1262662-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: pyrazino[2,3-h]dipyrido[3,2-a:2',3'-c]phenazine
• 英文别名: 6,9,15,18,21,26-Hexazahexacyclo[12.12.0.02,7.08,13.016,25.017,22]hexacosa-1(26),2(7),3,5,8(13),9,11,14,16(25),17,19,21,23-tridecaene
• CAS: 1262662-12-3
• 化学式: C₂₀H₁₀N₆
• 分子量: 334.34
• InChiKey: JNKDUUZRIRARCE-UHFFFAOYSA-N

物化性质

• 沸点：
  673.9±50.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  pyrazino[2,3-h]dipyrido[3,2-a:2',3'-c]phenazine 在 Amberlite ion exchange resin (chloride form) 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 pyrazino[2,3-h]ethylenedipyrido[3,2-a:2',3'-c]phenazilium dichloride
  参考文献：
  名称：

  Quaternarized pdppz: synthesis, DNA-binding and biological studies of a novel dppz derivative that causes cellular death upon light irradiation

  摘要：

  研究表明，季铵盐化 pdppz 衍生物 1 能与 DNA 紧密结合，其基态和激发态光物理特性也随之发生变化。此外，该化合物还能迅速被细胞吸收，并在光照下诱导多种癌细胞系在培养 24 小时后凋亡。

  DOI：

  10.1039/c0cc04303f
• 作为产物：
  描述：

  6-硝基喹喔啉 在 甲醇 、 palladium 10% on activated carbon 、 盐酸羟胺 、 sodium 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 生成 pyrazino[2,3-h]dipyrido[3,2-a:2',3'-c]phenazine
  参考文献：
  名称：

  Quaternarized pdppz: synthesis, DNA-binding and biological studies of a novel dppz derivative that causes cellular death upon light irradiation

  摘要：

  研究表明，季铵盐化 pdppz 衍生物 1 能与 DNA 紧密结合，其基态和激发态光物理特性也随之发生变化。此外，该化合物还能迅速被细胞吸收，并在光照下诱导多种癌细胞系在培养 24 小时后凋亡。

  DOI：

  10.1039/c0cc04303f

文献信息

• Detailed Biological Profiling of a Photoactivated and Apoptosis Inducing pdppz Ruthenium(II) Polypyridyl Complex in Cancer Cells
  作者：Suzanne M. Cloonan、Robert B. P. Elmes、MariaLuisa Erby、Sandra A. Bright、Fergus E. Poynton、Derek E. Nolan、Susan J. Quinn、Thorfinnur Gunnlaugsson、D. Clive Williams

  DOI：10.1021/acs.jmedchem.5b00451

  日期：2015.6.11

  Ruthenium polypyridyl complexes show great promise as new photodynamic therapy (PDT) agents. However, a lack of detailed understanding of their mode of action in cells poses a challenge to their development. We have designed a new Ru(II) PDT candidate that efficiently enters cells by incorporation of the lipophilic aromatic pdppz ([2,3-h]dipyrido[3,2-a:2',3'-c]phenazine) ligand and exhibits photoactivity through incorporation of 1,4,5,8-tetraazaphenanthrene ancillary ligands. Its photoreactivity toward biomolecules was studied in vitro, where light activation caused DNA cleavage. Cellular internalization occurred via an energy dependent mechanism. Confocal and transmission electron microscopy revealed that the complex localizes in various organelles, including the mitochondria. The complex is nontoxic in the dark, with cellular clearance within 96 h; however, upon visible light activation it induces caspase-dependent and reactive-oxygen-species-dependent apoptosis, with low micromolar IC50 values. This investigation greatly increases our understanding of such systems in cellulo, aiding development and realization of their application in cancer therapy.