benzo[i]dipyrido-[3,2-a:2',3'-c]phenazine

• 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: benzo[i]dipyrido-[3,2-a:2',3'-c]phenazine
• 英文别名: dppn；8b,14a-Dihydroquinoxalino[2,3-f][1,10]phenanthroline
• 化学式: C₁₈H₁₂N₄
• 分子量: 284.32
• InChiKey: MPBJNNZWLYASSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 bis(4,4'-dimethyl-2,2'-bipyridine)dichlororuthenium(II) 、 benzo[i]dipyrido-[3,2-a:2',3'-c]phenazine 以 乙二醇 为溶剂， 反应 0.17h， 以66%的产率得到4,4'-dimethyl-2,2'-bipyridine
  参考文献：
  名称：

  In Vitro Multiwavelength PDT with ³IL States: Teaching Old Molecules New Tricks

  摘要：

  The purpose of the present investigation was to ascertain whether (IL)-I-3 excited states with microsecond lifetimes are universally potent for photodynamic applications, and if these long-lived states are superior to their (MLCT)-M-3 counterparts as in vitro PDT agents. A family of blue-green absorbing, Ru(II)-based transition metal complexes derived from pi-expansive dppn ligand was prepared and characterized according to its photodynamic activity against HL-60 cells, and toward DNA in cell-free media. Complexes in this series that are characterized by low-energy and long-lived (IL)-I-3 excited states photocleaved DNA with blue, green, red, and near-IR light. This panchromatic photodynamic effect translated to in vitro multiwavelength photodynamic therapy (PDT) with red-light cytotmdcities as low as 1.5 mu M (EC50) for the parent complex and 400 nM for its more lipophilic counterpart. This potency is similar to that achieved with Ru(II)-based dyads containing long-lived (IL)-I-3 excitons located on appended pyrenyl units, and appears to be a general property of sufficiently long-lived excited states. Moreover, the red PDT observed for certain members of this family was almost S times more potent than Photofrin with therapeutic indices 30 times greater. Related Ru(II) complexes having lowest-lying (MLCT)-M-3 states of much shorter duration (<= 1 mu s) did not yield DNA photodamage or in vitro PDT with red or near-IR light, nor did the corresponding Os(II) complex with a submicrosecond (IL)-I-3 excited state lifetime. Therefore, metal complexes that utilize highly photosensitizing (IL)-I-3 excited states, with suitably long lifetimes (>> 1 mu s), are well-poised to elicit PDT at wavelengths even where their molar extinction coefficients are very low (<100 M-1 cm(-1)). Herein we demonstrate that such unexpected reactivity gives rise to very effective PDT in the typical therapeutic window (600-850 nm).

  DOI：

  10.1021/ic5002368

文献信息

• <i>In Vitro</i> Multiwavelength PDT with ³IL States: Teaching Old Molecules New Tricks
  作者：Huimin Yin、Mat Stephenson、Jordan Gibson、Eric Sampson、Ge Shi、Tariq Sainuddin、Susan Monro、Sherri A. McFarland

  DOI：10.1021/ic5002368

  日期：2014.5.5

  The purpose of the present investigation was to ascertain whether (IL)-I-3 excited states with microsecond lifetimes are universally potent for photodynamic applications, and if these long-lived states are superior to their (MLCT)-M-3 counterparts as in vitro PDT agents. A family of blue-green absorbing, Ru(II)-based transition metal complexes derived from pi-expansive dppn ligand was prepared and characterized according to its photodynamic activity against HL-60 cells, and toward DNA in cell-free media. Complexes in this series that are characterized by low-energy and long-lived (IL)-I-3 excited states photocleaved DNA with blue, green, red, and near-IR light. This panchromatic photodynamic effect translated to in vitro multiwavelength photodynamic therapy (PDT) with red-light cytotmdcities as low as 1.5 mu M (EC50) for the parent complex and 400 nM for its more lipophilic counterpart. This potency is similar to that achieved with Ru(II)-based dyads containing long-lived (IL)-I-3 excitons located on appended pyrenyl units, and appears to be a general property of sufficiently long-lived excited states. Moreover, the red PDT observed for certain members of this family was almost S times more potent than Photofrin with therapeutic indices 30 times greater. Related Ru(II) complexes having lowest-lying (MLCT)-M-3 states of much shorter duration (<= 1 mu s) did not yield DNA photodamage or in vitro PDT with red or near-IR light, nor did the corresponding Os(II) complex with a submicrosecond (IL)-I-3 excited state lifetime. Therefore, metal complexes that utilize highly photosensitizing (IL)-I-3 excited states, with suitably long lifetimes (>> 1 mu s), are well-poised to elicit PDT at wavelengths even where their molar extinction coefficients are very low (<100 M-1 cm(-1)). Herein we demonstrate that such unexpected reactivity gives rise to very effective PDT in the typical therapeutic window (600-850 nm).