3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine | 945975-87-1

• 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: 3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine
• 英文别名: 6-(2-pyridyl)-dipyrido-[3,2-a:2',3'-c]-phenazine；3-(pyrid-2'-yl)dipyrido[3,2-a:2':3'-c]phenazine；6-(2-pyridyl)dipyrido[3,2-a:2',3'-c]phenazine；pydppz；3-(Pyridin-2-yl)dipyrido[3,2-a:2',3'-c]phenazine；6-pyridin-2-ylquinoxalino[2,3-f][1,10]phenanthroline
• CAS: 945975-87-1
• 化学式: C₂₃H₁₃N₅
• 分子量: 359.39
• InChiKey: VCISBHJFHOBFAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine 、 iron(II) chloride 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到[Fe(3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine)₂]Cl₂
  参考文献：
  名称：

  Polypyridyl iron(II) complexes showing remarkable photocytotoxicity in visible light

  摘要：

  通过配位体B的铁(II)配合物，即N,N,N捐赠体2-(2-吡啶基)-1,10-菲啰啉（1中的pyphen）和3-(吡啶-2-基)双吡啶[3,2-a:2',3'-c]苯嗪（2中的pydppz），制备并表征了[Fe(B)2]Cl2（1和2）。它们在水相DMF中为1:2电解质。这些顺磁性配合物在DMF中显示出近570 nm的金属-配体电荷转移带。由于平面菲啰啉基团的存在，这些配合物与小牛胸腺DNA的结合常数(Kb)约为106 M−1，表明其具有显著的插层DNA结合能力。配合物2在永生化的人角质形成细胞HaCaT和乳腺癌细胞系MCF-7中表现出显著的光细胞毒性，在可见光（400-700 nm）下的IC50值分别为0.08和13 μM。配合物2在HaCaT细胞中仅显示出轻微的暗毒性，但在MCF-7癌细胞中则无毒性。光诱导的细胞损伤通过活性氧物质的生成遵循凋亡途径，DCFDA测定表明了这一点。

  DOI：

  10.1007/s12039-015-0815-0

文献信息

• Photocytotoxic Oxidovanadium(IV) Complexes of Polypyridyl Ligands Showing DNA‐Cleavage Activity in Near‐IR Light
  作者：Samya Banerjee、Akhtar Hussain、Puja Prasad、Imran Khan、Bhabatosh Banik、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1002/ejic.201200344

  日期：2012.8

  104 to 1.1 x 106 M1. The complexes show poor chemical nuclease activity in the dark and exhibit significant DNA-photocleaving activity in near-IR light of 705 and 785 nm forming .OH radicals. Complexes 2-4 show remarkable photocytotoxicity in HeLa cancer cells. FACS analysis of the HeLa cells treated with complex 4 shows cell death as highlighted by the sub G1 peak. Propidium iodide staining data indicate

  氧化钒 (IV) 配合物 VO(pyphen)(L)]Cl2 (1, 2) 和 VO(pydppz)(L)]Cl2 (3, 4)，其中 L 是 1,10-菲咯啉（phen 在 1 和 3）制备并表征了双吡啶并3,2-a:2',3'-c]吩嗪（2和4中的dppz）。VO(pyphen)(phen)](ClO4)2 (1a) 的晶体结构显示六配位的 VN5O 几何结构，其中多吡啶配体以经向方式结合，而 phen 配体显示出螯合结合模式与N-供体位点反式到氧化氧钒基。复合物在 DMF 中显示 720-750 nm 内的 dd 带。单电子顺磁复合物是 DMF 中的 1:2 电解质。在 DMF/0.1 M TBAP 中，复合物在 -0.85 V 与 SCE 附近表现出不可逆的 VIV/VIII 氧化还原响应。该复合物与小牛胸腺 (ct) DNA 结合，Kb 值在 7.5 x 104 到 1.1 x 106
• Photo-induced DNA cleavage activity and remarkable photocytotoxicity of lanthanide(iii) complexes of a polypyridyl ligand
  作者：Akhtar Hussain、Sudarshan Gadadhar、Tridib K. Goswami、Anjali A. Karande、Akhil R. Chakravarty

  DOI：10.1039/c1dt11400j

  日期：——

  photocleavage activity and photocytotoxicity studied. The crystal structure of complex 2 displays a GdO6N3 coordination. The pydppz complexes 3–5 show an electronic spectral band at ∼390 nm in DMF. The La(III) complexes are diamagnetic, while the Gd(III) complexes are paramagnetic with seven unpaired electrons. The molar conductivity data suggest 1 : 1 electrolytic nature of the complexes in aqueous DMF. They

  稀土（III） 配合物[Ln（吡啶）（acac）2（NO 3）]（1，2），[Ln（pydppz）（acac）2（NO 3）]（3，4），并[La（pydppz）（anacac）2（NO 3）]（5）其中Ln为La（III）（在1，3，5）和d（III）（在2，4），pyphen是6-（2-吡啶基）-1,10-菲咯啉， pydppz 是 6-（2-吡啶基）-二吡啶并[3,2- a：2'，3'- c ]吩嗪，anacac是 蒽基乙酰丙酮酸酯 和 acac 是 乙酰丙酮制备，表征并研究了它们的DNA光切割活性和光细胞毒性。配合物2的晶体结构显示GdO 6 N 3协调。这pydppz配合物3-5显示出在390 nm处的电子光谱带DMF。这La（III） 络合物是抗磁性的，而 d（III）络合物是顺磁性的，带有七个不成对的电子。摩尔电导率数据表明配合物在水溶液中具有1：1的电解性质DMF。它们是小牛胸腺DNA的狂热结合剂，K
• Marked Differences in Light-Switch Behavior of Ru(II) Complexes Possessing a Tridentate DNA Intercalating Ligand
  作者：Yao Liu、Richard Hammitt、Daniel A. Lutterman、Randolph P. Thummel、Claudia Turro

  DOI：10.1021/ic700484j

  日期：2007.7.1

  The tridentate ligand 3-(pyrid-2'-yl)dipyrido[3,2-a:2',3'-c]phenazine (pydppz) has been prepared in two steps by elaboration of 2-(pyrid-2'-yl)-1,10-phenanthroline. Both homoleptic [Ru(pydppz)(2)](2+) and heteroleptic [Ru(tpy)(pydppz)](2+) (tpy = 2,2';6',2' '-terpyridine) complexes have been prepared and characterized by H-1 NMR. The absorption and emission spectra are consistent with low-lying MLCT excited states, which are typical of Ru(II) complexes. Femtosecond transient absorption measurements show that that the (MLCT)-M-3 excited state of the heteroleptic complex [Ru(tpy)(pydppz)](2+) (tau approximate to 5 ns) is longer-lived than that of the homoleptic complex [Ru(pydppz)(2)](2+) (tau = 2.4 ns) and that these lifetimes are significantly longer than that of the (MLCT)-M-3 state of the parent complex [Ru(tpy)(2)](2+) (tau = 120 ps). These differences are explained by the lower-energy (MLCT)-M-3 excited state present in [Ru(tpy)(pydppz)](2+) and [Ru(pydppz)(2)](2+) compared to [Ru(tpy)(2)](2+), resulting in less deactivation of the former through the ligand-field state(s). DFT and TDDFT calculations are consistent with this explanation. [Ru(tpy)(pydppz)](2+) and [Ru(pydppz)(2)](2+) bind to DNA through the intercalation of the pydppz ligand; however, only the heteroleptic complex exhibits luminescence enhancement in the presence of DNA. The difference in the photophysical behavior of the complexes is explained by the inability of [Ru(pydppz)(2)](2+) to intercalate both pydppz ligands, such that one pydppz always remains exposed to the solvent. DNA photocleavage is observed for [Ru(tpy)(pydppz)](2+) in air, but not for [Ru(pydppz)(2)](2+). The DNA damage likely proceeds through the production of small amounts of O-1(2) by the longer-lived complex. Although both complexes possess the intercalating pydppz ligand, they exhibit different photophysical properties in the presence of DNA.
• Photo-induced anticancer activity of polypyridyl platinum(II) complexes
  作者：Basudev Maity、Sudarshan Gadadhar、Tridib K. Goswami、Anjali A. Karande、Akhil R. Chakravarty

  DOI：10.1016/j.ejmech.2012.09.025

  日期：2012.11

  Polypyridyl platinum(II) complexes (1-5), viz., [Pt(pyphen)Cl]Cl (1), [Pt(pyphen)(C CFc)]Cl (2), [Pt(pydppz)Cl]Cl (3), [Pt(pydppz)(C CPh)]Cl (4) and [Pt(pydppz)(C CFc)]Cl (5), where pyphen is 6-(2-pyridyl)-1,10-phenanthroline, pydppz is 6-(2-pyridyl)-dipyrido-[3,2-a:2',3'-c]-phenazine, FcC CH is ferrocenyl acetylene and PhC CH is phenyl acetylene, were synthesized, characterized and their DNA binding and photocytotoxic properties studied. The complexes showed strong binding affinity to calf-thymus DNA giving K-app of similar to 10(6)-10(7) M-1. Complexes 4 and 5 showed dual mode of binding to ct-DNA. The pydppz complexes 3-5 having a photoactive phenazine moiety showed photocytotoxicity in HeLa and MCF-7 cells in UV-A light of 365 nm with apoptotic cell death as evidenced from the acridine orange/ethidium bromide dual staining and the FACS data. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Polypyridyl iron(II) complexes showing remarkable photocytotoxicity in visible light
  作者：ADITYA GARAI、UTTARA BASU、ILA PANT、PATURU KONDAIAH、AKHIL R CHAKRAVARTY

  DOI：10.1007/s12039-015-0815-0

  日期：2015.4

  Iron(II) complexes of polypyridyl ligands (B), viz. [Fe(B)2]Cl2 (1 and 2) of N, N, N-donor 2-(2-pyridyl)-1,10-phenanthroline (pyphen in 1) and 3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine (pydppz in 2), are prepared and characterized. They are 1:2 electrolytes in aqueous DMF. The diamagnetic complexes exhibit metal to ligand charge transfer band near 570 nm in DMF. The complexes are avid binders to calf thymus DNA giving binding constant (K b) values of ∼106 M−1 suggesting significant intercalative DNA binding of the complexes due to presence of planar phenanthroline bases. Complex 2 exhibits significant photocytotoxicity in immortalized human keratinocyte cells HaCaT and breast cancer cell line MCF-7 giving IC50 values of 0.08 and 13 μM in visible light (400–700 nm). Complex 2 shows only minor dark toxicity in HaCaT cells but is non-toxic in dark in MCF-7 cancer cells. The light-induced cellular damage follows apoptotic pathway on generation of reactive oxygen species as evidenced from the dichlorofluorescein diacetate (DCFDA) assay.

  通过配位体B的铁(II)配合物，即N,N,N捐赠体2-(2-吡啶基)-1,10-菲啰啉（1中的pyphen）和3-(吡啶-2-基)双吡啶[3,2-a:2',3'-c]苯嗪（2中的pydppz），制备并表征了[Fe(B)2]Cl2（1和2）。它们在水相DMF中为1:2电解质。这些顺磁性配合物在DMF中显示出近570 nm的金属-配体电荷转移带。由于平面菲啰啉基团的存在，这些配合物与小牛胸腺DNA的结合常数(Kb)约为106 M−1，表明其具有显著的插层DNA结合能力。配合物2在永生化的人角质形成细胞HaCaT和乳腺癌细胞系MCF-7中表现出显著的光细胞毒性，在可见光（400-700 nm）下的IC50值分别为0.08和13 μM。配合物2在HaCaT细胞中仅显示出轻微的暗毒性，但在MCF-7癌细胞中则无毒性。光诱导的细胞损伤通过活性氧物质的生成遵循凋亡途径，DCFDA测定表明了这一点。