5-(4-bromohexyloxy)phenyl-10,15,20-triphenylporphyrin | 102202-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5-(4-bromohexyloxy)phenyl-10,15,20-triphenylporphyrin
• CAS: 102202-49-3
• 化学式: C₅₀H₄₁BrN₄O
• 分子量: 793.806
• InChiKey: MWBMEXWFHZOQIB-JXNHMKLYSA-N

物化性质

• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.66
• 重原子数：
  56.0
• 可旋转键数：
  11.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.59
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-bromohexyloxy)phenyl-10,15,20-triphenylporphyrin 、 fluorescein free acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-fluoresceinhexyloxy)phenyl-10,15,20-triphenylporphyrin
  参考文献：
  名称：

  DNA interactions, photocleavage, and cytotoxicity of fluorescein–porphyrinatozinc complexes with different lengths of links

  摘要：

  Three fluoresceinporphyrinatozinc complexes Zn(Fl-PPTPP) (1) (Fl-PPTPp=5-(4-fluoresceinpropyloxy)phenyl-10,15,20-triphenylporphyrin), Zn(Fl-HPTPP) (2) (Fl-HPTPp=5-(4-fluoresceinhexyloxy)phenyl-10,15,20-triphenylporphyrin) and Zn(Fl-DPTPP) (3) (Fl-DPTPp=5-(4-fluoresceindecoxy)phenyl-10,15,20-triphenylporphyrin) have been synthesized and characterized by elemental analysis, IR, UV/Vis, Electrospray mass spectra, and H-1 NMR. The DNA-binding behaviors of these complexes with calf-thymus DNA (CT-DNA) were investigated by UVvis absorption titration, fluorescence spectra, viscosity measurements, thermal denaturation, and circular dichroism. The results suggest that 1, 2, and 3 interact with CT-DNA by intercalation, and the conformation of fluoresceinporphyrin hybrids is an important factor affecting the DNA-binding affinities. The DNA-binding affinities (K-b values) follow the order 1>2>3. In addition, their photocleavage reactions with pBR322 supercoiled plasmid DNA were investigated by gel electrophoresis. All complexes exhibit significant DNA cleavage activity. These complexes have cytotoxic activities against myeloma cell (Ag8.653) and gliomas cell (U251) lines. Complex 1 was the most potent antitumor agent among the three complexes.

  DOI：

  10.1080/00958972.2013.786051

文献信息

• DNA-binding and photocleavage of fluorescein-porphyrinatozinc complexes
  作者：Jiazheng Lu、Haiwei Guo、Yongli Zhang、Jing Jiang、Yunjin Liu、Linquan Zang、Jinwang Huang

  DOI：10.1080/00958972.2012.681381

  日期：2012.5.20

  Three fluorescein-porphyrinatozinc(II) complexes, Zn(Fl-HPTTP) (1) (Fl-HPTTP = 5-(4-fluoresceinhexyloxy) phenyl-10,15,20-tritolylporphyrin), Zn(Fl-HPTPP) (2) (Fl-HPTPP = 5-(4-fluoresceinhexyloxy) phenyl-10,15,20-triphenylporphyrin), and Zn(Fl-HPTCPP) (3) (Fl-HPTCPP 5-(4-fluoresceinhexyloxy) phenyl-10,15,20-tri(4-chloro) phenylporphyrin), have been synthesized and characterized by elemental analysis, IR, UV-Vis, ES-MS, and H-1 NMR. The DNA-binding behaviors of these complexes with calf-thymus DNA (ct-DNA) were investigated by UV-Vis absorption titration, fluorescence spectra, viscosity measurements, thermal denaturation, and circular dichroism. The results suggest that 1, 2, and 3 interact with ct-DNA by intercalation and the DNA-binding affinities of these fluorescein-porphyrinatozinc(II) complexes may be closely associated with electronic effects of the substituent group introduced on the porphyrin ring of the ligands. The DNA-binding affinity (K-b values) follows the order 1 > 2 > 3. In addition, their photocleavage reactions with pBR322 supercoiled plasmid DNA were investigated by gel electrophoresis experiments. All complexes exhibit significant DNA cleavage activity. The cleavage ability of the fluorescein-porphyrinatozinc(II) complexes follows the order 1 > 2 > 3, in parallel to the magnitude of their intrinsic binding constants.