4,4'-(2,2':5',2''-terthiophene-5,5''-diyl)bis(3-butoxycyclobut-3-ene-1,2-dione) | 1212009-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,4'-(2,2':5',2''-terthiophene-5,5''-diyl)bis(3-butoxycyclobut-3-ene-1,2-dione)
• 英文别名: 3-Butoxy-4-[5-[5-[5-(2-butoxy-3,4-dioxocyclobuten-1-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]cyclobut-3-ene-1,2-dione
• CAS: 1212009-78-3
• 化学式: C₂₈H₂₄O₆S₃
• 分子量: 552.693
• InChiKey: HWQBFVITLYWBGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,4'-(2,2':5',2''-terthiophene-5,5''-diyl)bis(3-butoxycyclobut-3-ene-1,2-dione) 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 2.0h， 以91%的产率得到4,4'-(2,2':5',2''-terthiophene-5,5''-diyl)bis(3-hydroxycyclobut-3-ene-1,2-dione)
  参考文献：
  名称：

  Photooxidation and Phototoxicity of π-Extended Squaraines

  摘要：

  This paper describes the synthesis of pi-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules it,, photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis.

  DOI：

  10.1021/jm901727j
• 作为产物：
  描述：

  alpha-三联噻吩 、 方酸二正丁酯 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以37%的产率得到4,4'-(2,2':5',2''-terthiophene-5,5''-diyl)bis(3-butoxycyclobut-3-ene-1,2-dione)
  参考文献：
  名称：

  Photooxidation and Phototoxicity of π-Extended Squaraines

  摘要：

  This paper describes the synthesis of pi-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules it,, photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis.

  DOI：

  10.1021/jm901727j

文献信息

• Photooxidation and Phototoxicity of π-Extended Squaraines
  作者：Valentina Rapozzi、Luca Beverina、Patrizio Salice、Giorgio A. Pagani、Monica Camerin、Luigi E. Xodo

  DOI：10.1021/jm901727j

  日期：2010.3.11

  This paper describes the synthesis of pi-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules it,, photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis.