1,4,8,11,15,18,22,25-octakis[3-(pentyloxycarbonyl)propyloxy]phthalocyanine | 1309460-25-0

• 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: 1,4,8,11,15,18,22,25-octakis[3-(pentyloxycarbonyl)propyloxy]phthalocyanine
• 英文别名: Pentyl 4-[[8,14,17,23,26,32,35-heptakis(4-oxo-4-pentoxybutoxy)-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),3(40),4,6,8,10,12,14,16,18,20,22,24,26,28(38),29,31,33,35-nonadecaen-5-yl]oxy]butanoate；pentyl 4-[[8,14,17,23,26,32,35-heptakis(4-oxo-4-pentoxybutoxy)-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),3(40),4,6,8,10,12,14,16,18,20,22,24,26,28(38),29,31,33,35-nonadecaen-5-yl]oxy]butanoate
• CAS: 1309460-25-0
• 化学式: C₁₀₄H₁₄₆N₈O₂₄
• 分子量: 1892.34
• InChiKey: VTYZVPNQQMTOIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.9
• 重原子数：
  136
• 可旋转键数：
  80
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  393
• 氢给体数：
  2
• 氢受体数：
  30

反应信息

• 作为产物：
  描述：

  戊醇 、 3,6-bis[3-(ethyloxycarbonyl)propyloxy]-1,2-benzenedicarbonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 24.0h， 以1.6%的产率得到1,4,8,11,15,18,22,25-octakis[3-(pentyloxycarbonyl)propyloxy]phthalocyanine
  参考文献：
  名称：

  Photophysical properties and photocytotoxicity of novel phthalocyanines – potentially useful for their application in photodynamic therapy

  摘要：

  Two novel zinc(II) phthalocyanines bearing non-peripheral ester-alkyloxy substituents (Pc-4 and Pc-5) were synthesized, by a two-step procedure starting from 2,3-dicyanohydroquinone. Both sensitizers show promising photophysical properties, including solvatochromic study, qualitative evaluation of emission, aggregation behavior and singlet oxygen generation. It was proven that the photodynamic activity of the compounds studied depends on the molecular oxygen level. Comparison of the quantum yields of singlet oxygen generation as well as the oxidation rate constants using 1,3-diphenylisobenzofurane before and after deaeration proved the photodynamic effect of Pc-4 and Pc-5 to be governed by the photosensitization mechanism II. Changes in the quantities of the compounds exposed to irradiation were also estimated. Upon their exposure to light the changes in intensity of the Q band were monitored. The photodecomposition of Pc-4 and Pc-5 in DMSO or DMF solutions was found to proceed according to the first order kinetic reaction in two stages.The photosensitizing effect of Pc-4 in HSC-3 cells was significantly lower than that of ZnPc. Pc-4 was ineffective at 0.1 mu M, while a low, approx. 15% photocytotoxicity was observed at 5 mu M, at a distance of 5 and 10 cm. The efficacy of Pc-4 in photokilling of cultured cells is affected by hydrophobicity and the aggregation status of the photosensitizer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.03.003

文献信息

• Photophysical properties and photocytotoxicity of novel phthalocyanines – potentially useful for their application in photodynamic therapy
  作者：Tomasz Goslinski、Tomasz Osmalek、Krystyna Konopka、Marcin Wierzchowski、Piotr Fita、Jadwiga Mielcarek

  DOI：10.1016/j.poly.2011.03.003

  日期：2011.5

  Two novel zinc(II) phthalocyanines bearing non-peripheral ester-alkyloxy substituents (Pc-4 and Pc-5) were synthesized, by a two-step procedure starting from 2,3-dicyanohydroquinone. Both sensitizers show promising photophysical properties, including solvatochromic study, qualitative evaluation of emission, aggregation behavior and singlet oxygen generation. It was proven that the photodynamic activity of the compounds studied depends on the molecular oxygen level. Comparison of the quantum yields of singlet oxygen generation as well as the oxidation rate constants using 1,3-diphenylisobenzofurane before and after deaeration proved the photodynamic effect of Pc-4 and Pc-5 to be governed by the photosensitization mechanism II. Changes in the quantities of the compounds exposed to irradiation were also estimated. Upon their exposure to light the changes in intensity of the Q band were monitored. The photodecomposition of Pc-4 and Pc-5 in DMSO or DMF solutions was found to proceed according to the first order kinetic reaction in two stages.The photosensitizing effect of Pc-4 in HSC-3 cells was significantly lower than that of ZnPc. Pc-4 was ineffective at 0.1 mu M, while a low, approx. 15% photocytotoxicity was observed at 5 mu M, at a distance of 5 and 10 cm. The efficacy of Pc-4 in photokilling of cultured cells is affected by hydrophobicity and the aggregation status of the photosensitizer. (C) 2011 Elsevier Ltd. All rights reserved.