5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin copper | 81046-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin copper
• 英文别名: Cu[5-(4-hydroxylphenyl)-10,15,20-triphenylporphyrin]
• CAS: 81046-68-6
• 化学式: C₄₄H₂₈CuN₄O
• 分子量: 692.279
• InChiKey: UDTIQSLQWKBROR-DAJBKUBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin copper 、 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58 %的产率得到
  参考文献：
  名称：

  A Light‐Triggered J‐Aggregation‐Regulated Therapy Conversion: from Photodynamic/Photothermal Therapy to Long‐Lasting Chemodynamic Therapy for Effective Tumor Ablation

  摘要：

  Reactive oxygen species (ROS) have become an effective tool for tumor treatment. The combination of photodynamic therapy (PDT) and chemodynamic therapy (CDT) takes advantage of various ROS and enhances therapeutic effects. However, the activation of CDT usually occurs before PDT, which hinders the sustained maintenance of hydroxyl radicals (⋅OH) and reduces the treatment efficiency. Herein, we present a light‐triggered nano‐system based on molecular aggregation regulation for converting cancer therapy from PDT/photothermal therapy (PTT) to a long‐lasting CDT. The ordered J‐aggregation enhances the photodynamic properties of the cyanine moiety while simultaneously suppressing the chemodynamic capabilities of the copper‐porphyrin moiety. Upon light irradiation, Cu‐PCy JNPs demonstrate strong photodynamic and photothermal effects. Meanwhile, light triggers a rapid degradation of the cyanine backbone, leading to the destruction of the J‐aggregation. As a result, a long‐lasting CDT is sequentially activated, and the sustained generation of ⋅OH is observed for up to 48 hours, causing potent cellular oxidative stress and apoptosis. Due to their excellent tumor accumulation, Cu‐PCy JNPs exhibit effective in vivo tumor ablation through the converting therapy. This work provides a new approach for effectively prolonging the chemodynamic activity in ROS‐based cancer therapy.

  DOI：

  10.1002/anie.202404395
• 作为产物：
  描述：

  5-(4'-hydroxyphenyl)-10,15,20-triphenylporphyrin 、 copper(II) nitrate trihydrate 以 N,N-二甲基甲酰胺 为溶剂， 以51 %的产率得到5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin copper
  参考文献：
  名称：

  A Light‐Triggered J‐Aggregation‐Regulated Therapy Conversion: from Photodynamic/Photothermal Therapy to Long‐Lasting Chemodynamic Therapy for Effective Tumor Ablation

  摘要：

  Reactive oxygen species (ROS) have become an effective tool for tumor treatment. The combination of photodynamic therapy (PDT) and chemodynamic therapy (CDT) takes advantage of various ROS and enhances therapeutic effects. However, the activation of CDT usually occurs before PDT, which hinders the sustained maintenance of hydroxyl radicals (⋅OH) and reduces the treatment efficiency. Herein, we present a light‐triggered nano‐system based on molecular aggregation regulation for converting cancer therapy from PDT/photothermal therapy (PTT) to a long‐lasting CDT. The ordered J‐aggregation enhances the photodynamic properties of the cyanine moiety while simultaneously suppressing the chemodynamic capabilities of the copper‐porphyrin moiety. Upon light irradiation, Cu‐PCy JNPs demonstrate strong photodynamic and photothermal effects. Meanwhile, light triggers a rapid degradation of the cyanine backbone, leading to the destruction of the J‐aggregation. As a result, a long‐lasting CDT is sequentially activated, and the sustained generation of ⋅OH is observed for up to 48 hours, causing potent cellular oxidative stress and apoptosis. Due to their excellent tumor accumulation, Cu‐PCy JNPs exhibit effective in vivo tumor ablation through the converting therapy. This work provides a new approach for effectively prolonging the chemodynamic activity in ROS‐based cancer therapy.

  DOI：

  10.1002/anie.202404395

文献信息

• Synthesis of Diaryl Ether-Linked Porphyrin Dimers via Ullmann Coupling Reaction
  作者：Jian Wu、Xu-Liang Jiang、Hong-Liang Zhang

  DOI：10.3987/com-06-10816

  日期：——

  Diaryl ether-linked porphyrin dimers were synthesized by CuI-catalyzed Ullmann coupling reaction between 5-(4-hydroxylphenyl)-10,15,20-triphenylporphyrin and 5-(4-iodophenyl)-10,15,20- triphenylporphyrin as well as their metalated derivatives.

  采用CuI催化的5-(4-羟基苯基)-10,15,20-三苯基卟啉与5-(4-碘苯基)-10,15,20-三苯基卟啉的Ullmann偶联反应合成二芳基醚连接的卟啉二聚体。它们的金属化衍生物。
• Impact of different TiO 2 samples and porphyrin substituents on the photocatalytic performance of TiO 2 @copper porphyrin composites
  作者：Xiang-fei Lü、Hui Qian、Giuseppe Mele、Alberto De Riccardis、Ran Zhao、Jie Chen、Hao Wu、Nan-jiang Hu

  DOI：10.1016/j.cattod.2016.04.027

  日期：2017.3

  In this manuscript, the preparation and the comparison of the photocatalytic activity of novel TiO2@copper porphyrin composites obtained by impregnation of (5-(4-hydroxy) phenyl-10,15,20-triphenyl copper porphyrin la, 5-(4-ethylacetatatomethoxy) phenyl-10,15,20-triphenylcopper porphyrin 1b, and 5-(4-carboxylatomethoxy) phenyl-10,15,20-triphenyl copper porphyrin 1c respectively onto the surface of different TiO2 samples, commercial (cTiO(2)) and home-prepared (pTiO(2)), has been reported. The TiO2@copper porphyrin composites were characterized by XRD, BET, UV-vis, FT-IR and SEM-EDS techniques.For the first time, the formation of aggregated porphyrin, most likely in form of dimers 1a-1a, 1b-1b and 1c-1c, were detected on the lower and less hydroxylated surface area of cTiO(2).The photocatalytic activity of the samples was evaluated on the basis of the photodegradation of 4-nitrophenol (4-NP) in aqueous solution under metal halide lamp irradiation.The highest photocatalytic efficiency in the degradation of 4-NP, observed by using the carboxylporphyrin 1c as sensitizer supported onto the surface of both pTiO(2) or cTiO(2), was ascribed to the optimal combination of the anchoring mode with the efficient electron injection in the conduction band that carboxylic group produced at the surface of the TiO2 samples. (C) 2016 Elsevier B.V. All rights reserved.
• Spectroscopic investigations on the simulated solar light induced photodegradation of 4-nitrophenol by using three novel copper(II) porphyrin–TiO2 photocatalysts
  作者：Xiang-fei Lü、Wan-jun Sun、Jun Li、Wei-xia Xu、Feng-xing Zhang

  DOI：10.1016/j.saa.2013.02.021

  日期：2013.7

  Three porphyrins containing different functional groups (-OH, -CO2C2H5, -COOH), 5-(4-hydroxy) phenyl-10,15,20-triphenyl porphyrin (1a), 5-(4-ethylacetatatomethoxy) phenyl-10,15,20-triphenyl porphyrin (1b), 5-(4-carboxylatomethoxy) phenyl-10,15,20-triphenyl porphyrin (1c), were synthesized and characterized spectroscopically. The CuPp(2a, 2b, 2c)-TiO2 photocatalysts were then prepared and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), UV-vis diffuse reflectance spectroscopy (UV-vis-DRS), Fourier-transform infrared spectroscopy (FT-IR). The photocatalytic activities of the photocatalysts were investigated by carrying out the photodegradation of 4-nitrophenol in aqueous solution under simulated solar irradiation. It was found that the CuPp(2a, 2b, 2c)-TiO2 enhanced the photocatalytic efficiency of bare TiO2 in photo-degrading the 4-NP due to the interaction between CuPp(2a, 2b, 2c) and TiO2, resulted in the enhancement of the photogenerated electron-hole separation. The reasons of this enhanced photocatalytic activity were also discussed. Based on the present study, it could be considered as a promising photocatalyst for the further industrial application. (C) 2013 Elsevier B.V. All rights reserved.