2-trimethylsilylethyl 4-[bis(5-formyl-1H-pyrrol-2-yl)methyl]benzoate | 1275576-04-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-trimethylsilylethyl 4-[bis(5-formyl-1H-pyrrol-2-yl)methyl]benzoate
• CAS: 1275576-04-9
• 化学式: C₂₃H₂₆N₂O₄Si
• 分子量: 422.556
• InChiKey: YOKLBSMXDJTJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl 4-[bis(5-formyl-1H-pyrrol-2-yl)methyl]benzoate 在 zinc diacetate 、 sodium acetate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 26.67h， 生成
  参考文献：
  名称：

  Metallation of pentaphyrin with Lu(III) dramatically increases reactive-oxygen species production and cell phototoxicity

  摘要：

  Photodynamic therapy (PDT) is an emerging cancer treatment modality based on the excitation of a nontoxic photosensitizer with harmless visible light to produce reactive-oxygen species (ROS) that induce apoptosis and/or necrosis in cancer cells. As the efficacy of this therapy strongly depends of the nature of the photosensitizer, there is a great interest to develop new photoactive molecules. Here we report for the first time the synthesis, characterization and bioactivity of metal complexes between the non-aromatic expanded porphyrin, namely 20-[[4'-(Trimethylsilyl)ethoxycarbonyl]phenyl-2,13-dimethyl-3,12-diethyl-[24] iso-pentaphyrin (PCRed) and Zn(II) [Zn(II)-PCRed] or Lu(III) [Lu(III)-PCRed]. The complexation of these two diamagnetic heavy metal ions to PCRed improved the properties of the free photosensitizer as a PDT drug. We discovered that the 1:1 complex between PCRed and Lu(III) significantly increases the cellular uptake, ROS production and antiproliferative capacity in four cancer cell lines. Our study shows that metal complexation is a useful strategy to potentiate iso-pentaphyrin as a PDT drug. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.007

文献信息

• USE OF DERIVATIVES OF PENTAPHYRINE AS ANTIMICROBIAL AND DISINFECTANT AGENTS
  申请人：Fedele Rosalisa

  公开号：US20130172396A1

  公开（公告）日：2013-07-04

  The invention relates to the use of 20-(4-carboxyphenyl)-2,13-dimethyl-3,12-diethyl-[22] pentaphyrine as antibacterial agent in photodynamic treatment. This expanded porphyrin derivatized in position 4 with a carboxyphenyl group proved very active after photo-oxidation both against S. aureus and E. hirae . Its high antibacterial activity and its low toxicity make this pentaphyrine particularly useful as antimicrobial agent both for photodynamic therapy against bacterial infections and in the disinfection of microbiologically contaminated liquids.

  本发明涉及将20-(4-羧基苯基)-2,13-二甲基-3,12-二乙基-[22]五吡咯烷作为光动力治疗中的抗菌剂。该扩展卟啉在4位上衍生出羧基苯基后，在光氧化后对金黄色葡萄球菌和平滑链霉菌均表现出很高的活性。其高抗菌活性和低毒性使得这种五吡咯烷在光动力治疗细菌感染和消毒微生物污染液体方面特别有用。
• [EN] USE OF DERIVATIVES OF PENTAPHYRINE AS ANTIMICROBIAL AND DESINFECTANT AGENTS<br/>[FR] UTILISATION DE DÉRIVÉS DE PENTAPHYRINE COMME AGENTS ANTIMICROBIENS ET DÉSINFECTANTS
  申请人：UNIV DEGLI STUDI UDINE

  公开号：WO2012035489A9

  公开（公告）日：2012-07-19
• Metallation of pentaphyrin with Lu(III) dramatically increases reactive-oxygen species production and cell phototoxicity
  作者：Maurizio Ballico、Valentina Rapozzi、Luigi E. Xodo、Clara Comuzzi

  DOI：10.1016/j.ejmech.2010.12.007

  日期：2011.2

  Photodynamic therapy (PDT) is an emerging cancer treatment modality based on the excitation of a nontoxic photosensitizer with harmless visible light to produce reactive-oxygen species (ROS) that induce apoptosis and/or necrosis in cancer cells. As the efficacy of this therapy strongly depends of the nature of the photosensitizer, there is a great interest to develop new photoactive molecules. Here we report for the first time the synthesis, characterization and bioactivity of metal complexes between the non-aromatic expanded porphyrin, namely 20-[[4'-(Trimethylsilyl)ethoxycarbonyl]phenyl-2,13-dimethyl-3,12-diethyl-[24] iso-pentaphyrin (PCRed) and Zn(II) [Zn(II)-PCRed] or Lu(III) [Lu(III)-PCRed]. The complexation of these two diamagnetic heavy metal ions to PCRed improved the properties of the free photosensitizer as a PDT drug. We discovered that the 1:1 complex between PCRed and Lu(III) significantly increases the cellular uptake, ROS production and antiproliferative capacity in four cancer cell lines. Our study shows that metal complexation is a useful strategy to potentiate iso-pentaphyrin as a PDT drug. (C) 2010 Elsevier Masson SAS. All rights reserved.