4-(methyl(2,5,8,11-tetraoxatridecan-13-yl)amino)benzaldehyde | 1309461-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(methyl(2,5,8,11-tetraoxatridecan-13-yl)amino)benzaldehyde
• 英文别名: 4-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethyl-methylamino]benzaldehyde
• CAS: 1309461-50-4
• 化学式: C₁₇H₂₇NO₅
• 分子量: 325.405
• InChiKey: IUURBLZWRCYLRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(methyl(2,5,8,11-tetraoxatridecan-13-yl)amino)benzaldehyde 、 3-乙酰基-7-二乙基氨基-2H-色烯-2-酮 在 哌啶 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以62%的产率得到7-(diethylamino)-3-(3-(4-(methyl(2,5,8,11-tetraoxatridecan-13-yl)amino)phenyl)acryloyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and in Vitro Photocytotoxicity of Coumarin Derivatives for One- and Two-Photon Excited Photodynamic Therapy

  摘要：

  Triethylene glycol functionalized coumarin derivatives 1-5 were synthesized and investigated as photosensitizers for one- and two-photon excited photodynamic therapy (PDT). Their absorption, fluorescence, triplet-state quantum yields, and singlet oxygen quantum yields were found to be significantly related to the substituent at the 7-position of the coumarin ring. In vitro photocytotoxicity of these derivatives toward HepG2 cells was examined and compared with a clinical drug. In vitro generation of reactive oxygen species (ROS), cellular uptake, and intracellular distribution of these derivatives were also characterized to fully reveal their structure-property relationships. The results showed that derivative 5, with a two-photon absorption cross section value of 1556 GM, could be a powerful PDT agent for both superficial diseases and solid tumors.

  DOI：

  10.1021/jm400025g
• 作为产物：
  描述：

  N-甲基-N-(2-羟乙基)-4-氨基苯醛 、 对甲苯磺酸三缩乙二醇单甲醚酯 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以72%的产率得到4-(methyl(2,5,8,11-tetraoxatridecan-13-yl)amino)benzaldehyde
  参考文献：
  名称：

  Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy

  摘要：

  通过简单的工艺高产合成了一系列具有不同脂质/水分配系数的聚乙二醇官能化苯亚甲基环戊酮染料。对这些分子进行了详细表征和系统研究，包括线性和非线性光物理性质、活性氧产量和体外光动力疗法（PDT）活性。其中四种染料在 PBS 中具有良好的溶解性（大于 2 mg ml-1，足以用于临床静脉注射）、高活性氧产率、大双光子吸收和低暗毒性。其中，两种染料能被人类直肠癌 1116 细胞有效吸收，并在体外细胞实验中表现出很强的双光子激发光导治疗活性。

  DOI：

  10.1039/c0ob01278e

文献信息

• Effective Two-Photon Excited Photodynamic Therapy of Xenograft Tumors Sensitized by Water-Soluble Bis(arylidene)cycloalkanone Photosensitizers
  作者：Qianli Zou、Hongyou Zhao、Yuxia Zhao、Yanyan Fang、Defu Chen、Jie Ren、Xiaopu Wang、Ying Wang、Ying Gu、Feipeng Wu

  DOI：10.1021/acs.jmedchem.5b00731

  日期：2015.10.22

  bis(arylidene)cycloalkanone photosensitizers modified by polyethylene glycol (PEG) have been studied for two-photon excited photodynamic therapy (2PE-PDT). As compared with their prototype compounds, these PEGylated photosensitizers show enhanced water solubilities while their photophysical and photochemical properties, including linear absorption, two-photon absorption, fluorescence, and singlet oxygen

  已经研究了一系列由聚乙二醇（PEG）改性的双（亚芳基）环烷酮光敏剂，用于双光子激发光动力疗法（2PE-PDT）。与它们的原型化合物相比，这些PEG化的光敏剂显示出更高的水溶性，而它们的光物理和光化学特性（包括线性吸收，双光子吸收，荧光和单重态氧量子产率）保持不变。这些光敏剂的体外行为（细胞吸收，亚细胞定位，PDT和2PE-PDT中的光细胞毒性）表明，可以通过调节PEG链的长度和位置来获得最佳的脂质-水分配系数。其中，通过两条四甘醇链不对称改性的光敏剂作为2PE-PDT候选物表现出最佳性能。在静脉内注射该光敏剂后，体内2PE-PDT证实了选择性的血管封闭和明显的抑制肿瘤生长的治疗作用。经治疗的荷瘤小鼠的存活期显着延长。这项研究证明了使用简单分子构建2PE-PDT潜在候选人的可行性。
• Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy
  作者：Yuxia Zhao、Weijia Wang、Feipeng Wu、Yang Zhou、Naiyan Huang、Ying Gu、Qianli Zou、Wei Yang

  DOI：10.1039/c0ob01278e

  日期：——

  A series of polyethylene glycol-functionalized benzylidene cyclopentanone dyes with varying lipid/water partition coefficients were synthesized in high yields by a simple process. Detailed characterization and systematic studies of these molecules, including linear and nonlinear photophysical properties, reactive oxygen yields, and in vitro photodynamic therapy (PDT) activities, were conducted. Four of these dyes exhibited good solubility in PBS (>2 mg ml−1, which is sufficient for clinical venous injection), high reactive oxygen yields, large two-photon absorption and low dark toxicity, under the therapy dosage. Among them, two dyes could be absorbed efficiently by human rectal cancer 1116 cells, and presented strong two-photon excited PDT activity in in vitrocell experiments.

  通过简单的工艺高产合成了一系列具有不同脂质/水分配系数的聚乙二醇官能化苯亚甲基环戊酮染料。对这些分子进行了详细表征和系统研究，包括线性和非线性光物理性质、活性氧产量和体外光动力疗法（PDT）活性。其中四种染料在 PBS 中具有良好的溶解性（大于 2 mg ml-1，足以用于临床静脉注射）、高活性氧产率、大双光子吸收和低暗毒性。其中，两种染料能被人类直肠癌 1116 细胞有效吸收，并在体外细胞实验中表现出很强的双光子激发光导治疗活性。
• Synthesis and in Vitro Photocytotoxicity of Coumarin Derivatives for One- and Two-Photon Excited Photodynamic Therapy
  作者：Qianli Zou、Yanyan Fang、Yuxia Zhao、Hongyou Zhao、Ying Wang、Ying Gu、Feipeng Wu

  DOI：10.1021/jm400025g

  日期：2013.7.11

  Triethylene glycol functionalized coumarin derivatives 1-5 were synthesized and investigated as photosensitizers for one- and two-photon excited photodynamic therapy (PDT). Their absorption, fluorescence, triplet-state quantum yields, and singlet oxygen quantum yields were found to be significantly related to the substituent at the 7-position of the coumarin ring. In vitro photocytotoxicity of these derivatives toward HepG2 cells was examined and compared with a clinical drug. In vitro generation of reactive oxygen species (ROS), cellular uptake, and intracellular distribution of these derivatives were also characterized to fully reveal their structure-property relationships. The results showed that derivative 5, with a two-photon absorption cross section value of 1556 GM, could be a powerful PDT agent for both superficial diseases and solid tumors.