5-ethoxy-5-oxo-2-(tritylamino)pentanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-ethoxy-5-oxo-2-(tritylamino)pentanoic acid
• 英文别名: (2S)-5-ethoxy-5-oxo-2-(tritylamino)pentanoic acid
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: GFUPCOCRJAANAI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-ethoxy-5-oxo-2-(tritylamino)pentanoic acid 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 5-((4-(3,4-dicyanophenoxy)phenyl)amino)-5-oxo-4-(tritylamino)pentanoate
  参考文献：
  名称：

  Tumor microenvironment-responsive charge reversal zinc phthalocyanines based on amino acids for photodynamic therapy

  摘要：

  Amino acid substituted zinc phthalocyanines which are capable of reversing their charge from negative to positive in response to tumor microenvironment have been prepared by the isoelectric pHs regulation and charge reversal sensitivity enhancement. The charge reversal abilities of the prepared zinc phthalocyanines were judged by their isoelectric pHs and zeta potential values. The UV-Vis spectra, singlet oxygen generation ability, cellular uptake and in vitro anticancer ability of the prepared zinc phthalocyanines were investigated to study the influences of charge reversal on photodynamic activities. Charge reversible tetra- and octa-substituted glutamic acid ZnPcs showed enhanced singlet oxygen generation ability, cellular uptake and photocytotoxicity towards cancer cells, and were considered as promising photosensitizers for photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.12.009
• 作为产物：
  描述：

  L-谷氨酸5乙脂 、 三苯基氯甲烷 在 三甲基氯硅烷 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 5.5h， 以89.1%的产率得到5-ethoxy-5-oxo-2-(tritylamino)pentanoic acid
  参考文献：
  名称：

  Tumor microenvironment-responsive charge reversal zinc phthalocyanines based on amino acids for photodynamic therapy

  摘要：

  Amino acid substituted zinc phthalocyanines which are capable of reversing their charge from negative to positive in response to tumor microenvironment have been prepared by the isoelectric pHs regulation and charge reversal sensitivity enhancement. The charge reversal abilities of the prepared zinc phthalocyanines were judged by their isoelectric pHs and zeta potential values. The UV-Vis spectra, singlet oxygen generation ability, cellular uptake and in vitro anticancer ability of the prepared zinc phthalocyanines were investigated to study the influences of charge reversal on photodynamic activities. Charge reversible tetra- and octa-substituted glutamic acid ZnPcs showed enhanced singlet oxygen generation ability, cellular uptake and photocytotoxicity towards cancer cells, and were considered as promising photosensitizers for photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.12.009

文献信息

• Tumor microenvironment-responsive charge reversal zinc phthalocyanines based on amino acids for photodynamic therapy
  作者：Ao Wang、Li Gui、Shan Lu、Lin Zhou、Jiahong Zhou、Shaohua Wei

  DOI：10.1016/j.dyepig.2015.12.009

  日期：2016.3

  Amino acid substituted zinc phthalocyanines which are capable of reversing their charge from negative to positive in response to tumor microenvironment have been prepared by the isoelectric pHs regulation and charge reversal sensitivity enhancement. The charge reversal abilities of the prepared zinc phthalocyanines were judged by their isoelectric pHs and zeta potential values. The UV-Vis spectra, singlet oxygen generation ability, cellular uptake and in vitro anticancer ability of the prepared zinc phthalocyanines were investigated to study the influences of charge reversal on photodynamic activities. Charge reversible tetra- and octa-substituted glutamic acid ZnPcs showed enhanced singlet oxygen generation ability, cellular uptake and photocytotoxicity towards cancer cells, and were considered as promising photosensitizers for photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.