Zn(pyropheophorbide-a allyl ester(-2H)) | 1345966-90-6

• 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: Zn(pyropheophorbide-a allyl ester(-2H))
• CAS: 1345966-90-6
• 化学式: C₃₆H₃₆N₄O₃Zn
• 分子量: 638.097
• InChiKey: VLBWOEVSXUYWGQ-OGZMHEHASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 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：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  Zn(pyropheophorbide-a allyl ester(-2H)) 在 四(三苯基膦)钯 、 diethylammonium hydrogencarbonate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide d
  参考文献：
  名称：

  Control of the Photocatalytic Activity of Bimetallic Complexes of Pyropheophorbide-a by Nucleic Acids

  摘要：

  Photo catalytic activity of a photosensitizer (PS) in an oligodeoxyribonucleotide duplex 5'-PS similar to ODN1/ODN2 similar to Q-3' is inhibited because of close proximity of a quencher Q, The ODN2 in this duplex is selected to be longer than the ODN1. Therefore, in the presence of a nucleic acid (analyte), which is fully complementary to the ODN2 strand, the duplex is decomposed with formation of an analyte/ODN2Q duplex and a catalytically active, single stranded PS similar to ODN1. In this way the catalytic activity of the PS can be controlled by the specific nucleic acids. We applied this reaction earlier for the amplified detection of ribonucleic acids in live cells (Arian, D.; Clo, E.; Gothelf, K; Mokhir, A. Chem.- Ear J. 2010, 16(1), 288). As a photosensitizer (PS) we used In3+(pyropheophorbide-a)chloride and as a quencher (Q) - Black-Hole-Quencher-3 (BHQ-3). The In3+ complex is a highly active photocatalyst in aqueous solution. However, it can coordinate additional ligands containing thiols (e.g., proteins, peptides, and aminoacids), that modulate properties of the complex itself and of the corresponding bio- molecules. These possible interactions can lead to undesired side effects of nucleic acid controlled photocatalysts (PS similar to ODN1/ODN2-Q) in live cells. In this work we explored the possibility to substitute the In3+ complex for those ones of divalent metal ions, Zn2+ and Pd2+, which exhibit lower or no tendency to coordinate the fifth ligand. We found that one of the compounds tested (Pd(pyropheophorbide-a) is as potent and as stable photosensitizer as its In3+ analogue, but does not coordinate additional ligands that makes it more suitable for cellular applications. When the Pd complex was introduced in the duplex PS similar to ODN1/ODN2-Qas a PS, its photocatalytic activity could be controlled by nucleic acids as efficiently as that of the corresponding In3+ complex.

  DOI：

  10.1021/ic201408h
• 作为产物：
  描述：

  pyropheophorbide a allyl ester 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以75%的产率得到Zn(pyropheophorbide-a allyl ester(-2H))
  参考文献：
  名称：

  Control of the Photocatalytic Activity of Bimetallic Complexes of Pyropheophorbide-a by Nucleic Acids

  摘要：

  Photo catalytic activity of a photosensitizer (PS) in an oligodeoxyribonucleotide duplex 5'-PS similar to ODN1/ODN2 similar to Q-3' is inhibited because of close proximity of a quencher Q, The ODN2 in this duplex is selected to be longer than the ODN1. Therefore, in the presence of a nucleic acid (analyte), which is fully complementary to the ODN2 strand, the duplex is decomposed with formation of an analyte/ODN2Q duplex and a catalytically active, single stranded PS similar to ODN1. In this way the catalytic activity of the PS can be controlled by the specific nucleic acids. We applied this reaction earlier for the amplified detection of ribonucleic acids in live cells (Arian, D.; Clo, E.; Gothelf, K; Mokhir, A. Chem.- Ear J. 2010, 16(1), 288). As a photosensitizer (PS) we used In3+(pyropheophorbide-a)chloride and as a quencher (Q) - Black-Hole-Quencher-3 (BHQ-3). The In3+ complex is a highly active photocatalyst in aqueous solution. However, it can coordinate additional ligands containing thiols (e.g., proteins, peptides, and aminoacids), that modulate properties of the complex itself and of the corresponding bio- molecules. These possible interactions can lead to undesired side effects of nucleic acid controlled photocatalysts (PS similar to ODN1/ODN2-Q) in live cells. In this work we explored the possibility to substitute the In3+ complex for those ones of divalent metal ions, Zn2+ and Pd2+, which exhibit lower or no tendency to coordinate the fifth ligand. We found that one of the compounds tested (Pd(pyropheophorbide-a) is as potent and as stable photosensitizer as its In3+ analogue, but does not coordinate additional ligands that makes it more suitable for cellular applications. When the Pd complex was introduced in the duplex PS similar to ODN1/ODN2-Qas a PS, its photocatalytic activity could be controlled by nucleic acids as efficiently as that of the corresponding In3+ complex.

  DOI：

  10.1021/ic201408h