(6-(((2-((anthracen-9-ylmethyl)(methyl)amino)ethyl)(methyl)amino)methyl)pyridin-2-yl)-methanol | 1342295-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (6-(((2-((anthracen-9-ylmethyl)(methyl)amino)ethyl)(methyl)amino)methyl)pyridin-2-yl)-methanol
• CAS: 1342295-68-4
• 化学式: C₂₆H₂₉N₃O
• 分子量: 399.536
• InChiKey: BZAXXRHETDHZRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6-(((2-((anthracen-9-ylmethyl)(methyl)amino)ethyl)(methyl)amino)methyl)pyridin-2-yl)-methanol 、 二甲胺 在 氯化亚砜 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以70%的产率得到N-(anthracen-9-ylmethyl)-N'-((6-((dimethylamino)methyl)pyridin-2-yl)methyl)-N,N'-dimethylethane-1,2-diamine
  参考文献：
  名称：

  Physiologically Relevant Concentrations of NaCl and KCl Increase DNA Photocleavage by an N-Substituted 9-Aminomethylanthracene Dye

  摘要：

  This paper describes the synthesis of a new 9-aminomethylanthracene dye N-substituted with a pyridinylpoly-amine side chain (4). The effects of NaCl and KCl on anthracene/DNA interactions were then studied, with the goal of simulating the conditions of high ionic strength that a DNA photosensitizer might encounter in the cell nucleus (similar to 450 mM of NaCl and 260 mM of KCl). As exemplified by methylene blue (5), the expected effect of increasing ionic strength is to decrease DNA binding and photocleavage yields. In contrast, the addition of 150 mM of NaCl in combination with 260 mM of KCl to photodeavage reactions containing micromolar concentrations of 4 triggers the conversion of supercoiled, nicked, and linear forms of pUC19 plasmid into a highly degraded band of DNA fragments (350 nm hv, pH 7.0). Circular dichroism spectra point to a correlation between salt-induced unwinding of the DNA helix and the increase in DNA photocleavage yields. The results of circular dichroism, UV-vis absorption, fluorescence emission, thermal denaturation, and photodeavage inhibition experiments suggest that the combination of salts causes a change in the DNA binding mode of 4 from intercalation to an external interaction. This in turn leads to an increase in the anthracene-sensitized production of DNA-damaging reactive oxygen species.

  DOI：

  10.1021/bi200972c
• 作为产物：
  描述：

  6-溴甲基-2-吡啶甲醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 52.5h， 生成 (6-(((2-((anthracen-9-ylmethyl)(methyl)amino)ethyl)(methyl)amino)methyl)pyridin-2-yl)-methanol
  参考文献：
  名称：

  Physiologically Relevant Concentrations of NaCl and KCl Increase DNA Photocleavage by an N-Substituted 9-Aminomethylanthracene Dye

  摘要：

  This paper describes the synthesis of a new 9-aminomethylanthracene dye N-substituted with a pyridinylpoly-amine side chain (4). The effects of NaCl and KCl on anthracene/DNA interactions were then studied, with the goal of simulating the conditions of high ionic strength that a DNA photosensitizer might encounter in the cell nucleus (similar to 450 mM of NaCl and 260 mM of KCl). As exemplified by methylene blue (5), the expected effect of increasing ionic strength is to decrease DNA binding and photocleavage yields. In contrast, the addition of 150 mM of NaCl in combination with 260 mM of KCl to photodeavage reactions containing micromolar concentrations of 4 triggers the conversion of supercoiled, nicked, and linear forms of pUC19 plasmid into a highly degraded band of DNA fragments (350 nm hv, pH 7.0). Circular dichroism spectra point to a correlation between salt-induced unwinding of the DNA helix and the increase in DNA photocleavage yields. The results of circular dichroism, UV-vis absorption, fluorescence emission, thermal denaturation, and photodeavage inhibition experiments suggest that the combination of salts causes a change in the DNA binding mode of 4 from intercalation to an external interaction. This in turn leads to an increase in the anthracene-sensitized production of DNA-damaging reactive oxygen species.

  DOI：

  10.1021/bi200972c