4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2,2'-bipyridine | 1584692-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2,2'-bipyridine
• 英文别名: bpy-2-nitroIm；4-[3-(2-nitroimidazol-1-yl)propyl]-2-pyridin-2-ylpyridine
• CAS: 1584692-50-1
• 化学式: C₁₆H₁₅N₅O₂
• 分子量: 309.327
• InChiKey: JVVGVLDKCNQOKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ru(4,7-diphenyl-1,10-phenanthroline)₂Cl₂*DMF*H₂O 、 4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2,2'-bipyridine 在 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 31.0h， 以72%的产率得到[Ru(4,7-diphenyl-1,10-phenanthroline)₂(4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2,2′-bipyridine)]Cl₂
  参考文献：
  名称：

  2-Nitroimidazole-ruthenium polypyridyl complex as a new conjugate for cancer treatment and visualization

  摘要：

  A novel long-lifetime highly luminescent ruthenium polypyridyl complex containing 2-nitroimidazole moiety [Ru(dip)(2)(bpy-2-nitrolm)]Cl-2 (dip = 4,7-dipheny1-1,10-phenanthroline, bpy-2-nitroIm = 4-[3-(2-nitro-1Himidazol-1-yl)propyl]-2,2'-bipyridine) has been designed cancer treatment and imaging. The luminescence properties of the synthesized compound strongly depend on the oxygen concentration. Under oxygen-free conditions quantum yield of luminescence and the average lifetime of emission were found to be 0.034 and 1.9 mu s, respectively, which is ca. three times higher in comparison to values obtained in air-equilibrated solution. The binding properties of the investigated ruthenium complex to human serum albumin have been studied and the apparent binding constant for the formation of the protein-ruthenium adduct was determined to be 1.1 x 10(5) M-1. The quantum yield and the average lifetime of emission are greatly enhanced upon binding of ruthenium compound to the protein. The DNA binding studies revealed two distinguished binding modes which lead to a decrease in luminescence intensity of ruthenium complex up to 60% for [DNA]/[Ru] < 2, and enhancement of emission for [DNA]/[Ru] > 80. Preliminary biological studies confirmed fast and efficient accumulation of the ruthenium complex inside cells. Furthermore, the ruthenium complex was found to be relatively cytotoxic with LD50 of 12 and 13 mu M for A549 and CT26 cell lines, respectively, under normoxic conditions. The retention and cellular uptake of ruthenium complex is enhanced under hypoxic conditions and its LD50 decreases to 8 mu M for A549 cell line. (c) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.02.001
• 作为产物：
  描述：

  3-(2,2'-bipyridin-4-yl)prop-2-yn-1-ol 在 palladium on activated charcoal 、 氢溴酸 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2,2'-bipyridine
  参考文献：
  名称：

  2-Nitroimidazole-ruthenium polypyridyl complex as a new conjugate for cancer treatment and visualization

  摘要：

  A novel long-lifetime highly luminescent ruthenium polypyridyl complex containing 2-nitroimidazole moiety [Ru(dip)(2)(bpy-2-nitrolm)]Cl-2 (dip = 4,7-dipheny1-1,10-phenanthroline, bpy-2-nitroIm = 4-[3-(2-nitro-1Himidazol-1-yl)propyl]-2,2'-bipyridine) has been designed cancer treatment and imaging. The luminescence properties of the synthesized compound strongly depend on the oxygen concentration. Under oxygen-free conditions quantum yield of luminescence and the average lifetime of emission were found to be 0.034 and 1.9 mu s, respectively, which is ca. three times higher in comparison to values obtained in air-equilibrated solution. The binding properties of the investigated ruthenium complex to human serum albumin have been studied and the apparent binding constant for the formation of the protein-ruthenium adduct was determined to be 1.1 x 10(5) M-1. The quantum yield and the average lifetime of emission are greatly enhanced upon binding of ruthenium compound to the protein. The DNA binding studies revealed two distinguished binding modes which lead to a decrease in luminescence intensity of ruthenium complex up to 60% for [DNA]/[Ru] < 2, and enhancement of emission for [DNA]/[Ru] > 80. Preliminary biological studies confirmed fast and efficient accumulation of the ruthenium complex inside cells. Furthermore, the ruthenium complex was found to be relatively cytotoxic with LD50 of 12 and 13 mu M for A549 and CT26 cell lines, respectively, under normoxic conditions. The retention and cellular uptake of ruthenium complex is enhanced under hypoxic conditions and its LD50 decreases to 8 mu M for A549 cell line. (c) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.02.001