4-(3-bromopropyl)-2,2'-bipyridine | 1231718-59-4

• 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-bromopropyl)-2,2'-bipyridine
• CAS: 1231718-59-4
• 化学式: C₁₃H₁₃BrN₂
• 分子量: 277.164
• InChiKey: MKJCUXYUPXKNKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-硝基咪唑 、 4-(3-bromopropyl)-2,2'-bipyridine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以35%的产率得到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
• 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 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 4-(3-bromopropyl)-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

文献信息

• Synthesis and DNA photocleavage study of Ru(bpy)32+-(CH2)n-MV2+ complexes
  作者：Shiguo Sun、Yanxia He、Zhigang Yang、Yi Pang、Fengyu Liu、Jiangli Fan、Licheng Sun、Xiaojun Peng

  DOI：10.1039/b927568a

  日期：——

  A series of Ru(bpy)32+-(CH2)n-MV2+ complexes (1, n = 3, 4, 7) used for DNA photocleavage have been designed and synthesized. Under the irradiation of visible light, complexes 1 can cleave supercoiled plasmid DNA (pBR322) both in air and under Ar atmosphere. Radical species such as O2−˙, ˙OH and the light-induced charge-separated (CS) oxidation state Ru(bpy)33+-(CH2)n-MV+˙ are responsible for the cleavage. The longer the carbon chain linkage, the higher the DNA photocleavage efficiency. It is noted that backwards intramolecular electron transfer (ET) that exist in complexes 1 can lead to some decreasing effect on the cleavage result, while inclusion of complexes 1 with cucurbit[8]uril (CB[8]) inhibits the backwards ET to some extent, thereby increasing photocleavage efficiency.

  设计并合成了一系列用于 DNA 光裂解的 Ru(bpy)32+-(CH2)n-MV2+ 复合物 (1, n = 3, 4, 7)。在可见光照射下，复合物1无论在空气中还是在Ar气氛下都能裂解超螺旋质粒DNA（pBR322）。 O2−˙、˙OH 等自由基物种和光诱导电荷分离 (CS) 氧化态 Ru(bpy)33+-( )n-MV+˙ 负责裂解。碳链越长，DNA光裂解效率越高。值得注意的是，配合物 1 中存在的反向分子内电子转移 (ET) 可能会导致对裂解结果的影响有所减弱，而配合物 1 与葫芦[8]脲 (CB[8]) 的结合会抑制向后 ET 的某些影响。程度，从而提高光裂解效率。