4-(3-hydroxypropyl)-2,2'-bipyridine | 614753-98-9

• 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-hydroxypropyl)-2,2'-bipyridine
• 英文别名: 3-[2,2']-bipyridinyl-4-yl-propan-1-ol；3-(2-pyridin-2-ylpyridin-4-yl)propan-1-ol
• CAS: 614753-98-9
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: UNLYICJAHHINQG-UHFFFAOYSA-N

物化性质

• 沸点：
  394.7±32.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 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：
  46.01
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxypropyl)-2,2'-bipyridine 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以50%的产率得到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
• 作为产物：
  描述：

  N-氧代-4-硝基-2，2’联吡啶 在 四(三苯基膦)钯 、 乙酰溴 、 palladium on activated charcoal 、 氢气 、 三溴化磷 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 7.25h， 生成 4-(3-hydroxypropyl)-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

• Intramolecular Electrocatalysis of 8-Oxo-Guanine Oxidation:  Secondary Structure Control of Electron Transfer in Osmium-Labeled Oligonucleotides
  作者：Rebecca C. Holmberg、Mark T. Tierney、Patricia A. Ropp、Eric E. Berg、Mark W. Grinstaff、H. Holden Thorp

  DOI：10.1021/ic030004f

  日期：2003.10.1

  A phosphoramidite containing Os(bpy)(3)(2+) (Os; bpy, 2,2'-bipyridine) with a three-carbon linker was synthesized and used to prepare oligonucleotides with the Os redox catalyst appended to the 5'-end. The electrogenerated Os(III) is capable of oxidizing 7,8-dihydro-8-oxo-guanine (8G), but 8G is not electrochemically reactive at indium tin oxide electrodes because of poor electrode kinetics for the direct reaction. The hairpin-forming oligonucleotide Os-5'-ATG TCA GAT TAG CAG GCC TGA CAT 8G was synthesized and characterized by thermal denaturation and native gel electrophoresis both in the hairpin form and when hybridized to its Watson-Crick complement. The redox potential in both forms of the appended Os(III/II) couple was 0.63 V (all potentials vs Ag/AgCl), which is identical to that for the free complex. The diffusion coefficients of the hairpin form (10.2 x 10(-7) cm(2)/s) and the duplex form (8.7 x 10(-7) cm(2)/s) were consistent with values expected from studies of noncovalently bound redox labels, which suggest that the measured diffusion coefficient should be that of the appended DNA molecule. The oligonucleotide was designed such that in the duplex form, the 8G is far from the Os(III/II) couple, but in the hairpin form, the 8G is situated close to the redox center. For the duplex form, cyclic voltammetry studies showed that mediated oxidation of the 8G nucleobase occurred only through bimolecular reaction of the electrogenerated Os(III) of one duplex with the 8G of another duplex. However, in the hairpin form, intramolecular electron transfer from 8G to Os(III) in the same molecule was apparent in both chronoamperometry and cyclic voltammetry.