2-(2,2':6',2''-terpyridine-4'-yloxy)ethyl-N,N-bis(2-pyridylmethyl)amine | 1246377-14-9

• 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: 2-(2,2':6',2''-terpyridine-4'-yloxy)ethyl-N,N-bis(2-pyridylmethyl)amine
• 英文别名: 2-(2,6-dipyridin-2-ylpyridin-4-yl)oxy-N,N-bis(pyridin-2-ylmethyl)ethanamine
• CAS: 1246377-14-9
• 化学式: C₂₉H₂₆N₆O
• 分子量: 474.565
• InChiKey: OGSKELOCFUEGOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(双-(2-吡啶甲基)-氨基)-乙醇 、 4'-氯-2,2':6',2''-三联吡啶 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以58%的产率得到2-(2,2':6',2''-terpyridine-4'-yloxy)ethyl-N,N-bis(2-pyridylmethyl)amine
  参考文献：
  名称：

  Two Metals Are Better than One: Investigations on the Interactions between Dinuclear Metal Complexes and Quadruplex DNA

  摘要：

  Twelve mono-and dimetallic complexes (the metals being Cu-II, Pt-II, and Zn-II) with terpyridine-based ligands have been prepared and fully characterized. The X-ray crystal structures of two of the complexes (monometallic Cu-II and Zn-II complexes with a morpholino-substituted terpyridine ligand) are reported. The affinities of the 12 complexes toward duplex and quadruplex (HTelo and c-myc) DNA have been investigated using a combination of techniques including fluorescent indicator displacement (FID) assay, UV-vis spectroscopy and circular dichroism (CD). These studies revealed that the dicopper and diplatinum complexes 11 and 12 bind very strongly to quadruplex DNA (up to K 7.97 x 10(6) M-1) and with good selectivity (up to 100-fold) over duplex DNA. In these dimetallic complexes, one of the metals is coordinated to a terpyridine moiety yielding square based pyramidal (with Cu-II) or square planar (with Pt-II) geometries. The second metal is coordinated to a dipicolyl amine linked to terpyridine by a three-atom spacer. We propose that these complexes bind to quadruplex DNA via a combination of interactions: pi-pi end-stacking between the metal-terpyridine fragment and the guanine quartet, and electrostatic/metal-phosphate interactions (between the metal-dipicolyl amine fragment and DNA's backbone).

  DOI：

  10.1021/ic100884p

文献信息

• Two Metals Are Better than One: Investigations on the Interactions between Dinuclear Metal Complexes and Quadruplex DNA
  作者：Kogularamanan Suntharalingam、Andrew J. P. White、Ramon Vilar

  DOI：10.1021/ic100884p

  日期：2010.9.20

  Twelve mono-and dimetallic complexes (the metals being Cu-II, Pt-II, and Zn-II) with terpyridine-based ligands have been prepared and fully characterized. The X-ray crystal structures of two of the complexes (monometallic Cu-II and Zn-II complexes with a morpholino-substituted terpyridine ligand) are reported. The affinities of the 12 complexes toward duplex and quadruplex (HTelo and c-myc) DNA have been investigated using a combination of techniques including fluorescent indicator displacement (FID) assay, UV-vis spectroscopy and circular dichroism (CD). These studies revealed that the dicopper and diplatinum complexes 11 and 12 bind very strongly to quadruplex DNA (up to K 7.97 x 10(6) M-1) and with good selectivity (up to 100-fold) over duplex DNA. In these dimetallic complexes, one of the metals is coordinated to a terpyridine moiety yielding square based pyramidal (with Cu-II) or square planar (with Pt-II) geometries. The second metal is coordinated to a dipicolyl amine linked to terpyridine by a three-atom spacer. We propose that these complexes bind to quadruplex DNA via a combination of interactions: pi-pi end-stacking between the metal-terpyridine fragment and the guanine quartet, and electrostatic/metal-phosphate interactions (between the metal-dipicolyl amine fragment and DNA's backbone).