11-[11-[Bis(2-methoxy-2-oxoethyl)amino]undecanoylamino]undecanoic acid | 933448-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 11-[11-[Bis(2-methoxy-2-oxoethyl)amino]undecanoylamino]undecanoic acid
• CAS: 933448-53-4
• 化学式: C₂₈H₅₂N₂O₇
• 分子量: 528.73
• InChiKey: ZFTFJUQBJJBOCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11-[11-[Bis(2-methoxy-2-oxoethyl)amino]undecanoylamino]undecanoic acid 在 sodium hydroxide 、 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Synthesis, in vitro and in silico assessment of organometallic Rhenium(I) and Technetium(I) thymidine complexes

  摘要：

  Thymidine kinases have been identified as suitable targets for non-invasive imaging of gene therapy and cancer. Thus, there is a high interest in new, reliable and inexpensive radiolabeled thymidine analogues for these applications. In this study we present the synthesis and in vitro evaluation of M(CO)(3)-complexes of thymidine (M = Tc-99m, Re) for potential use in SPECT tumor imaging. 5'-amino-5'-deoxythymidine was derivatized at position C5' with spacers of various lengths (similar to 0-30 angstrom) carrying tridentate metal chelating entities such as iminodiacetic acid and picolylamine-N-monoacetic acid. The nucleoside derivatives were reacted with the precursors [ReBr3(CO)(3)](2-) and [Tc-99m(OH2)(3)(CO)(3)](+), respectively. The organometallic thymidine complexes have been fully characterized by means of IR, NMR and mass spectrometry. Enzyme kinetic studies revealed mixed inhibition of the human cytosolic thymidine kinase with K-i values ranging from 4.4 to 334 mu M for all thymidine complexes. Competitive inhibition of herpes simplex virus type 1 thymidine kinase was only achieved when thymidine and the metal core were separated by a spacer of approximately 30 angstrom length. These findings were supported by in silico molecular docking and molecular dynamic experiments. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.101
• 作为产物：
  描述：

  11-氨基十一酸 在 N-羟基丁二酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 11-[11-[Bis(2-methoxy-2-oxoethyl)amino]undecanoylamino]undecanoic acid
  参考文献：
  名称：

  Synthesis, in vitro and in silico assessment of organometallic Rhenium(I) and Technetium(I) thymidine complexes

  摘要：

  Thymidine kinases have been identified as suitable targets for non-invasive imaging of gene therapy and cancer. Thus, there is a high interest in new, reliable and inexpensive radiolabeled thymidine analogues for these applications. In this study we present the synthesis and in vitro evaluation of M(CO)(3)-complexes of thymidine (M = Tc-99m, Re) for potential use in SPECT tumor imaging. 5'-amino-5'-deoxythymidine was derivatized at position C5' with spacers of various lengths (similar to 0-30 angstrom) carrying tridentate metal chelating entities such as iminodiacetic acid and picolylamine-N-monoacetic acid. The nucleoside derivatives were reacted with the precursors [ReBr3(CO)(3)](2-) and [Tc-99m(OH2)(3)(CO)(3)](+), respectively. The organometallic thymidine complexes have been fully characterized by means of IR, NMR and mass spectrometry. Enzyme kinetic studies revealed mixed inhibition of the human cytosolic thymidine kinase with K-i values ranging from 4.4 to 334 mu M for all thymidine complexes. Competitive inhibition of herpes simplex virus type 1 thymidine kinase was only achieved when thymidine and the metal core were separated by a spacer of approximately 30 angstrom length. These findings were supported by in silico molecular docking and molecular dynamic experiments. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.101

文献信息

• Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1
  作者：D. Desbouis、P.A. Schubiger、R. Schibli

  DOI：10.1016/j.jorganchem.2006.10.011

  日期：2007.2

  Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium complexes of a 5'-carboxamide 5-ethyl-2'-deoxyuridine derivative able to selectively inhibit HSV1-TK is presented. The 5-ethyl-2'-deoxyuridine functionalized with a suitable tridentate chelating system at position 5' was synthesized from commercial 2'-deoxyuridine in seven steps. The 5-ethyl-2'-deoxyuridine derivative was labeled with the fac-M(CO)(3)-core (M = Tc, Re). The resulting rhenium complex was found to be a selective competitive inhibitor of HSV1-TK (K-i = 4.56 mu M). Inhibition of the human cytosolic thymidine kinase (hTK1) previously reported with organometallic rhenium and technetium complexes of 5'-carboxamide thymidine derivative was not observed. The uptake of the technetium-99m complex in transfected cells expressing HSV1-TK has been evaluated to assess its possible use as reporter. (C) 2006 Elsevier B.V. All rights reserved.