(carboxymethyl-{2-[2-(4,7,10-tris-{[2-(bis-carboxymethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraazacyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid | 352689-31-7

• 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: (carboxymethyl-{2-[2-(4,7,10-tris-{[2-(bis-carboxymethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraazacyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid
• 英文别名: 2-[Carboxymethyl-[2-[[2-[4,7,10-tris[2-[2-[bis(carboxymethyl)amino]ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]ethyl]amino]acetic acid；2-[carboxymethyl-[2-[[2-[4,7,10-tris[2-[2-[bis(carboxymethyl)amino]ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]ethyl]amino]acetic acid
• CAS: 352689-31-7
• 化学式: C₄₀H₆₈N₁₂O₂₀
• 分子量: 1037.05
• InChiKey: KLHWWUZRVNNMRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -23.8
• 重原子数：
  72
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  441
• 氢给体数：
  12
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 (carboxymethyl-{2-[2-(4,7,10-tris-{[2-(bis-carboxymethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraazacyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid 以 甲醇 、 水 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Surface Recognition of a Protein Using Designed Transition Metal Complexes

  摘要：

  Each protein has a unique pattern of histidine residues on the surface. This paper describes the design, synthesis, and binding studies of transition metal complexes to target the surface histidine pattern of carbonic anhydrase (bovine erythrocyte). When the pattern of cupric ions on a complex matches the surface pattern of histidines of the protein, strong and selective binding can be achieved in aqueous buffer (pH = 7.0). The described method of protein recognition is applicable to proteins of known structures. With rapidly increasing number of solved protein structures, the method has wide applicability in purification, targeting, and sensing of proteins.

  DOI：

  10.1021/ja003193z
• 作为产物：
  描述：

  1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (carboxymethyl-{2-[2-(4,7,10-tris-{[2-(bis-carboxymethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraazacyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid
  参考文献：
  名称：

  Surface Recognition of a Protein Using Designed Transition Metal Complexes

  摘要：

  Each protein has a unique pattern of histidine residues on the surface. This paper describes the design, synthesis, and binding studies of transition metal complexes to target the surface histidine pattern of carbonic anhydrase (bovine erythrocyte). When the pattern of cupric ions on a complex matches the surface pattern of histidines of the protein, strong and selective binding can be achieved in aqueous buffer (pH = 7.0). The described method of protein recognition is applicable to proteins of known structures. With rapidly increasing number of solved protein structures, the method has wide applicability in purification, targeting, and sensing of proteins.

  DOI：

  10.1021/ja003193z

文献信息

• Calcium-responsive paramagnetic CEST agents
  作者：Goran Angelovski、Thomas Chauvin、Rolf Pohmann、Nikos K. Logothetis、Éva Tóth

  DOI：10.1016/j.bmc.2010.07.023

  日期：2011.2

  The assessment of changes in the extracellular calcium concentration by magnetic resonance imaging would be a valuable biomedical research tool to monitor brain neuronal activity. In this perspective, we report here the synthesis of novel ligands consisting of tetraamide and bisamide derivatives of cyclen, L(1) and L(2), respectively, each bearing imino(diacetate) moieties for Ca(2+) binding. Yb(3+) and Eu(3+) complexes are investigated as chemical exchange saturation transfer (CEST) agents that respond to the presence of Ca(2+). A CEST effect is observed for both YbL(1) and EuL(1) complexes (B = 11.7 T), originating from the slow exchange of the amide protons and those of the coordinated water, respectively, whilst no CEST is detected for complexes of L(2). Upon calcium binding. the CEST effect decreases considerably (from 60% to 20% for YbL(1) and from 35% to 10% for EuL(1)). A similar variation is observed in the presence of Mg(2+). The affinity constants between the lanthanide complexes and the alkaline earth metal ions have been estimated from the variation of the CEST effect to be K(aff)(YbL1) (-Ca) = 8 +/- 2 M(-1), K(aff)(YbL1) (-Mg) = 23 +/- 3 M(-1) and K(aff)(EUL1) (-Ca) = 10 +/- 3 M(-1) These low values imply the coordination of the alkaline earth ions to a single iminodiacetate arm. Ca(2+)/Mg(2+) binding to the lanthanide complexes slows down the exchange of the amide protons on YbL(1) which is responsible for the diminished CEST effect. This has been evidenced by assessing the proton exchange rates from the dependency of the CEST effect on the saturation time and the saturation power, in the absence and in the presence of Ca(2+) and Mg(2+). The applicability of the PARACEST MRI agents for Ca(2+) detection has been evaluated on a 16 T MRI scanner. (C) 2010 Elsevier Ltd. All rights reserved.
• Surface Recognition of a Protein Using Designed Transition Metal Complexes
  作者：Md. Abul Fazal、Bidhan C. Roy、Shuguang Sun、Sanku Mallik、Kenton R. Rodgers

  DOI：10.1021/ja003193z

  日期：2001.7.1

  Each protein has a unique pattern of histidine residues on the surface. This paper describes the design, synthesis, and binding studies of transition metal complexes to target the surface histidine pattern of carbonic anhydrase (bovine erythrocyte). When the pattern of cupric ions on a complex matches the surface pattern of histidines of the protein, strong and selective binding can be achieved in aqueous buffer (pH = 7.0). The described method of protein recognition is applicable to proteins of known structures. With rapidly increasing number of solved protein structures, the method has wide applicability in purification, targeting, and sensing of proteins.