1,4,7-tris[4'-(ethoxycarbonyl)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane | 957142-91-5

• 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: 1,4,7-tris[4'-(ethoxycarbonyl)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane
• 英文别名: 2-[4,7-Bis(1-carboxy-5-ethoxy-5-oxopentyl)-1,4,7,10-tetrazacyclododec-1-yl]-6-ethoxy-6-oxohexanoic acid；2-[4,7-bis(1-carboxy-5-ethoxy-5-oxopentyl)-1,4,7,10-tetrazacyclododec-1-yl]-6-ethoxy-6-oxohexanoic acid
• CAS: 957142-91-5
• 化学式: C₃₂H₅₆N₄O₁₂
• 分子量: 688.816
• InChiKey: MRRBMNOEBJGIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  48
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1,4,7-tris[4'-(ethoxycarbonyl)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane 、 yttrium(III) chloride hexahydrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以93%的产率得到yttrium(III) 1,4,7-tris[4'-(ethoxycarbonyl)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Luminescence Study of Eu(III) Analogues of Esterase-Activated Magnetic Resonance Contrast Agents

  摘要：

  A model for an accumulation and enzyme-activation strategy of a magnetic resonance contrast agent was investigated via the luminescence of Eu(III) analogues. Neutral q = 2 Eu(III) ethyl and acetoxymethyl ester LnaDO3A-based complexes showed increased emission intensity in the presence of serum concentrations of carbonate because of inner-sphere water molecule displacement by the anion. The affinity for carbonate is suppressed by the introduction of negative charge to the complex following enzymatic hydrolysis of the ester groups, resulting in quenching of Eu(Ill) luminescence and changes in spectral form. The conversion of neutral, catoxylic ester-containing complexes into free acid forms by enzymatic hydrolysis using pig liver esterase was demonstrated by luminescence (Eu) and H-1 NMR spectroscopic investigations (Y). These studies demonstrated that the concept of inhibition of anion binding as a result of enzyme activation is feasible.

  DOI：

  10.1021/ic901284t
• 作为产物：
  描述：

  1,4,7-tris[4'-(ethoxycarbonyl)-1'-(tert-butoxycarbonyl)butyl]-1,4,7,10-tetraazacyclododecane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以38%的产率得到1,4,7-tris[4'-(ethoxycarbonyl)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  An esterase-activated magnetic resonance contrast agent

  摘要：

  一个带有悬挂乙酰氧甲酯的Gd(III)配合物在暴露于猪肝酯酶时被激活；其弛豫性提高了84%，这是由于生成的负电荷抑制了HCO3−/CO32−的结合。

  DOI：

  10.1039/b711989e

文献信息

• An esterase-activated magnetic resonance contrast agent
  作者：Marco Giardiello、Mark P. Lowe、Mauro Botta

  DOI：10.1039/b711989e

  日期：——

  A Gd(III) complex bearing pendant acetoxymethyl esters is activated on exposure to porcine liver esterase; the 84% increase in relaxivity is a result of suppression of HCO3−/CO32− binding by the resulting negative charge.

  一个带有悬挂乙酰氧甲酯的Gd(III)配合物在暴露于猪肝酯酶时被激活；其弛豫性提高了84%，这是由于生成的负电荷抑制了HCO3−/CO32−的结合。
• Luminescence Study of Eu(III) Analogues of Esterase-Activated Magnetic Resonance Contrast Agents
  作者：Marco Giardiello、Mark P. Lowe

  DOI：10.1021/ic901284t

  日期：2009.9.7

  A model for an accumulation and enzyme-activation strategy of a magnetic resonance contrast agent was investigated via the luminescence of Eu(III) analogues. Neutral q = 2 Eu(III) ethyl and acetoxymethyl ester LnaDO3A-based complexes showed increased emission intensity in the presence of serum concentrations of carbonate because of inner-sphere water molecule displacement by the anion. The affinity for carbonate is suppressed by the introduction of negative charge to the complex following enzymatic hydrolysis of the ester groups, resulting in quenching of Eu(Ill) luminescence and changes in spectral form. The conversion of neutral, catoxylic ester-containing complexes into free acid forms by enzymatic hydrolysis using pig liver esterase was demonstrated by luminescence (Eu) and H-1 NMR spectroscopic investigations (Y). These studies demonstrated that the concept of inhibition of anion binding as a result of enzyme activation is feasible.