tetra-tert-butyl 2,2',2'',2'''-((((4-amino-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(azanetriyl))tetraacetate | 1000991-94-5

• 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: tetra-tert-butyl 2,2',2'',2'''-((((4-amino-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(azanetriyl))tetraacetate
• CAS: 1000991-94-5
• 化学式: C₃₄H₅₇N₃O₁₀
• 分子量: 667.841
• InChiKey: MWQIPSPEWIYALY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  156.16
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  tetra-tert-butyl 2,2',2'',2'''-((((4-amino-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(azanetriyl))tetraacetate 、 十八烷酰氯 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以91%的产率得到tetra-tert-butyl 2,2',2'',2'''-((((4-stearamido-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(azanetriyl))tetraacetate
  参考文献：
  名称：

  刚性和功能化EGTA衍生物的合成及溶液热力学研究。

  摘要：

  描述了一系列新的EGTA（乙二醇-双（2-氨基乙基醚）-N，N，N'，N'-四乙酸）衍生物的合成，这些衍生物将芳族和官能化的芳族部分引入了氧乙烯烯桥中。进行了溶液热力学研究，以确定结构修饰对镧系元素和碱土金属离子配位能力的影响。芳族部分上远程官能团的存在将使复合物与大分子或其他生物靶标结合。

  DOI：

  10.1039/b804195d
• 作为产物：
  描述：

  二(2-甲基-2-丙基)2,2'-[(2-羟基乙基)亚氨基]二乙酸酯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 tetra-tert-butyl 2,2',2'',2'''-((((4-amino-1,2-phenylene)bis(oxy))bis(ethane-2,1-diyl))bis(azanetriyl))tetraacetate
  参考文献：
  名称：

  Calcium depletion-mediated protease inhibition and apical-junctional-complex disassembly via an EGTA-conjugated carrier for oral insulin delivery

  摘要：

  Calcium (Ca2+) has a crucial role in maintaining the intestinal protease activity and in forming the apical junctional complex (AJC) that preserves epithelial barrier function. Ethylene glycol tetraacetic acid (EGTA) is a Ca2+-specific chelating agent. To maintain the concentration of this chelator in areas where enzyme inhibition and paracellular permeation enhancement are needed, this study synthesized a poly(gamma-glutamic acid)-EGTA conjugate (gamma PGA-EGTA) to form nanoparticles (NPs) with chitosan (CS) for oral insulin delivery. The results of our molecular dynamic (MD) simulations indicate that Ca2+ ions could be specifically chelated to the nitrogen atoms, ether oxygen atoms, and carboxylate oxygen atoms in [Ca(EGTA)](2-) anions. By chelating Ca2+, gamma PGA-EGTA conferred a significant insulin protection effect against proteases in intestinal tracts isolated from rats. Additionally, calcium depletion by gamma PGA-EGTA could stimulate the endocytosis of AJC components in Caco-2 cell monolayers, which led to a reversible opening of AJCs and thus increased their paracellular permeability. Single-photon emission computed tomography images performed in the biodistribution study clearly show the I-123-insulin orally delivered by CS/gamma PGA-EGTA NPs in the heart, aorta, renal cortex, renal pelvis and liver, which ultimately produced a significant and prolonged hypoglycemic effect in diabetic rats. The above results confirm that this gamma PGA-EGTA conjugate is a promising candidate for oral insulin delivery. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2012.11.011

文献信息

• Maximizing the relaxivity of HSA-bound gadolinium complexes by simultaneous optimization of rotation and water exchange
  作者：Stefano Avedano、Lorenzo Tei、Alberto Lombardi、Giovanni B. Giovenzana、Silvio Aime、Dario Longo、Mauro Botta

  DOI：10.1039/b714438e

  日期：——

  Two new GdEGTA (EGTA = ethylene glycol-bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid) derivatives incorporating aromatic moieties into the oxoethylenic bridge have been prepared and characterised, their conjugates to HSA investigated and an unprecedented high relaxivity, close to that predicted by theory, interpreted in terms of the combined effect of restricted local rotation and fast rate of water exchange.

  我们制备并表征了两种新的 GdEGTA（EGTA = 乙二醇-双（2-氨基乙基醚）-N,N,N′,N′-四乙酸）衍生物，它们在氧代乙烯桥中加入了芳香分子，并对它们与 HSA 的共轭物进行了研究，发现它们具有前所未有的高弛豫性，接近理论预测的弛豫性。