N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid | 147666-97-5

• 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: N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid
• 英文别名: DTPA(HTA)2；2-[Bis[2-[carboxymethyl-[2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxoethyl]amino]ethyl]amino]acetic acid
• CAS: 147666-97-5
• 化学式: C₃₀H₄₁N₅O₁₂
• 分子量: 663.682
• InChiKey: YWHMUQCCKLRFDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  261
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid 、 gadolinium(III) chloride hexahydrate 以 吡啶 、 水 为溶剂， 以95%的产率得到2-[bis[2-[carboxylatomethyl-[2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxoethyl]amino]ethyl]amino]acetate;gadolinium(3+);hydrate
  参考文献：
  名称：

  Heterobimetallic gadolinium(III)–iron(III) complex of DTPA-bis(3-hydroxytyramide)

  摘要：

  A derivative of diethylenetriamine-N,N,N',N",N"-pentaacetic acid (DTPA), carrying two catechol functional groups has been synthesised by the reaction between DTPA-bis(anhydride) and 3-hydroxytyramine (dopamine). The ligand DTPA-bis(3-hydroxytyramide), [DTPA(HTA)(2)], is able to form stable heterobimetallic complexes with gadolinium(III) and iron(III) ions. The gadolinium(III) occupies the internal coordination cage of DTPA formed by three nitrogens, two carboxylate and two amide oxygens, while the [Fe(NTA)(H2O)(2)] (nitrilotri acetic acid, NTA) binds to catechol units by the substitution of two water ligands. The formation of polymeric species was avoided by using the tripodal NTA ligand. The heterobimetallic complex was characterised by means of visible absorption spectroscopy, electron spray ionisation-mass spectrometry (ESI-MS), and nuclear magnetic resonance (NMR) spectroscopy. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jallcom.2003.11.102
• 作为产物：
  描述：

  二乙烯三胺五醋酸 在 乙酸酐 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N,N'-bis(3-hydroxytyramide)diethylenetriamine N,N',N''-triacetic Acid
  参考文献：
  名称：

  EDTA and DTPA modified ligands as sequestering agents for uranyl decorporation

  摘要：

  Synthesis of modified EDTA and DTPA ligands and determination of their binding affinities for the uranyl cation are described.Thanks to a screening method, based on a chromophoric complex displacement procedure, chelating properties were studied in aqueous media under various pH conditions for evaluation of their in vivo uranyl-removal efficacy. Each ligand showed a more or less pronounced affinity for uranium. Specific ligands based on EDTA or DTPA analogues containing sulfocatecholamide (CAMS) were found to exhibit a significant affinity towards uranyl ion in acidic, neutral or basic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.065

文献信息

• Bis(phenylethylamide) Derivatives of Gd‐DTPA as Potential Receptor‐Specific MRI Contrast Agents
  作者：Sophie Laurent、Tatjana N. Parac‐Vogt、Kristof Kimpe、Coralie Thirifays、Koen Binnemans、Robert N. Muller、Luce Vander Elst

  DOI：10.1002/ejic.200601170

  日期：2007.5

  DTPA-bis(amide) derivatives bearing phenyl, phenol or catechol groups that mimic side chains of naturally occurring amino acids, such as phenylalanine, tyrosine or dopamine, were synthesized and characterized by elemental analysis, electrospray mass spectrometry, NMR spectroscopy and IR spectroscopy. The gadolinium(III) complexes of the ligands DTPA-bis(tyramide) [DTPA-(TA)2], DTPA-bis(3-hydroxytyramide)

  DTPA-双（酰胺）衍生物带有苯基、苯酚或邻苯二酚基团，可模拟天然氨基酸（如苯丙氨酸、酪氨酸或多巴胺）的侧链，并通过元素分析、电喷雾质谱、核磁共振光谱和红外光谱进行表征。配体DTPA-双(酪酰胺)[DTPA-(TA)2]、DTPA-双(3-羟基酪酰胺)[DTPA-(HTA)2]和DTPA-双(苯丙氨酸乙酯)的钆(III)配合物[ DTPA-(PAE)2]，然后通过 17O NMR 光谱和核磁弛豫色散 (NMRD) 测量进行体外研究。停留时间
• Luminescent Eu ^III and Tb ^III Complexes Containing Dopamine Neurotransmitter: Biological Interactions, Antioxidant Activity and Cellular‐Imaging Studies
  作者：Khushbu Singh、Anshika Goenka、Subramaniam Ganesh、Ashis K. Patra

  DOI：10.1002/ejic.201800732

  日期：2018.9.23

  studied for their antioxidant activity, ability to interact with calf‐thymus DNA (CT‐DNA) and bovine serum albumin (BSA), hydrolytic cleavage of pUC19 supercoiled plasmid DNA and as cellular‐imaging probes for both cancer cells and neuroblastoma cells. Both the EuIII and TbIII complexes exhibit potent antioxidant activity. These complexes show moderate binding affinity towards CT‐DNA (Kb ≈ 104 m–1) and BSA

  通过与二亚乙基三胺五乙酸反应生成的两种发光水溶性镧系元素（III）配合物[Ln（DTPA-DOPA）（H 2 O）]（1-2），其中Ln = Eu III（1），Tb III（2） （DTPA）带有带有邻苯二酚官能团[即DTPA-双（3-羟基酪酰胺）]的神经递质多巴胺，并对其光物理性质进行了研究。光激发后，在1和2处观察到强烈的红色和绿色发光特性，随后从多巴胺到Ln III进行有效的能量转移，从而导致内部构型f – f过渡。它们显示出由于intraconfigurational区分的尖锐的发射频带5 d 0 → 7 ˚F Ĵ跃迁在铕III和5 d 4 → 7个˚F Ĵ跃迁铽III。它们表现出长的激发态寿命[ τ = 0.52 MS（1）和0.33毫秒（2）]和计算出的量子产率，Φ整体，0.022（1）和0.038（2）。研究了发光复合物的抗氧化活性，与小牛胸腺DNA（CT-DNA）和牛血清