2-[Bis[2-[carboxymethyl-[2-(dimethylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid | 163494-48-2

• 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: 2-[Bis[2-[carboxymethyl-[2-(dimethylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid
• CAS: 163494-48-2
• 化学式: C₁₈H₃₃N₅O₈
• 分子量: 447.489
• InChiKey: WAZDWNALALCLNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.7
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  水 、 氯化钆 、 2-[Bis[2-[carboxymethyl-[2-(dimethylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid 生成 gadolinium(III) 5,8-bis(carboxylatomethyl)-11-(2-(dimethylamino)-2-oxoethyl)-2-methyl-3-oxo-2,5,8,11-tetraazatridecan-13-oate hydrate
  参考文献：
  名称：

  [(Gd-DTPA)(H2O)]2 的双（烷基酰胺）衍生物的合成、变温 17O NMR 研究 - 对水交换动力学的取代效应的评估

  摘要：

  参考 LCIB-ARTICLE-2002-003在 Web of Science 记录中查看记录，创建于 2006-02-15，修改于 2017-05-12

  DOI：

  10.1002/1099-0682(200210)2002:10<2686::aid-ejic2686>3.0.co;2-d
• 作为产物：
  描述：

  二亚乙基三胺五乙酸二酐 、 二甲胺 以 二甲基亚砜 为溶剂， 以74.6%的产率得到2-[Bis[2-[carboxymethyl-[2-(dimethylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid
  参考文献：
  名称：

  比较Gd-DTPA和几种双酰胺衍生物作为潜在的MRI造影剂。

  摘要：

  合成并表征了四亚乙基三胺五乙酸（DTPA）-双酰胺衍生物的中性g配合物。已通过体外和体内实验评估了它们作为组织特异性和低渗MRI造影剂的潜在应用。他们在D（2）O，牛血清白蛋白和人血清转铁蛋白溶液中测得的弛豫度显示出良好的弛豫能力。体内研究证明，Gd（DTPA-BDMA），Gd（DTPA-BIN）和Gd（环状-DTPA-1,2-pn）可能是有前途的肝脏特异性MRI造影剂和Gd（DTPA-BDMA），和Gd（cyclic-DTPA-1,2-pn）具有良好的肾脏排泄能力。其中，Gd（环状-DTPA-1,2-pn）是一种功能更强大的肝造影剂，Gd（DTPA-BIN）提供了几个小时的稳定成像对比度。它们还显示出较低的毒性。

  DOI：

  10.1016/s0968-0896(03)00263-3

文献信息

• Synthesis of Two<i>N,N</i>′-bis(<i>N,N</i>-dialkylamide) Derivatives of Diethylenetriaminepentaacetic Acid and the Stabilities of Their Complexes with Gd³⁺, Ca²⁺, Cu²⁺, and Zn²⁺
  作者：Yun-Ming Wang、Yueh-Ju Wang、Gin-Chung Liu、Yu-Ting Kuo

  DOI：10.1002/jccs.199900075

  日期：1999.8

  AbstractTwo bis(N,N‐dialkylamide) derivatives of DTPA [(carboxymethyl)iminobis (ethylenenitrilo) tetraacetic acid], DTPA‐BDMA = the bis(N,N‐dimethylamide) and DTPA‐BDEA = the bis(N,N‐diethylamide) were synthesized. Their protonation constants were determined by potentiometric titration in 0.10 M Me4NNO3 and by NMR pH titration at 25.0 ± 0.1 °C. Stability and selectivity constants were measured to evaluate the possibility of using the corresponding gadolinium(III) complexes for magnetic resonance imaging contrast agents. The stability constants of gadolinium(III), copper(II), zinc(II), and calcium(II) complexes with DTPA‐BDMA and DTPA‐BDEA were investigated quantitatively by potentiometry. The stability constant for gadolinium(III) complexes is larger than those for Ca(II), Zn(II), and Cu(II) complexes. The selectivity constants and modified selectivity constants of the amides for Gd3+ over endogenously available metal ions were calculated. Effectiveness of these two ligands in binding divalent and trivalent metal ions in biological media is assessed by comparing pM values at physiological pH 7.4. Spin‐lattice relaxivity values R1 for Gd(III) complexes were also determined. The observed relaxivity values were found to decrease with increasing pH in the acid range below pH 4 and relaxivity values became invariant with respect to pH changes over the range of 4–10. 17O NMR shifts showed that the [Dy(DTPA‐BDMA)] and [Dy(DTPA‐BDEA)] complexes had one inner‐sphere water molecule. Water proton spin‐lattice relaxation rates for the [Gd(DTPA‐BDMA)] and [Gd(DTPA‐BDEA)] complexes were also consistent with one inner‐sphere gadolinium(III) coordination position.
• Amid-Komplexe
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0263059B1

  公开（公告）日：1992-11-11
• Synthesis, Variable Temperature and Pressure 17O NMR Study of Bis(alkylamide) Derivatives of [(Gd-DTPA)(H2O)]2 − An Assessment of the Substitution Effect on Water Exchange Kinetics
  作者：François Botteman、Gaëlle M. Nicolle、Luce Vander Elst、Sophie Laurent、André E. Merbach、Robert N. Muller

  DOI：10.1002/1099-0682(200210)2002:10<2686::aid-ejic2686>3.0.co;2-d

  日期：2002.10

  Reference LCIB-ARTICLE-2002-003View record in Web of Science Record created on 2006-02-15, modified on 2017-05-12

  参考 LCIB-ARTICLE-2002-003在 Web of Science 记录中查看记录，创建于 2006-02-15，修改于 2017-05-12
• Comparison between Gd-DTPA and several bisamide derivatives as potential MRI contrast agents
  作者：Jianghua Feng、Guoying Sun、Fengkui Pei、Maili Liu

  DOI：10.1016/s0968-0896(03)00263-3

  日期：2003.7

  Four neutral gadolinium complexes of diethylenetriaminepentaacetic acid (DTPA)-bisamide derivatives have been synthesized and characterized. Their potential application as tissue-specific and low-osmolarity MRI contrast agents has been evaluated by in vitro and in vivo experiments. Their measured relaxivities in D(2)O, bovine serum albumin and human serum transferrin solutions showed favorable relaxation

  合成并表征了四亚乙基三胺五乙酸（DTPA）-双酰胺衍生物的中性g配合物。已通过体外和体内实验评估了它们作为组织特异性和低渗MRI造影剂的潜在应用。他们在D（2）O，牛血清白蛋白和人血清转铁蛋白溶液中测得的弛豫度显示出良好的弛豫能力。体内研究证明，Gd（DTPA-BDMA），Gd（DTPA-BIN）和Gd（环状-DTPA-1,2-pn）可能是有前途的肝脏特异性MRI造影剂和Gd（DTPA-BDMA），和Gd（cyclic-DTPA-1,2-pn）具有良好的肾脏排泄能力。其中，Gd（环状-DTPA-1,2-pn）是一种功能更强大的肝造影剂，Gd（DTPA-BIN）提供了几个小时的稳定成像对比度。它们还显示出较低的毒性。