Gd-DOTA | 83678-67-5

• 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: Gd-DOTA
• 英文别名: Gadolinium-DOTA；gadolinium(3+);2-[4,7,10-tris(carboxylatomethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetate
• CAS: 83678-67-5
• 化学式: C₁₆H₂₄GdN₄O₈
• 分子量: 557.639
• InChiKey: GFSTXYOTEVLASN-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -7.79
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  12

ADMET

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用总结：目前没有关于母乳喂养期间使用钆喷酸葡胺的已发表经验。一些专业组织制定的指南指出，哺乳母亲在接受含钆对比剂后，不需要中断哺乳。钆喷酸葡胺是最稳定的钆剂之一，理论上使其成为在哺乳期间使用的较安全的药物。然而，由于没有关于在母乳喂养期间使用钆喷酸葡胺的已发表经验，可能更倾向于使用其他药物，特别是在哺乳新生儿或早产儿时。 ◉ 对哺乳婴儿的影响：截至修订日期，未找到相关的已发表信息。 ◉ 对泌乳和母乳的影响：截至修订日期，未找到相关的已发表信息。

◉ Summary of Use during Lactation:There is no published experience with gadoterate during breastfeeding. Guidelines developed by several professional organizations state that breastfeeding need not be disrupted after a nursing mother receives a gadolinium-containing contrast medium. Gadoterate is one of the most stable gadolinium agents, theoretically making it one of the safer drugs to use during breastfeeding. However, because there is no published experience with gadoterate during breastfeeding, other agents may be preferred, especially while nursing a newborn or preterm infant. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  氢化铕 、 Gd-DOTA 以 盐酸 为溶剂， 生成 [Eu-DOTA](1-)
  参考文献：
  名称：

  Tóth, Éva; Brücher, Ernö; Lázár, István, Inorganic Chemistry, 1994, vol. 33, # 18, p. 4070 - 4076

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸 、 gadolinium(III) trifluoromethanesulfonate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以55%的产率得到Gd-DOTA
  参考文献：
  名称：

  High-Relaxivity Gd(III)–Hemicryptophane Complex

  摘要：

  The polytopic hemicryptophane cage HC1 combining a cyclotriveratrylene (CTV) unit and a tris(2-aminoethyl)amine (tren) moiety connected by three 2-hydroxyisophthalamide linkers was synthesized in 12 steps. The resulting highly functionalized covalent host is soluble in aqueous medium and has been used to complex Gd(III) ion. The Gd(III)@HC1 complex presents promising relaxivity properties when compared to the clinically used Dotarem MRI agent.

  DOI：

  10.1021/acs.orglett.9b00081

文献信息

• Lanthanide(III) Complexes of Phosphorus Acid Analogues of H ₄ DOTA as Model Compounds for the Evaluation of the Second‐Sphere Hydration
  作者：Zuzana Kotková、Giovannia A. Pereira、Kristina Djanashvili、Jan Kotek、Jakub Rudovský、Petr Hermann、Luce Vander Elst、Robert N. Muller、Carlos F. G. C. Geraldes、Ivan Lukeš、Joop A. Peters

  DOI：10.1002/ejic.200800859

  日期：2009.1

  were observed for all other complexes. Ln III -induced 17 O NMR shift data reveal that the spatial location of the second-sphere water molecules for the two groups of complexes differs. The parameters governing the effect of the second hydration sphere on the relaxivity of the Gd III complexes of all ligands were evaluated by EPR, variable-temperature 17 O NMR spectroscopy and 1 H NMRD re-laxometry.

  五个类似 DOTA 的配体在其 Gd III 复合物的第一配位球中缺乏水分子，即次膦酸盐 H 4 DOTP H 、H 4 DOTP hm 和 H 4 DOTP Et 以及膦酸酯单酯 H 4 DOTP OEt 和 H 4 DOTP合成 OBu 的目的是探索第二水合球对 Gd III 配合物弛豫率的影响。H 4 DOTP H 、H 4 DOTP hm 和H 4 DOTP OEt 配体及其Ln III 配合物通过电位和时间分辨发光表征；Gd III 配合物在热力学上远不如 H 4 DOTA 稳定，并且在内球中没有水配位。游离配体H 4 DOTP OEt和H 4 DOTP H和H 4 DOTP OEt的Gd III复合物的晶体结构通过X射线衍射确定。配合物具有预期的八齿配位模式，具有 N 4 O 4 排列；没有水分子与 Gd III 离子结合。从 1 H 和 31 P NMR 光谱中获得了水溶液中所有五种配体的
• Solution Structure and Relaxivity of Ln‐DOTXAZA Derivatives
  作者：Malte Holzapfel、Torben Baldau、Svenja Kerpa、Gianmarco Guadalupi、Bing Qi、Yang Liu、Wolfgang J. Parak、Wolfgang Maison

  DOI：10.1002/ejic.202200432

  日期：2022.11.17

  Gd-Based contrast agents (GBCAs) are essential reagents in clinical diagnosis via MRI. We report four members of the DOTXAZA series, which are valuable scaffolds for the assembly of new GBCAs with improved relaxivity and tailored pharmacokinetic or targeting properties by Cu-catalyzed alkyne-azide cycloaddition (CuAAC).

  Gd 基造影剂(GBCA) 是通过 MRI 进行临床诊断的重要试剂。我们报告了 DOTXAZA 系列的四个成员，它们是用于组装新 GBCA 的有价值的支架，通过 Cu 催化的炔烃-叠氮化物环加成 (CuAAC) 具有改善的弛豫性和定制的药代动力学或靶向特性。
• Gd(III) complexes for electron–electron dipolar spectroscopy: Effects of deuteration, pH and zero field splitting
  作者：Luca Garbuio、Kaspar Zimmermann、Daniel Häussinger、Maxim Yulikov

  DOI：10.1016/j.jmr.2015.08.009

  日期：2015.10

  Spectral parameters of Gd(III) complexes are intimately linked to the performance of the Gd(III)nitroxide or Gd(III)-Gd(III) double electron-electron resonance (DEER or PELDOR) techniques, as well as to that of relaxation induced dipolar modulation enhancement (RIDME) spectroscopy with Gd(III) ions. These techniques are of interest for applications in structural biology, since they can selectively detect site-to-site distances in biomolecules or biomolecular complexes in the nanometer range. Here we report relaxation properties, echo detected EPR spectra, as well as the magnitude of the echo reduction effect in Gd(III)-nitroxide DEER for a series of Gadolinium(III) complexes with chelating agents derived from tetraazacyclododecane. We observed that solvent deuteration does not only lengthen the relaxation times of Gd(III) centers but also weakens the DEER echo reduction effect. Both of these phenomena lead to an improved signal-to-noise ratios or, alternatively, longer accessible distance range in pulse EPR measurements. The presented data enrich the knowledge on paramagnetic Gd(III) chelate complexes in frozen solutions, and can help optimize the experimental conditions for most types of the pulse measurements of the electron-electron dipolar interactions. (C) 2015 Elsevier Inc. All rights reserved.
• High-Relaxivity Gd(III)–Hemicryptophane Complex
  作者：Estelle Godart、Augustin Long、Roselyne Rosas、Gilles Lemercier、Marion Jean、Sébastien Leclerc、Sabine Bouguet-Bonnet、Célia Godfrin、Laure-Lise Chapellet、Jean-Pierre Dutasta、Alexandre Martinez

  DOI：10.1021/acs.orglett.9b00081

  日期：2019.4.5

  The polytopic hemicryptophane cage HC1 combining a cyclotriveratrylene (CTV) unit and a tris(2-aminoethyl)amine (tren) moiety connected by three 2-hydroxyisophthalamide linkers was synthesized in 12 steps. The resulting highly functionalized covalent host is soluble in aqueous medium and has been used to complex Gd(III) ion. The Gd(III)@HC1 complex presents promising relaxivity properties when compared to the clinically used Dotarem MRI agent.
• Tóth, Éva; Brücher, Ernö; Lázár, István, Inorganic Chemistry, 1994, vol. 33, # 18, p. 4070 - 4076
  作者：Tóth, Éva、Brücher, Ernö、Lázár, István、Tóth, Imre

  DOI：——

  日期：——