[Gd(HPN3DO3A)] | 1264655-47-1

• 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(HPN3DO3A)]
• 英文别名: [Gd(HPN₃DO3A)]
• CAS: 1264655-47-1
• 化学式: C₁₇H₂₈GdN₇O₇
• 分子量: 599.702
• InChiKey: IHTJXVQAIPLLQM-UQKRIMTDSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,3,5-triethynyl-2-(tetradecyloxy)benzene 、 [Gd(HPN3DO3A)] 在 甲醇 、 copper(l) iodide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到5-(2,4,6-tris(1-(2-hydroxy-3-(1H-1,2,3-triazol-1-yl)propyl)-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecylgadolinium(III))phenoxy)tetradecyl
  参考文献：
  名称：

  Cell Labeling via Membrane-Anchored Lipophilic MR Contrast Agents

  摘要：

  Cell tracking in vivo with MR imaging requires the development of contrast agents with increased sensitivity that effectively label and are retained by cells. Most clinically approved Gd(III)-based contrast agents require high incubation concentrations and prolonged incubation times for cellular internalization. Strategies to increase contrast agent permeability have included conjugating Gd(III) complexes to cell penetrating peptides, nanoparticles, and small molecules which have greatly improved cell labeling but have not resulted in improved cellular retention. To overcome these challenges, we have synthesized a series of lipophilic Gd(III)-based MR contrast agents that label cell membranes in vitro. Two of the agents were synthesized with a multiplexing strategy to contain three Gd(III) chelates (1 and 2) while the third contains a single Gd(III) chelate (3). These new agents exhibit significantly enhanced labeling and retention in HeLa and MDA-MB-231-mcherry cells compared to agents that are internalized by cells (4 and Prohance).

  DOI：

  10.1021/bc500083t

文献信息

• Graphene Oxide Cellular Delivery of Hydrophilic Small Molecules
  申请人：Northwestern University

  公开号：US20170074859A1

  公开（公告）日：2017-03-16

  Unmodified graphene oxide conjugated with hydrophilic small molecules for cellular delivery.

  未经修改的氧化石墨烯与亲水性小分子结合用于细胞传递。
• Synthesis and Evaluation of Gd^III-Based Magnetic Resonance Contrast Agents for Molecular Imaging of Prostate-Specific Membrane Antigen
  作者：Sangeeta Ray Banerjee、Ethel J. Ngen、Matthew W. Rotz、Samata Kakkad、Ala Lisok、Richard Pracitto、Mrudula Pullambhatla、Zhengping Chen、Tariq Shah、Dmitri Artemov、Thomas J. Meade、Zaver M. Bhujwalla、Martin G. Pomper

  DOI：10.1002/anie.201503417

  日期：2015.9.7

  Magnetic resonance (MR) imaging is advantageous because it concurrently provides anatomic, functional, and molecular information. MR molecular imaging can combine the high spatial resolution of this established clinical modality with molecular profiling in vivo. However, as a result of the intrinsically low sensitivity of MR imaging, high local concentrations of biological targets are required to generate

  磁共振成像（MR）具有优势，因为它同时提供了解剖，功能和分子信息。MR分子成像可以将这种既定临床模式的高空间分辨率与体内分子谱相结合。但是，由于MR成像固有的低灵敏度，需要高局部浓度的生物靶标才能产生可​​分辨的MR对比度。我们假设前列腺特异性膜抗原（PSMA）是前列腺癌成像和治疗的有吸引力的靶标，可以作为基于MR的分子成像的合适生物标记。我们已经合成了三种新的基于高亲和力，低分子量Gd III的PSMA靶向造影剂，其中包含一到三种Gd III 每分子螯合。我们评估了这些试剂在溶液，前列腺癌细胞和体内实验模型中的弛豫特性，以证明基于PSMA的MR分子成像的可行性。
• Optimization of ZD2 Peptide Targeted Gd(HP-DO3A) for Detection and Risk-Stratification of Prostate Cancer with MRI
  作者：Nadia R. Ayat、Jing-Can Qin、Han Cheng、Sarah Roelle、Songqi Gao、Yajuan Li、Zheng-Rong Lu

  DOI：10.1021/acsmedchemlett.8b00172

  日期：2018.7.12

  LNCaP tumors. It produced 400% and 100% CNR increases in the T1-weighted 2D spin-echo MR images and 3D FLASH images of PC3 tumors, respectively, for at least 30 min at a dose of 0.1 mmol/kg. In contrast, less than 20% CNR increase was observed in the LNCaP tumors with both sequences. The optimized targeted contrast agent has higher relaxivities and are effective to detect aggressive PC3 tumors and differentiate

  这项工作的目的是优化肽靶向大环 MRI 造影剂，用于侵袭性前列腺癌的检测和风险分层。在室温下，在 CuSO4 和抗坏血酸盐的存在下，使用点击化学制备优化的试剂。ZD2-N3-Gd(HP-DO3A) 的 T1 和 T2 弛豫在 1.4 T 时分别为 5.44 和 7.10 mM-1 s-1，在 7 T 时分别为 5.53 和 7.81 mM-1 s-1，高于之前的报道了 ZD2-Gd(HP-DO3A)。在携带侵袭性 PC3 人前列腺癌异种移植物和缓慢生长的 LNCaP 肿瘤异种移植物的雄性裸鼠中研究了该试剂的特异性肿瘤增强作用。使用 2D 自旋回波序列和 3D FLASH 序列与 7 T 小动物扫描仪获取对比增强 MR 图像。ZD2-N3-Gd(HP-DO3A) 在侵袭性 PC3 肿瘤中产生强烈的对比度增强，而在缓慢生长的 LNCaP 肿瘤中几乎没有增强。它使 PC3 肿瘤的 T1 加权 2D