bis(2,5-dioxopyrrolidin-1-yl) 5-iodoisophthalate | 1411597-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(2,5-dioxopyrrolidin-1-yl) 5-iodoisophthalate
• 英文别名: Bis(2,5-dioxopyrrolidin-1-yl) 5-iodobenzene-1,3-dicarboxylate
• CAS: 1411597-37-9
• 化学式: C₁₆H₁₁IN₂O₈
• 分子量: 486.176
• InChiKey: XLLDBQZSSYROGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis(2,5-dioxopyrrolidin-1-yl) 5-iodoisophthalate 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  WO2023/278592

  摘要：

  公开号：
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 5-碘间苯二甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以73.3%的产率得到bis(2,5-dioxopyrrolidin-1-yl) 5-iodoisophthalate
  参考文献：
  名称：

  SIB-DOTA: A trifunctional prosthetic group potentially amenable for multi-modal labeling that enhances tumor uptake of internalizing monoclonal antibodies

  摘要：

  A major drawback of internalizing monoclonal antibodies (mAbs) radioiodinated with direct electrophilic approaches is that tumor retention of radioactivity is compromised by the rapid washout of iodo-tyrosine, the primary labeled catabolite for mAbs labeled via this strategy. In our continuing efforts to develop more versatile residualizing labels that could overcome this problem, we have designed SIB-DOTA, a prosthetic labeling template that combines the features of the prototypical, dehalogenation-resistant N-succinimidyl 3-iodobenzoate (SIB) with DOTA, a useful macrocyclic chelator for labeling with radiometals. Herein we describe the synthesis of the unlabeled standard of this prosthetic moiety, its protected tin precursor, and radioiodinated SIB-DOTA. An anti-EGFRvIII-reactive mAb, L8A4 was radiolabeled with [I-131]SIB-DOTA in 27.1 +/- 6.2% (n = 2) conjugation yields and its targeting properties to the same mAb labeled with [I-125]SGMIB both in vitro and in vivo using U87MG.Delta EGFR cells and xenografts were compared. In vitro paired-label internalization assays showed that the intracellular radioactivity from [I-131]SIB-DOTA-L8A4 was 21.4 +/- 0.5% and 26.2 +/- 1.1% of initially bound radioactivity at 16 and 24 h, respectively. In comparison, these values for [I-125]SGMIB-L8A4 were 16.7 +/- 0.5% and 14.9 +/- 1.1%. Similarly, the SIB-DOTA prosthetic group provided better tumor targeting in vivo than SGMIB over 8 d period. These results suggest that SIB-DOTA warrants further evaluation as a residualizing agent for labeling internalizing mAbs including those targeted to EGFRvIII. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.025

文献信息

• [EN] RADIOLABELED BIOMOLECULES AND THEIR USE<br/>[FR] BIOMOLÉCULES RADIOMARQUÉES ET LEUR UTILISATION
  申请人：UNIV DUKE

  公开号：WO2018178936A1

  公开（公告）日：2018-10-04

  The application is drawn to radiolabeled biomolecules and methods for radiolabeling biomolecules with radioactive halogen atoms that minimizes loss of the radioactive halogen due to dehalogenation in vivo, preserves the biological activity of the biomolecule, maximizes retention of radioactivity in cancer cells, and minimizes the retention of radioactivity in normal tissues after in vivo administration. Some such radiolabeled biomolecules comprise a radioactive metal atom in place of, or in addition to the radioactive halogen. The biomolecules have an affinity for particular types of cells and may specifically bind a certain cell, such as cancer cells. Relevant biomolecules include antibodies, monoclonal antibodies, antibody fragments, peptides, other proteins, nanoparticles and aptamers.

  该应用程序涉及放射性标记的生物分子和使用放射性卤素原子对生物分子进行放射性标记的方法，从而最小化由于体内脱卤而导致的放射性卤素损失，保留生物分子的生物活性，最大限度地保留癌细胞中的放射性活性，并在体内给药后最小化正常组织中的放射性活性保留。一些这样的放射性标记的生物分子包括放射性金属原子代替或附加在放射性卤素原子上。这些生物分子具有亲和力，可以特异性地结合某些细胞，例如癌细胞。相关的生物分子包括抗体、单克隆抗体、抗体片段、肽、其他蛋白质、纳米颗粒和适配体。
• RADIOLABELED BIOMOLECULES AND THEIR USE
  申请人：DUKE UNIVERSITY

  公开号：US20200188541A1

  公开（公告）日：2020-06-18

  The application is drawn to radiolabeled biomolecules and methods for radiolabeling biomolecules with radioactive halogen atoms that minimizes loss of the radioactive halogen due to dehalogenation in vivo, preserves the biological activity of the biomolecule, maximizes retention of radioactivity in cancer cells, and minimizes the retention of radioactivity in normal tissues after in vivo administration. Some such radiolabeled biomolecules comprise a radioactive metal atom in place of, or in addition to the radioactive halogen. The biomolecules have an affinity for particular types of cells and may specifically bind a certain cell, such as cancer cells. Relevant biomolecules include antibodies, monoclonal antibodies, antibody fragments, peptides, other proteins, nanoparticles and aptamers.