N'N"N"'-triacetyl-fusarimine | 20186-12-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: N'N"N"'-triacetyl-fusarimine
• 英文别名: TAF；N-(15,27-diacetamido-7,19,31-trihydroxy-10,22,34-trimethyl-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-trien-3-yl)acetamide
• CAS: 20186-12-3
• 化学式: C₃₉H₆₀N₆O₁₅
• 分子量: 852.937
• InChiKey: VGXYDZCCQDSGLZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  60
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  288
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N'N"N"'-triacetyl-fusarimine 、 zirconium oxalate 在 potassium carbonate 作用下， 以 aq. buffer 为溶剂， 反应 1.55h， 生成
  参考文献：
  名称：

  Novel Bifunctional Cyclic Chelator for ⁸⁹Zr Labeling–Radiolabeling and Targeting Properties of RGD Conjugates

  摘要：

  Within the last years Zr-89 has attracted considerable attention as long-lived radionuclide for positron emission tomography (PET) applications. So far desferrioxamine B (DFO) has been mainly used as bifunctional chelating system. Fusarinine C (FSC), having complexing properties comparable to DFO, was expected to be an alternative with potentially higher stability due to its cyclic structure. In this study, as proof of principle, various FSC-RGD conjugates targeting alpha(v)beta(3) integrins were synthesized using different conjugation strategies and labeled with Zr-89. In vitro stability, biodistribution, and microPET/CT imaging were evaluated using [Zr-89]FSC-RGD conjugates or [Zr-89]triacetylfusarinine C (TAFC). Quantitative Zr-89 labeling was achieved within 90 min at room temperature. The distribution coefficients of the different radioligands indicate hydrophilic character. Compared to [Zr-89]DFO, [Zr-89]FSC derivatives showed excellent in vitro stability and resistance against transchelation in phosphate buffered saline (PBS), ethylenediaminetetraacetic acid solution (EDTA), and human serum for up to 7 days. Cell binding studies and biodistribution as well as microPET/CT imaging experiments showed efficient receptor-specific targeting of [Zr-89]FSC-RGD conjugates. No bone uptake was observed analyzing PET images indicating high in vivo stability. These findings indicate that FSC is a highly promising chelator for the development of Zr-89-based PET imaging agents.

  DOI：

  10.1021/acs.molpharmaceut.5b00128

文献信息

• Novel Bifunctional Cyclic Chelator for ⁸⁹Zr Labeling–Radiolabeling and Targeting Properties of RGD Conjugates
  作者：Chuangyan Zhai、Dominik Summer、Christine Rangger、Gerben M. Franssen、Peter Laverman、Hubertus Haas、Milos Petrik、Roland Haubner、Clemens Decristoforo

  DOI：10.1021/acs.molpharmaceut.5b00128

  日期：2015.6.1

  Within the last years Zr-89 has attracted considerable attention as long-lived radionuclide for positron emission tomography (PET) applications. So far desferrioxamine B (DFO) has been mainly used as bifunctional chelating system. Fusarinine C (FSC), having complexing properties comparable to DFO, was expected to be an alternative with potentially higher stability due to its cyclic structure. In this study, as proof of principle, various FSC-RGD conjugates targeting alpha(v)beta(3) integrins were synthesized using different conjugation strategies and labeled with Zr-89. In vitro stability, biodistribution, and microPET/CT imaging were evaluated using [Zr-89]FSC-RGD conjugates or [Zr-89]triacetylfusarinine C (TAFC). Quantitative Zr-89 labeling was achieved within 90 min at room temperature. The distribution coefficients of the different radioligands indicate hydrophilic character. Compared to [Zr-89]DFO, [Zr-89]FSC derivatives showed excellent in vitro stability and resistance against transchelation in phosphate buffered saline (PBS), ethylenediaminetetraacetic acid solution (EDTA), and human serum for up to 7 days. Cell binding studies and biodistribution as well as microPET/CT imaging experiments showed efficient receptor-specific targeting of [Zr-89]FSC-RGD conjugates. No bone uptake was observed analyzing PET images indicating high in vivo stability. These findings indicate that FSC is a highly promising chelator for the development of Zr-89-based PET imaging agents.