1-(1-[(18)F]fluoro-3,6,9,12,15,18,21-heptaoxatricos-23-yl)-4-(1-(2,5-pyrroledione-1-yl)-3,6,9,12,15,18-hexaoxanonadeca-19-yl)-1,2,3-triazole | 1190206-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(1-[(18)F]fluoro-3,6,9,12,15,18,21-heptaoxatricos-23-yl)-4-(1-(2,5-pyrroledione-1-yl)-3,6,9,12,15,18-hexaoxanonadeca-19-yl)-1,2,3-triazole
• 英文别名: [(18)F]FPEGMA；1-[2-[2-[2-[2-[2-[2-[[1-[2-[2-[2-[2-[2-[2-[2-(2-(18F)fluoranylethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]triazol-4-yl]methoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]pyrrole-2,5-dione
• CAS: 1190206-04-2
• 化学式: C₃₅H₆₁FN₄O₁₅
• 分子量: 795.887
• InChiKey: LCAXWLIGYJONIM-QBZPUJSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  55
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  188
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1-(3,6,9,12,15,18-hexaoxahenicos-20-yn-1-yl)-2,5-pyrroledione 、 1-azido-2-[2-[2-[2-[2-[2-[2-(2-(18F)fluoranylethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethane 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙腈 为溶剂， 生成 1-(1-[(18)F]fluoro-3,6,9,12,15,18,21-heptaoxatricos-23-yl)-4-(1-(2,5-pyrroledione-1-yl)-3,6,9,12,15,18-hexaoxanonadeca-19-yl)-1,2,3-triazole
  参考文献：
  名称：

  A Modular Platform for the Rapid Site-Specific Radiolabeling of Proteins with ¹⁸F Exemplified by Quantitative Positron Emission Tomography of Human Epidermal Growth Factor Receptor 2

  摘要：

  Receptor-specific proteins produced by genetic engineering are attractive as PET imaging agents, but labeling with conventional F-18-based prosthetic groups is problematic due to long synthesis times, poor radiochemical yields, and low specific activities. Therefore, we developed a modular platform for the rapid preparation of water-soluble prosthetic groups capable of efficiently introducing F-18 into proteins. The utility of this platform is demonstrated by the thiol-specific prosthetic group, [F-18]FPEGMA, which was used to produce site-specifically F-18-labeled protein (F-18-trastuzumab-ThioFab) in 82 min with a total radiochemical yield of 13 +/- 3% and a specific activity of 2.2 +/- 0.2 Ci/mu mol. F-18-trastuzumab-ThioFab retained the biological activity of native protein and was successfully validated in vivo with microPET imaging of Her2 expression in a xenograft tumor-bearing murine model modulated by. the Hsp90 inhibitor, 17-(allylamino)-17-demethoxygeldanamycin.

  DOI：

  10.1021/jm900420c

文献信息

• US8435488B2
  申请人：——

  公开号：US8435488B2

  公开（公告）日：2013-05-07
• A Modular Platform for the Rapid Site-Specific Radiolabeling of Proteins with ¹⁸F Exemplified by Quantitative Positron Emission Tomography of Human Epidermal Growth Factor Receptor 2
  作者：Herman S. Gill、Jeff N. Tinianow、Annie Ogasawara、Judith E. Flores、Alexander N. Vanderbilt、Helga Raab、Justin M. Scheer、Richard Vandlen、Simon-P. Williams、Jan Marik

  DOI：10.1021/jm900420c

  日期：2009.10.8

  Receptor-specific proteins produced by genetic engineering are attractive as PET imaging agents, but labeling with conventional F-18-based prosthetic groups is problematic due to long synthesis times, poor radiochemical yields, and low specific activities. Therefore, we developed a modular platform for the rapid preparation of water-soluble prosthetic groups capable of efficiently introducing F-18 into proteins. The utility of this platform is demonstrated by the thiol-specific prosthetic group, [F-18]FPEGMA, which was used to produce site-specifically F-18-labeled protein (F-18-trastuzumab-ThioFab) in 82 min with a total radiochemical yield of 13 +/- 3% and a specific activity of 2.2 +/- 0.2 Ci/mu mol. F-18-trastuzumab-ThioFab retained the biological activity of native protein and was successfully validated in vivo with microPET imaging of Her2 expression in a xenograft tumor-bearing murine model modulated by. the Hsp90 inhibitor, 17-(allylamino)-17-demethoxygeldanamycin.