1-[(18)F]fluoro-3,6,9,12,15,18-hexaoxahenicos-20-yne | 1190206-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(18)F]fluoro-3,6,9,12,15,18-hexaoxahenicos-20-yne
• 英文别名: 3-[2-[2-[2-[2-[2-(2-(18F)fluoranylethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]prop-1-yne
• CAS: 1190206-07-5
• 化学式: C₁₅H₂₇FO₆
• 分子量: 321.376
• InChiKey: YUQVIBPOQUCLNS-GKTGUEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  叠氮-PEG4-NHS酯 、 1-[(18)F]fluoro-3,6,9,12,15,18-hexaoxahenicos-20-yne 在 2,6-二甲基吡啶 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 [(18)F]FPEGNHS
  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
• 作为产物：
  描述：

  丙炔-七聚乙二醇-对甲苯磺酸酯 在 四丁基铵碳酸氢酯 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.05h， 生成 1-[(18)F]fluoro-3,6,9,12,15,18-hexaoxahenicos-20-yne
  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

• METHODS AND COMPOSITIONS FOR PROTEIN LABELLING
  申请人：Gill Herman

  公开号：US20100221176A1

  公开（公告）日：2010-09-02

  A modular platform is provided for rapid preparation of various water-soluble prosthetic groups capable to efficiently introduce 18 F into proteins with 18 F labelling reagents.

  提供了一个模块化平台，用于快速准备各种水溶性假体基团，能够有效地将 18 F引入蛋白质中，使用 18 F标记试剂。
• 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.