1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol
• 英文别名: 1-(8-[18F]fluorooctanoyl)-2-palmitoylglycerol；[1-(8-(18F)fluoranyloctanoyloxy)-3-hydroxypropan-2-yl] hexadecanoate
• 化学式: C₂₇H₅₁FO₅
• 分子量: 473.699
• InChiKey: BXNWHFLEWUAPCO-GLOFJIOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  33
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [1-(8-(18F)fluoranyloctanoyloxy)-3-trityloxypropan-2-yl] hexadecanoate 在 boron trifluoride methanol complex 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以60%的产率得到1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol
  参考文献：
  名称：

  Furumoto; Nagata; Iwata, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S644-S645

  摘要：

  DOI：

文献信息

• [F-18]labeling of 1,2-diacylglycerols
  作者：Toshihiro Takahashi、Tatsuo Ido、Shinji Nagata、Ren Iwata

  DOI：10.1002/1099-1344(200008)43:9<943::aid-jlcr379>3.0.co;2-v

  日期：2000.8

  We have developed two kinds of [F-18]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(omega-[F-18]fluoroacyl)-2-acylglycerols (1*,2-[F-18]FDAGs) and 2-(omega-[F-18]fluoroacyl)-1-acylglycerols (1,2*-[F-18]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[F-18]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with omega-[F-18]fluoroacyl chlorides (method A) and 1-(16-[F-18]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C16,C16)) and 1-(8-[F-18]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[F-18]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(omega-[F-18]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(omega-bromoacyl)-1-acylglycerol with [F-18]F- (method B) and 2-(16-[F-18]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C16)) and [F-18]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[F-18]FDAGs were obtained in radiochemical yields of 8-35 % (based on [F-18]F-) with radiochemical purities of > 97 % and the purified 1,2*-[F-18]FDAGs were in radiochemical yields of 5-15 % with radiochemical purities of > 95 %. The total synthesis time from the start of the reactive [F-18]F- production, including HPLC purification, was 100 - 135 min (method A) and 115 - 175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[F-18]FDAG(C16,C16), 1*,2-[F-18]FDAG(C8, C16), and 1,2*-[F-18]FDAG(C16,C16), 1,2*-[F-18]FDAG(C16,C8) for animal studies.
• Synthesis of 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for imaging intracellular signal transduction
  作者：Shozo Furumoto、Ren Iwata、Tatsuo Ido

  DOI：10.1002/1099-1344(20001030)43:12<1159::aid-jlcr402>3.0.co;2-z

  日期：2000.10.30

  An improved approach to the synthesis of 1-O-(8-[F-18]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol (rac-1,2-[F-18]FDAG) has been developed. We designed and synthesized two new types of precursors for the radiosynthesis and investigated their general utility. Each precursor was smoothly radiofluorinated (5 min) and the protecting soup at the 3-O-position was rapidly removed (1 min). The resulting rac-1,2-[F-18]FDAG was obtained in overall radiochemical yields of 20-30% (EOB) within 70 min including final preparative HPLC separation.
• Ido, Tatsuo; Nagata, Shinnji; Mukoyoshi, Masanori, Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 631 - 633
  作者：Ido, Tatsuo、Nagata, Shinnji、Mukoyoshi, Masanori、Yamaguchi, Koji、Iwata, Ren、et al.

  DOI：——

  日期：——
• Furumoto; Nagata; Iwata, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S644-S645
  作者：Furumoto、Nagata、Iwata、Ido

  DOI：——

  日期：——