[F-18]labeiing of 1,2-diacylglycerols

Toshihiro Takahashi, Tatsuo Ido, Shinji Nagata, Ren Iwata

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

We have developed two kinds of [18F]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(ω-[18F]fluoroacyl)-2-acylglycerols (1*,2-[18F]FDAGs) and 2-(ω[18F]fluoroacyl)-1-acylglycerols (1,2*-[18F]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[18F]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with ω-[18F]fluoroacyl chlorides (method A) and 1-(16-[18F]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C16,C16)) and 1-(8-[18F]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[18F]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(ω-[18F]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(ω-bromoacyl)-1-acylglycerol with [18F]F- (method B) and 2-(16-[18F]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C16)) and 2-(8-[18F]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[18F]FDAGs were obtained in radiochemical yields of 8-35% (based on [18F]F-) with radiochemical purities of > 97% and the purified 1,2*-[18F]FDAGs were in radiochemical yields of 5-15% with radiochemical purities of > 95%. The total synthesis time from the start of the reactive [18F]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-[18F]FDAG(C16,C16), 1*,2-[18F]FDAG (C8,C16), and 1,2*-[18F]FDAG(C16,C16), 1,2*-[18F]FDAG(C16,C8) for animal studies.

Original languageEnglish
Pages (from-to)943-969
Number of pages27
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume43
Issue number9
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • 1-(ω-[F]fluoroacyl)-2-acylglycerol
  • 2-(ω-[F]fluoroacyl)-1-acylglycerol
  • Phosphatidyl-inositol (PI) turnover
  • Positron emission tomography (PET)
  • [F]labeled 1,2-diacylglycerols

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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