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Synthesis of a F-18 labeled analog of antitumor prostaglandin delta 7-PGA1 methyl ester using p-[18F]fluorobenzylamine.

Authors
  • Haradahira, T
  • Hasegawa, Y
  • Furuta, K
  • Suzuki, M
  • Watanabe, Y
  • Suzuki, K
Type
Published Article
Journal
Applied Radiation and Isotopes
Publisher
Elsevier
Publication Date
Dec 01, 1998
Volume
49
Issue
12
Pages
1551–1556
Identifiers
PMID: 9745691
Source
Medline
License
Unknown

Abstract

A fluorine-18 labeled analog of an antitumor prostaglandin delta 7-PGA1 methyl ester, 15-deoxy-13,14-dihydro-delta 7-PGA1 4-[18F]fluorobenzyl amide ([18F]3), was synthesized as a tracer candidate for detecting tumors with positron emission tomography. p-[18F]Fluorobenzylamine (p-[18F]FBnA) used as a labeled precursor for the synthesis of [18F]3 was prepared by fluorination of a 4-N, N, N-trimethylammonium-benzonitrile triflate with [18F]fluoride and subsequent reduction with borane-dimethylsulfide. Radiochemical yield and purity of p-[18F]FBnA obtained were 39-49% (decay uncorrected) and 91-96%, respectively, after C18 Sep-Pak purification. Treatment of p-[18F]FBnA with a 15-deoxy-13,14-dihydro-delta 7-PGA1 N-succinimidyl ester in acetonitrile and subsequent HPLC purification gave radiochemically pure (> 99%) [18F]3 with a 58% decay uncorrected yield. The total synthesis time was 70 min from the start of the radiosynthesis of p-[18F]FBnA.

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