Synthesis of a F-18 labeled analog of antitumor prostaglandin delta 7-PGA1 methyl ester using p-[18F]fluorobenzylamine.
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.
Haradahira
T
T
Division of Advanced Technology for Medical Imaging, National Institute of Radiological Sciences, Chiba, Japan.
Hasegawa
Y
Y
Furuta
K
K
Suzuki
M
M
Watanabe
Y
Y
Suzuki
K
K
D000970:Antineoplastic Agents; D001549:Benzamides / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D005462:Fluorine Radioisotopes; D007202:Indicators and Reagents; D011455:Prostaglandins A, Synthetic; D016719:Radioimmunodetection
D000970:Antineoplastic Agents; D001549:Benzamides; D005462:Fluorine Radioisotopes; D007202:Indicators and Reagents; D011455:Prostaglandins A, Synthetic; C114760:4-fluorobenzylamine; C048481:9-oxo-15-hydroxy-delta 7,10,13-prostatrienoic acid methyl ester; C114759:4-fluorobenzamide