Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of O-(3-[18F]Fluoropropyl)-L-tyrosine (L-[18F]FPT) and Its Biological Evaluation in 9L Tumor Bearing Rat

  • Moon, Byung-Seok (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Kim, Sang-Wook (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Lee, Tae-Sup (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Ahn, Soon-Hyuk (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Lee, Kyo-Chul (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • An, Gwang-Il (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Yang, Seung-Dae (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences) ;
  • Chi, Dae-Yoon (Department of Chemistry, Inha University) ;
  • Choi, Chang-Woon (Department of Nuclear Medicine, Korea Institute of Radiological and Medical Sciences) ;
  • Lim, Sang-Moo (Department of Nuclear Medicine, Korea Institute of Radiological and Medical Sciences) ;
  • Chun, Kwon-Soo (Laboratory of Cyclotron Application, Korea Institute of Radiological and Medical Sciences)
  • Published : 2005.01.20
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Abstract

O-(3-[$^{18}$F]Fluoropropyl)-L-tyrosine (L-[$^{18}$F]FPT) was synthesized by nucleophilic radiofluorination followed by acidic hydrolysis of protective groups and evaluated with 9 L tumor bearing rat. L-[$^{18}$F]FPT is an homologue of O-(2-[$^{18}$F]fluoroethyl)-L-tyrosine (L-[$^{18}$F]FET) which recently is studied as a tracer for tumor imaging using positron emission tomography (PET). [$^{18}$F]FPT was directly prepared from the precursor of O-(3-ptoluenesulfonyloxypropyl)- N-(tert-butoxycarbonyl)-L-tyrosine methyl ester. FPT-PET image was obtained at 60 min in 9 L tumor bearing rats. The radiochemical yield of [$^{18}$F]FPT was 0-45% (decay corrected) and the radiochemical purity was more than 95% after HPLC purification. The total time elapsed for the synthesis of [$^{18}$F]FPT was 100 min from EOB (End-of-bombardment). A comparison of uptake studies between [$^{18}$F]FPT and [$^{18}$F]FET was performed. In biodistribution, [$^{18}$F]FPT showed similar pattern with [$^{18}$F]FET in various tissues, but [$^{18}$F]FPT showed low uptake in brain. Furthermore, [$^{18}$F]FPT showed higher tumor-to-brain ratio than [$^{18}$F]FET. In conclusion, [$^{18}$F]FPT seems to be more useful amino acid tracer than [$^{18}$F]FET for brain tumors imaging with PET.

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