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The development of an efficient, rapid method for [^<18>F] fluorobenzyl iodide as a versatile labeling precursor.

Research Project

Project/Area Number 11670861
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Radiation science
Research InstitutionTohoku University

Principal Investigator

IWATA Ren  Tohoku University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (60143038)

Co-Investigator(Kenkyū-buntansha) YANAI Kazuhiko  Tohoku University, Graduate School of Medicine, Professor, 大学院・医学系研究科, 教授 (50192787)
IDO Tatsuo  Tohoku University, Cyclotron & Radioisotope Center, Professor, サイクロトロン・ラジオアイソトーフセンター, 教授 (80134063)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2000: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1999: ¥2,000,000 (Direct Cost: ¥2,000,000)
KeywordsPET / Fluorine-18 / Radiopharmaceutical / Labeling precursor / Positron emitter / Fluorobenzyl halide / ポジトロン放出核種 / 標識薬剤合成前駆体
Research Abstract

[^<18>F] Fluorobenzyl iodide and bromide ([^<18>F] fluorobenzyl halide) have been expected to be as versatile a precursor for ^<18>F-fluorobenzylation as ^<11>C-labled methyl iodide for ^<11>C-methylation. In the present study, we have aimed at developing a convenient, rapid method for automated preparation of the target compound from [^<18>F] fluoride. Attempts have been made to adapt the following three steps, constituting the synthesis procedure, to on-column processing.
1) Synthesis of [^<18>F] fluorobenzaldehyde from [^<18>F] fluoride : Starting substrates were immobilized on solid-phase-supports and examined for aromatic nucleophilic substitution by [^<18>F] fluoride. However, radiochemical yields of [^<18>F] fluorobenzaldehyde obtained by this method were not high enough for successive reactions. Consequently the on-column method was abandoned.
2) Reduction of [^<18>F] fluorobenzaldehyde into [^<18>F] fluorobenzyl alcohol : Sodium borohydride was chosen among many reductive reagents as it was used in aqueous solutions. While NaBH_4 on alumina gave rather lower yields, a simple on-column method of just flowing a NaBH_4 solution through a C18 cartridge retaining [^<18>F] fluorobenzaldehyde yielded [^<18>F] fluorobenzyl alcohol almost quantitatively. Thus after the reduction [^<18>F] fluorobenzyl alcohol was eluted with CH_2Cl_2.
3) Synthesis of [^<18>F] fluorobenzyl halide from [^<18>F] fluorobenzyl alcohol : Halogenation reagents immobilized to a resin or adsorbed on silica gel were investigated for the reaction. It was observed that radiochemical yields of [^<18>F] fluorobenzyl halide were very dependent on the dryness of the solvent eluting from the C18 cartridge. A semi-automated system was constructed on the basis of the above results and evaluated by preparing new ^<18>F-labeled radioligands from [^<18>F] fluorobenzyl halide.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] R.Iwata,C.Pascali,A.Bogni,G.Horvath,Z.Kovacs,K.Yanai,T.Ido.: "A new convenient method for the preparation of 4-[^<18>F]fluorobenzyl halides"Applied Radiation Isotopes. 52. 87-92 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Wada,R.Iwata.T.Ido and Y.Takai: "Synthesis of 1-[2-[^<18>F]fluoro-1-(hydroxymethyl)-ethoxy]methyl-2-nitro-imidazole ([^<18>F]FENI), a potential agent for imaging hypoxic tissues by PET"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 785-793 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata,G.Horvath,C.Pascali,A.Bogni,K.Yanai.Z.Kovacs T.Ido: "Synthesis of 3-[1H-imidazol-4-yl]propyl 4-[^<18>F]fluorobenzyl ether ([^<18>F]fluoro-proxyfan): a potential radioligand for imaging histamine H_3 receptors"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 873-882 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Furumoto,R.Iwata and T.Ido: "Synthesis of 1-O-(8-[^<18>F]fluorooctanoyl)-2-O-palmitoyl -rac-glycerol for Imaging Intracellular Signal Transduction"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 1159-1172 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata,C.Pascali,A.Bogni,Y.Miyake,K.Yanai,T.Ido: "A Simple Loop Method for the Automated Preparation of [^<11>C] Raclopride from [^<11>C] Methyl Triflate"Applied Radiation Isotopes. 55. 23-28 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata, C.Pascali, A.Bogni, G.Horvath, Z.Kovacs, K.Yanai and T.Ido: "A new convenient method for the preparation of 4-[^<18>F] fluorobenzyl halides."Appl. Radiat. Isot.. 52. 87-92 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Wada, R.Iwata, T.Ido and Y.Takai: "Synthesis of 1-[2-[^<18>F] fluoro-1-(hydroxymethyl)-ethoxy] methyl-2-nitroimidazole ([^<18>F] FENI), a potential agent for imaging hypoxic tissues by PET."J.Labeld. Compd. Radiopharm.. 43. 785-793 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata, G.Horvath, C.Pascali, A.Bogni, K.Yanai, Z.Kovacs and T.Ido: "Synthesis of 3-[1H-imidazol-4-yl] propyl 4-[^<18>F] fluorobenzyl ether ([^<18>F] fluoroproxyfan) : a potential radioligand for imaging histamine H_3 receptors."J.Labeld. Compd. Radiopharm.. 43. 873-882 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Furumoto, R.Iwata and T.Ido: "Synthesis of 1-O-(8-[^<18>F] fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for Imaging Intracellular Signal Transd."J.Labeld. Compd. Radiopharm.. 43. 1159-1172 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata, C.Pascali, A.Bogni, Y.Miyake, K.Yanai, and T.Ido: "A Simple Loop Method for the Automated Preparation of [^<11>C] Raclopride from [^<11>C] Methyl Triflate."Appl. Radiat. Isot.. 55. 23-28 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Iwata,C.Pascali,A.Bogni,G.Horvath,Z.Kovacs,K.Yanai,T.Ido.: "A new convenient method for the preparation of 4-[^<18>F] fluorobenzyl halides "Applied Radiation Isotopes. 52. 87-92 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.Wada,R.Iwata,T.Ido and Y.Takai: "Synthesis of 1-[2-[^<18>F] fluoro-1-(hydroxymethyl)-ethoxy]methyl-2-nitro-imidazole ([^<18>F]FENI), a potential agent for imaging hypoxic tissues by PET"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 785-793 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] R.Iwata,G.Horvath,C.Pascali,A.Bogni,K.Yanai,Z.Kovacs T.Ido: "Synthesis of 3-[1H-imidazol-4-yl] propyl 4-[^<18>F]fluorobenzyl ether([^<18>F]fluoroproxyfan): a potential radioligand for imaging histamine H_3 receptors"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 873-882 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Furumoto,R.Iwata and T.Ido: "Synthesis of 1-O-(8-[^<18>F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for Imaging Intracellular Signal Transduction"Journal of Labeled Compounds and Radiopharmaceuticals. 43. 1159-117 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] R.Iwata,C.Pascali,A.Bogni,Y.Miyake,K.Yanai,T.Ido: "A Simple Loop Method for the Automated Preparation of [^<11>C]Raclopride from [^<11>C]Methyl Triflate"Applied Radiation Isotopes. 53(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 岩田 練、井戸達雄他1名: "^<18>F-標識前駆体、4-[^<18>]fluorobenzyl bromideの迅速合成法の開発"核医学. 36・6. 611 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] R.Iwata,C.Pascali 他5名: "A new, convenient method for the preparation of 4-[^<18>]fluorobenzyl halides"Applied Radiation Isotopes. 52. 87-92 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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