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Design of Radiotracers Labeled with Short-Lived Nuclides as Brain Radiopharmaceuticals

Research Project

Project/Area Number 59570440
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Radiation science
Research InstitutionKyushu University

Principal Investigator

MAEDA MINORU  Kyushu University, Faculty of Pharmaceutical Sciences, 薬学部, 助教授 (70101178)

Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1986: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1985: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1984: ¥800,000 (Direct Cost: ¥800,000)
KeywordsIodine-131 / Solid-phase triazene reaction / Dimethylsulfonium salt / Fluoride ion / Bromofluorination; <^(11)C> -ethanolamine / 炭素-11フェニルエタノールアミン / 酵素法
Research Abstract

The research has been aimed at the development of new radiopharmaceuticals with high specific activity for brain functional imaging, where the development of new reaction systems for preparing such radiotracers is essentially needed. No-carrieradded 2-(4-[ <^(131)I> ]iodophenyl)- and 8-[ <^(131)I> ]iodo-2-phenylpyrazolo[4,3-c]quinolin-3(5H)-one were prepared in isolated radiochemical yields of 11.6 and 5.4%, respectively, by acid decomposition of aryl triazenes in acetonitrile. A modified triazene method involving solid-phase decomposition reactions increased the yields to 15-35%. This modified procedure can be also applied to the high specific activity synthesis of other aromatic radiohalide compounds where difficulties occurs in obtaining satisfactory yields by decomposition of diazonium salt in an organic solvent. The utility of aromatic dimethylsulfonium group as a leaving group in nucleophilic substitution with fluoride ion has been investigated and this new fluorination gives an alternative method for preparing aromatic precursors for <^(18)F> radiopharmaceuticals. The recent preparation and successful use of <^(18)F> tetra-n-butylammonium fluoride led to also investigate the labeling reaction system consisting of this agent in conjunction with N-bromoimides for bromofluorination of double bonds and this method provides satisfactory yields of bromo-fluoride adducts. NCA [1- <^(11)C> ]phenylethanolamine was prepared by the oxynitrilase-catalyzed addition of [ <^(11)C> ]HCN to benzaldehyde followed by reduction of the [ <^(11)C> ]cyanohydrin. Radiochemical yields of 2-7% at end-of-synthesis were obtained in a synthesis time of 50-60 min. The enantiomeric composition was determined through its conversion to the MTPA diastereomers; the enantiomeric purity of the [ <^(11)C> ]phenylethanolamine produced via Co <Cl_2> -NaB <H_4> reduction was 60% e.e. while that prepared through boran-THF complex reduction was 80% e.e.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] M.Maeda: Chem.Pharm.Bull.33. 1301-1303 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M.Maeda: J.Label.Compds.Radiopharm.22. 487-501 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M.Maeda: J.Fluorine.Chem.34. 337-346 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M.Maeda: Radiat.Isot.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M. Maeda: "Synthesis of Radioiodinated Analogs of 2-Phenylpyrazolo[4,3-c]-quinolin-3(5H)-one by A Modified Triazene Method" J. Label. Compds. Radiopharm.22. 487-501 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M. Maeda: "Dimethylsulfonium Salts as Substrates in Aromatic Nucleophilic Substitution with Fluoride Ions" Chem. Pharm. Bull.33. 1301-1303 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M. Maeda: "Bromofluorination of Double Bonds Using N-Bromoimides and Tetra-n-butylammonium fluoride as A Source of Fluoride" J. Fluorine Chem.34. 337-346 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] M. Maeda: "Enantioselective Synthesis of Caron-11 Labeled Phenylethanolamine" Radiat. Iso.(1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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