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Chemical Synthesis of Biologically Active Substances Labeled with Positron Emitting Radionuclides for Diagnoses of Deceases of Brain and Heart, and Cancer

Research Project

Project/Area Number 62480236
Research Category

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

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

Principal Investigator

TADA Masao  Tohoku Univ., Res.Inst. for TB and Cancer, Assoc.Prof., 抗酸菌病研究所, 助教授 (10006083)

Co-Investigator(Kenkyū-buntansha) KUBOTA Kazuo  Tohoku Univ., Res.Inst. for TB and Cancer, Instr., 抗酸菌病研究所, 講師 (40161674)
ITO Masatoshi  Tohoku Univ., Cyclotron and RI Center, Assoc.Prof., サイクロトロンラジオアイソトープセンター, 助教授 (00125501)
SUGIYAMA Hiroshi  Tohoku Univ., Chem.Res.Inst. of Non-aq.Solu., Assoc.Prof., 非水溶液化学研究所, 助教授 (90006304)
MATSUZAWA Taiju  Tohoku Univ., Res.Inst. for TB and Cancer, Prof., 抗酸菌病研究所, 教授 (10006108)
Project Period (FY) 1987 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥6,700,000 (Direct Cost: ¥6,700,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1988: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1987: ¥3,400,000 (Direct Cost: ¥3,400,000)
KeywordsChemical Synthesis / Diagnosis / Radiopharmaceutical / PET / Positron / Labeled Sugar / 標識アミノ糖 / 放射性薬剤 / 陽電子CT / 六炭糖 / 陽電子コンピュータトモグラフィー
Research Abstract

1. Improved synthesis of 2-deoxy-2-[^<18>F]fluoro-D-galactose.
Chemical synthesis of 2-deoxy-2-fluoro-D-galactose and its ^<18>F-labeled compound, a new radiopharmaceutical for liver imaging, using the acetyl hypofluorite procedure has been achieved.
2. Liver function studies using 2-deoxy-2-[^<18>F]fluoro-D-galactose and PET.
Both metabolite study and clinical Pet study on 2-deoxy-2-[^<18>F]fluoro-D-galactose show that the sugar is a very useful radiopharmceutical for the liver function studies. The detailed study on the sugar is in progress.
3. Synthesis of D-[1-^<11>C]hexoses.
(1). D-[1-^<11>C]Glucose. A mixture of D-arabinose and [^<11>C]cyanide was heated for 10 min in presence of alkali, passed through a column of cation exchange resine, and evaporated to dryness. The residue was treated with the diborane for 10 min to afford the desired sugar.
(2). D-[1-^<11>C]Galactose. A mixture of D-lyxose and [^<11>C]cyanide was treated in a similar manner as in (1) to give D-[1-^<11>C]galactose.
4. Synthesis of 2-deoxy-2-[^<18>F]fluoroacetamido-D-hexoses.
(1). 2-Deoxy-2-[^<18>F]fluoroacetamido-D-glucose. An efficient, one-pot synthesis the sugar starting from [^<18>F]fluoride and ethyl bromoacetate has been achieved. The synthesis is accomplished by a combination of halogen exchange, alkaline hydrolysis, and condensation. The sugar showed the diagnostic tumor-imaging activity.
(2). 2-Deoxy-2-[^<18>F]fluoroacetamido-D-mannose and -D-galactose. Rapid synthesis of theses sugars, respectively, have been developed,and their biological characteristics are being further investigated.

Report

(4 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • 1987 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] Masao Tada: "Synthesis of ^<18>F-Labelled 2-Deoxy-2-fluoro-D-galacto-pyranose Using the Acetyl Hypofluorite Procedure" Carbohydr.Res.161. 314-317 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masao Tada: "Synthesis of 3-Amino-1-methyl-9H-〔4-^<14>Clpyrido〔3,4-b〕-indole(3-Amino〔4-^<14>C〕harman)" J.Labelled Compds,Radiopharm.24. 631-636 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 福田寛: "新しいポジトロン標識肝診断薬剤-2-デオキシ-2-〔^<18>F〕フルオロ-Dガラクト-ス 第一報:急性毒性および被爆線量の評価" 核医学. 24. 165-169 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Keiichiro Yamaguchi: "Differential Diagnosis between Hepatocellular Carcinoma and Metastatic Liver Tumor Using 2-Deoxy-2-(^<18>F)fluoro-D-galactose with Positron Emission Tomography" CYRIC Ann.Rep.303-311 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiichi Ishiwata: "Application of 2-Deoxy-2-〔^<18>F〕fluoro-D-galctose for Experimental Tumor study" CYRIC Ann.Rep.196-203 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiichi Ishiwata: "Accumulation of 2-Deoxy-2-〔^<18>F〕fluoro-D-galctose in the Liver by Phosphate and Uridylate Trapping" Nucl.Med.Biol.15. 271-276 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 松沢大樹: "PETによる早期微小癌診断法の開発" 図説臨床癌シリ-ズ. 22. 127-133 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masao Tada: "A Convenient Synthesis of D-〔1-^<11>C〕Glucopyranose and -D-〔1-^<11>C〕Galactopyranose Using Diborane" J.Labelled Compds.Radiopharm.27. 1-7 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiichi Ishiwata: "2-Deoxy-2-〔^<18>F〕fluoro-D-galactose as an In Vivo Tracer for Imaging Galactose Metabolism in Tumors with Positron Emisson Tomography" Nucl.Med.Biol.16. 247-254 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 窪田和雄: "診断技術の進歩と微小癌の診断能力:X線CTとPET" 日本臨床. 47. 1037-1043 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazuo Kubota: "Differential Diagnosis of AH109A Tumor and Inflammation by Radioscintigraphy with L-〔methyl-^<11>C〕Methionine" Jpn.J.Cancer Res.80. 778-782 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takehiko Fujiwara: "N-〔^<18>F〕Fluoroacetly-D-glucosamine:A New Positron Labeled Pharmaceutical for Cancer Diagnosis.Preliminary Study" CYRIC Ann.Rep.174-177 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masao Tada: "An Efficient,One-pot synthesis of 2-Deoxy-2-〔温18F〕fluoro acetamido-D-glucopyranose(N-〔^<18>F〕Fluoroacetyl-D-glucosamine),Potential Diagnostic Imaging Agent" J.Labelled Compds Radiopharm.27. 1317-1324 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazuo Kubota: "Rapid and Sensitive Response of ^<11>C-L-Methionine Tumor Uptake to Irradiation" J.Nucl.Med.(in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Tada, Masao: "Synthesis of ^<18>F-Labelled 2-Deoxy-2-fluoro-D-galactopyranose Using the Acetyl Hypofluorite Procedure" Carbohydr. Res., 24, 314-317, 1987.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Tada, Masao: "Synthesis of 3-Amino-1-methyl-9H-[4-^<14>C]-pyrido[3,4-b]indole (3-Amino[^<14>C]harman)" J.Labeled Compds.Radiopharm., 24, 631-636, 1987.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fukuda, Hiroshi: "2-Deoxy-2-[^<18>F]fluoro-D-galactose: A New Tracer for the Evaluation for Liver Function by PET. -- I. Evaluation of Toxicity and Radiation Dose (in Japanese)" Kaku Igaku, 24, 165-169, 1987.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yamaguchi, Keiichiro: "Differential Diagnosis between Hepatocellular Carcinoma and Metastatic Liver Tumor Using 2-Deoxy-2-[^<18>F]fluoro-D-galactose with Positron Emission Tomography" CYRIC Ann. Rep., 303-311, 1987.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Ishiwata, Kiichi: "Application of 2-Deoxy-2-[^<18>F]fluoro-D-galactose for Experimental Tumor Study" CYRIC Ann. Rep., 196-203, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Ishiwata, Kiichi: "Accumulation of 2-Deoxy-2-[^<18>F]fluoro-D-galactose for Experimental Tumor Study" Nucl. Med. Biol., 15, 271-276, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Matsuzawa, Taiju: "Development of PET for the Diagnosis of Early Cancer (in Japanese)" Progress in Cancer Clinics., 22, 127-133, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Tada, Masao: "A Convenient Synthesis of D-[1-^<11>C]Glucopyranose and D-[1-^<11>C]Galactose Using Diborane" J.Labeled Compds.Radiopharm., 27, 1-7, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Ishiwata, Kiichi: "2-Deoxy-2-[^<18>F]fluoro-D-galactose as an In Vivo Tracer for Imaging Galactose Metabolism in Tumors with Positron Emission Tomography" Nucl. Med. Biol., 16, 247-254, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kubota, Kazuo: "Recent Advances of Positron Emission Tomography and CT Scan for the Diagnosis of Early Cancer (in Japanese)" Nihon Rinsho, 47, 1037-1043, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kubota, Kazuo: "Differential Diagnosis of AH109A Tumor and Inflammation by Radioscintigraphy with L-[methyl-^<11>C]Methionine" Jpn. J. Cancer Res., 80, 778-782, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fujiwara, Takehiko: "N-[^<18>F]Fluoroacetyl-D-glucosamine: A New Positron Labeled Pharmaceutical for Cancer Diagnosis. Preliminary Study" CYRIC Ann. Rep., 174-177, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Tada, Masao: "An Efficient, One-pot Synthesis of 2-Deoxy-2-[^<18>F]fluoroacetamido-D-glucopyranose (N-[^<18>F]Fluoroacetyl-D-glucosamine), Potential Diagnostic Imaging Agent" J.Labeled Compds.Radiopharm., 27, 1317-1324, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kubota, Kazuo: "Rapid and Sensitive Response of ^<11>C-L-Methionine Tumor Uptake to Irradiation" J. Nucl. Med.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiichi Ishiwata: "2-Deoxy-2-〔^<18>F〕fluoro-D-galactose as an In Vivo Tracer for Imaging Galactose Metabolism in Tumors with Positron Emisson Tomography" Nucl.Med.Biol.16. 247-254 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 窪田和雄: "診断技術の進歩と微小癌の診断能力:X線CTとPET" 日本臨床. 47. 1037-1043 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kazuo Kubota: "Differential Diagnosis of AH109A Tumor and Inflammation by Radioscintigraphy with L-〔methy1-^<11>C〕Methionine" Jpn.J.Cancer Res.80. 778-782 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takehiko Fujiwara: "N-〔^<18>F〕Fluoroacetyl-D-glucosamine:A New Positron Labeled Pharmaceutical for Cancer Diagnosis.Preliminary Study" CYRIC Ann.Rep.174-177 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masao Tada: "An Efficient,One-Pot Synthesis of 2-Deoxy-2-〔^<18>F〕fluoroacetamido-D-glucopyranose(N〔^<18>F〕Fluoroacetyl-D-glucosamine),Potential Diagnostic Imaging Agent" J.Labelled Compds.Radiopharm.27. 1317-1324 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kazuo Kubota: "Rapid and Sensitive Response of ^<11>C-L-Methionine Tumor Uptake to Irradiation" J.Nucl.Med.

    • Related Report
      1989 Annual Research Report
  • [Publications] 松沢大樹: 図説臨床癌シリーズ. 22. 127-133 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Tada,Masao: J.Labelled Compds.Radiopharm.27. 1-7 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] TADA.Masao: Carbohydr.Res. 161. 314-317 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] ISHIWATA.Kiichi: Nucl.Med.Biol. 15. 271-276 (1988)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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