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Radiosynthesis and evaluation of peptide probe containing short-lived positron-emitting radionuclides via a Pictet-Spengler reaction

Research Project

Project/Area Number 24791357
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Radiation science
Research InstitutionNational Institute of Radiological Sciences

Principal Investigator

HANYU Masayuki  独立行政法人放射線医学総合研究所, 分子イメージング研究センター, 研究員 (80435552)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
KeywordsPETイメージング / ピクテスペングラー反応 / 遠隔合成装置 / オリゴペプチド / PET
Research Abstract

A procedure for the synthesis of a carbon-11 labeled oligopeptide containing [1-11C]1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid ([1-11C]Tpi) from the corresponding TrpHCl-containing peptides has been developed involving a Pictet-Spengler reaction with [11C]formaldehyde. The radiolabeling of a TrpHCl-containing RGD peptide using the Pictet-Spengler reaction was successful. Furthermore, the remote-controlled synthesis of a [1-11C]Tpi-containing RGD (1) peptide was attempted using an automatic production system to generate [11C]CH3I. The radiochemical yield of the compound 1 at the end of synthesis was 5.9 % (n=4), for a total synthesis time of about 35 min. The usefulness of our synthesis was demonstrated PET studies using the compound 1 for the mouse bearing MIAPaca-2 and BxPC-3, a small cell pancreatic cancer cell line. The BxPC-3 cell-to-muscle and MIAPaca-2 cell-to-muscle of 1 at 22 min were retained at a low level of 2.8 and 1.3, respectively.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (16 results)

All 2014 2013 2012

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (9 results)

  • [Journal Article] Radiolabeling and Preliminary PET Study of Carbon-11 Labeled Amino Acids and Oligopeptides by Using Carbon-11 Formaldehyde; Peptide Science 2013, Y. Nishiuchi and T. Teshima (Ed.)2014

    • Author(s)
      Masayuki Hanyu, Aya Sugyou, Aung U Winn, Atsushi Tsuji, Kazunori Kawamura, Tsuneo Saga, Ming-Rong Zhang, Toshimitsu Fukumura
    • Journal Title

      The Japanese Peptide Society

      Pages: 181-182

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Radiolabeling and Preliminary PET Study of Carbon-11 Labeled Amino Acids and Oligopeptides by Using Carbon-11 Formaldehyde2014

    • Author(s)
      Masayuki Hanyu, Aya Sugyou, Aung U Winn, Atsushi Tsuji, Kazunori Kawamura, Tsuneo Saga, Ming-Rong Zhang, Toshimitsu Fukumura
    • Journal Title

      Peptide Science 2013

      Volume: 50 Pages: 181-182

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbon-11 radiolabeling of an oligopeptide containing tryptophan hydrochloride via a Pictet-Spengler reaction using carbon-11 formaldehyde2013

    • Author(s)
      Masayuki Hanyu, Yuuki Takada, Hiroki Hashimoto, Kazunori Kawamura, Ming-Rong Zhang, Toshimitsu Fukumura
    • Journal Title

      Journal of Peptide Science

      Volume: 19(10) Pages: 663-668

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Radiolabeling of oligopeptides containing [1-<11>^C]-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxyl ic acid via a Pictet-Spengler reaction; Peptide Science 2012, K. Sugimura (Ed.)2013

    • Author(s)
      Masayuki Hanyu, Yuuki Takada, Hiroki Hashimoto, Kazunori Kawamura, Ming-Rong Zhang, Toshimitsu Fukumura
    • Journal Title

      The Japanese Peptide Society

      Pages: 303-304

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Radiolabeling of Oligopeptides Containing [1-11C]-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic Acid via a Pictet-Spengler Reaction2013

    • Author(s)
      Masayuki Hanyu
    • Journal Title

      PEPTIDE SCIENCE 2012

      Volume: 49 Pages: 303-304

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Radiolabeling of aromatic compounds using K[*Cl]Cl and OXONE2012

    • Author(s)
      Yuuki Takada, Masayuki Hanyu, Koutarou Nagatsu, Toshimitsu Fukumura
    • Journal Title

      Journal of Labeled Compounds & Radiopharmaceuticals

      Volume: 55(10) Pages: 383-386

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Radiolabeling of aromatic compounds using K[*Cl]Cl and OXONE2012

    • Author(s)
      Yuuki Takada
    • Journal Title

      Journal of Labelled Compounds and Radiopharmaceuticals

      Volume: 55 Issue: 10 Pages: 383-386

    • DOI

      10.1002/jlcr.2957

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Radiolabeling and Preliminary PET Study of Carbon-11 Labeled Amino Acids and Oligopeptides by Using Carbon-11 Formaldehyde2013

    • Author(s)
      Masayuki Hanyu, Aya Sugyou, Aung U Winn, Atsushi Tsuji, Kazunori Kawamura, Tsuneo Saga, Ming-Rong Zhang, Toshimitsu Fukumura
    • Organizer
      4th Asia-Pacific International Peptide Symposium, in conjunction with the 50th Japanese Peptide Symposium
    • Place of Presentation
      OSAKA
    • Year and Date
      2013-11-08
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] Radiosynthesis and preliminary PET study of an <11>^C-labelled RGD peptide containing [1-<11>^C]1, 2, 3, 4-tetrahydro-beta-carboline-3-carbox ylic acid2013

    • Author(s)
      Masayuki Hanyu, Atsushi Tsuji, Kazunori Kawamura, Ming-Rong Zhang, Toshimitsu Fukumura
    • Organizer
      10th Australian Peptide Conference
    • Place of Presentation
      Penang, MALAYSIA
    • Year and Date
      2013-09-13
    • Related Report
      2013 Final Research Report
  • [Presentation] Radiosynthesis and preliminary PET study of an 11C-labelled RGD peptide containing [1-11C]1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid2013

    • Author(s)
      Masayuki Hanyu, Atsushi Tsuji, Kazunori Kawamura, Ming-Rong Zhang, Toshimitsu Fukumura
    • Organizer
      10th Australian Peptide Conference
    • Place of Presentation
      Penang, MALAYSIA
    • Related Report
      2013 Annual Research Report
  • [Presentation] Pictet-Spengler 反応を経由した[1-<11>^C]1, 2, 3, 4-テトラヒドロ-β-カルボリン-3-カルボン酸を含むオリゴペプチドの標識反応2012

    • Author(s)
      破入正行, 高田由貴, 橋本裕輝, 河村和紀, 張明栄, 福村利光
    • Organizer
      第49回日本ペプチド学会
    • Place of Presentation
      鹿児島
    • Year and Date
      2012-11-09
    • Related Report
      2013 Final Research Report
  • [Presentation] オキソンを用いた芳香族化合物への放射性塩素標識に関する研究2012

    • Author(s)
      高田由貴, 破入正行, 福村利光
    • Organizer
      日本核医学会
    • Place of Presentation
      札幌
    • Year and Date
      2012-10-12
    • Related Report
      2013 Final Research Report
  • [Presentation] ピクテ-スペングラー反応を用いた[<11>^C]-テトラヒドロカルボリン誘導体の合成2012

    • Author(s)
      破入正行, 橋本裕輝, 河村和紀, 福村利光
    • Organizer
      日本核医学会
    • Place of Presentation
      札幌
    • Year and Date
      2012-10-11
    • Related Report
      2013 Final Research Report
  • [Presentation] ピクテ-スペングラー反応を用いた[11C]-テトラヒドロカルボリン誘導体の合成2012

    • Author(s)
      破入正行
    • Organizer
      第52回日本核医学会学術総会
    • Place of Presentation
      札幌
    • Related Report
      2012 Research-status Report
  • [Presentation] オキソンを用いた芳香族化合物への放射性塩素標識に関する研究2012

    • Author(s)
      高田由貴
    • Organizer
      第52回日本核医学会学術総会
    • Place of Presentation
      札幌
    • Related Report
      2012 Research-status Report
  • [Presentation] Pictet-Spenglar反応を経由した[1-11C]-1,2,3,4-テトラヒドロ-β-カルボリン3-カルボン酸を含むオリゴペプチドの標識反応2012

    • Author(s)
      破入正行
    • Organizer
      第49回ペプチド討論会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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