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Conformation analysis and target molecule identification of PF1171 hexapeptides in vivo

Research Project

Project/Area Number 16K07707
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionMie University

Principal Investigator

MASUDA Yuichi  三重大学, 生物資源学研究科, 准教授 (90617755)

Research Collaborator AKAGI Ken-ichi  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords環状ペプチド / カイコ / 立体配座 / 三次元構造 / 核磁気共鳴 / 安定同位体標識 / 分子プローブ / 有機化学 / NMR / アミノ酸 / 生理活性 / ケミカルバイオロジー
Outline of Final Research Achievements

PF1171F is a cyclic hexapeptide with paralytic activity against silkworm larvae via oral administration. To elucidate its conformation in pseudo body’s internal environment (aqueous solution and silkworm’s hemolymph), PF1171F whose nitrogen atoms were labeled with 15N was analyzed by 1H-15N 2-dimentional Nuclear Magnetic Resonance (NMR) experiments. The conformation in aqueous solution was found to be quite different from those in organic solvents. On the other hand, no NMR signals were observed in the 2D spectrum of PF1171F in silkworm’s hemolymph. This might be because PF1171F sticks to large biomolecules such as hemocytes.

Academic Significance and Societal Importance of the Research Achievements

環状ペプチドの立体配座は、標的分子結合や体内動態と密接に関係しているが、実際に活性が発現する生体環境中における立体配座研究は、これまでほとんど行われていなかった。
本研究では、15N標識したPF1171Fを有機合成し、二次元NMRを駆使することにより、疑似生体環境中の立体配座解析を実現した。本解析法は、薬の候補分子として注目されている環状ペプチドの活性発現機構研究に有効である。また、本研究で得られた疑似生体環境中における立体配座の知見は、環状ペプチドの合理的設計につながる。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (19 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (6 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 5 results,  Open Access: 5 results,  Acknowledgement Compliant: 1 results) Presentation (9 results) (of which Int'l Joint Research: 1 results) Remarks (3 results)

  • [Int'l Joint Research] University of Salerno(イタリア)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides2018

    • Author(s)
      D’Amato Assunta、Della Sala Giorgio、Izzo Irene、Costabile Chiara、Masuda Yuichi、De Riccardis Francesco
    • Journal Title

      Molecules

      Volume: 23 Issue: 7 Pages: 1779-1779

    • DOI

      10.3390/molecules23071779

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Conformation-Based Design and Synthesis of Apratoxin A Mimetics Modified at the α,β-Unsaturated Thiazoline Moiety2017

    • Author(s)
      Onda Yuichi、Masuda Yuichi、Yoshida Masahito、Doi Takayuki
    • Journal Title

      J. Med. Chem.

      Volume: 60 Issue: 15 Pages: 6751-6765

    • DOI

      10.1021/acs.jmedchem.7b00833

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Systematic Analysis of the Relationship among 3D Structure, Bioactivity, and Membrane Permeability of PF1171F, a Cyclic Hexapeptide with Paralyzing Effects on Silkworms2017

    • Author(s)
      Masuda Yuichi、Tanaka Ren、Ganesan A.、Doi Takayuki
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 21 Pages: 11447-11463

    • DOI

      10.1021/acs.joc.7b01975

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids2016

    • Author(s)
      Masuda Y, Aoyama K, Yoshida M, Kobayashi K, Ohshiro T, Tomoda H, Doi T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 754-765

    • DOI

      10.1248/cpb.c16-00095

    • NAID

      130005160040

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase.2016

    • Author(s)
      Masuda, Y., Maruyama, C., Kawabata, K., Hamano, Y., Doi, T.
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 36 Pages: 5602-5611

    • DOI

      10.1016/j.tet.2016.07.050

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 生物活性環状ペプチドPF1171類とapratoxin Cの全合成と三次元構造解析2016

    • Author(s)
      増田裕一,土井隆行:
    • Journal Title

      化学工業

      Volume: 67 Pages: 18-25

    • Related Report
      2016 Research-status Report
  • [Presentation] Cherimolacyclopeptide Eの全合成と生物活性評価2019

    • Author(s)
      吉田 優香,増田 裕一
    • Organizer
      日本農芸化学会2019年度大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] アミロイドβの凝集を阻害するβ -ストランド配座固定ペプチドの設計と合成:ベンゼン環と配座固定の位置の検討2019

    • Author(s)
      田中 郁也,柴田 果奈,増田 裕一
    • Organizer
      日本農芸化学会2019年度大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 3D Structure-activity relationship study of naturally occurring peptides and its application to drug design.2018

    • Author(s)
      Yuichi Masuda
    • Organizer
      第10回国際ペプチドシンポジウム/第55回ペプチド討論会
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] アミロイドβの凝集を阻害するβ-ストランド配座固定ペプチドの設計と合成2018

    • Author(s)
      田中 郁也、柴田 果奈、増田 裕一
    • Organizer
      日本農芸化学会 2018年度大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 環状ペプチドPF1171ペンタペプチドとavellanin類の全合成と生物活性評価2018

    • Author(s)
      本田 将也、増田 裕一
    • Organizer
      日本農芸化学会 2018年度大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 環状ペプチドPF1171Fの生体内環境における立体配座のNMRによる解析2018

    • Author(s)
      増田 裕一、佐野 萌佳、本田 将也、赤木 謙一
    • Organizer
      日本農芸化学会 2018年度大会
    • Related Report
      2017 Research-status Report
  • [Presentation] (2S,3R,4R)-3,4-dihydroxyarginineの合成と一酸化窒素合成酵素の阻害活性2017

    • Author(s)
      増田 裕一,丸山 千登勢,川畑 球一,濱野 吉十,土井 隆行
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大学(京都府京都市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] Total synthesis and biological evaluation of PF1171B, D, E, and avellanins A, B, C.2017

    • Author(s)
      Masaya Honda, Yuichi Masuda
    • Organizer
      第54回 ペプチド討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 環状ペプチドの三次元構造に着目した構造-活性相関研究2016

    • Author(s)
      増田 裕一
    • Organizer
      第51回 天然物化学談話会
    • Place of Presentation
      湯沢東映ホテル(新潟県南魚沼群)
    • Year and Date
      2016-07-06
    • Related Report
      2016 Research-status Report
  • [Remarks] 創薬化学研究室の紹介ページ

    • URL

      http://www.cc.mie-u.ac.jp/~masuda/

    • Related Report
      2018 Annual Research Report 2017 Research-status Report 2016 Research-status Report
  • [Remarks] 生理活性化学・創薬化学研究室のページ

    • URL

      http://bfcmc.bio.mie-u.ac.jp/

    • Related Report
      2018 Annual Research Report
  • [Remarks] 三重大学教員紹介

    • URL

      http://kyoin.mie-u.ac.jp/profile/3065.html

    • Related Report
      2017 Research-status Report 2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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