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Multifaceted approaches to develop novel antibacterial seeds against drug-resistant bacterial pathogens

Research Project

Project/Area Number 25293026
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Drug development chemistry
Research InstitutionHokkaido University

Principal Investigator

ICHIKAWA Satoshi  北海道大学, 薬学研究科(研究院), 教授 (60333621)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000)
Fiscal Year 2015: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2013: ¥7,020,000 (Direct Cost: ¥5,400,000、Indirect Cost: ¥1,620,000)
Keywords天然物 / 抗菌剤 / 有機合成 / 抗菌薬 / 薬剤耐性 / 創薬化学
Outline of Final Research Achievements

a) Structural simplification of muraymycins and caprazamycins have been investigated to develop analogues possessing antibacterial activity against drug-resistant bacteria such as MRSA and VRE with enough metabolic stability as well as reduced toxicity against human cells. b) Efficient synthetic strategy toward the synthesis of plusbacin A3, which is applicable to the synthesis of a range of analogues, has been developed. c) Total synthesis of quinaldopeptin has been developed via solid-phase synthesis. A range of analogues was synthesized and their antibacterial activity was evaluated to find a potent analogue with superior antibacterial activity than that of natural product.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (44 results)

All 2016 2015 2014 2013

All Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (32 results) (of which Invited: 1 results)

  • [Journal Article] Design, synthesis and biological evaluation of 5′-C-piperidinyl-5′-O-aminoribosyluridines as a potential antibacterial agent.2015

    • Author(s)
      Nakaya, Takeshi; Matsuda, Akira; Ichikawa, Satoshi*
    • Journal Title

      Org. Biomol. Chem

      Volume: 14 Issue: 28 Pages: 7720-7735

    • DOI

      10.1039/c5ob01037c

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structure and activity relationship study of syringolin A as a potential anticancer agent.2015

    • Author(s)
      Chiba, Takuya; Matsuda, Akira; Ichikawa, Satoshi*
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 25 Issue: 21 Pages: 4872-4877

    • DOI

      10.1016/j.bmcl.2015.06.015

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Carbacaprazamycins: Chemically Stable Analogues of the Caprazamycin Nucleoside Antibiotics.2015

    • Author(s)
      Satoshi Ichikawa,* Mayumi Yamaguchi, Lee Shang Hsuan, Yuta Kato, and Akira Matsuda.
    • Journal Title

      ACS Infect. Dis.

      Volume: 1 Issue: 4 Pages: 151-156

    • DOI

      10.1021/id5000376

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Antibacterial nucleoside natural products inhibiting phospho-MurNAc-pentapeptide translocase; chemistry and structure-activity relationship.2015

    • Author(s)
      Ichikawa, Satoshi; Yamaguchi, Mayumi; Matsuda, Akira.
    • Journal Title

      Current Med. Chem.

      Volume: 22 Issue: 34 Pages: 3951-3979

    • DOI

      10.2174/0929867322666150818103502

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Isoxazolidine-containing Uridine Derivatives as Caprazamycin Analogues.2014

    • Author(s)
      Yamaguchi, Mayumi; Matsuda, Akira; Ichikawa, Satoshi*.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 4 Pages: 1187-1197

    • DOI

      10.1039/c4ob02142h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Expansion of Antibacterial Spectrum of Muraymycins toward Pseudomonas aeruginosa.2014

    • Author(s)
      Takeoka, Yusuke; Tanino, Tetsuya; Sekiguchi, Mitsuaki; Yonezawa, Shuji; Sakagami, Masahiro; Takahashi, Fumiyo; Togame, Hiroko; Tanaka, Yoshikazu; Takemoto, Hiroshi; Ichikawa, Satoshi*; Matsuda. Akira.
    • Journal Title

      ACS Med. Chem. Lett.

      Volume: 5 Issue: 5 Pages: 556-560

    • DOI

      10.1021/ml5000096

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of syringolin A and its improvement of biological activity.2014

    • Author(s)
      Chiba, Takuya; Hosono, Hidetaka; Nakagawa, Koji; Asaka, Masahiro; Takeda, Hiroshi; Matsuda, Akira; Ichikawa, Satoshi.*
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 126 Issue: 19 Pages: 4936-4939

    • DOI

      10.1002/ange.201402428

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Biological Evaluation of Quinaldopeptin.2014

    • Author(s)
      Katayama, Katsushi; Okamura, Takuya; Sunadome, Takuya; Nakagawa, Koji; Takeda, Hiroshi; Shiro, Motoo; Matsuda, Akira; Ichikawa, Satoshi
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 6 Pages: 2580-2590

    • DOI

      10.1021/jo500039d

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Function-oriented Synthesis of Liponucleoside Natural Products.2014

    • Author(s)
      Tanino, Tetsuya; Yamaguchi, Mayumi; Matsuda, Akira; Ichikawa, Satoshi
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 9 Issue: 9 Pages: 1836-1840

    • DOI

      10.1002/ejoc.201400140

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Sandramycin and Its Analogues via a Multi-component Assemblage.2013

    • Author(s)
      Katayama, Katsushi; Nakagawa, Koji; Takeda, Hiroshi; Matsuda, Akira; Ichikawa, Satoshi
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 2 Pages: 428-431

    • DOI

      10.1021/ol403319m

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Quinaldopeptin and Its Analogues.2013

    • Author(s)
      Ichikawa, Satoshi*; Takuya Okamura, and Matsuda, Akira.
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 24 Pages: 12662-12670

    • DOI

      10.1021/jo402267r

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of C-Glycosyl Pyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as a Scaffold for Check Point 1 Kinase Inhibitors.2013

    • Author(s)
      Ichikawa, Satoshi*; Tatebayashi, Nana and Matsuda, Akira.
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 23 Pages: 12065-12075

    • DOI

      10.1021/jo4020672

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 芳香族求核置換反応を利用したDNAメチル化酵素阻害剤の創製研究2016

    • Author(s)
      笠井由起子、佐藤浩輔、市川聡
    • Organizer
      日本薬学会第136年会 (口頭発表)
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] エピジェネティック制御を指向した非環式C-ヌクレオシドの合成と性質2016

    • Author(s)
      内海翔平、佐藤浩輔、市川聡
    • Organizer
      日本薬学会第136年会 (口頭発表)
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] Design and synthesis of simplified caprazamycin analogs.2015

    • Author(s)
      Nakaya, T.; Matsuda, A.; Ichikawa, S.
    • Organizer
      PACIFICHEM, The International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu (Hawaii, USA)
    • Year and Date
      2015-12-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] Design and synthesis of conformationally restricted caprazamycin analogs as antibacterial agents.2015

    • Author(s)
      Yamaguchi, M.; Ichikawa, S.; Matsuda, A.
    • Organizer
      PACIFICHEM, The International Chemical Congress of Pacific Basin Societies 2015 (Poster Presentation)
    • Place of Presentation
      Honolulu (Hawaii, USA)
    • Year and Date
      2015-12-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic study of plusbacin A32015

    • Author(s)
      Katsuyama, A.; Matsuda, A.; Ichikawa, S.
    • Organizer
      PACIFICHEM, The International Chemical Congress of Pacific Basin Societies 2015 (Poster Presentation)
    • Place of Presentation
      Honolulu (Hawaii, USA)
    • Year and Date
      2015-12-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] PImprovement of biological activities of syringolin A2015

    • Author(s)
      Chiba, T.; Matsuda, A.; Ichikawa, S.
    • Organizer
      PACIFICHEM, The International Chemical Congress of Pacific Basin Societies 2015 (Poster Presentation)
    • Place of Presentation
      Honolulu (Hawaii, USA)
    • Year and Date
      2015-12-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] syrbactin類を基盤とした新規プロテアソーム阻害剤の開発研究2015

    • Author(s)
      北畑舜、千葉拓也、市川聡
    • Organizer
      第33回メディシナルケミストリーシンポジウム(口頭発表&ポスター発表)
    • Place of Presentation
      幕張国際研修センター(千葉県・幕張市)
    • Year and Date
      2015-11-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic study of plusbacin A32015

    • Author(s)
      Katsuyama, A.; Matsuda, A.; Ichikawa, S.
    • Organizer
      第52回ペプチド討論会( 口頭発表)
    • Place of Presentation
      中央公民館(神奈川県・平塚市)
    • Year and Date
      2015-11-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] Syringolin類の合成と構造活性相関研究2015

    • Author(s)
      Nakaya, T.; Matsuda, A.; Ichikawa, S.
    • Organizer
      第57回天然物有機化学討論会 (ポスター発表)
    • Place of Presentation
      イーグレ姫路(兵庫県・姫路市)
    • Year and Date
      2015-09-23
    • Related Report
      2015 Annual Research Report
  • [Presentation] Syringolin類の合成と構造活性相関研究2015

    • Author(s)
      北畑舜、千葉拓也、市川聡
    • Organizer
      第57回天然物有機化学討論会 (ポスター発表)
    • Place of Presentation
      神奈川県民ホール(神奈川県・横浜市)
    • Year and Date
      2015-09-10
    • Related Report
      2015 Annual Research Report
  • [Presentation] Plusbacin A3の全合成研究2015

    • Author(s)
      勝山彬、松田彰、市川聡
    • Organizer
      第27回万有札幌シンポジウム (ポスター発表、ベストポスター賞)
    • Place of Presentation
      北海道大学(北海道・札幌市)
    • Year and Date
      2015-07-04
    • Related Report
      2015 Annual Research Report
  • [Presentation] 新規抗菌剤開発を指向したリポヌクレオシド系抗菌抗生物質の単純化研究2015

    • Author(s)
      山口繭美、松田彰、市川聡
    • Organizer
      第13回次世代を担う有機化学シンポジウム (口頭発表)
    • Place of Presentation
      立命館大学(滋賀県・草津市)
    • Year and Date
      2015-05-22
    • Related Report
      2015 Annual Research Report
  • [Presentation] Plusbacin A3の全合成研究2015

    • Author(s)
      勝山 彬、松田 彰、市川 聡
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-28 – 2015-03-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] Syringolin誘導体の合成2015

    • Author(s)
      北畑 舜、松田 彰、市川 聡
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-28 – 2015-03-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] ネプラノシン A 誘導体によるエピジェネティクスコントロール2014

    • Author(s)
      砂留 拓矢、新城 恵子、市川 聡、近藤 豊、周東 智、松田 彰
    • Organizer
      第32回メディシナルケミストリーシンポジウム
    • Place of Presentation
      神戸
    • Year and Date
      2014-11-27 – 2014-11-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新規抗菌剤開発を指向したisoxazolidinyl uridine誘導体の設計と合成2014

    • Author(s)
      山口 繭美、松田 彰、市川 聡
    • Organizer
      第32回メディシナルケミストリーシンポジウム
    • Place of Presentation
      神戸
    • Year and Date
      2014-11-27 – 2014-11-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 抗腫瘍活性増強を目指したプロテアソーム阻害剤シリンゴリンAの分子変換2014

    • Author(s)
      千葉 拓也、市川 聡、松田 彰
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] Jollié-Ugi反応を用いたplusbacinA3の合成研究2014

    • Author(s)
      勝山 彬、松田 彰、市川 聡
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Design and Synthesis of Isoxazolidine-containing Uridine Derivatives as Antibacterial Agents2014

    • Author(s)
      Yamaguchi, M.; Matsuda, A.; Ichikawa, S.
    • Organizer
      ACS 248th National Meeting
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-14 – 2014-08-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] Total Synthesis of Syringolin A and Its Structure-activity Relationship Study2014

    • Author(s)
      Chiba, T.; Ichikawa, S.; Matsuda, A.
    • Organizer
      ACS 248th National Meeting
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-14 – 2014-08-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of piperidine analogues of caprazamycins by aza-Prins-Ritter reaction2014

    • Author(s)
      Nakaya, T.; Ichikawa, S.; Matsuda, A
    • Organizer
      ACS 248th National Meeting
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-14 – 2014-08-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] Scaffold hoppingによる新規caprazamycin誘導体の合成研究2014

    • Author(s)
      仲谷 岳志、市川 聡、松田 彰
    • Organizer
      第26回万有札幌シンポジウム
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] ヌクレオシド系天然物による創薬基盤研究2014

    • Author(s)
      市川 聡
    • Organizer
      日本薬学会134年会シンポジウム
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] シリンゴリンAを基盤とした新規プロテアソーム阻害剤の創製研究2014

    • Author(s)
      千葉拓也、松田彰、市川聡
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
  • [Presentation] aza-Prins反応を用いた新規カプラザマイシン誘導体の合成研究2014

    • Author(s)
      仲谷岳志、松田彰、市川聡
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ジアステレオ選択的Ugi三成分反応による3-ヒドロキシプロリンの合成とPlusbacin A3の全合成への応用2014

    • Author(s)
      勝山彬、松田彰、市川聡
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Quinaldopeptin誘導体の合成2014

    • Author(s)
      藤沼雅巳、松田彰、市川聡
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
  • [Presentation] シリンゴリンAの全合成とその構造活性相関研究2013

    • Author(s)
      千葉拓也、松田彰、市川聡
    • Organizer
      第十一回 次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Total Synthesis of Syringolin A, a Potent Proteasome Inhibitor2013

    • Author(s)
      千葉拓也、松田彰、市川聡
    • Organizer
      13th International Conference on the Chemistry of Antibiotics and other bioactive compounds
    • Place of Presentation
      富士ビューホテル(山梨)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis and propaties of functionalized dumbbell oligodeoxynucleotides by Cu(I) catalyzed alkyne-azide cycloaddition2013

    • Author(s)
      砂留拓矢、市川聡、松田彰
    • Organizer
      The 40th International Symposium on Nucleic Acids Chemistry 2013
    • Place of Presentation
      神奈川大学(横浜)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ムレイドマイシンA誘導体の合成研究2013

    • Author(s)
      中村公佑、松田彰、市川聡
    • Organizer
      日本薬学会 北海道支部第140回例会
    • Place of Presentation
      札幌コンベンションセンター(北海道)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ムレイドマイシンA誘導体の合成研究2013

    • Author(s)
      中村公佑、松田彰、市川聡
    • Organizer
      第55回 天然有機化合物討論会
    • Place of Presentation
      同志社大学寒梅館(京都)
    • Related Report
      2013 Annual Research Report

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Published: 2013-05-21   Modified: 2019-07-29  

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