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2018 Fiscal Year Annual Research Report

ドナーアクセプター連結型中分子による生物機能/光機能分子創出

Publicly Offered Research

Project AreaMiddle molecular strategy: Creation of higher bio-functional molecules by integrated synthesis.
Project/Area Number 18H04376
Research InstitutionHokkaido University

Principal Investigator

鈴木 孝紀  北海道大学, 理学研究院, 教授 (70202132)

Project Period (FY) 2018-04-01 – 2020-03-31
Keywords中分子 / 酸化還元 / ヘテロ環 / 近赤外吸収
Outline of Annual Research Achievements

有機酸化還元系は、生体電子伝達系への関与(除草剤パラコート)やDNAインターカレーション能(アントラキノン系抗がん剤)などの特性により、医農薬分野で活躍する生物機能分子として高いポテンシャルを持つ化合物群である。π電子系化合物を利用した分子創薬に於いては、新規な低分子酸化還元系分子骨格の開発ばかりでなく、その骨格の連結(中分子化)による酸化還元機能/生物活性の調節と複合化が有効なアプローチであると考えた。このような複数サイトの連結型中分子は、電子授受以外の外部刺激(溶媒極性、光照射)によっても分子特性の変調が可能なため、モノマーには無い特異な制御性を持つ。また、ドナーとアクセプターの組み合わせなど、電子的特性が大きく異なる骨格の連結では、中分子内電荷移動/電子移動を通して新たな生物機能が期待できる。
本年度は、上記の研究目的にそった検討を進める一方、合わせて、京都大学 大野浩章教授とインドロカルバゾール類の合成と特性開発について、また、信州大学 大神田淳子教授とヘテロ縮環型キノンの生理活性について、京都大学 永木愛一郎准教授とのフローリアクターによる非対称ジオール合成について、それぞれ領域内共同研究を行い、それらについて共著論文発表を行った。さらに、アクセプターであるパーフルオロフェニル基を持つある種のジカチオンが、電荷移動的な近赤外吸収体を持つために、生体内での酸化還元応答や光化学療法へ利用できると考え、初期の計画と合わせ、近赤外の吸収体を持つ色素を利用したin vitroおよび in vivoでの検討を共同研究により行った。有機エレクトロクロミズム系とナノカプセルに共存する近赤外発光性ポリマーとのFRETを鍵としたセンシングは前例のないものであり、今後殺ガン細胞特性への展開が期待される。

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

おおむね順調に進展している

Strategy for Future Research Activity

最終年度は、領域内の多くのグループとの共同研究を進め、その成果をより多くの論文発表という形にする。

  • Research Products

    (22 results)

All 2019 2018 Other

All Int'l Joint Research (1 results) Journal Article (19 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 19 results) Presentation (2 results) (of which Invited: 2 results)

  • [Int'l Joint Research] Nanjing University(中国)

    • Country Name
      CHINA
    • Counterpart Institution
      Nanjing University
  • [Journal Article] Dual dynamic chirality generated in the assembly of three achiral rods through the three-fold twisting of a macrocycle2019

    • Author(s)
      Katoono Ryo、Sakamoto Kazuki、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 55 Pages: 5503~5506

    • DOI

      10.1039/C9CC02226K

    • Peer Reviewed
  • [Journal Article] Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge2019

    • Author(s)
      Katoono Ryo、Kusaka Keiichi、Saito Yuki、Sakamoto Kazuki、Suzuki Takanori
    • Journal Title

      Chemical Science

      Volume: 10 Pages: 4782~4791

    • DOI

      10.1039/C9SC00972H

    • Peer Reviewed
  • [Journal Article] Synthesis of the cyclohexene segment of portimine2019

    • Author(s)
      Saito Takafumi、Fujiwara Kenshu、Kondo Yoshihiko、Akiba Uichi、Suzuki Takanori
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Pages: 386~389

    • DOI

      10.1016/j.tetlet.2018.12.063

    • Peer Reviewed
  • [Journal Article] A Novel Condensed Heterocyclic Quinone with a Dibezofuranobisthiadiazole Skeleton.2019

    • Author(s)
      K. Sugawara, W. Nojo, Y. Ishigaki, J. Ohkanda, T. Suzuki
    • Journal Title

      Heterocycles

      Volume: - Pages: -

    • DOI

      10.3987/COM-19-S(F)7

    • Peer Reviewed
  • [Journal Article] Two-way Chromic Systems Based on Tetraarylanthraquinodimethanes: Electrochromism in Solution and Mechanofluorochromism in a Solid State.2019

    • Author(s)
      Y. Ishigaki, K. Sugawara, M. Yoshida, M. Kato, T. Suzuki
    • Journal Title

      Bull. Chem. Soc. Jpn。

      Volume: - Pages: -

    • DOI

      10.1246/bcsj.20190094

    • Peer Reviewed
  • [Journal Article] Total synthesis of kehokorins A and B2019

    • Author(s)
      Fujiwara Kenshu、Motousu Ryosuke、Sato Daisuke、Kondo Yoshihiko、Akiba Uichi、Suzuki Takanori、Tokiwano Tetsuo
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Pages: 1299~1301

    • DOI

      10.1016/j.tetlet.2019.04.011

    • Peer Reviewed
  • [Journal Article] Selective Formation of a Mixed‐valence State from Linearly‐bridged Oligo(aromatic diamines): Drastic Structural Change into a Folded Columnar Stack for Half‐filled Polycations**2019

    • Author(s)
      Nojo Wataru、Ishigaki Yusuke、Takeda Takashi、Akutagawa Tomoyuki、Suzuki Takanori
    • Journal Title

      Chemistry A European Journal

      Volume: - Pages: -

    • DOI

      10.1002/chem.201901272

    • Peer Reviewed
  • [Journal Article] Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes2018

    • Author(s)
      Kawada Yuiki、Ohmura Shunsuke、Kobayashi Misaki、Nojo Wataru、Kondo Masaki、Matsuda Yuka、Matsuoka Junpei、Inuki Shinsuke、Oishi Shinya、Wang Chao、Saito Tatsuo、Uchiyama Masanobu、Suzuki Takanori、Ohno Hiroaki
    • Journal Title

      Chemical Science

      Volume: 9 Pages: 8416~8425

    • DOI

      10.1039/C8SC03525C

    • Peer Reviewed
  • [Journal Article] Engineering of Electrochromic Materials as Activatable Probes for Molecular Imaging and Photodynamic Therapy2018

    • Author(s)
      Wu Luyan、Sun Yidan、Sugimoto Keisuke、Luo Zhiliang、Ishigaki Yusuke、Pu Kanyi、Suzuki Takanori、Chen Hong-Yuan、Ye Deju
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Pages: 16340~16352

    • DOI

      10.1021/jacs.8b10176

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Expandability of a long C-O bond by a scissor effect in acenaphthofuran2018

    • Author(s)
      Uchimura Yasuto、Shimajiri Takuya、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 54 Pages: 10300~10303

    • DOI

      10.1039/C8CC05998E

    • Peer Reviewed
  • [Journal Article] Molecular Wires with Controllable π-Delocalization Incorporating Redox-Triggered π-Conjugated Switching Units2018

    • Author(s)
      Nojo Wataru、Tamaoki Hitomi、Ishigaki Yusuke、Katoono Ryo、Fujiwara Kenshu、Fukushima Takanori、Suzuki Takanori
    • Journal Title

      ChemPlusChem

      Volume: ー Pages: ー

    • DOI

      10.1002/cplu.201800341

    • Peer Reviewed
  • [Journal Article] Transmission of Point Chirality to Axial Chirality for Strong Circular Dichroism in Triarylmethylium-o,o-dimers2018

    • Author(s)
      Suzuki Takanori、Ishigaki Yusuke、Iwai Tomohiro、Hayashi Yuki、Nagaki Aiichiro、Katoono Ryo、Fujiwara Kenshu、Yoshida Jun-ichi
    • Journal Title

      Synlett

      Volume: 29 Pages: 2147~2154

    • DOI

      10.1055/s-0037-1610190

    • Peer Reviewed
  • [Journal Article] An improved synthesis of the C42-C52 segment of ciguatoxin 3C2018

    • Author(s)
      Saito Takafumi、Fujiwara Kenshu、Sano Yusuke、Sato Takuto、Kondo Yoshihiko、Akiba Uichi、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Pages: 1372~1376

    • DOI

      10.1016/j.tetlet.2018.02.052

    • Peer Reviewed
  • [Journal Article] Double bond formation based on nitroaldol reaction and radical elimination: A prototype segment connection method for the total synthesis of nigricanoside A dimethyl ester2018

    • Author(s)
      Tsunoda Takayuki、Fujiwara Kenshu、Okamoto Satoshi、Kondo Yoshihiko、Akiba Uichi、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Pages: 1846~1850

    • DOI

      10.1016/j.tetlet.2018.03.091

    • Peer Reviewed
  • [Journal Article] Narrower HOMO-LUMO gap attained by conformational switching through peripheral polyarylation in 1,4,5,8-tetraaza-9,10-anthraquinodimethanes2018

    • Author(s)
      Suzuki Takanori、Ishigaki Yusuke、Sugawara Kazuma、Umezawa Yu、Katoono Ryo、Shimoyama Atsushi、Manabe Yoshiyuki、Fukase Koichi、Fukushima Takanori
    • Journal Title

      Tetrahedron

      Volume: 74 Pages: 2239~2244

    • DOI

      10.1016/j.tet.2018.03.041

    • Peer Reviewed
  • [Journal Article] Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Chemical Science

      Volume: 9 Pages: 2222~2229

    • DOI

      10.1039/C7SC05242A

    • Peer Reviewed
  • [Journal Article] Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source2018

    • Author(s)
      Katoono Ryo、Kusaka Keiichi、Tanaka Yuki、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Pages: 1167~1171

    • DOI

      10.1039/C7OB03057F

    • Peer Reviewed
  • [Journal Article] Longest C-C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.80A2018

    • Author(s)
      Ishigaki Yusuke、Shimajiri Takuya、Takeda Takashi、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Chem

      Volume: 4 Pages: 795~806

    • DOI

      10.1016/j.chempr.2018.01.011

    • Peer Reviewed
  • [Journal Article] Dynamic or undynamic chirality generated by helical arrangement of a shape-persistent ring and rod doubly bridged in a molecule2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Kusaka Keiichi、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 54 Pages: 735~738

    • DOI

      10.1039/C7CC09485J

    • Peer Reviewed
  • [Presentation] Studies on Dynamic Redox Systems: Construction of Record-breaking Strained Compounds and Development of Unimolecular Memory2019

    • Author(s)
      鈴木孝紀
    • Organizer
      第99回日本化学会春季年会(受賞講演)
    • Invited
  • [Presentation] 超結合:共有結合の限界を超えた化学2019

    • Author(s)
      鈴木孝紀
    • Organizer
      第99回日本化学会春季年会(特別企画)
    • Invited

URL: 

Published: 2019-12-27  

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