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Design and synthesis of heavy atom-free photosensitizers based on the biradical intersystem crossing mechanism and its application to photodynamic therapy

Research Project

Project/Area Number 16H04176
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bio-related chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

YUASA HIDEYA  東京工業大学, 生命理工学院, 教授 (90261156)

Project Period (FY) 2016-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Fiscal Year 2020: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2019: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2018: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2017: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2016: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Keywords光増感剤 / 光線力学治療 / CT吸収 / ビフェニル誘導体 / 項間交差 / ビフェニル化合物 / 分子内CT / ビラジカル / 光線力学治療効果 / ランタニドナノ粒子 / 三重項生成機構 / 生体機能材料 / 分子内電荷移動
Outline of Final Research Achievements

We succeeded in the development of biphenyl derivatives as a new intramolecular CT photosensitizer on the basis of our own triplet-producing mechanism. We exploited this photosensitizer for the photodynamic damage of cancer cells. We also found that the biphenyl photosensitizer can be excited by two-photon excitation with a near-infrared laser, which enables deep-tissue entry. Overall, we have accomplished almost all the goals first planned, except for animal experiments.

Academic Significance and Societal Importance of the Research Achievements

これまでの多くの増感剤は、分子量が500以上であり、チャネルタンパク質の孔、DNAメジャーグルーブ、酵素ポケットなど狭い空間に収まりにくく、増感剤の生体応用の選択肢が狭かった。研究代表者らが開発したビフェニル誘導体は分子量がグルコースを付けても435と非常に小さく、グルコース輸送体の孔などを標的にできる。そのため、今後、種々の生体応用が期待できる。また、医薬品としても体内滞留時間を短くできるなどの利点があげられる。

Report

(6 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (46 results)

All 2021 2020 2019 2018 2017 2016 Other

All Journal Article (14 results) (of which Peer Reviewed: 12 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (29 results) (of which Int'l Joint Research: 5 results,  Invited: 8 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] 小さな光増感剤への期待と課題2021

    • Author(s)
      湯浅英哉、金森功史
    • Journal Title

      JPA日本光線力学学会NEWS LETTER

      Volume: 24 Pages: 5-7

    • Related Report
      2020 Annual Research Report
  • [Journal Article] Photo effect on the CD1d-binding ability of azobenzene-attached analogues of α-GalCer2020

    • Author(s)
      Takashi Kanamori, Tomoki Numata, Satoshi Kuwabara, Yasuyuki Ishii, Hiroshi Watarai, Hideya Yuasa
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 5 Pages: 126960-126960

    • DOI

      10.1016/j.bmcl.2020.126960

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Affinity Control of Monosaccharide Conjugated Peptides against Lectins with a Set of Amino Acid Substitutions on alpha Helical Structures2020

    • Author(s)
      Yusuke Maeda, Toshiki Sawada, Tsuyoshi Takahashi, Hideya Yuasa, and Hisakazu Mihara
    • Journal Title

      Bioconjugate Chem.

      Volume: 31 Issue: 11 Pages: 2533-2540

    • DOI

      10.1021/acs.bioconjchem.0c00480

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Twist‐Assisted Biphenyl Photosensitizer Passable Through Glucose Channel2019

    • Author(s)
      Tsuga Yuki、Katou Masataka、Kuwabara Satoshi、Kanamori Takashi、Ogura Shun‐ichiro、Okazaki Shigetoshi、Ohtani Hiroyuki、Yuasa Hideya
    • Journal Title

      Chemistry An Asian Journal

      Volume: 14 Issue: 12 Pages: 2067-2071

    • DOI

      10.1002/asia.201900378

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New photosensitisers for photodynamic therapy2019

    • Author(s)
      Hideya Yuasa
    • Journal Title

      Research OUTREACH

      Volume: 109 Issue: 109 Pages: 110-113

    • DOI

      10.32907/ro-109-110113

    • Related Report
      2019 Annual Research Report
  • [Journal Article] 重原子不要な励起三重項生成法:スピン軌道電荷移動2019

    • Author(s)
      湯浅英哉、津賀雄輝
    • Journal Title

      光化学

      Volume: 50 Pages: 185-188

    • NAID

      40022116054

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Large Timescale Interrogation of Neuronal Function by Fiberless Optogenetics Using Lanthanide Micro-particles2019

    • Author(s)
      Toh Miyazaki, Srikanta Chowdhury, Takayuki Yamashita, Takanori Matsubara, Hiromu Yawo, Hideya Yuasa and Akihiro Yamanaka
    • Journal Title

      Cell Reports

      Volume: 26 Issue: 4 Pages: 1033-1043

    • DOI

      10.1016/j.celrep.2019.01.001

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of and triplex formation in oligonucleotides containing 2’-deoxy-6-thioxanthosine2018

    • Author(s)
      akeshi Inde, Shuhei Nishizawa, Yuusaku Hattori, Takashi Kanamori, Hideya Yuasa, Kohji Seio, Mitsuo Sekine, Akihiro Ohkubo
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 26 Issue: 13 Pages: 3785-3790

    • DOI

      10.1016/j.bmc.2018.06.004

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Water-Soluble Glucosyl Pyrene Photosensitizers: An Intramolecularly Synthesized 2-C-Glucoside and an O-Glucoside2018

    • Author(s)
      Takashi Kanamori, Akira Matsuyama, Hidenori Naito, Yuki Tsuga, Yoshiki Ozako, Shun-ichiro Ogura, Shigetoshi Okazaki, Hideya Yuasa
    • Journal Title

      Journal of Organic Chemistry

      Volume: 83 Issue: 22 Pages: 13765-13775

    • DOI

      10.1021/acs.joc.8b02066

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] pH-Dependent Switching of Base Pairs Using Artificial Nucleobases with Carboxyl Groups2018

    • Author(s)
      Kaewsomboon T, Nishizawa S, Kanamori T, Yuasa H, Ohkubo A
    • Journal Title

      The Journal of Organic CHemistry

      Volume: 83 Issue: 3 Pages: 1320-1320

    • DOI

      10.1021/acs.joc.7b02828

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intersystem Crossing Mechanisms in the Room Temperature Phosphorescence of Crystalline Organic Compounds2018

    • Author(s)
      Hideya Yuasa and Shinichi Kuno
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 91 Issue: 2 Pages: 223-229

    • DOI

      10.1246/bcsj.20170364

    • NAID

      130006350279

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 室温燐光を発する有機化合物結晶とその項間交差メカニズム2017

    • Author(s)
      久野信一、湯浅英哉
    • Journal Title

      光化学

      Volume: 48 Pages: 155-161

    • NAID

      40021423213

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Long persistent Phosphorescence of crystalline phenylboronic acid derivatives and its mechanistic study2017

    • Author(s)
      Shinichi Kuno, Takashi Kanamori, Zhao Yijing, Hiroyuki Ohtani, Hideya Yuasa
    • Journal Title

      ChemPhotoChem

      Volume: 1 Issue: 3 Pages: 102-106

    • DOI

      10.1002/cptc.201600031

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Coating lanthanide nanoparticles with carbohydrate ligands elicits affinity for HeLa and RAW264.7 cells, enhancing their photodamaging effect2017

    • Author(s)
      Takashi Kanamori, Takashi Sawamura, Tatsumi Tanaka, Izumi Sotokawa, Ryota Mori, Kotaro Inada, Akihiro Ohkubo, Shun-Ichiro Ogura, Yasutoshi Murayama, Eigo Otsuji, Hideya Yuasa
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 25 Issue: 2 Pages: 743-749

    • DOI

      10.1016/j.bmc.2016.11.050

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] グアノシンの配列選択的光酸化を指向した核酸-光増感剤複合体の開発2020

    • Author(s)
      金森功吏、津賀雄輝、汪潮、浜本航治、遊部智大、湯浅英哉
    • Organizer
      第14回バイオ関連化学シンポジウム2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] リガンド連結型有機光触媒を用いた標的タンパク質の酸化的不活性化と抗腫瘍活性2020

    • Author(s)
      對馬理彦、Wen Yijin、津賀雄輝、金森功吏、湯浅英哉、中村浩之
    • Organizer
      LASER WEEK IN KOCHI
    • Related Report
      2020 Annual Research Report
  • [Presentation] 小さな光増感剤開発による癌細胞標的と核酸点変異への応用2020

    • Author(s)
      湯浅英哉 金森功史
    • Organizer
      LASER WEEK IN KOCHI
    • Related Report
      2020 Annual Research Report
  • [Presentation] 小型高効率光増感剤の開発とグアノシンの配列選択的光酸化への応用2020

    • Author(s)
      金森功吏・津賀雄輝・浜本航治・汪潮・遊部智大・李若瑜・金子翔大・湯浅英哉
    • Organizer
      日本化学会第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Development of Novel Photoactivatable Glycolipid Analogues Controlling the Immune Activity of iNKT Cells2019

    • Author(s)
      Tomoki Numata, Satoshi Kuwabara, Takashi Kanamori, Hiroshi Watarai, Yasuyuki Ishii, and Hideya Yuasa
    • Organizer
      6th International Conference on Chemical and Biological Sciences
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 東工大発光機能分子・素子の医学応用への潜在力2019

    • Author(s)
      湯浅英哉
    • Organizer
      高知大学医学部附属病院・光線医療センター 開設2周年 記念式典
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] がん治療を指向した光応答低分子デバイス2019

    • Author(s)
      湯浅英哉
    • Organizer
      PhotoDynamic Medicine PDM 2019
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 光線力学治療を志向した低分子光増感剤の開発2019

    • Author(s)
      加藤正隆・津賀雄輝・桑原 聖・金森功吏・湯浅英哉
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] Photosensitizers in Photodynamic Therapy2018

    • Author(s)
      Hideya Yuasa
    • Organizer
      The 2nd US-Japan-China Collaborative Workshop on Advanced Medical Technologies
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A small photosensitizer with a novel intersystem-crossing mechanism2018

    • Author(s)
      Hideya Yuasa
    • Organizer
      The 2nd Russia-Japan Joint Forum for Education and Research Program
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 光増感剤応用を指向した水溶性グルコシルピレン:分子内グリコシル化反応を利用した2-C-グルコシドおよびO-グルコシド2018

    • Author(s)
      金森功史・松山央・小倉俊一郎・岡崎茂俊・湯浅英哉
    • Organizer
      GlycoTOKYO2018シンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Development of a small photosensitizer for pPhotodynamic therapy using biphenyl derivatives with an intramolecular charge transfer character2018

    • Author(s)
      Yuki Tsuga, Shigetoshi Okazaki, Hiroyuki Ohtani, Hideya Yuasa
    • Organizer
      10th Asian Photochemistry Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Novel Photoactivatable Glycolipid Analogues Controlling the Immune Activity of iNKT Cells2018

    • Author(s)
      Tomoki Numata, Satoshi Kuwabara, Takashi Kanamori, Hiroshi Watarai, Yasuyuki Ishii, and Hideya Yuasa
    • Organizer
      6th International Conference on Chemical and Biological Sciences
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] グルコース修飾ピレン誘導体を用いた光増感剤の開発2018

    • Author(s)
      内藤秀則、尾迫佳樹、金森功吏、小倉俊一郎、湯浅英哉
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] GFP色素誘導体を用いた糖鎖受容体のturn-on型蛍光プローブの設計と合成2018

    • Author(s)
      稲田宏太郎・金森功吏・大窪章寛・小倉俊一郎・湯浅英哉
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ピレン誘導体を用いた無洗浄タンパク質ゲル染色剤2018

    • Author(s)
      森保 太貴・宮川 まどか・金森 功吏・林 宣宏・湯浅 英哉
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ラジカルイオン対機構を利用した光線力学治療用光増感剤と糖の複合体開発2017

    • Author(s)
      津賀雄輝・趙奕靖・金森功吏・小倉俊一郎・大谷弘之・湯浅英哉
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 5´および3´末端にアシル基を有する環状オリゴヌクレオチドの合成2017

    • Author(s)
      西澤周平・橋本律・金森功吏・湯浅英哉・大窪章寛
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] In silico screening and synthesis of carbohydrate-modified fluorescent probes for the detection of selectins2017

    • Author(s)
      KANAMORI, Takashi; KUWABARA, Satoshi; OGURA, Shunichiro
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Structure-photosensitizing property relationship of biphenyl derivatives2017

    • Author(s)
      ZHAO, Yijing; TSUGA, Yuki; KANAMORI, Takashi; YUASA, Hideya
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of water soluble C-glycosylated pyrene complexes by intramolecular C-glycosylation.2017

    • Author(s)
      MATSUYAMA, Akira; KANAMORI, Takashi; YUASA, Hideya
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of low molecular-weight photosensitizer by intramolecular charge transfer2017

    • Author(s)
      津賀雄輝、趙奕靖、金森功吏、小倉俊一郎、大谷弘之、湯浅英哉
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ピレンC-グリコシド誘導体の合成と光増感剤への応用2017

    • Author(s)
      金森功吏、松山央、内藤秀則、尾迫佳樹、小倉俊一郎、湯浅英哉
    • Organizer
      第11回バイオ関連化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 5’および3’末端にアシル基を有する環状オリゴヌクレオチドの合成と性質2017

    • Author(s)
      西澤周平、橋本律、三宅優、金森功吏、湯浅英哉、大窪章寛
    • Organizer
      第11回バイオ関連化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 2-アミノキノリン誘導体を含む三重鎖形成核酸の合成と性質2017

    • Author(s)
      大西達也、西村ゆり、金森功吏、湯浅英哉、大窪章寛
    • Organizer
      第11回バイオ関連化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光による生命機能の制御と治療への応用2017

    • Author(s)
      湯浅英哉
    • Organizer
      BioJapan2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 分子メス:刃先が鋭い光増感剤2017

    • Author(s)
      湯浅英哉
    • Organizer
      SPACC(先端錯体工学研究会)ミニシンポジウム
    • Place of Presentation
      東京工業大学 すずかけ台キャンパス 大学会館二階集会室1(神奈川県横浜市)
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Development of new photosensitizer using intramolecular charge transfer mechanism and application for photodynamic therapy targeting glucose transporter2016

    • Author(s)
      Yuki Tsuga, Zhao Yijing, Takashi Kanamori, Akihiro Ohkubo, Shun-ichiro Ogura, Hiroyuki Ohtani, Hideya Yuasa
    • Organizer
      第10回バイオ関連化学シンポジウム
    • Place of Presentation
      石川県立音楽堂(石川県金沢市)
    • Year and Date
      2016-09-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新しい光増感メカニズムと光線力学治療2016

    • Author(s)
      湯浅英哉
    • Organizer
      BioJapan2016
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Remarks] 湯浅・大窪研究室ホームページ

    • URL

      http://www.yuasa-lab.bio.titech.ac.jp/

    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] 光で免疫活性を制御できる糖脂質2019

    • Inventor(s)
      光で免疫活性を制御できる糖脂質
    • Industrial Property Rights Holder
      光で免疫活性を制御できる糖脂質
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report
  • [Patent(Industrial Property Rights)] 分子内電荷移動化合物を含む光線力学的治療剤2016

    • Inventor(s)
      湯浅英哉、津賀雄輝
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-102568
    • Filing Date
      2016-05-23
    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2022-01-27  

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