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Development of Photofunctional Molecules Based on Flexible Controls of the Excited Multiplet States of Chromophore-Radical Systems

Research Project

Project/Area Number 16H04128
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional solid state chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

ISHII Kazuyuki  東京大学, 生産技術研究所, 教授 (20282022)

Co-Investigator(Kenkyū-buntansha) 榎本 恭子  東京大学, 生産技術研究所, 技術専門職員 (50772711)
Research Collaborator YOKOI Takanori  
KARASAWA Masanobu  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,940,000 (Direct Cost: ¥13,800,000、Indirect Cost: ¥4,140,000)
Fiscal Year 2018: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2017: ¥8,060,000 (Direct Cost: ¥6,200,000、Indirect Cost: ¥1,860,000)
Fiscal Year 2016: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywords色素 / ラジカル / 光励起多重項 / 光機能
Outline of Final Research Achievements

After a groundbreaking study demonstrated that a high dose of ascorbic acid selectively kills cancer cells, the compound has been tested in the clinic against various forms of cancers, with some success. However, in vivo tracing of intravenously injected ascorbic acid has not been achieved. In this study, we successfully imaged ascorbic acid intravenously injected into mice based on the discovery of a novel, highly sensitive, and appropriately selective fluorescent probe consisting of silicon phthalocyanine and two nitroxide radicals, i.e., R2c. The radicals in this R2c were encapsulated in dimeric bovine serum albumin, and the sensitivity was >100-fold higher than those of other R2c-based probes. Ascorbic acid intravenously injected into mice was efficiently transported to the liver, heart, lung, and cholecyst. The present results provide opportunities to advance the use of ascorbic acid as cancer therapy.

Academic Significance and Societal Importance of the Research Achievements

本研究成果により、投与されたビタミンCが活性な状態でどの臓器に輸送されるかを知ることができるようになるため、高濃度ビタミンC療法への有用な知見が期待できるとともに、アルブミン二量体との複合化法は、蛍光プローブ開発における新たな分子設計指針として有用と考えられる。
本研究成果は、Scientific Reports誌に論文が掲載(2018, 8, 1560)され、日本経済新聞、日経産業新聞、海外web記事等に紹介された。社会的Impact FactorであるAltmericは93となり、本誌Top 10 in Biochemistry and Molecular Biologyにも選出された。

Report

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

    (56 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (18 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 13 results,  Open Access: 4 results,  Acknowledgement Compliant: 1 results) Presentation (33 results) (of which Int'l Joint Research: 6 results,  Invited: 7 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 2 results)

  • [Int'l Joint Research] ルーヴェンカトリック大学(ベルギー)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] KU Leuven(Belgium)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Encapsulation of zinc phthalocyanine into bovine serum albumin aggregates2019

    • Author(s)
      Takanori Yokoi, Shingo Hattori, Kazuyuki Ishii
    • Journal Title

      J. Coord. Chem.

      Volume: 72 Issue: 4 Pages: 707-715

    • DOI

      10.1080/00958972.2019.1566538

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Power Spring: Circular Dichroism Inversion of Polythiophene Aggregates from the Right-Handed Helix to Left-Handed Helix2019

    • Author(s)
      Shingo Hattori, Stefaan Vandendriessche, Toshiyuki Hirano, Fumitoshi Sato, Guy Koeckelberghs, Thierry Verbiest, Kazuyuki Ishii
    • Journal Title

      J. Phys. Chem. B

      Volume: 123 Issue: 13 Pages: 2925-2929

    • DOI

      10.1021/acs.jpcb.8b11832

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] フタロシアニンの新規光機能開拓2019

    • Author(s)
      石井和之
    • Journal Title

      化学工業

      Volume: 70 Pages: 59-64

    • Related Report
      2018 Annual Research Report
  • [Journal Article] フタロシアニンとヒト血清アルブミンの複合化2019

    • Author(s)
      服部伸吾, 村田康輔, 石井和之
    • Journal Title

      生産研究

      Volume: 71

    • NAID

      130007685294

    • Related Report
      2018 Annual Research Report
    • Open Access
  • [Journal Article] フタロシアニンを用いたビタミンC検出用蛍光プローブの開発2019

    • Author(s)
      横井孝紀, 石井和之
    • Journal Title

      生産研究

      Volume: 71

    • NAID

      130007685295

    • Related Report
      2018 Annual Research Report
    • Open Access
  • [Journal Article] Dependence of phthalocyanine-based fluorescence on albumin structure: A fluorescent probe for ascorbic acid2018

    • Author(s)
      Takanori Yokoi, Kazuyuki Ishii
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 364 Pages: 1-5

    • DOI

      10.1016/j.jphotochem.2018.05.036

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transient absorption studies on photothermal energy transfer and heat dissipation:Phthalocyanine-based thin films on Bi, Al-substituted DyIG substrates2018

    • Author(s)
      Masanobu Karasawa, Kazuyuki Ishii
    • Journal Title

      Chem. Phys. Lett.

      Volume: 704 Pages: 1-4

    • DOI

      10.1016/j.cplett.2018.05.031

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 体内のビタミンCを検出する技術2018

    • Author(s)
      石井和之
    • Journal Title

      PHARM STAGE

      Volume: 18 Pages: 41-44

    • NAID

      40021573556

    • Related Report
      2018 Annual Research Report
  • [Journal Article] 濃縮速度に基づく超分子キラリティ選択2018

    • Author(s)
      服部伸吾, 石井和之
    • Journal Title

      光化学協会誌

      Volume: 49 Pages: 24-27

    • NAID

      40021561401

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Pulsed laser induced heat transfer from phthalocyanine-based thin film to a Bi, Al-substituted DyIG substrate: photothermal demagnetization observed by magnetic circular dichroism and numerical analysis2018

    • Author(s)
      M. Karasawa, K. Ishii
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 未定 Issue: 17 Pages: 12241-12247

    • DOI

      10.1039/c8cp01789a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In vivo fluorescence bioimaging of ascorbic acid in mice: Development of an efficient probe consisting of phthalocyanine, TEMPO, and albumin2018

    • Author(s)
      T. Yokoi, T. Otani, K. Ishii
    • Journal Title

      Scientific Reports

      Volume: 8 Issue: 1 Pages: 1560-1560

    • DOI

      10.1038/s41598-018-19762-8

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Photoelectrochemical oxygen reduction reactions using phthalocyanine-based thin films on an ITO electrode2018

    • Author(s)
      N. T. Hong Trang, K. Ishii
    • Journal Title

      J. Phys. Chem. C

      Volume: 122 Issue: 6 Pages: 3539-3547

    • DOI

      10.1021/acs.jpcc.7b10201

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Near infra-red S0⇔T1 transitions of iridium(III) phthalocyanine: Degeneracy of the T1 state evidenced by magnetic circular dichroism2017

    • Author(s)
      K. Murata, K. Ishii
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 44 Issue: 44 Pages: 5103-5107

    • DOI

      10.1002/ejic.201700668

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Magneto-chiral dichroism measurements using a pulsed electromagnet2017

    • Author(s)
      S. Hattori, Y. Yamamoto, T. Miyatake, *K. Ishii
    • Journal Title

      Chem. Phys. Lett.

      Volume: 674 Pages: 38-41

    • DOI

      10.1016/j.cplett.2017.02.033

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Evaporation Rate-Based Selection of Supramolecular Chirality2017

    • Author(s)
      S. Hattori, S. Vandendriessche, G. Koeckelberghs, *T. Verbiest, *K. Ishii
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 21 Pages: 3066-3069

    • DOI

      10.1039/c6cc09842h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Catalytic Transformation of Dinitrogen into Ammonia and Hydrazine by Iron-Dinitrogen Complexes Bearing Pincer Ligand2016

    • Author(s)
      S. Kuriyama, K. Arashiba, K. Nakajima, Y. Matsuo, H. Tanaka, K. Ishii, K. Yoshizawa, Y. Nishibayashi
    • Journal Title

      Nature Communications

      Volume: 7 Issue: 1 Pages: 12181-12181

    • DOI

      10.1038/ncomms12181

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Magnetic Hysteresis of Molecular Faraday Effects of Phthalocyanine-Based Thin Films on Bi, Al-Substituted DyIG Substrates at Room Temperature and Demagnetization of the Ferrimagnetic Substrates by Photothermal Effects of Phthalocyanines2016

    • Author(s)
      M. Karasawa, *K. Ishii
    • Journal Title

      J. Phys. Chem. C

      Volume: 120 Issue: 38 Pages: 21811-21817

    • DOI

      10.1021/acs.jpcc.6b07316

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Determination of the Absolute Configuration of Side Chains of Basic Amino Acid Residues Using the Water-Soluble Porphyrin-Based Exciton Chirality Method2016

    • Author(s)
      S. Hattori, K. Akagawa, K. Kudo, *K. Ishii
    • Journal Title

      J. Phys. Chem. B

      Volume: 120 Issue: 39 Pages: 10280-10287

    • DOI

      10.1021/acs.jpcb.6b07925

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] Photofunctions of Phthalocyanine Complexes2018

    • Author(s)
      Kazuyuki Ishii
    • Organizer
      233rd ECS Meeting
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Soft Crystals with Superior Physical Properties & Functions2018

    • Author(s)
      Kazuyuki Ishii
    • Organizer
      The 1st International Symposium on Soft Crystals
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photochemistry of Porphyrins Based on Orbital and Spin Angular Momenta2018

    • Author(s)
      Kazuyuki Ishii
    • Organizer
      10th Asian Photochemistry Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chirality Induced by Aggregation of Aromatic Compounds2018

    • Author(s)
      Kazuyuki Ishii
    • Organizer
      SOLVAY WORKSHOP Chiral Symmetry Breaking at Molecular Level
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Magneto-Optical Effects of Phthalocyanine Complexes2018

    • Author(s)
      Kazuyuki Ishii, Kazutaka Ozawa, Masanobu Karasawa, Kei Murata
    • Organizer
      43rd International Conference on Coordination Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機金属フタロシアニンの赤色光励起によるホルムアルデヒド生成2018

    • Author(s)
      齊部佑紀、村田慧、石井和之
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラル会合体薄膜を前駆体としたフタロシアニンのキラル寡量化2017

    • Author(s)
      黒羽みずき, 石井和之
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス、横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 疎水性フタロシアニンを用いたアルブミン寡量体の合成2017

    • Author(s)
      村田康輔, 石井和之
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス、横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] カーボンナノチューブ修飾電極を用いた電気化学的小分子活性化2017

    • Author(s)
      田中隼人, 石井和之
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス、横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 光で操る分子の機能2017

    • Author(s)
      石井和之
    • Organizer
      第7回光電子融合ワークショップ
    • Place of Presentation
      東京大学生産技術研究所、東京
    • Year and Date
      2017-02-13
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Fluorescence bioimaging of ascorbic acid intravenously injected into mice: Silicon phthalocyanine covalently linked to TEMPO radicals2017

    • Author(s)
      K. Ishii, T. Yokoi
    • Organizer
      22nd International Symposium on Photochemistry and Photophysics of Coordination Compounds (ISPPCC 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Novel rhenium phthalocyanine complexes CO release by red light-irradiation2017

    • Author(s)
      K. Murata, Y, Koike, K. Ishii
    • Organizer
      22nd International Symposium on Photochemistry and Photophysics of Coordination Compounds (ISPPCC 2017)
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポルフィリン類縁体とアルブミンの複合化2017

    • Author(s)
      村田康輔、石井和之
    • Organizer
      錯体化学会第67回討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 電子吸収スペクトルによるアルブミンと複合化したフタロシアニン会合体の解析2017

    • Author(s)
      村田康輔、石井和之
    • Organizer
      第29回配位化合物の光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ir(III)フタロシアニン錯体の磁気円偏光二色性による励起三重項状態の観測2017

    • Author(s)
      村田慧、石井和之
    • Organizer
      第56回電子スピンサイエンス学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光機能性レニウムフタロシアニン錯体の合成と性質2017

    • Author(s)
      村田慧、小池洋輔、石井和之
    • Organizer
      第8回光電子融合ワークショップ
    • Related Report
      2017 Annual Research Report
  • [Presentation] Near Infra-Red S0⇔T1 Transitions of Ir(III) Phthalocyanine: Degeneracy of the T1 State Evidenced by MCD2017

    • Author(s)
      村田慧、石井和之
    • Organizer
      錯体化学会第67回討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] レニウムフタロシアニン錯体による光CO放出反応2017

    • Author(s)
      村田慧、小池洋輔、石井和之
    • Organizer
      東京大学生産技術研究所光電子融合研究センター公開シンポジウム~光量子技術の新たな展開~
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリチオフェンキラル会合体の光物性2016

    • Author(s)
      服部伸吾,S. VANDENDRIESSCHE, G. KOECKELBERGHS,T. VERBIEST,石井和之
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場Iキャンパス、東京東京
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] Demagnetization of Bi, Al-substituted DyIG substrates by photothermal effects of phthalocyanines2016

    • Author(s)
      M. Karasawa,K. Ishii
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場Iキャンパス、東京東京
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] Fluorescence bioimaging of ascorbic acid in mice: Development of a phthalocyanine-based fluorescence probe encapsulated into serum albumin2016

    • Author(s)
      T. Yokoi, K. Ishii
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場Iキャンパス、東京東京
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] 液晶性分子中におけるフタロシアニン錯体のサーモクロミック特性2016

    • Author(s)
      石田虎太郎,石井和之
    • Organizer
      第28回 配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] ネオジムポルフィリン錯体の励起状態ダイナミクス2016

    • Author(s)
      山下雄己,石井和之
    • Organizer
      第28回 配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] レニウムフタロシアニンの合成と光化学反応2016

    • Author(s)
      小池洋輔,石井和之
    • Organizer
      第28回 配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] フタロシアニン薄膜の光照射による無機磁性基板の消磁2016

    • Author(s)
      唐澤正信,石井和之
    • Organizer
      第28回配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] 亜鉛フタロシアニン色素を用いた血清アルブミンの会合の誘起2016

    • Author(s)
      横井孝紀,石井和之
    • Organizer
      第28回配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] 水溶性ポルフィリンを用いた 超分子励起子キラリティー法の開発:ペプチド側鎖絶対配置の決定2016

    • Author(s)
      服部伸吾,赤川賢吾,工藤一秋,石井和之
    • Organizer
      第28回配位化合物の光化学討論会
    • Place of Presentation
      京都工芸繊維大学、京都
    • Year and Date
      2016-08-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] フタロシアニンの会合挙動制御を利用したサーモクロミック材料2016

    • Author(s)
      石田虎太郎,石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] ネオジムポルフィリン錯体の二重発光特性2016

    • Author(s)
      山下雄己,石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] 励起子キラリティーを用いたペプチドの円偏光二色性解析2016

    • Author(s)
      服部伸吾,赤川賢吾,工藤一秋,石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] フタロシアニン薄膜の磁気光学効果を利用した新規光磁気記録の提案2016

    • Author(s)
      唐澤正信,石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] フタロシアニン誘導体を用いたビタミンC検出用蛍光プローブの開発2016

    • Author(s)
      横井孝紀,石井和之
    • Organizer
      光電子融合研究センター公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] 分子を用いた光機能材料開発2016

    • Author(s)
      石井和之
    • Organizer
      光電子融合研究センター 公開シンポジウム~光電子融合と先端材料~
    • Place of Presentation
      東京大学先端科学技術研究センター、東京
    • Year and Date
      2016-04-21
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Patent(Industrial Property Rights)] 階層構造を利用した流水圧損低減型吸着システム2018

    • Inventor(s)
      石井和之、榎本恭子
    • Industrial Property Rights Holder
      東京大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 放射性物質吸着フィルタ及び放射性物質吸着装置2017

    • Inventor(s)
      高木和夫、石井和之
    • Industrial Property Rights Holder
      東京大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017
    • Acquisition Date
      2019
    • Related Report
      2018 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 温度応答性色材2017

    • Inventor(s)
      石井和之,石田虎太郎
    • Industrial Property Rights Holder
      東京大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017-02-06
    • Related Report
      2016 Annual Research Report

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

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