Updated on 2026/04/29

写真a

 
FUJIOKA HIROYOSHI
 
Organization
Institute of Integrated Research Laboratory for Chemistry and Life Science Assistant Professor
Title
Assistant Professor
External link

News & Topics

Research Interests

  • ラマンプローブ

  • 蛍光プローブ

Research Areas

  • Life Science / Bioorganic chemistry  / ケミカルバイオロジー

Education

  • The University of Tokyo   Graduate School of Pharmaceutical Sciences

    2021.4 - 2023.3

      More details

  • The University of Tokyo   Graduate School of Pharmaceutical Sciences

    2019.4 - 2021.3

      More details

  • The University of Tokyo   Faculty of Pharmaceutical Sciences   Department of Pharmaceutical Sciences

    2015.4 - 2019.3

      More details

  • 私立 甲陽学院高等学校

    2011.4 - 2014.3

      More details

  • Institute of Science Tokyo   Department of Life Science and Technology

    2024.10

      More details

  • Tokyo Institute of Technology   School of Life Science and Technology

    2023.4

      More details

▼display all

Research History

  • Institute of Science Tokyo   Institute of Integrated Research, Laboratory for Chemistry and Life Science   Assistant Professor

    2025.4

      More details

  • Institute of Science Tokyo   Department of Life Science and Technology   Assistant Professor

    2024.10

      More details

  • Tokyo Institute of Technology   School of Life Science and Technology   Assistant Professor

    2023.4

      More details

  • 日本学術振興会   特別研究員(DC1)

    2021.4 - 2023.3

      More details

Papers

  • Diversification of the 10th core atom of 9-cyanopyronins expands the resonance Raman vibrational palette

    Shun-suke Kanai, Hiroyoshi Fujioka, Minoru Kawatani, Spencer John Spratt, Shun-suke Fukuta, Zhihao Zhan, Yang Ma, Kazuhiro Kuruma, Daisuke Asanuma, Yuichi Asada, Masayasu Taki, Shigehiro Yamaguchi, Yasuyuki Ozeki, Mako Kamiya

    Communications Chemistry   2026.4

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s42004-026-02019-1

    researchmap

  • Functional Raman Probes for Detecting Enzyme Activities Based on Aggregation Control

    Momoko Okinaka, Minoru Kawatani, Hiroyoshi Fujioka, Spencer John Spratt, Hiroki Ito, Yoshihiro Misawa, Reika Otake, Aoi Ishikawa, Ryosuke Kojima, Yasuteru Urano, Yasuyuki Ozeki, Mako Kamiya

    Analytical Chemistry   2025.9

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.analchem.5c02231

    researchmap

  • Near-Infrared Coumarin-Hemicyanine Hybrid Dyes Bearing an Intramolecular Nucleophile for Activatable Fluorescence and Raman Imaging

    Hiroyoshi Fujioka, Ryo Sakamoto, Kotaro Hiramatsu, Yusuke Murakami, Minori Masaki, Minoru Kawatani, Satoshi Matsumoto, Ryosuke Kojima, Yasuteru Urano, Hideaki Kano, Mako Kamiya

    Analytical Chemistry   2025.8

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.analchem.5c02714

    researchmap

  • Photocatalytic and Chemoselective H/D Exchange at α-Thio C(sp3)-H Bonds

    Riku Ogasahara, Miyu Mae, Yuki Itabashi, Kei Ohkubo, Keisuke Matsuura, Hyoga Shimizu, Kazuho Ban, Masaki Togami, Taro Udagawa, Hiroyoshi Fujioka, Mako Kamiya, Shuji Akai, Yoshinari Sawama

    Journal of the American Chemical Society   2025.5

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.5c01894

    researchmap

  • Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide. International journal

    Riku Ogasahara, Miyu Mae, Keisuke Matsuura, Sota Yoshimura, Takayoshi Ishimoto, Taro Udagawa, Kazuo Harada, Hiroyoshi Fujioka, Mako Kamiya, Rio Asada, Hiromasa Uchiyama, Yuichi Tozuka, Shuji Akai, Yoshinari Sawama

    Chemistry (Weinheim an der Bergstrasse, Germany)   31 ( 14 )   e202404204   2025.3

     More details

    Language:English   Publishing type:Research paper (scientific journal)  

    Deuterated molecules are of growing interest because of the specific characteristics of deuterium, such as stronger C-D bonds being stronger than C-H bonds. Polyethylene glycols (PEGs) are widely utilized in scientific fields (e. g., drug discovery and material sciences) as linkers and for the improvement of various properties (solubility in water, stability, etc.) of mother compounds. Therefore, deuterated PEGs can be used as novel tools for drug discovery. Although the H/D exchange reaction (deuteration) is a powerful and straightforward method to produce deuterated compounds, the deuteration of PEGs bearing many unactivated C(sp3)-H bonds has not been developed. Herein, we report the photocatalytic deuteration of multiple sites of PEGs using tetra-n-butylammonium decatungstate (TBADT) and D2O as an inexpensive deuterium source. This deuteration can be adapted to PEG derivatives bearing various substituents ((hetero)aryl, benzoyl, alkyl, etc.). The deuteration efficiencies of the α-oxy C(sp3)-H bonds at the terminal positions of the PEGs were strongly influenced by the substituents. These reactivities were elucidated by density functional theory calculations of the reaction barriers towards the formation of radical intermediates, induced by the excited state of TBADT and the PEG substrate. In addition, the applicability of deuterated PEGs to internal standard experiments and Raman spectroscopy was demonstrated.

    DOI: 10.1002/chem.202404204

    PubMed

    researchmap

  • Cyano-Hydrol green derivatives: Expanding the 9-cyanopyronin-based resonance Raman vibrational palette

    Hiroyoshi Fujioka, Yuta Murao, Momoko Okinaka, Spencer John Spratt, Jingwen Shou, Minoru Kawatani, Ryosuke Kojima, Ryo Tachibana, Yasuteru Urano, Yasuyuki Ozeki, Mako Kamiya

    Bioorganic & Medicinal Chemistry Letters   2024.7

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.bmcl.2024.129757

    researchmap

  • Modular Design Platform for Activatable Fluorescence Probes Targeting Carboxypeptidases Based on ProTide Chemistry

    Yugo Kuriki, Mari Sogawa, Toru Komatsu, Minoru Kawatani, Hiroyoshi Fujioka, Kyohhei Fujita, Tasuku Ueno, Kenjiro Hanaoka, Ryosuke Kojima, Rumi Hino, Hiroki Ueo, Hiroaki Ueo, Mako Kamiya, Yasuteru Urano

    Journal of the American Chemical Society   2023.12

     More details

    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/jacs.3c10086

    researchmap

  • Impact of multiple H/D replacements on the physicochemical properties of flurbiprofen. International journal

    Hiromasa Uchiyama, Kazuho Ban, Shiho Nozaki, Yui Ikeda, Takayoshi Ishimoto, Hiroyoshi Fujioka, Mako Kamiya, Ryugo Amari, Hirofumi Tsujino, Masayoshi Arai, Sachi Yamazoe, Keiko Maekawa, Takuma Kato, Mitsunobu Doi, Kazunori Kadota, Yuichi Tozuka, Naohito Tomita, Hironao Sajiki, Shuji Akai, Yoshinari Sawama

    RSC medicinal chemistry   14 ( 12 )   2583 - 2592   2023.12

     More details

    Language:English   Publishing type:Research paper (scientific journal)  

    Although deuterium incorporation into pharmaceutical drugs is an attractive way to expand drug modalities, their physicochemical properties have not been sufficiently examined. This study focuses on examining the changes in physicochemical properties between flurbiprofen (FP) and flurbiprofen-d8 (FP-d8), which was successfully prepared by direct and multiple H/D exchange reactions at the eight aromatic C-H bonds of FP. Although the effect of deuterium incorporation was not observed between the crystal structures of FP and FP-d8, the melting point and heat of fusion of FP-d8 were lower than those of FP. Additionally, the solubility of FP-d8 increased by 2-fold compared to that of FP. Calculation of the interaction energy between FP/FP-d8 and water molecules using the multi-component density functional theory method resulted in increased solubility of FP-d8. These novel and valuable findings regarding the changes in physicochemical properties triggered by deuterium incorporation can contribute to the further development of deuterated drugs.

    DOI: 10.1039/d3md00357d

    PubMed

    researchmap

  • Super-resolution vibrational imaging based on photoswitchable Raman probe. International journal

    Jingwen Shou, Ayumi Komazawa, Yuusaku Wachi, Minoru Kawatani, Hiroyoshi Fujioka, Spencer John Spratt, Takaha Mizuguchi, Kenichi Oguchi, Hikaru Akaboshi, Fumiaki Obata, Ryo Tachibana, Shun Yasunaga, Yoshio Mita, Yoshihiro Misawa, Ryosuke Kojima, Yasuteru Urano, Mako Kamiya, Yasuyuki Ozeki

    Science advances   9 ( 24 )   eade9118   2023.6

     More details

    Language:English   Publishing type:Research paper (scientific journal)  

    Super-resolution vibrational microscopy is promising to increase the degree of multiplexing of nanometer-scale biological imaging because of the narrower spectral linewidth of molecular vibration compared to fluorescence. However, current techniques of super-resolution vibrational microscopy suffer from various limitations including the need for cell fixation, high power loading, or complicated detection schemes. Here, we present reversible saturable optical Raman transitions (RESORT) microscopy, which overcomes these limitations by using photoswitchable stimulated Raman scattering (SRS). We first describe a bright photoswitchable Raman probe (DAE620) and validate its signal activation and depletion characteristics when exposed to low-power (microwatt level) continuous-wave laser light. By harnessing the SRS signal depletion of DAE620 through a donut-shaped beam, we demonstrate super-resolution vibrational imaging of mammalian cells with excellent chemical specificity and spatial resolution beyond the optical diffraction limit. Our results indicate RESORT microscopy to be an effective tool with high potential for multiplexed super-resolution imaging of live cells.

    DOI: 10.1126/sciadv.ade9118

    PubMed

    researchmap

  • Activatable Raman Probes Utilizing Enzyme-Induced Aggregate Formation for Selective Ex Vivo Imaging. International journal

    Hiroyoshi Fujioka, Minoru Kawatani, Spencer John Spratt, Ayumi Komazawa, Yoshihiro Misawa, Jingwen Shou, Takaha Mizuguchi, Hina Kosakamoto, Ryosuke Kojima, Yasuteru Urano, Fumiaki Obata, Yasuyuki Ozeki, Mako Kamiya

    Journal of the American Chemical Society   2023.4

     More details

    Language:English   Publishing type:Research paper (scientific journal)  

    Detecting multiple enzyme activities simultaneously with high spatial specificity is a promising strategy to investigate complex biological phenomena, and Raman imaging would be an excellent tool for this purpose due to its high multiplexing capabilities. We previously developed activatable Raman probes based on 9CN-pyronins, but specific visualization of cells with target enzyme activities proved difficult due to leakage of the hydrolysis products from the target cells after activation. Here, focusing on rhodol bearing a nitrile group at the position of 9 (9CN-rhodol), we established a novel mechanism for Raman signal activation based on a combination of aggregate formation (to increase local dye concentration) and the resonant Raman effect along with the bathochromic shift of the absorption, and utilized it to develop Raman probes. We selected the 9CN-rhodol derivative 9CN-JCR as offering a suitable combination of increased stimulated Raman scattering (SRS) signal intensity and high aggregate-forming ability, resulting in good retention in target cells after probe activation. By using isotope-edited 9CN-JCR-based probes, we could simultaneously detect β-galactosidase, γ-glutamyl transpeptidase, and dipeptidyl peptidase-4 activities in live cultured cells and distinguish cell regions expressing target enzyme activity in Drosophila wing disc and fat body ex vivo.

    DOI: 10.1021/jacs.2c12381

    PubMed

    researchmap

  • Unprecedented Regioselective Deuterium‐Incorporation of Alkyltrimethylammonium Chlorides and Raman Analysis

    Yoshinari Sawama, Takumi Matsuda, Shogo Moriyama, Kazuho Ban, Hiroyoshi Fujioka, Mako Kamiya, Jingwen Shou, Yasuyuki Ozeki, Shuji Akai, Hironao Sajiki

    Asian Journal of Organic Chemistry   12 ( 3 )   2023.2

     More details

    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ajoc.202200710

    researchmap

    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.202200710

  • 9‐Cyano‐10‐telluriumpyronin Derivatives as Red‐light‐activatable Raman Probes

    Minoru Kawatani, Spencer J. Spratt, Hiroyoshi Fujioka, Jingwen Shou, Yoshihiro Misawa, Ryosuke Kojima, Yasuteru Urano, Yasuyuki Ozeki, Mako Kamiya

    Chemistry – An Asian Journal   2023.1

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/asia.202201086

    researchmap

  • Homemade Solution of NaOD in D 2 O: Applications in the Field of Stilbene‐ d 1 Synthesis

    Keisuke Imai, Naohito Tomita, Hiroyoshi Fujioka, Mako Kamiya, Riku Ogasahara, Kazuho Ban, Hyoga Shimizu, Takayoshi Ishimoto, Hironao Sajiki, Shuji Akai, Yoshinari Sawama

    Asian Journal of Organic Chemistry   12 ( 3 )   2023.1

     More details

    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ajoc.202200690

    researchmap

    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.202200690

  • Near-infrared imaging in fission yeast using a genetically encoded phycocyanobilin biosynthesis system

    Keiichiro Sakai, Yohei Kondo, Hiroyoshi Fujioka, Mako Kamiya, Kazuhiro Aoki, Yuhei Goto

    Journal of Cell Science   134 ( 24 )   2021.12

     More details

    Publishing type:Research paper (scientific journal)   Publisher:The Company of Biologists  

    DOI: 10.1242/jcs.259315

    researchmap

  • Multicolor Activatable Raman Probes for Simultaneous Detection of Plural Enzyme Activities

    Hiroyoshi Fujioka, Jingwen Shou, Ryosuke Kojima, Yasuteru Urano, Yasuyuki Ozeki, Mako Kamiya

    Journal of the American Chemical Society   142 ( 49 )   20701 - 20707   2020.12

     More details

    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    DOI: 10.1021/jacs.0c09200

    researchmap

  • Companion Diagnosis for Retinal Neuroprotective Treatment by Real-Time Imaging of Calpain Activation Using a Novel Fluorescent Probe

    Toshifumi Asano, Yuri Nagayo, Satoru Tsuda, Azusa Ito, Wataru Kobayashi, Kosuke Fujita, Kota Sato, Koji M. Nishiguchi, Hiroshi Kunikata, Hiroyoshi Fujioka, Mako Kamiya, Yasuteru Urano, Toru Nakazawa

    Bioconjugate Chemistry   31 ( 9 )   2241 - 2251   2020.9

     More details

    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.bioconjchem.0c00435

    Scopus

    PubMed

    researchmap

  • Activatable fluorescent probes for hydrolase enzymes based on coumarin–hemicyanine hybrid fluorophores with large Stokes shifts

    Hiroyoshi Fujioka, Shin-nosuke Uno, Mako Kamiya, Ryosuke Kojima, Kai Johnsson, Yasuteru Urano

    Chemical Communications   2020

     More details

    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D0CC00559B

    researchmap

  • Design of spontaneously blinking fluorophores for live-cell super-resolution imaging based on quantum-chemical calculations

    Ryo Tachibana, Mako Kamiya, Akihiko Morozumi, Yoshiyuki Miyazaki, Hiroyoshi Fujioka, Aika Nanjo, Ryosuke Kojima, Toru Komatsu, Tasuku Ueno, Kenjiro Hanaoka, Toshitada Yoshihara, Seiji Tobita, Yasuteru Urano

    Chemical Communications   2020

     More details

    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D0CC05126H

    researchmap

▼display all

Research Projects

  • GSH検出型ラマンプローブを用いた超多重生体機能解析

    Grant number:23K19240  2023.8 - 2025.3

    日本学術振興会  科学研究費助成事業  研究活動スタート支援

    藤岡 礼任

      More details

    Grant amount:\2860000 ( Direct Cost: \2200000 、 Indirect Cost:\660000 )

    本研究では、化合物の吸収特性に基づいて共鳴ラマン効果の有無によって検出感度が変化することを利用し、ローダミン色素とGSHの付加乖離反応によって引き起こされるダイナミックな吸収変化をラマン信号の変化に結び付けて検出を行う、新規GSH定量型ラマンプローブの開発を行う。この時、ラマン顕微法の多重検出能を利用すれば吸収蛍光特性の近い2つの色素を分離よく検出できる可能性があり、2波長を検出するために可視光の波長領域を占有してしまう従来のratio型蛍光プローブの課題を解決し、複数の蛍光プローブと併用可能なGSH定量ラマンプローブの開発を目指す。
    当該年度においては、合成した複数のローダミン色素のラマンピークが色素骨格の構造によって異なるスペクトルパターンを示すことを見出し、ラマンスペクトルで同時に検出可能なローダミン色素のペアを選定した。その後、選定した色素を用いて細胞内のGSH濃度をratiometricに定量するために、片方の色素は細胞内のGSH濃度に対して適切な応答性となるように、またもう片方の色素はGSHと非応答性となるように構造展開した。この時、GSH濃度依存的に吸収スペクトルを変化させるGSH応答性色素が、吸収スペクトルの変化に伴ってラマン信号も変化させることを確認した。さらに、これらの色素を適当なリンカーで結合することによってそれぞれの色素が細胞内で同一に局在するような設計でプローブを合成した。今後は開発したプローブの基本的な特性を取得しつつ、実際に細胞内でそのGSH濃度の変化をラマンイメージングで評価可能か検討を行っていく予定である。

    researchmap