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In vivo Click Reaction of Acrolein: Application to In vivo Synthetic Chemistry and Cancer Imaging

Research Project

Project/Area Number 18K14341
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 37010:Bio-related chemistry
Research InstitutionTokyo Institute of Technology (2020)
Institute of Physical and Chemical Research (2018-2019)

Principal Investigator

PRADIPTA AMBARA  東京工業大学, 物質理工学院, 助教 (90631648)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywordsアクロレイン / アリールアジド / 乳がん / 1,3-双極子環化付加 / Acrolein / Phenyl azide / Click reaction / Breast cancer / TAMRA / Intraoperative detection / Imaging / Cancer surgery / Diazo / Cancer / Drug release / がん / クリックケミストリー / イメージング
Outline of Final Research Achievements

A rapid and accurate intraoperative method to diagnose the presence of breast cancer on the edge of the surgically resected tissues, is highly required. However, the current histological analysis method for determining surgical margins is time-consuming. Other groups have also reported a chemistry-based fluorescent probe that can be activated in cancer lesions. However, most of the methods rely on the time-dependent increase of fluorescence, making it difficult to use in breast-conserving surgery.
Herein, we utilized the azide-acrolein reaction-based method to discriminate breast cancer lesion from the normal breast gland. This method is the first example of an organic synthetic chemistry-based approach that can be used not only to visualize the cancer tissue but also to distinguish morphology of the resected tissue only within a few minutes. The ability to perform chemical reactions with cancer metabolites only at the desired cancer site is highly advantageous for cancer therapy.

Academic Significance and Societal Importance of the Research Achievements

Our method has the potential to become a highly selective margin management method for live tissues. It could be used as a low-cost, and easy-to-perform method for cancer sensing during surgery. The clinical significance of our probe deserves further investigation in hospitals worldwide.

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (38 results)

All 2021 2020 2019 2018

All Journal Article (16 results) (of which Int'l Joint Research: 16 results,  Peer Reviewed: 16 results,  Open Access: 9 results) Presentation (20 results) (of which Int'l Joint Research: 4 results,  Invited: 1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Targeted 1,3-dipolar cycloaddition with acrolein for cancer prodrug activation2021

    • Author(s)
      Pradipta, A. R., Ahmadi, P., Terashima, K., Muguruma, K., Fujii, M., Ichino, T., Maeda, S., Tanaka, K.
    • Journal Title

      Chem. Sci.

      Volume: - Issue: 15 Pages: 5438-5449

    • DOI

      10.1039/d0sc06083f

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Application of acrolein imines to organic synthesis, biofunctional studies, and clinical practice2021

    • Author(s)
      Pradipta, A. R., Tanaka, K.
    • Journal Title

      Chem. Rec.

      Volume: 21 Issue: 4 Pages: 646-662

    • DOI

      10.1002/tcr.202000146

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A strategy for tumor targeting by higher-order glycan pattern recognition: Synthesis and in vitro and in vivo properties of glycoalbumins conjugated with four different N-glycan molecules2020

    • Author(s)
      Smirnov, I., Sibgatullina, R., Urano, S., Tahara, T., Ahmadi, P., Watanabe, Y., Pradipta, A. R., Kurbangalieva, A., Tanaka, K.
    • Journal Title

      Small

      Volume: 16 Issue: 46 Pages: 2004831-2004831

    • DOI

      10.1002/smll.202004831

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Enantioselective synthesis of cyclic and linear diamines by imine cycloadditions2020

    • Author(s)
      Chang Tsung‐Che、Pradipta Ambara R.、Tanaka Katsunori
    • Journal Title

      Chirality

      Volume: 32 Issue: 9 Pages: 1160-1168

    • DOI

      10.1002/chir.23265

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Methods for acrolein detection: Recent advances and applications2020

    • Author(s)
      Pradipta, A. R., Tanaka, K.
    • Journal Title

      J. Idn. Chem. Soc.

      Volume: 3 Issue: 2 Pages: 73-80

    • DOI

      10.34311/jics.2020.03.2.73

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Disease-associated acrolein: A possible diagnostic and therapeutic substrate for in vivo synthetic chemistry2020

    • Author(s)
      Muguruma, K., Pradipta, A. R., Ode, Y., Terashima, K., Michiba, H., Fujii, M., Tanaka, K.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 28 Issue: 24 Pages: 115831-115831

    • DOI

      10.1016/j.bmc.2020.115831

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stereochemical features of the crystallization of eight-membered 1,5-diazaheterocycles with chiral aminoindanol fragments at nitrogen atoms2020

    • Author(s)
      O. A. Lodochnikova, D. R. Chulakova, D. P. Gerasimova, I. A. Litvinov, A. R. Pradipta, K. Tanaka, A. R. Kurbangalieva
    • Journal Title

      J. Struct. Chem.

      Volume: 61 Issue: 1 Pages: 125-131

    • DOI

      10.26902/jsc_id49649

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Emerging Technologies for Real‐Time Intraoperative Margin Assessment in Future Breast‐Conserving Surgery.2020

    • Author(s)
      Pradipta AR, Tanei T, Morimoto K, Shimazu K, Noguchi S, Tanaka K.
    • Journal Title

      Advanced Science (Weinh)

      Volume: 10.1002 Issue: 9 Pages: 201901519-201901519

    • DOI

      10.1002/advs.201901519

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Tetramethylrhodamine is an essential scaffold of azide probe in detecting cellular acrolein2019

    • Author(s)
      Pradipta AR, Fujii M, Tanei T, Morimoto K, Shimazu K, Noguchi S, Tanaka K.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: - Issue: 11 Pages: 2228-2234

    • DOI

      10.1016/j.bmc.2019.04.026

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Facile Access to Optically Active 2,6‐Dialkyl‐1,5‐Diazacyclooctanes2019

    • Author(s)
      Chulakova Dilyara R.、Pradipta Ambara R.、Lodochnikova Olga A.、Kuznetsov Danil R.、Bulygina Kseniya S.、Smirnov Ivan S.、Usachev Konstantin S.、Latypova Liliya Z.、Kurbangalieva Almira R.、Tanaka Katsunori
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 14 Issue: 22 Pages: 4048-4054

    • DOI

      10.1002/asia.201900938

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Poster Abstracts I2019

    • Author(s)
      Tomonori Tanei, Ambara R. Pradipta, Koji Morimoto, Motoko Fujii, Jun-ichiro Ikeda, Eiichi Morii, Shinzaburo Noguchi, Koichi Tanaka,
    • Journal Title

      The Breast

      Volume: 44 Pages: S15-S78

    • DOI

      10.1016/s0960-9776(19)30046-3

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Expanding the applicability of metal-labeling of biomolecules by RIKEN click reaction: A case study with 68Ga-PET2018

    • Author(s)
      Y. Nakamoto, A. R. Pradipta, H. Mukai, M. Zouda, Y. Watanabe, A. Kurbangalieva, P. Ahmadi, Y. Manabe, K. Fukase, K. Tanaka
    • Journal Title

      ChemBioChem.

      Volume: 19 Issue: 19 Pages: 2055-2060

    • DOI

      10.1002/cbic.201800335

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] In vitro and in vivo cancer cell apoptosis triggered by competitive binding of Cinchona alkaloids to the RING domain of TRAF62018

    • Author(s)
      Y. Qi, X. Zhao, J. Chen, A. R. Pradipta, J. Wei, H. Ruan, R. P. Hsung, K. Tanaka, L. Zhou
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: - Issue: 6 Pages: 1-16

    • DOI

      10.1080/09168451.2018.1559030

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Cascade Reaction in Human Live Tissue Allows Clinically Applicable Diagnosis of Breast Cancer Morphology2018

    • Author(s)
      Tanei Tomonori、Pradipta Ambara R.、Morimoto Koji、Fujii Motoko、Arata Mayumi、Ito Akihiro、Yoshida Minoru、Saigitbatalova Elena、Kurbangalieva Almira、Ikeda Jun-ichiro、Morii Eiichi、Noguchi Shinzaburo、Tanaka Katsunori
    • Journal Title

      Advanced Science

      Volume: 6 Issue: 2 Pages: 1801479-1801479

    • DOI

      10.1002/advs.201801479

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Cycloaddition reactions of N-alkyl-α,β-unsaturated imines: Facile preparation of azaheterocycles for synthesis and biological applications2018

    • Author(s)
      A. R. Pradipta, L. Latypova, D. Chulakova, I. Smirnov, A. Kurbangalieva, K. Tanaka
    • Journal Title

      Heterocycles

      Volume: 97 Issue: 2 Pages: 668-685

    • DOI

      10.3987/rev-18-sr(t)4

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Poster Abstract2018

    • Author(s)
      Ambara R. Pradipta, Elena Saigitbatalova, Almira Kurbangalieva, Katsunori Tanaka
    • Journal Title

      European Journal of Clinical Investigation

      Volume: 48 Issue: S1 Pages: 219-219

    • DOI

      10.1111/eci.12926

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Reactivity of Endogenous Acrolein: Application for Therapy and Diagnosis2021

    • Author(s)
      A. R. Pradipta
    • Organizer
      新学術領域「ケモユビキチン 」第4回総括班会議
    • Related Report
      2020 Annual Research Report
  • [Presentation] Reactivity of Acrolein Released from Cancer Cells: Application for Selective Cancer Therapy and Diagnosis2021

    • Author(s)
      A. R. Pradipta, P. Ahmadi, K. Tanaka
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Acrolein Sensor for Rapid and Accurate Intraoperative Diagnosis of Breast Cancer Morphology2020

    • Author(s)
      A. R. Pradipta, K. Tanaka
    • Organizer
      The 22nd Interdisciplinary Exchange Evening
    • Related Report
      2020 Annual Research Report
  • [Presentation] がんが普遍的に過剰生産するアクロレイン代謝物:ヒト生組織でのカスケード反応による乳がん術中迅速診断の臨床成果2020

    • Author(s)
      A. R. Pradipta, T. Tanei, K. Morimoto, K. Shimazu, S. Noguchi, K. Tanaka
    • Organizer
      第62回天然有機化合物討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Reactivity of Acrolein Released from Cancer Cells: Application for Selective Cancer Therapy2020

    • Author(s)
      A. R. Pradipta, K. Tanaka
    • Organizer
      Chemical Probe 第3回合同合宿セミナー
    • Related Report
      2020 Annual Research Report
  • [Presentation] Reactivity and Application of Acrolein Released from Cancer Cells2020

    • Author(s)
      A. R. Pradipta
    • Organizer
      The 6th International Symposium on Applied Chemistry
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Acrolein Click Chemistry-Mediated Cancer Diagnosis2020

    • Author(s)
      A. R. Pradipta
    • Organizer
      令和元年度 基礎科学特別研究員成果発表会
    • Related Report
      2019 Research-status Report
  • [Presentation] Synthetic Chemistry for Clinical Trials: Azide-Acrolein Click Reaction for Intraoperative Diagnosis of Breast Cancer Patients2019

    • Author(s)
      A. R. Pradipta, M. Fujii, K. Tanaka
    • Organizer
      RIKEN-Max Planck Joint Research Center for Systems Chemical Biology the Seventh Symposium
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Acrolein Sensor for Rapid Intraoperative Diagnosis of Breast Cancer2019

    • Author(s)
      A. R. Pradipta, K. Tanaka
    • Organizer
      Chemical Probe 第2回合同合宿セミナー
    • Related Report
      2019 Research-status Report
  • [Presentation] 新規 UbTACs のためのリガンド化合物探索とキメラ化法開発2019

    • Author(s)
      A. R. Pradipta
    • Organizer
      新学術領域「ケモユビキチン 」第3回総括班会議
    • Related Report
      2019 Research-status Report
  • [Presentation] Reactivity of Acrolein Released from Cancer Cells: Application for Selective Cancer Therapy2019

    • Author(s)
      A. R. Pradipta, P. Ahmadi, M. Fujii, K. Tanaka
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 実臨床合成化学:乳癌の術中断端迅速診断2019

    • Author(s)
      Ambara R. Pradipta, Tomonori Tanei, Motoko Fujii, Koji Morimoto, Shinzaburo Noguchi, Katsunori Tanaka
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 実臨床合成化学:乳癌の術中断端迅速診断2019

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      第1回新学術「ケモユビキチン」班会議・第2回ユビキチン研究会
    • Related Report
      2018 Research-status Report
  • [Presentation] 弥生キャンパス. A. R. Pradipta, K. Tanaka, Synthetic Chemistry for Clinical Trials: Azide-Acrolein Click Reaction for Intraoperative Diagnosis of Breast Cancer Patients2018

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Clinical Organic Synthesis: Rapid Intraoperative Diagnosis of Breast Cancer2018

    • Author(s)
      Ambara R. Pradipta, Motoko Fujii, Katsunori Tanaka
    • Organizer
      日本化学会新領域研究グループ「有機合成化学を起点とするものづくり戦略」最終研究成果発表シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] 実臨床合成化学:乳癌の術中断端迅速診断2018

    • Author(s)
      Ambara R. Pradipta, Tomonori Tanei, Motoko Fujii, Koji Morimoto, Shinzaburo Noguchi, Katsunori Tanaka
    • Organizer
      第12回バイオ関連化学シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] Acrolein Sensor for Rapid Intraoperative Diagnosis of Breast Cancer2018

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      The All-RIKEN Workshop 2018
    • Related Report
      2018 Research-status Report
  • [Presentation] Acrolein Click Chemistry-Mediated Cancer Imaging and Treatment2018

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      GlycoTOKYO2018シンポジウム (東京糖鎖研究会)
    • Related Report
      2018 Research-status Report
  • [Presentation] Acrolein Click Chemistry-Mediated Cancer Imaging and Treatment2018

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      ケミカルプローブ合同合宿セミナー
    • Related Report
      2018 Research-status Report
  • [Presentation] Acrolein Click Chemistry-Mediated Cancer Imaging and Treatment2018

    • Author(s)
      Ambara R. Pradipta, Katsunori Tanaka
    • Organizer
      The 54th International Conference on Medicinal Chemistry: Interfacing Chemical Biology and Drug Discovery
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Patent(Industrial Property Rights)] HARAKENZO2020

    • Inventor(s)
      A. R. Pradipta, K. Tanaka
    • Industrial Property Rights Holder
      A. R. Pradipta, K. Tanaka
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Acquisition Date
      2020
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] 国立研究開発法人理化学研究所2018

    • Inventor(s)
      田中克典, Ambara R. Pradipta
    • Industrial Property Rights Holder
      田中克典, Ambara R. Pradipta
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Acquisition Date
      2018
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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