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2020 Fiscal Year Annual Research Report

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

Research Project

Project/Area Number 18K14341
Research InstitutionTokyo Institute of Technology

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
KeywordsAcrolein / Phenyl azide / Click reaction / Breast cancer / TAMRA / Intraoperative detection / Imaging / Cancer surgery
Outline of Annual Research Achievements

We developed the fluorescence-labeled aryl azide in the previous fiscal year, namely click-to-sense (CTS) probe, for acrolein detection in cancer cells. This method selectively labels the cellular contents of cancer cells within live tissues and visualizes their morphology. The CTS probe has been used in a clinical study as a highly selective and straightforward cancer screening method during breast cancer surgery. In the fiscal year 2021, we further enhanced azide's reactivity by developing the second generation of CTS probe. Moreover, we found that the addition of a metal catalyst could enhance the sensitivity of cancer diagnosis. The improved method could eliminate the false positive observation and realize rapid intraoperative diagnosis during breast-conserving surgery in the hospital.

  • Research Products

    (13 results)

All 2021 2020

All Journal Article (6 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (6 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Patent(Industrial Property Rights) (1 results)

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

    • Author(s)
      Pradipta Ambara R.、Ahmadi Peni、Terashima Kazuki、Muguruma Kyohei、Fujii Motoko、Ichino Tomoya、Maeda Satoshi、Tanaka Katsunori
    • Journal Title

      Chemical Science

      Volume: - Pages: -

    • DOI

      10.1039/D0SC06083F

    • 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 Ambara R.、Tanaka Katsunori
    • Journal Title

      The Chemical Record

      Volume: - Pages: 1-18

    • DOI

      10.1002/tcr.202000146

    • 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 Ivan、Sibgatullina Regina、Urano Sayaka、Tahara Tsuyoshi、Ahmadi Peni、Watanabe Yasuyoshi、Pradipta Ambara R.、Kurbangalieva Almira、Tanaka Katsunori
    • Journal Title

      Small

      Volume: 16 Pages: 2004831~2004831

    • DOI

      10.1002/smll.202004831

    • 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 Pages: 1160~1168

    • DOI

      10.1002/chir.23265

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Methods for Acrolein Detection: Recent Advances and Applications2020

    • Author(s)
      Pradipta Ambara R.、Tanaka Katsunori
    • Journal Title

      Journal of the Indonesian Chemical Society

      Volume: 3 Pages: 73~73

    • DOI

      10.34311/jics.2020.03.2.73

    • 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 Kyohei、Pradipta Ambara R.、Ode Yudai、Terashima Kazuki、Michiba Hiroyuki、Fujii Motoko、Tanaka Katsunori
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 28 Pages: 115831~115831

    • DOI

      10.1016/j.bmc.2020.115831

    • 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
  • [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
  • [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
  • [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
  • [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
  • [Presentation] Reactivity and Application of Acrolein Released from Cancer Cells2020

    • Author(s)
      A. R. Pradipta
    • Organizer
      The 6th International Symposium on Applied Chemistry
    • Int'l Joint Research / Invited
  • [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
    • Industrial Property Number
      PCT/JP2020/178209

URL: 

Published: 2021-12-27  

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