Takao, Kenichi

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry (Yagami)

Position

Professor

Related Websites

External Links
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Career 【 Display / hide 】

  • 1995.04
    -
    1996.03

    Research Chemist in Sagami Chemical Research Center

  • 1996.04
    -
    1998.03

    Instructor in Faculty of Pharmaceutical Sciences, Science University of Tokyo

  • 1998.04
    -
    2001.03

    Instructor in Faculty of Science and Technology, Keio University

  • 2001.04
    -
    2008.03

    Assistant Professor in Faculty of Science and Technology, Keio University

  • 2005.08
    -
    2006.07

    Research Associate, Scripps Florida, USA

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Academic Background 【 Display / hide 】

  • 1990.03

    Keio University, Faculty of Science and Technology, 応用化学科

    University, Graduated

  • 1992.03

    Keio University, Graduate School, Division of Science and Technology, 応用化学専攻

    Graduate School, Completed, Master's course

  • 1995.03

    Keio University, Graduate School, Division of Science and Technology, 応用化学専攻

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • Ph.D., Keio University, Coursework, 1995.03

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Organic Chemistry)

  • Nanotechnology/Materials / Synthetic organic chemistry (Synthetic Chemistry)

  • Life Science / Bioorganic chemistry (Organic Chemistry)

  • Life Science / Pharmaceutical chemistry and drug development sciences (Chemical Pharmaceutics)

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Books 【 Display / hide 】

  • 有機合成実験法ハンドブック　第２版

    高尾 賢一, 丸善出版, 2015.11

    Scope: 15.2.1　ヒドロキシ基の保護と脱保護

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Ken-ichi Takao and Kin-ichi Tadano, Elsevier: Amsterdam, 2013.04

    Scope: 161-187

  • ベーシックマスター有機化学

    高尾 賢一, オーム社, 2011.11

    Scope: 第14章　有機合成化学

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Yoshikazu Suzuki, Ken-ichi Takao, and Kin-ichi Tadano, Elsevier: Amsterdam, 2003.12

    Scope: 127-167

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Ken-ichi Takao, Jun Ishihara, Kin-ichi Tadano, Elsevier: Amsterdam, 2000.12

    Scope: 3-51

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Papers 【 Display / hide 】

  • Antiproliferative activities through accelerating autophagic flux by basidalin and its analogs in human cancer cells

    Matagawa T., Sasazawa Y., Agui K., Fujimaki M., Kawano S., Ogura A., Takao K.i., Igarashi M., Simizu S.

    Bioorganic and Medicinal Chemistry Letters (Bioorganic and Medicinal Chemistry Letters)  104 2024.05

    ISSN  0960894X

    　View Summary

    Basidalin, isolated from the basidiomycete Leucoagaricus naucina, has previously demonstrated antibacterial and antitumor properties against murine cancer cells in vivo, but its effects on human cancer cells remain unknown. In this study, we found that basidalin possesses antiproliferative activity against human cancer cell lines. To elucidate the antiproliferative mechanism of basidalin, we focused on autophagy. Treatment with basidalin led to an increase in LC3-II expression level, and accelerated autophagic flux through an mTOR-independent pathway. Moreover, according to the structure–activity relationship analysis—including newly synthesized basidalin analogs—the formyl group, not the amino group, contributes to the antiproliferative activities of basidalin against human cancer cells. Additionally, the antiproliferative activity of basidalin analogs was strongly correlated with autophagy-inducing activity, indicating that basidalin exhibits antiproliferative activity through autophagy induction. These data suggest that basidalin, characterized by its ability to upregulate autophagic flux, emerges as a novel anticancer drug.

  • Open system massive synthesis of narrow-band blue and green fluorescent graphene quantum dots and their application in water sensing

    Ochi Y., Otani A., Katakami R., Ogura A., Takao K.I., Iso Y., Isobe T.

    Journal of Materials Chemistry C (Journal of Materials Chemistry C)  12 ( 18 ) 6548 - 6558 2024.04

    ISSN  20507526

    　View Summary

    Graphene quantum dots (GQDs) are environmentally friendly fluorescent carbon-based nanomaterials. However, there is no report on the massive synthesis of GQDs with narrow-band fluorescence and a high photoluminescence quantum yield (PLQY) using a simple liquid-phase method under atmospheric conditions. In this study, GQDs were successfully synthesized in ∼100% product yield by heating phloroglucinol (PG) with Na3PO4·12H2O in 1,2-pentanediol at 180 °C for 6 h in an open system with air flow, followed by dialysis purification. The high product yield was attributed to the addition of Na3PO4·12H2O as a base catalyst, which promoted the dehydration-condensation reaction between PG molecules. The dispersion of PG derived GQDs (PG-GQDs) in ethanol resulted in blue fluorescence with a full width at half maximum of 32 nm and a PLQY of 54%. Further purification of PG-GQDs by silica gel column chromatography improved the PLQY to 75%. Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and X-ray photoelectron spectroscopy confirmed that dehydration-condensation reactions occurred not only between PGs but also between GQDs and 1,2-pentanediol. The binding of 1,2-pentanediol to the edges of GQDs suppressed the stacking of GQDs and prevented concentration quenching, resulting in a high PLQY. PG-GQDs exhibited negative fluorescence solvatochromism, i.e., the fluorescence wavelength blue-shifted with increasing solvent polarity. Dispersion of PG-GQDs in N-methyl-2-pyrrolidone (MP) resulted in green fluorescence with a PLQY of 96%. Dispersion of PG-GQDs in water resulted in blue fluorescence and a low PLQY of 6% at pH 7, while the PLQY was more than 50% at pH ≥ 11. Using these properties, the sensing of water (pH 13) in MP was investigated. The results showed that as the water content was increased from 0% to 100%, the fluorescence color gradually changed from green to blue and the fluorescence wavelength continuously shifted from 514 nm to 466 nm, indicating their applicability in water sensing.

  • Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

    Yamamoto H., Yamaoka K., Shinohara A., Shibata K., Takao K.I., Ogura A.

    Chemical Science (Chemical Science)  14 ( 40 ) 11243 - 11250 2023.09

    ISSN  20416520

    　View Summary

    In organic chemistry, selecting mild conditions for transformations and saving energy are increasingly important for achieving sustainable development goals. Herein, we describe a red-light-mediated Barton decarboxylation using readily available red-light-emitting diodes as the energy source and zinc tetraphenylporphyrin as the catalyst, avoiding explosive or hazardous reagents or external heating. Mechanistic studies suggest that the reaction probably proceeds via Dexter energy transfer between the activated catalyst and the Barton ester. Furthermore, a one-pot wavelength-selective reaction within the visible light range is developed in combination with a blue-light-mediated photoredox reaction, demonstrating the compatibility of two photochemical transformations based on mechanistic differences. This one-pot process expands the limits of the decarboxylative Giese reaction beyond polarity matching.

  • Open system synthesis of narrow-bandwidth red-fluorescent carbon quantum dots with a function of multi-metal ion sensing

    Katakami R., Sato K., Ogura A., Takao K.I., Iso Y., Isobe T.

    Journal of Materials Chemistry C (Journal of Materials Chemistry C)  11 ( 12 ) 4143 - 4152 2023.03

    ISSN  2050-7526

    　View Summary

    Carbon quantum dots (CQDs) are environmentally friendly phosphors. However, there have been few reports on red-emitting CQDs with narrow-bandwidths, all of which were synthesized via solvothermal methods using autoclaves. Here, red-emitting CQDs were synthesized from 4,6-diaminoresorcinol dihydrochloride (DAR), which is an aromatic compound with electron-donating hydroxy and amino groups. The synthesis involved heating at 180 °C for 6 h in a high-boiling-point 1,2-pentanediol solvent in an open system without using autoclaves and catalysts. The DAR-derived-CQDs in ethanol exhibited red photoluminescence with a 0.14 eV full width at half-maximum that was comparable to that of narrow-bandwidth blue-fluorescent phloroglucinol (PG)-derived-CQDs. The red emission was attributed to a weakened quantum-size effect and electron-donating NH2 groups. The hydroxy groups of PG-derived-CQDs interacted with Al3+ and Fe3+ ions, resulting in fluorescence quenching. DAR-derived-CQDs have hydroxy and amino groups, which facilitate the fluorescence quenching for Al3+, Fe3+, Cu2+, and Pb2+ ions.

  • Synthesis of Indoles via Sigmatropic Rearrangements and Olefin Isomerization

    Uchida T., Saito R., Takao K.i., Ogura A.

    Advanced Synthesis and Catalysis (Advanced Synthesis and Catalysis)  366 ( 3 ) 465 - 472 2023

    ISSN  16154150

    　View Summary

    Indoles are important heterocycles in pharmaceuticals and agrochemicals, and their atom-economical synthesis is needed. Herein, we describe the synthesis of indoles using sigmatropic rearrangements. The N-allylaniline was oxidized by environmentally benign hydrogen peroxide, and spontaneous [2,3]-Meisenheimer rearrangement gave N-allyloxyaniline. Subsequent treatment with a ruthenium catalyst afforded N-vinyloxyaniline, which underwent [3,3]-sigmatropic rearrangement to give indoles, expelling water as the only byproduct. The whole sequence is free of quantitative salt byproducts, thereby avoiding aqueous work up and cutting off the inorganic waste.

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Papers, etc., Registered in KOARA 【 Display / hide 】

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Reviews, Commentaries, etc. 【 Display / hide 】

  • 分子内野崎-檜山-高井-岸反応を用いた天然物の全合成

    高尾賢一

    THE CHEMICAL TIMES  ( No.3 ) 12 - 16 2018.07

    Article, review, commentary, editorial, etc. (scientific journal), Single Work

  • 有機化学の反応のしくみ

    高尾賢一・只野金一

    化学と教育 Vol.65   620 - 623 2017.12

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work

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Presentations 【 Display / hide 】

  • ステルヒルスチンAおよびBの全合成研究

    南友紀子・野村亮太・小椋章弘・高尾賢一

    第66回天然有機化合物討論会 (京都市) , 

    2024.09
    , 

    Poster presentation

  • グッチフェロンAの全合成研究

    滝本実里・七瀧智俊・小椋章弘・高尾賢一

    日本化学会第104春季年会 (船橋市) , 

    2024.03
    , 

    Oral presentation (general)

  • 赤色光照射で駆動する新規ラジカル開始剤の開発

    谷川麟太郎・篠原　杏・高尾賢一・小椋章弘

    日本化学会第104春季年会 (船橋市) , 

    2024.03
    , 

    Oral presentation (general)

  • ステルヒルスチンAおよびBの全合成研究

    南友紀子・野村亮太・小椋章弘・高尾賢一

    日本化学会第104春季年会 (船橋市) , 

    2024.03
    , 

    Oral presentation (general)

  • 分子内野崎-檜山-高井-岸反応を用いた天然物の全合成

    高尾賢一

    有機合成化学協会関東支部ミニシンポジウム多摩2023 (八王子市) , 

    2023.11
    , 

    Oral presentation (invited, special)

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Research Projects of Competitive Funds, etc. 【 Display / hide 】

  • 立体選択的な第四級不斉炭素構築法の開発とそれに基づく生物活性物質の合成

    2021.04
    -
    2025.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

  • Development and Application of Methods for Constructing New Skeletons by Use of Ring-Rearrangement Metathesis and Biomimetic Reactions

    2015.04
    -
    2018.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Principal investigator

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Awards 【 Display / hide 】

  • Astellas Award in Synthetic Organic Chemistry, Japan

    Ken-ichi Takao, 2006.11, 社団法人 有機合成化学協会, Development of Methods for Asymmetric Synthesis of Cyclobutanes and Application to Total Synthesis of Natural Products

    Type of Award： Award from Japanese society, conference, symposium, etc.

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Courses Taught 【 Display / hide 】

  • TOPICS IN ORGANIC SYNTHETIC CHEMISTRY

    2024

  • SEMINAR IN APPLIED CHEMISTRY

    2024

  • LABORATORIES IN APPLIED CHEMISTRY B

    2024

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2024

  • GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

    2024

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Memberships in Academic Societies 【 Display / hide 】

  • The Chemical Society of Japan, 

    1990.04
    -
    Present

  • The Society of Synthetic Organic Chemistry, Japan, 

    1990.04
    -
    Present

  • The Pharmaceutical Society of Japan, 

    1996.04
    -
    Present

  • American Chemical Society, 

    1999.01
    -
    Present

  • The Japanese Society for Process Chemistry, 

    2003.04
    -
    Present
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Committee Experiences 【 Display / hide 】

  • 2023.02
    -
    2024.02

    事業委員長, 有機合成化学協会

  • 2022.02
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    2024.02

    理事（事業担当）, 有機合成化学協会

  • 2021.02
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    2023.02

    関東支部常任幹事, 有機合成化学協会

  • 2019.02
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    2021.02

    関東支部幹事, 有機合成化学協会

  • 2016.12
    -
    2021.12

    幹事, 新規素材探索研究会

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