Details of a Researcher - Nishiyama, Shigeru

Nishiyama, Shigeru

写真a

Affiliation: Faculty of Science and Technology (Mita)

Position: Professor Emeritus

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Career 【 Display / hide 】

1978.01

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1979.12

Alexander von Humboldt （西ドイツ，ダルムシュタット工科大学） ,研究員
1980.01

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1980.06

ダルムシュタット工科大学 ,共同研究員
1980.07

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1981.03

慶應義塾大学（工学部） ,助手
1981.04

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1985.03

慶應義塾大学（理工学部） ,助手
1985.04

-

1991.03

慶應義塾大学（理工学部） ,専任講師

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Academic Background 【 Display / hide 】

1971.03

Keio University, Faculty of Engineering, 応用化学

University, Graduated
1973.03

Keio University, Graduate School, Division of Engineering, 応用化学専攻

Graduate School, Completed, Master's course
1976.03

Keio University, Graduate School, Division of Engineering, 応用化学専攻

Graduate School, Withdrawal after completion of doctoral course requirements, Doctoral course

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Academic Degrees 【 Display / hide 】

工学　, Keio University, 1977.09

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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)
Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules (生物有機科学)
Life Science / Bioorganic chemistry (organic chemistry)

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Research Themes 【 Display / hide 】

synthesis and biologicalactivity of heliannuols, allelopathogenic substance of sunflower,

2002

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Present
Synthesis of a-mangostin derivatives and their inhibitory activity against sphingomyelinase,

2000

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Present

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Books 【 Display / hide 】

未来を拓く元素戦略、CSJカレントレビュー11

NISHIYAMA SHIGERU, 化学同人, 2013

Scope: 62-67
天然物合成で活躍した反応

NISHIYAMA SHIGERU, 化学同人, 2011.10

Scope: 158-159
新規素材探索—医薬品リード化合物・食品素材を求めてー

NISHIYAMA SHIGERU, シーエムシー出版, 2008

Scope: 154-164
有機電解合成の新展開II

NISHIYAMA SHIGERU, シーエムシー出版, 2004

Scope: 89 - 102
生命科学のための基礎シリーズ　化学（監修　大島泰郎）

太田博道、岩村道子、大場　茂、西山　繁, 実教出版, 2002.03

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Papers 【 Display / hide 】

Oxidative Cleavage of the Acyl-Carbon Bond in Phenylacetone with Electrogenerated Superoxide Anions

Zhang Y., Sugai T., Yamamoto T., Yamamoto N., Kutsumura N., Einaga Y., Nishiyama S., Saitoh T., Nagase H.

ChemElectroChem (ChemElectroChem) 6 ( 16 ) 4194 - 4198 2019

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An oxidative cleavage reaction of the acyl−carbon bond in phenylacetone derivatives under cathodic reduction is reported. This particular transformation is driven by the cathodic reduction of dissolved molecular oxygen to superoxide anions. Various cathode materials were examined, and we discovered that boron-doped diamond (BDD) enables highly efficient molecular conversion, owing to BDD's outstanding electrochemical property for utilizing the small amounts of molecular oxygen effectively. The scope of the reaction is broad and can be applied to a variety of substrates, ranging from ketones to esters and amides. As an electric current is directly employed to generate the superoxide anion, the reaction is metal- and catalyst-free. Electro-organic synthesis using the carbon-based BDD electrode thus provides access to sustainable molecular transformations.
- Access to Document (DOI)
Near-Infrared Bioluminescence Imaging with a through-Bond Energy Transfer Cassette

Abe M., Nishihara R., Ikeda Y., Nakajima T., Sato M., Iwasawa N., Nishiyama S., Paulmurugan R., Citterio D., Kim S., Suzuki K.

ChemBioChem (ChemBioChem) 20 ( 15 ) 1919 - 1923 2019

ISSN 14394227

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A coelenterazine (CTZ) analogue emitting near-infrared (NIR) bioluminescence was synthesized for through-bond energy transfer (TBET)-based imaging modalities. The analogue, named Cy5-CTZ, was prepared by conjugating cyanine-5 (Cy5) dye to CTZ through an acetylene linker. This novel derivative is intrinsically fluorescent and emits NIR-shifted luminescence upon reacting with an appropriate luciferase, the Renilla luciferase. This Cy5-CTZ substrate is optically stable in physiological samples and rapidly permeabilize through the plasma membrane into the cytosolic compartment of live cells.
- Access to Document (DOI)
Highly bright and stable NIR-BRET with blue-shifted coelenterazine derivatives for deep-tissue imaging of molecular events in vivo

Nishihara R., Paulmurugan R., Nakajima T., Yamamoto E., Natarajan A., Afjei R., Hiruta Y., Iwasawa N., Nishiyama S., Citterio D., Sato M., Kim S., Suzuki K.

Theranostics (Theranostics) 9 ( 9 ) 2646 - 2661 2019

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© Ivyspring International Publisher. Background: Bioluminescence imaging (BLI) is one of the most widely used optical platforms in molecular imaging, but it suffers from severe tissue attenuation and autoluminescence in vivo. Methods: Here, we developed a novel BLI platform on the basis of bioluminescence resonance energy transfer (BRET) for achieving a ∼300 nm blue-to-near infrared shift of the emission (NIR-BRET) by synthesizing an array of 18 novel coelenterazine (CTZ) derivatives, named “Bottle Blue (BBlue)” and a unique iRFP-linked RLuc8.6-535SG fusion protein as a probe. Results: The best NIR-BRET was achieved by tuning the emission peaks of the CTZ derivatives to a Soret band of the iRFP. In mammalian cells, BBlue2.3, one of the CTZ derivatives, emits light that is ∼50-fold brighter than DBlueC when combined with RLuc8.6-535SG, which shows stable BL kinetics. When we used a caged version of BBLue2.3, it showed a BL half decay time of over 60 minutes while maintaining the higher signal sensitivity. This NIR BL is sufficiently brighter to be used for imaging live mammalian cells at single cell level, and also for imaging metastases in deep tissues in live mice without generating considerable autoluminescence. A single-chain probe developed based on this BLI platform allowed us to sensitively image ligand antagonist-specific activation of estrogen receptor in the NIR region. Conclusion: This unique optical platform provides the brightest NIR BLI template that can be used for imaging a diverse group of cellular events in living subjects including protein‒protein interactions and cancer metastasis.
- Access to Document (DOI)
Electrochemical Pinacol Coupling of Acetophenone Using Boron-Doped Diamond Electrode

Nakahara K., Naba K., Saitoh T., Sugai T., Obata R., Nishiyama S., Einaga Y., Yamamoto T.

ChemElectroChem (ChemElectroChem) 6 ( 16 ) 4153 - 4157 2019

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An electrochemical pinacol coupling reaction of acetophenone using a boron-doped diamond (BDD) electrode has been reported. This transformation is driven by the one-electron reduction of acetophenone on the BDD cathode, followed by an intermolecular radical coupling. Owing to the BDD's outstanding electrochemical properties, the pinacol-type compound has been obtained in good conversion yield. The roles of a supporting electrolyte and solvent were addressed; (1) lithium ions contribute to increase in the reactivity of the radical intermediate. (2) Addition of water promotes the electron transfer process at the BDD surface. The reaction is relatively tolerant to para-substituted acetophenone derivatives. Since electric current is directly employed as reducing reagents to generate a radical intermediate, the reaction is metal-free, sustainable, and inherently safe.
- Access to Document (DOI)
Azide- and Dye-Conjugated Coelenterazine Analogues for a Multiplex Molecular Imaging Platform

Nishihara R., Hoshino E., Kakudate Y., Kishigami S., Iwasawa N., Sasaki S., Nakajima T., Sato M., Nishiyama S., Citterio D., Suzuki K., Kim S.

Bioconjugate Chemistry (Bioconjugate Chemistry) 29 ( 6 ) 1922 - 1931 2018.06

ISSN 10431802

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© 2018 American Chemical Society. Native coelenterazine (nCTZ) is a common substrate to most marine luciferases and photoproteins. In this study, nine novel dye- and azide-conjugated CTZ analogues were synthesized by conjugating a series of fluorescent dyes or an azide group to the C-2 or C-6 position of the nCTZ backbone to obtain bulkiness-driven substrate specificity and potential chemiluminescence/bioluminescence resonance energy transfer (C/BRET). The investigation on the optical properties revealed that azide-conjugated CTZs emit greatly biased bioluminescence to ALucs and ca. 130 nm blue-shifted bioluminescence with RLuc8.6 in living animal cells or lysates. The corresponding kinetic study explains that azide-conjugated CTZ exerts higher catalytic efficiency than nCTZ. Nile red-conjugated CTZ completely showed red-shifted CRET spectra and characteristic BRET spectra with artificial luciferase 16 (ALuc16). No or less spectral overlap occurs among [Furimazine-NanoLuc], [6-N 3 -CTZ-ALuc26], [6-pi-OH-CTZ-RLuc8.6], and [6-N 3 -CTZ-RLuc8.6] pairs, because of the substrate-driven luciferase specificity and color shifts, providing a crosstalk-free multiplex bioassay platform. The unique bioluminescence system appends a new toolbox to bioassays and multiplex molecular imaging platforms. This study is the first example that systematically synthesized fluorescent dye-conjugated CTZs and applied them for a bioluminescence assay system.
- Access to Document (DOI)

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

Synthesis of biologically important molecules by means of elencrochemical procedures

Nishiyama, Shigeru

科学研究費補助金研究成果報告書 2013
Development of environmentally benign synthesis towards new biologically active substance

Nishiyama, Shigeru

科学研究費補助金研究成果報告書 2010

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Presentations 【 Display / hide 】

ベンジルグリコシド誘導体を活用した電解グリコシル化反応の開発

NISHIYAMA SHIGERU

第５５回天然有機化合物討論会 (京都) ,

2013.09
,
Poster presentation
電気化学を活用する有機合成

NISHIYAMA SHIGERU

理研シンポジウム：第８回有機合成化学のフロンティア　JST-ERATO シンポジウム：生細胞分子化学 (和光) ,

2013.07
,
Oral presentation (invited, special), 理化学研究所
糖誘導体の電解反応および不斉炭素構築に関する合成化学的研究

NISHIYAMA SHIGERU

第３７回有機電子移動化学討論会 (岡山) ,

2013.06
,
Poster presentation
ベンジルグリコシド誘導体を活用した電解グリコシル化反応の開発

NISHIYAMA SHIGERU

第３７回有機電子移動化学討論会 (岡山) ,

2013.06
,
Oral presentation (general)
ホタルルシフェリンの構造活性相関と新規ルシフェリンアナログの開発

NISHIYAMA SHIGERU

第３７回有機電子移動化学討論会 (岡山) ,

2013.06
,
Poster presentation