Teruyuki Kondo

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Organization: Kyoto University

Department: Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering

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TOPICS

Polymer

Dendrimers

Inorganic Chemistry

Functional Complex

Chemicals
References

Dioxetane formation and chemiluminescent emission upon the combination of a vinylphenol derivative with naphthalene endoperoxide

Co-reporter:Yui Umehara;Aoi Son;Kazuhito Tanabe

RSC Advances (2011-Present) 2017 vol. 7(Issue 16) pp:9472-9475

Publication Date(Web):2017/01/30

DOI:10.1039/C6RA28079J

We designed a chemiluminescent system using nanoparticles. We prepared mesoporous nanoparticles bearing naphthalene endoperoxide as a singlet oxygen generator in the pore and vinyl phenol derivative as an emission unit. The combination of these functional molecules gave highly efficient and bright chemiluminescence through the formation of a 1,2-dioxetane intermediate.

Ruthenium- and Rhodium-Catalyzed Strain-Driven Cleavage and Reconstruction of the CC Bond

Co-reporter:Teruyuki Kondo

European Journal of Organic Chemistry 2016 Volume 2016( Issue 7) pp:1232-1242

Publication Date(Web):

DOI:10.1002/ejoc.201501291

Abstract

The synthesis of new functional organic molecules that cannot be obtained by a simple combination of conventional synthetic methods is a challenging subject in organic, organometallic, and industrial chemistry as well as in atom-efficient and environmental organic synthesis. Among the various possibilities that have been considered, the catalytic cleavage and reconstruction of the C–C bond has opened the door to a new branch of synthetic organic chemistry. This microreview summarizes progress on the ruthenium- and rhodium-catalyzed strain-driven cleavage of the C–C bond, the methods of which were mostly developed by the author. The direct oxidative addition of 2,5-norbornadienes, cyclopropenones, cyclobutenones, and cyclobutenediones, and to catalytically active metal species followed by the construction of the C–C bond has been used for the preparation of new organic molecules.

13C/15N-Enriched l-Dopa as a Triple-Resonance NMR Probe to Monitor Neurotransmitter Dopamine in the Brain and Liver Extracts of Mice

Co-reporter:Dr. Hisatsugu Yamada;Tetsuro Kameda;Dr. Yu Kimura;Dr. Hirohiko Imai;Dr. Tetsuya Matsuda;Dr. Shinsuke So;Dr. Akio Toshimitsu;Dr. Yasuhiro Aoyama;Dr. Teruyuki Kondo

ChemistryOpen 2016 Volume 5( Issue 2) pp:

Publication Date(Web):

DOI:10.1002/open.201500196

Abstract

In an attempt to monitor μm-level trace constituents, we applied here ¹H-{¹³C-¹⁵N} triple-resonance nuclear magnetic resonance (NMR) to ¹³C/¹⁵N-enriched l-Dopa as the inevitable precursor of the neurotransmitter dopamine in the brain. The perfect selectivity (to render endogenous components silent) and μm-level sensitivity (700 MHz spectrometer equipped with a cryogenic probe) of triple-resonance allowed the unambiguous and quantitative metabolic and pharmacokinetic analyses of administered l-Dopa/dopamine in the brain and liver of mice. The level of dopamine generated in the brain (within the range 7–76 μm, which covers the typical stimulated level of ∼30 μm) could be clearly monitored ex vivo, but was slightly short of the detection limit of a 7 T MR machine for small animals. This work suggests that μm-level trace constituents are potential targets of ex vivo monitoring as long as they contain N atom(s) and their appropriate ¹³C/¹⁵N-enrichment is synthetically accessible.

Magnetic Resonance Imaging of Tumor with a Self-Traceable Phosphorylcholine Polymer

Co-reporter:Hisatsugu Yamada; Yoshinori Hasegawa; Hirohiko Imai; Yuki Takayama; Fuminori Sugihara; Tetsuya Matsuda; Hidehito Tochio; Masahiro Shirakawa; Shinsuke Sando; Yu Kimura; Akio Toshimitsu; Yasuhiro Aoyama

Journal of the American Chemical Society 2015 Volume 137(Issue 2) pp:799-806

Publication Date(Web):January 6, 2015

DOI:10.1021/ja510479v

Polymers are concentration-amplified with respect to the monomeric units. We show here that a phosphorylcholine polymer enriched with 13C/15N at the methyl groups is self-traceable by multiple-resonance (heteronuclear-correlation) NMR in tumor-bearing mice inoculated with the mouse rectal cancer cell line (colon 26). Preliminary measurements indicated that the present polymeric nanoprobe was satisfactorily distinguished from lipids and detectable with far sub-micromolar spectroscopic and far sub-millimolar imaging sensitivities. Detailed ex vivo and in vivo studies for the tumor-bearing mice administered the probe with a mean molecular weight of 63 000 and a mean size of 13 nm, revealed the following: (1) this probe accumulates in the tumor highly selectively (besides renal excretion) and efficiently (up to 30% of the injected dose), (2) the tumor can thus be clearly in vivo imaged, the lowest clearly imageable dose of the probe being 100 mg/kg or 2.0 mg/20-g mouse, and (3) the competition between renal excretion and tumor accumulation is size-controlled; that is, the larger (higher molecular-weight) and smaller (lower molecular-weight) portions of the probe undergo tumor accumulation and renal excretion, respectively. The observed size dependence suggests that the efficient tumor-targeting of the present probe is stimulated primarily by the so-called enhanced permeability and retention (EPR) effect, that is, size-allowed invasion of the probe into the tumor tissue via defective vascular wall. Self-traceable polymers thus open an important area of magnetic resonance imaging (MRI) of tumors and may provide a highly potential tool to visualize various delivery/localization processes using synthetic polymers.

Magnetic resonance imaging of tumor with a self-traceable polymer conjugated with an antibody fragment

Co-reporter:Hisatsugu Yamada, Yoshinori Hasegawa, Yuki Suzuki, Hirohiko Imai, Tetsuya Matsuda, Yu Kimura, Akio Toshimitsu, Yasuhiro Aoyama, Teruyuki Kondo

Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 13) pp:2675-2678

Publication Date(Web):1 July 2015

DOI:10.1016/j.bmcl.2015.04.072

A 13C-enriched phosphorylcholine polymer (13C-PMPC) as a self-traceable MR (magnetic resonance) tag was conjugated with a fragment (scFv) of Herceptin, a clinical antibody against antigen Her2. When injected in model mice bearing Her2(+) (gastric) and Her2(−) (pancreatic) tumors, the antibody-tag conjugate 13C-PMPC-scFv selectively accumulated in the Her2(+) tumor with a rapid build-up/decay (accumulation/clearance) profile and, with the use of the 1H–13C double-resonance (heteronuclear correlation) technique, the Her2(+) gastric tumor was clearly MR imaged.Figure optionsDownload full-size imageDownload as PowerPoint slide

Synthesis and functional evaluation of chiral dendrimer-triamine-coordinated Gd complexes with polyaminoalcohol end groups as highly sensitive MRI contrast agents

Co-reporter:Yuka Miyake, Yu Kimura, Naomi Orito, Hirohiko Imai, Tetsuya Matsuda, Akio Toshimitsu, Teruyuki Kondo

Tetrahedron 2015 Volume 71(26–27) pp:4438-4444

Publication Date(Web):1 July 2015

DOI:10.1016/j.tet.2015.04.050

Novel chiral dendrimer-triamine-coordinated Gd complexes with polyaminoalcohol end groups were synthesized and shown to have longitudinal relaxivity (r1) values 5 times higher than that of clinically used Gd-DTPA. The affinities of Gd-4a and Gd-4b for bovine serum albumin (BSA), respectively, were estimated by a quartz crystal microbalance (QCM) measurement. The amino groups of the dendrimer were then conjugated with PEG. This conjugation with PEG strongly affected its ability to attenuate signals in T1-weighted MRI.

Size-Controlled and Biocompatible Gd2O3 Nanoparticles for Dual Photoacoustic and MR Imaging

Co-reporter:Yu Kimura;Ryota Kamisugi;Michiko Narazaki;Tetsuya Matsuda;Yasuhiko Tabata;Akio Toshimitsu

Advanced Healthcare Materials 2012 Volume 1( Issue 5) pp:657-660

Publication Date(Web):

DOI:10.1002/adhm.201200103

Synthesis and functional evaluation of chiral dendrimer–triamine-coordinated Gd complexes as highly sensitive MRI contrast agents

Co-reporter:Yuka Miyake, Yu Kimura, Syungo Ishikawa, Hiroshi Tsujita, Hiroki Miura, Michiko Narazaki, Tetsuya Matsuda, Yasuhiko Tabata, Tetsuya Yano, Akio Toshimitsu, Teruyuki Kondo

Tetrahedron Letters 2012 Volume 53(Issue 34) pp:4580-4583

Publication Date(Web):22 August 2012

DOI:10.1016/j.tetlet.2012.06.072

Novel chiral dendrimer–triamine-coordinated Gd complexes were synthesized and shown to have longitudinal relaxivity (r1) 3 times higher than that of clinically used Gd-DTPA. The pharmacokinetic differences between optical isomers were estimated from the affinity of 2-(R) and 2-(S) with bovine serum albumin (BSA), respectively, by a quartz crystal microbalance (QCM) measurement. As a result, the association constant Ka of 2-(S) was about 4 times higher than that of 2-(R), which means that 2-(S) is retained in the vascular retention for a longer time after administration. This result was also supported by T1-weighted MR images of mice before and after the intravenous injection of 2-(R) and 2-(S), as well as the time-course of the signal intensities (SI) at the blood vessels and quantification of Gd3+ concentration in the blood and urine.

Selective Trimerization of Ethylene to Isohexenes Catalyzed by a Ruthenium(0) Complex

Co-reporter:Dr. Teruyuki Kondo;Keisuke Yamamoto;Daisuke Takagi;Lingfeng Shen;Yuki Yoshida;Dr. Yu Kimura;Dr. Akio Toshimitsu;Masahiko Kuramoto;Dr. Yasushi Shiraki

ChemCatChem 2010 Volume 2( Issue 12) pp:1565-1568

Publication Date(Web):

DOI:10.1002/cctc.201000219

Rhodium-Catalyzed Decarbonylative Coupling Reactions of Diphenylketene with Alkenes

Co-reporter:Teruyuki Kondo Dr.;Yukiko Tokoro;Yasuyuki Ura Dr.;Kenji Wada Dr.;Take-aki Mitsudo Dr.

ChemCatChem 2009 Volume 1( Issue 1) pp:82-84

Publication Date(Web):

DOI:10.1002/cctc.200900075

Inside Cover: Regio- and Stereoselective Synthesis of Enamides and Dienamides by Ruthenium-Catalyzed Co-Oligomerization of N-Vinylamides with Alkenes or Alkynes (Angew. Chem. Int. Ed. 27/2007)

Co-reporter:Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Shingo Matsuki;Kenji Wada Dr.;Take-aki Mitsudo Dr. Dr.

Angewandte Chemie International Edition 2007 Volume 46(Issue 27) pp:

Publication Date(Web):22 JUN 2007

DOI:10.1002/anie.200790123

Just as with the Chimera, a creature from Greek mythology that has the head of a lion, a goat, and a snake, three distinct monomers can be combined to make one molecule. In their Communication on page 5160 ff., T. Kondo, Y. Ura, and co-workers describe a series of ruthenium-catalyzed co-oligomerization reactions, including the cotrimerization of N-vinylamides with acrylates and ethylene, as a route to biologically and synthetically important enamides and dienamides.

Highly Selective Dimerization of Styrenes and Linear Co-dimerization of Styrenes with Ethylene Catalyzed by a Ruthenium Complex

Co-reporter:Teruyuki Kondo Dr.;Daisuke Takagi;Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Kenji Wada Dr.;Take-aki Mitsudo Dr.

Angewandte Chemie International Edition 2007 Volume 46(Issue 31) pp:

Publication Date(Web):25 JUN 2007

DOI:10.1002/anie.200701583

Heads you win: An unusual head-to-head dimerization of styrenes has been developed using the zero-valent ruthenium catalyst [Ru(η⁶-cot)(η²-dmfm)₂] (cot=1,3,5-cyclooctatriene, dmfm=dimethyl fumarate) in the presence of primary alcohols to give the homo-dimer in high regio- and stereoselectivity. The catalyst system is also effective for the selective co-dimerization of styrenes with ethylene to give the co-dimer in high yield.

Highly Selective Dimerization of Styrenes and Linear Co-dimerization of Styrenes with Ethylene Catalyzed by a Ruthenium Complex

Co-reporter:Teruyuki Kondo Dr.;Daisuke Takagi;Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Kenji Wada Dr.;Take-aki Mitsudo Dr.

Angewandte Chemie 2007 Volume 119(Issue 31) pp:

Publication Date(Web):25 JUN 2007

DOI:10.1002/ange.200701583

Kopf gewinnt: Eine ungewöhnliche Kopf-Kopf-Dimerisierung von Styrolen gelingt mit dem nullwertigen Rutheniumkatalysator [Ru(η⁶-cot)(η²-dmfm)₂] (cot=1,3,5-Cyclooctatrien, dmfm=Dimethylfumarat) in Gegenwart primärer Alkohole; dabei entsteht das Homodimer mit hoher Regio- und Stereoselektivität. Das Katalysatorsystem eignet sich auch für die selektive Codimerisierung von Styrolen mit Ethen in hoher Ausbeute.

Innentitelbild: Regio- and Stereoselective Synthesis of Enamides and Dienamides by Ruthenium-Catalyzed Co-Oligomerization of N-Vinylamides with Alkenes or Alkynes (Angew. Chem. 27/2007)

Co-reporter:Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Shingo Matsuki;Kenji Wada Dr.;Take-aki Mitsudo Dr. Dr.

Angewandte Chemie 2007 Volume 119(Issue 27) pp:

Publication Date(Web):22 JUN 2007

DOI:10.1002/ange.200790123

Die Chimäre, eine Kreatur aus der griechischen Mythologie mit einem Löwen-, einem Ziegen- und einem Schlangenkopf, findet ihre chemische Entsprechung in einem molekularen Konstrukt aus drei unterschiedlichen Monomeren. In ihrer Zuschrift auf S. 5252 ff. beschreiben T. Kondo, Y. Ura und Mitarbeiter eine Reihe von rutheniumkatalysierten Cooligomerisierungen – darunter auch die Cotrimerisierung von N-Vinylamiden, Acrylaten und Ethen – als Weg zu biologisch und synthetisch nützlichen Enamiden und Dienamiden.

Regio- and Stereoselective Synthesis of Enamides and Dienamides by Ruthenium-Catalyzed Co-Oligomerization of N-Vinylamides with Alkenes or Alkynes

Co-reporter:Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Shingo Matsuki;Kenji Wada Dr.;Take-aki Mitsudo Dr. Dr.

Angewandte Chemie 2007 Volume 119(Issue 27) pp:

Publication Date(Web):25 MAY 2007

DOI:10.1002/ange.200701356

Der nullwertige Rutheniumkomplex (η⁶-1,3,5-Cyclooctatrien)bis(η²-dimethylfumarat)ruthenium katalysiert die hoch selektive Codimerisierung von N-Vinylamiden mit Alkenen oder Alkinen und ermöglicht die Cotrimerisierung von N-Vinylamiden mit Ethylacrylat und Ethen (siehe Schema). Auf diese Art gelingt die rasche und atomökonomische Synthese von biologisch und für die Synthesechemie wichtigen Enamiden und Dienamiden.

Regio- and Stereoselective Synthesis of Enamides and Dienamides by Ruthenium-Catalyzed Co-Oligomerization of N-Vinylamides with Alkenes or Alkynes

Co-reporter:Hiroshi Tsujita Dr.;Yasuyuki Ura Dr.;Shingo Matsuki;Kenji Wada Dr.;Take-aki Mitsudo Dr. Dr.

Angewandte Chemie International Edition 2007 Volume 46(Issue 27) pp:

Publication Date(Web):25 MAY 2007

DOI:10.1002/anie.200701356

The zero-valent ruthenium complex (η⁶-1,3,5-cyclooctatriene)bis(η²-dimethyl fumarate)ruthenium effectively catalyzes the highly selective codimerization of N-vinylamides with alkenes or alkynes and was successfully applied in the cotrimerization of N-vinylamides with ethyl acrylate and ethylene (see scheme). These reactions offer a rapid and atom-economical synthesis of biologically and synthetically important enamides and dienamides.

Ru- and Rh-Catalyzed CC Bond Cleavage of Cyclobutenones: Reconstructive and Selective Synthesis of 2-Pyranones, Cyclopentenes, and Cyclohexenones

Co-reporter:Teruyuki Kondo Dr.;Yoshinori Taguchi;Yushi Kaneko;Masatsugu Niimi;Take-aki Mitsudo Dr.

Angewandte Chemie 2004 Volume 116(Issue 40) pp:

Publication Date(Web):5 OCT 2004

DOI:10.1002/ange.200461002

η⁴-Vinylketen- und/oder Metallacyclopentenonkomplexe dürften die Schlüsselzwischenstufen der Ruthenium- und Rhodium-katalysierten Ringöffnungsdimerisierung von Cyclobutenonen zu 2-Pyranonen wie auch der Rhodium-katalysierten Kupplungen von Cyclobutenonen mit 2-Norbornen sein (siehe Schema).

Ru- and Rh-Catalyzed CC Bond Cleavage of Cyclobutenones: Reconstructive and Selective Synthesis of 2-Pyranones, Cyclopentenes, and Cyclohexenones

Co-reporter:Teruyuki Kondo Dr.;Yoshinori Taguchi;Yushi Kaneko;Masatsugu Niimi;Take-aki Mitsudo Dr.

Angewandte Chemie International Edition 2004 Volume 43(Issue 40) pp:

Publication Date(Web):5 OCT 2004

DOI:10.1002/anie.200461002

η⁴-Vinylketene and/or metallacyclopentenone complexes can be considered key intermediates in the ruthenium- and rhodium-catalyzed ring-opening dimerization of cyclobutenones to give 2-pyranones as well as in the rhodium-catalyzed coupling reactions of cyclobutenones with 2-norbornene (see scheme).