start-ver=1.4
cd-journal=joma
no-vol=14
cd-vols=
no-issue=1
article-no=
start-page=621
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2023
dt-pub=20230204
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Pivotal role for S-nitrosylation of DNA methyltransferase 3B in epigenetic regulation of tumorigenesis
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=DNA methyltransferases (DNMTs) catalyze methylation at the C5 position of cytosine with S-adenosyl-l-methionine. Methylation regulates gene expression, serving a variety of physiological and pathophysiological roles. The chemical mechanisms regulating DNMT enzymatic activity, however, are not fully elucidated. Here, we show that protein S-nitrosylation of a cysteine residue in DNMT3B attenuates DNMT3B enzymatic activity and consequent aberrant upregulation of gene expression. These genes include Cyclin D2 (Ccnd2), which is required for neoplastic cell proliferation in some tumor types. In cell-based and in vivo cancer models, only DNMT3B enzymatic activity, and not DNMT1 or DNMT3A, affects Ccnd2 expression. Using structure-based virtual screening, we discovered chemical compounds that specifically inhibit S-nitrosylation without directly affecting DNMT3B enzymatic activity. The lead compound, designated DBIC, inhibits S-nitrosylation of DNMT3B at low concentrations (IC50 <= 100nM). Treatment with DBIC prevents nitric oxide (NO)-induced conversion of human colonic adenoma to adenocarcinoma in vitro. Additionally, in vivo treatment with DBIC strongly attenuates tumor development in a mouse model of carcinogenesis triggered by inflammation-induced generation of NO. Our results demonstrate that de novo DNA methylation mediated by DNMT3B is regulated by NO, and DBIC protects against tumor formation by preventing aberrant S-nitrosylation of DNMT3B.
en-copyright=
kn-copyright=
en-aut-name=OkudaKosaku
en-aut-sei=Okuda
en-aut-mei=Kosaku
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=NakaharaKengo
en-aut-sei=Nakahara
en-aut-mei=Kengo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=ItoAkihiro
en-aut-sei=Ito
en-aut-mei=Akihiro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=IijimaYuta
en-aut-sei=Iijima
en-aut-mei=Yuta
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=NomuraRyosuke
en-aut-sei=Nomura
en-aut-mei=Ryosuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=KumarAshutosh
en-aut-sei=Kumar
en-aut-mei=Ashutosh
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
en-aut-name=FujikawaKana
en-aut-sei=Fujikawa
en-aut-mei=Kana
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=7
ORCID=
en-aut-name=AdachiKazuya
en-aut-sei=Adachi
en-aut-mei=Kazuya
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=8
ORCID=
en-aut-name=ShimadaYuki
en-aut-sei=Shimada
en-aut-mei=Yuki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=9
ORCID=
en-aut-name=FujioSatoshi
en-aut-sei=Fujio
en-aut-mei=Satoshi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=10
ORCID=
en-aut-name=YamamotoReina
en-aut-sei=Yamamoto
en-aut-mei=Reina
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=11
ORCID=
en-aut-name=TakasugiNobumasa
en-aut-sei=Takasugi
en-aut-mei=Nobumasa
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=12
ORCID=
en-aut-name=OnumaKunishige
en-aut-sei=Onuma
en-aut-mei=Kunishige
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=13
ORCID=
en-aut-name=OsakiMitsuhiko
en-aut-sei=Osaki
en-aut-mei=Mitsuhiko
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=14
ORCID=
en-aut-name=OkadaFutoshi
en-aut-sei=Okada
en-aut-mei=Futoshi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=15
ORCID=
en-aut-name=UkegawaTaichi
en-aut-sei=Ukegawa
en-aut-mei=Taichi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=16
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=17
ORCID=
en-aut-name=YasuiNorihisa
en-aut-sei=Yasui
en-aut-mei=Norihisa
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=18
ORCID=
en-aut-name=YamashitaAtsuko
en-aut-sei=Yamashita
en-aut-mei=Atsuko
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=19
ORCID=
en-aut-name=MarusawaHiroyuki
en-aut-sei=Marusawa
en-aut-mei=Hiroyuki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=20
ORCID=
en-aut-name=MatsushitaYosuke
en-aut-sei=Matsushita
en-aut-mei=Yosuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=21
ORCID=
en-aut-name=KatagiriToyomasa
en-aut-sei=Katagiri
en-aut-mei=Toyomasa
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=22
ORCID=
en-aut-name=ShibataTakahiro
en-aut-sei=Shibata
en-aut-mei=Takahiro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=23
ORCID=
en-aut-name=UchidaKoji
en-aut-sei=Uchida
en-aut-mei=Koji
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=24
ORCID=
en-aut-name=NiuSheng-Yong
en-aut-sei=Niu
en-aut-mei=Sheng-Yong
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=25
ORCID=
en-aut-name=LangNhi B.
en-aut-sei=Lang
en-aut-mei=Nhi B.
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=26
ORCID=
en-aut-name=NakamuraTomohiro
en-aut-sei=Nakamura
en-aut-mei=Tomohiro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=27
ORCID=
en-aut-name=ZhangKam Y. J.
en-aut-sei=Zhang
en-aut-mei=Kam Y. J.
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=28
ORCID=
en-aut-name=LiptonStuart A.
en-aut-sei=Lipton
en-aut-mei=Stuart A.
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=29
ORCID=
en-aut-name=UeharaTakashi
en-aut-sei=Uehara
en-aut-mei=Takashi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=30
ORCID=
affil-num=1
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=2
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=3
en-affil=Chemical Genomics Research Group, RIKEN Center for Sustainable Resource Science
kn-affil=
affil-num=4
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=5
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=6
en-affil=Laboratory for Structural Bioinformatics, Center for Biosystems Dynamics Research, RIKEN
kn-affil=
affil-num=7
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=8
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=9
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=10
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=11
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=12
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=13
en-affil=Division of Experimental Pathology, Faculty of Medicine, Tottori University
kn-affil=
affil-num=14
en-affil=Division of Experimental Pathology, Faculty of Medicine, Tottori University
kn-affil=
affil-num=15
en-affil=Division of Experimental Pathology, Faculty of Medicine, Tottori University
kn-affil=
affil-num=16
en-affil=Department of Synthetic and Medicinal Chemistry, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=17
en-affil=Department of Synthetic and Medicinal Chemistry, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=18
en-affil=Laboratory of Structural Biology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=19
en-affil=Laboratory of Structural Biology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=20
en-affil=Department of Gastroenterology and Hepatology, Graduate School of Medicine, Kyoto University
kn-affil=
affil-num=21
en-affil=Division of Genome Medicine, Institute of Advanced Medical Sciences, Tokushima University
kn-affil=
affil-num=22
en-affil=Division of Genome Medicine, Institute of Advanced Medical Sciences, Tokushima University
kn-affil=
affil-num=23
en-affil=Graduate School of Bioagricultural Sciences, Nagoya University
kn-affil=
affil-num=24
en-affil=Laboratory of Food Chemistry, Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo
kn-affil=
affil-num=25
en-affil=Broad Institute of MIT and Harvard
kn-affil=
affil-num=26
en-affil=Neurodegeneration New Medicines Center, and Departments of Molecular Medicine and Neuroscience, The Scripps Research Institute
kn-affil=
affil-num=27
en-affil=Neurodegeneration New Medicines Center, and Departments of Molecular Medicine and Neuroscience, The Scripps Research Institute
kn-affil=
affil-num=28
en-affil=Laboratory for Structural Bioinformatics, Center for Biosystems Dynamics Research, RIKEN
kn-affil=
affil-num=29
en-affil=Neurodegeneration New Medicines Center, and Departments of Molecular Medicine and Neuroscience, The Scripps Research Institute
kn-affil=
affil-num=30
en-affil=Department of Medicinal Pharmacology, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University
kn-affil=
END
start-ver=1.4
cd-journal=joma
no-vol=8
cd-vols=
no-issue=
article-no=
start-page=794948
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2021
dt-pub=20211220
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Exploring the Retinal Binding Cavity of Archaerhodopsin-3 by Replacing the Retinal Chromophore With a Dimethyl Phenylated Derivative
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=Rhodopsins act as photoreceptors with their chromophore retinal (vitamin-A aldehyde) and they regulate light-dependent biological functions. Archaerhodopsin-3 (AR3) is an outward proton pump that has been widely utilized as a tool for optogenetics, a method for controlling cellular activity by light. To characterize the retinal binding cavity of AR3, we synthesized a dimethyl phenylated retinal derivative, (2E,4E,6E,8E)-9-(2,6-Dimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal (DMP-retinal). QM/MM calculations suggested that DMP-retinal can be incorporated into the opsin of AR3 (archaeopsin-3, AO3). Thus, we introduced DMP-retinal into AO3 to obtain the non-natural holoprotein (AO3-DMP) and compared some molecular properties with those of AO3 with the natural A1-retinal (AO3-A1) or AR3. Light-induced pH change measurements revealed that AO3-DMP maintained slow outward proton pumping. Noteworthy, AO3-DMP had several significant changes in its molecular properties compared with AO3-A1 as follows; 1) spectroscopic measurements revealed that the absorption maximum was shifted from 556 to 508 nm and QM/MM calculations showed that the blue-shift was due to the significant increase in the HOMO-LUMO energy gap of the chromophore with the contribution of some residues around the chromophore, 2) time-resolved spectroscopic measurements revealed the photocycling rate was significantly decreased, and 3) kinetical spectroscopic measurements revealed the sensitivity of the chromophore binding Schiff base to attack by hydroxylamine was significantly increased. The QM/MM calculations show that a cavity space is present at the aromatic ring moiety in the AO3-DMP structure whereas it is absent at the corresponding beta-ionone ring moiety in the AO3-A1 structure. We discuss these alterations of the difference in interaction between the natural A1-retinal and the DMP-retinal with binding cavity residues.
en-copyright=
kn-copyright=
en-aut-name=TsuneishiTaichi
en-aut-sei=Tsuneishi
en-aut-mei=Taichi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=TakahashiMasataka
en-aut-sei=Takahashi
en-aut-mei=Masataka
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=TsujimuraMasaki
en-aut-sei=Tsujimura
en-aut-mei=Masaki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=KojimaKeiichi
en-aut-sei=Kojima
en-aut-mei=Keiichi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=IshikitaHiroshi
en-aut-sei=Ishikita
en-aut-mei=Hiroshi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
en-aut-name=SudoYuki
en-aut-sei=Sudo
en-aut-mei=Yuki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=7
ORCID=
affil-num=1
en-affil=Laboratory of Biophysical Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=2
en-affil=Laboratory of Synthetic and Medicinal Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=3
en-affil=Department of Applied Chemistry, The University of Tokyo
kn-affil=
affil-num=4
en-affil=Laboratory of Biophysical Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=5
en-affil=Department of Applied Chemistry, The University of Tokyo
kn-affil=
affil-num=6
en-affil=Laboratory of Synthetic and Medicinal Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=7
en-affil=Laboratory of Biophysical Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
en-keyword=retinal
kn-keyword=retinal
en-keyword=rhodopsin
kn-keyword=rhodopsin
en-keyword=proton pump
kn-keyword=proton pump
en-keyword=derivative
kn-keyword=derivative
en-keyword=photoreceptor
kn-keyword=photoreceptor
END
start-ver=1.4
cd-journal=joma
no-vol=62
cd-vols=
no-issue=19
article-no=
start-page=8809
end-page=8818
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2019
dt-pub=20190904
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Competitive Binding Assay with an Umbelliferone-Based Fluorescent Rexinoid for Retinoid X Receptor Ligand Screening
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract= Ligands for retinoid X receptors (RXRs), "rexinoids", are attracting interest as candidates for therapy of type 2 diabetes and Alzheimer's and Parkinson's diseases. However, current screening methods for rexinoids are slow and require special apparatus or facilities. Here, we created 7-hydroxy-2-oxo-6-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2H-chromene-3-carboxylic acid (10, CU-6PMN) as a new fluorescent RXR agonist and developed a screening system of rexinoids using 10. Compound 10 was designed based on the fact that umbelliferone emits strong fluorescence in a hydrophilic environment, but the fluorescence intensity decreases in hydrophobic environments such as the interior of proteins. The developed assay using 10 enabled screening of rexinoids to be performed easily within a few hours by monitoring changes of fluorescence intensity with widely available fluorescence microplate readers, without the need for processes such as filtration.
en-copyright=
kn-copyright=
en-aut-name=YamadaShoya
en-aut-sei=Yamada
en-aut-mei=Shoya
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=KawasakiMayu
en-aut-sei=Kawasaki
en-aut-mei=Mayu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=FujiharaMichiko
en-aut-sei=Fujihara
en-aut-mei=Michiko
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=WatanabeMasaki
en-aut-sei=Watanabe
en-aut-mei=Masaki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=TakamuraYuta
en-aut-sei=Takamura
en-aut-mei=Yuta
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=TakiokuMaho
en-aut-sei=Takioku
en-aut-mei=Maho
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
en-aut-name=NishiokaHiromi
en-aut-sei=Nishioka
en-aut-mei=Hiromi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=7
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=8
ORCID=
en-aut-name=MakishimaMakoto
en-aut-sei=Makishima
en-aut-mei=Makoto
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=9
ORCID=
en-aut-name=MotoyamaTomoharu
en-aut-sei=Motoyama
en-aut-mei=Tomoharu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=10
ORCID=
en-aut-name=ItoSohei
en-aut-sei=Ito
en-aut-mei=Sohei
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=11
ORCID=
en-aut-name=TokiwaHiroaki
en-aut-sei=Tokiwa
en-aut-mei=Hiroaki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=12
ORCID=
en-aut-name=NakanoShogo
en-aut-sei=Nakano
en-aut-mei=Shogo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=13
ORCID=
en-aut-name=KakutaHiroki
en-aut-sei=Kakuta
en-aut-mei=Hiroki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=14
ORCID=
affil-num=1
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=2
en-affil=
kn-affil=
affil-num=3
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=4
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=5
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=6
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=7
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=8
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
affil-num=9
en-affil=Division of Biochemistry, Department of Biomedical Sciences, Nihon University School of Medicine
kn-affil=
affil-num=10
en-affil=Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka
kn-affil=
affil-num=11
en-affil=Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka
kn-affil=
affil-num=12
en-affil=Department of Chemistry and Research Center of Smart Molecules, Rikkyo University
kn-affil=
affil-num=13
en-affil=Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka
kn-affil=
affil-num=14
en-affil=Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences
kn-affil=
END
start-ver=1.4
cd-journal=joma
no-vol=29
cd-vols=
no-issue=5
article-no=
start-page=2150
end-page=2156
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2017
dt-pub=20170302
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Real-Time, in Situ Monitoring of the Oxidation of Graphite: Lessons Learned
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract= Graphite oxide (GO) and its constituent layers (i.e., graphene oxide) display a broad range of functional groups and, as such, have attracted significant attention for use in numerous applications. GO is commonly prepared using the “Hummers method” or a variant thereof in which graphite is treated with KMnO4 and various additives in H2SO4. Despite its omnipresence, the underlying chemistry of such oxidation reactions is not well understood and typically affords results that are irreproducible and, in some cases, unsafe. To overcome these limitations, the oxidation of graphite under Hummers-type conditions was monitored over time using in situ X-ray diffraction and in situ X-ray absorption near edge structure analyses with synchrotron radiation. In conjunction with other atomic absorption spectroscopy, UV–vis spectroscopy and elemental analysis measurements, the underlying mechanism of the oxidation reaction was elucidated, and the reaction conditions were optimized. Ultimately, the methodology for reproducibly preparing GO on large scales using only graphite, H2SO4, and KMnO4 was developed and successfully adapted for use in continuous flow systems.
en-copyright=
kn-copyright=
en-aut-name=MorimotoNaoki
en-aut-sei=Morimoto
en-aut-mei=Naoki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=SuzukiHideyuki
en-aut-sei=Suzuki
en-aut-mei=Hideyuki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=KawaguchiShogo
en-aut-sei=Kawaguchi
en-aut-mei=Shogo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=KunisuMasahiro
en-aut-sei=Kunisu
en-aut-mei=Masahiro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=BielawskiChristopher W.
en-aut-sei=Bielawski
en-aut-mei=Christopher W.
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
en-aut-name=NishinaYuta
en-aut-sei=Nishina
en-aut-mei=Yuta
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=7
ORCID=
affil-num=1
en-affil=Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Division of Pharmaceutical Sciences, Okayama University
kn-affil=
affil-num=2
en-affil=Research Core for Interdisciplinary Sciences, Okayama University
kn-affil=
affil-num=3
en-affil=Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Division of Pharmaceutical Sciences, Okayama Universit
kn-affil=
affil-num=4
en-affil=Japan Synchrotron Radiation Research Institute (JASRI), SPring-8
kn-affil=
affil-num=5
en-affil=Toray Research Center, Inc., Surface Science Laboratories
kn-affil=
affil-num=6
en-affil=Center for Multidimensional Carbon Materials (CMCM), Institute for Basic Science (IBS)
kn-affil=
affil-num=7
en-affil=Research Core for Interdisciplinary Sciences, Okayama University
kn-affil=
END
start-ver=1.4
cd-journal=joma
no-vol=45
cd-vols=
no-issue=11
article-no=
start-page=2327
end-page=2329
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2004
dt-pub=20043
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Enantioselective construction of biaryl part in the synthesis of stegane related compounds
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed.
Stegane and related compounds are important because of their interesting biological activities such as antileukemic properties.1 One of the most outstanding features of their chemical structures is an unsymmetrical 2,2’-disubstituted biphenyl moiety with an axial chirality (Figure 1). For the formation of such a biphenyl part in the syntheses of the stegane families, several approaches have been attempted such as photocyclization,2 Suzuki coupling,3 oxidative biaryl coupling,4 the SNAr reaction,5 Ullmann coupling,6 and the [2+2+2] three-component cyclization reaction.7
en-copyright=
kn-copyright=
en-aut-name=AbeHitoshi
en-aut-sei=Abe
en-aut-mei=Hitoshi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=TakedaShigemitsu
en-aut-sei=Takeda
en-aut-mei=Shigemitsu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=FujitaTakuro
en-aut-sei=Fujita
en-aut-mei=Takuro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=NishiokaKeisuke
en-aut-sei=Nishioka
en-aut-mei=Keisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=HarayamaTakashi
en-aut-sei=Harayama
en-aut-mei=Takashi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
affil-num=1
en-affil=
kn-affil=Okayama University
affil-num=2
en-affil=
kn-affil=Okayama University
affil-num=3
en-affil=
kn-affil=Okayama University
affil-num=4
en-affil=
kn-affil=Okayama University
affil-num=5
en-affil=
kn-affil=Okayama University
affil-num=6
en-affil=
kn-affil=Okayama University
en-keyword=steganone
kn-keyword=steganone
en-keyword=palladium
kn-keyword=palladium
en-keyword=phenyl benzoate
kn-keyword=phenyl benzoate
en-keyword=lactone concept
kn-keyword=lactone concept
en-keyword=biary
kn-keyword=biary
END
start-ver=1.4
cd-journal=joma
no-vol=46
cd-vols=
no-issue=18
article-no=
start-page=3197
end-page=3200
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2005
dt-pub=20055
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=The chemical synthesis of graphislactones A-D was achieved through the Pd-mediated intramolecular biaryl coupling reaction of phenyl benzoate derivatives.
en-copyright=
kn-copyright=
en-aut-name=AbeHitoshi
en-aut-sei=Abe
en-aut-mei=Hitoshi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=
en-aut-name=NishiokaKeisuke
en-aut-sei=Nishioka
en-aut-mei=Keisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=
en-aut-name=TakedaShigemitsu
en-aut-sei=Takeda
en-aut-mei=Shigemitsu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=
en-aut-name=AraiMasatsugu
en-aut-sei=Arai
en-aut-mei=Masatsugu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=
en-aut-name=HarayamaTakashi
en-aut-sei=Harayama
en-aut-mei=Takashi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=
affil-num=1
en-affil=
kn-affil=Okayama University
affil-num=2
en-affil=
kn-affil=Okayama University
affil-num=3
en-affil=
kn-affil=Okayama University
affil-num=4
en-affil=
kn-affil=Okayama University
affil-num=5
en-affil=
kn-affil=Okayama University
affil-num=6
en-affil=
kn-affil=Okayama University
en-keyword=Palladium
kn-keyword=Palladium
en-keyword=Phenyl benzoate
kn-keyword=Phenyl benzoate
en-keyword=Graphislactone
kn-keyword=Graphislactone
en-keyword=Biaryl coupling
kn-keyword=Biaryl coupling
END
start-ver=1.4
cd-journal=joma
no-vol=7
cd-vols=
no-issue=
article-no=
start-page=20
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=1985
dt-pub=19851101
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=有機廃液の貯蔵について
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=
en-copyright=
kn-copyright=
en-aut-name=TakeuchiYasuo
en-aut-sei=Takeuchi
en-aut-mei=Yasuo
kn-aut-name=竹内靖雄
kn-aut-sei=竹内
kn-aut-mei=靖雄
aut-affil-num=1
ORCID=
affil-num=1
en-affil=
kn-affil=岡山大学薬学部
END