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Authors = Michio Yamada

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16 pages, 5813 KiB  
Article
Photoreactions of Sc3N@C80 with Disilirane, Silirane, and Digermirane: A Photochemical Method to Separate Ih and D5h Isomers
by Masahiro Kako, Kyosuke Miyabe, Shinpei Fukazawa, Shinji Kanzawa, Masanori Yasui, Michio Yamada, Yutaka Maeda, Zdeněk Slanina, Filip Uhlík, Ludwik Adamowicz, Ilias Papadopoulos, Dirk M. Guldi, Makoto Furukawa, Shigeru Nagase and Takeshi Akasaka
Photochem 2022, 2(1), 122-137; https://doi.org/10.3390/photochem2010010 - 7 Feb 2022
Cited by 1 | Viewed by 2979
Abstract
Under photoirradiation, Sc3N@Ih-C80 reacted readily with disilirane 1, silirane 4, and digermirane 7 to afford the corresponding 1:1 adducts, whereas Sc3N@D5h-C80 was recovered without producing those adducts. Based [...] Read more.
Under photoirradiation, Sc3N@Ih-C80 reacted readily with disilirane 1, silirane 4, and digermirane 7 to afford the corresponding 1:1 adducts, whereas Sc3N@D5h-C80 was recovered without producing those adducts. Based on these results, we described a novel method for the exclusive separation of Ih and D5h isomers of Sc3N@C80. The method includes three procedures: selective derivatization of Sc3N@Ih-C80 using 1, 4, and 7, facile HPLC separation of pristine Sc3N@D5h-C80 and Sc3N@Ih-C80 derivatives, and thermolysis of Sc3N@Ih-C80 derivatives to collect pristine Sc3N@Ih-C80. In addition, laser flash photolysis experiments were conducted to elucidate the reaction mechanism. Decay of the transient absorption of 3Sc3N@Ih-C80* was observed to be enhanced in the presence of 1, indicating the quenching process. When Sc3N@D5h-C80 was used, the transient absorption was much less intensive. Therefore, the quenching of 3Sc3N@D5h-C80* by 1 could not be confirmed. Furthermore, we applied time-dependent density functional theory (TD-DFT) calculations of the photoexcited states of Sc3N@C80 to obtain insights into the reaction mechanism. Full article
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13 pages, 2414 KiB  
Article
Relaxin-2 May Suppress Endometriosis by Reducing Fibrosis, Scar Formation, and Inflammation
by Osamu Yoshino, Yosuke Ono, Masako Honda, Kyoko Hattori, Erina Sato, Takehiro Hiraoka, Masami Ito, Mutsumi Kobayashi, Kenta Arai, Hidekazu Katayama, Hiroyoshi Tsuchida, Kaori Yamada-Nomoto, Shunsuke Iwahata, Yoshiyuki Fukushi, Shinichiro Wada, Haruko Iwase, Kaori Koga, Yutaka Osuga, Michio Iwaoka and Nobuya Unno
Biomedicines 2020, 8(11), 467; https://doi.org/10.3390/biomedicines8110467 - 31 Oct 2020
Cited by 14 | Viewed by 4793
Abstract
Background: Relaxin (RLX)-2, produced by the corpus luteum and placenta, is known to be potentially effective in fibrotic diseases of the heart, lungs, kidneys, and bladder; however, its effectiveness in endometriosis has not yet been investigated. In the present study, we conducted a [...] Read more.
Background: Relaxin (RLX)-2, produced by the corpus luteum and placenta, is known to be potentially effective in fibrotic diseases of the heart, lungs, kidneys, and bladder; however, its effectiveness in endometriosis has not yet been investigated. In the present study, we conducted a comprehensive study on the effect of RLX-2 on endometriosis. We checked the expressions of LGR-7, a primary receptor of RLX-2, in endometriomas using immunohistochemistry. Endometriotic stromal cells (ESCs) purified from surgical specimens were used in in vitro experiments. The effects of RLX-2 on ESCs were evaluated by quantitative-PCR, ELISA, and Western blotting. Gel contraction assay was used to assess the contraction suppressive effect of RLX-2. The effect of RLX-2 was also examined in the endometriosis mouse model. LGR-7 was expressed in endometriotic lesions. In ESCs, RLX-2 increased the production of cAMP and suppressed the secretion of interleukin-8, an inflammatory cytokine, by 15% and mRNA expression of fibrosis-related molecules, plasminogen activator inhibitor-1 (PAI-1), and collagen-I by approximately 50% (p < 0.05). In the gel contraction assay, RLX-2 significantly suppressed the contraction of ESCs, which was cancelled by removing RLX-2 from the medium or by adding H89, a Protein Kinase A (PKA) inhibitor. In ESCs stimulated with RLX-2, p38 MAPK phosphorylation was significantly suppressed. In the endometriosis mouse model, administration of RLX-2 significantly decreased the area of the endometriotic-like lesion with decreasing fibrotic component compared to non-treated control (p = 0.01). RLX-2 may contribute to the control of endometriotic lesion by suppressing fibrosis, scar formation, and inflammation. Full article
(This article belongs to the Special Issue Advanced Research in Endometriosis)
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14 pages, 1457 KiB  
Review
New Horizons in Chemical Functionalization of Endohedral Metallofullerenes
by Michio Yamada, Michael T. H. Liu, Shigeru Nagase and Takeshi Akasaka
Molecules 2020, 25(16), 3626; https://doi.org/10.3390/molecules25163626 - 10 Aug 2020
Cited by 19 | Viewed by 3509
Abstract
This overview explains some new aspects of chemical functionalization of endohedral metallofullerenes (EMFs) that have been unveiled in recent years. After differences in chemical reactivity between EMFs and the corresponding empty fullerenes are discussed, cage-opening reactions of EMFs are examined. Then, the selective [...] Read more.
This overview explains some new aspects of chemical functionalization of endohedral metallofullerenes (EMFs) that have been unveiled in recent years. After differences in chemical reactivity between EMFs and the corresponding empty fullerenes are discussed, cage-opening reactions of EMFs are examined. Then, the selective bisfunctionalization of EMFs is explained. Finally, single-bonding derivatization of EMFs is addressed. The diversity and applicability of the chemical functionalization of endohedral metallofullerenes are presented to readers worldwide. Full article
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10 pages, 1027 KiB  
Article
Photoreactions of Endohedral Metallofullerene with Siliranes: Electronic Properties of Carbosilylated Lu3N@Ih-C80
by Masahiro Kako, Kazuya Minami, Taiki Kuroiwa, Shinpei Fukazawa, Yuki Arikawa, Michio Yamada, Yutaka Maeda, Qiao-Zhi Li, Shigeru Nagase and Takeshi Akasaka
Molecules 2017, 22(5), 850; https://doi.org/10.3390/molecules22050850 - 20 May 2017
Cited by 3 | Viewed by 4473
Abstract
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino [...] Read more.
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino adducts. The electronic effect of the silirane addends on Lu3N@Ih-C80 was verified on the basis of density functional theory calculations. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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16 pages, 1418 KiB  
Article
Preparation of Photocrosslinked Fish Elastin Polypeptide/Microfibrillated Cellulose Composite Gels with Elastic Properties for Biomaterial Applications
by Shinya Yano, Megumi Mori, Naozumi Teramoto, Makoto Iisaka, Natsumi Suzuki, Masanari Noto, Yasuko Kaimoto, Masashi Kakimoto, Michio Yamada, Eri Shiratsuchi, Toshiaki Shimasaki and Mitsuhiro Shibata
Mar. Drugs 2015, 13(1), 338-353; https://doi.org/10.3390/md13010338 - 9 Jan 2015
Cited by 15 | Viewed by 9483
Abstract
Photocrosslinked hydrogels reinforced by microfibrillated cellulose (MFC) were prepared from a methacrylate-functionalized fish elastin polypeptide and MFC dispersed in dimethylsulfoxide (DMSO). First, a water-soluble elastin peptide with a molecular weight of ca. 500 g/mol from the fish bulbus arteriosus was polymerized by N [...] Read more.
Photocrosslinked hydrogels reinforced by microfibrillated cellulose (MFC) were prepared from a methacrylate-functionalized fish elastin polypeptide and MFC dispersed in dimethylsulfoxide (DMSO). First, a water-soluble elastin peptide with a molecular weight of ca. 500 g/mol from the fish bulbus arteriosus was polymerized by N,N′-dicyclohexylcarbodiimide (DCC), a condensation reagent, and then modified with 2-isocyanatoethyl methacrylate (MOI) to yield a photocrosslinkable fish elastin polypeptide. The product was dissolved in DMSO and irradiated with UV light in the presence of a radical photoinitiator. We obtained hydrogels successfully by substitution of DMSO with water. The composite gel with MFC was prepared by UV irradiation of the photocrosslinkable elastin polypeptide mixed with dispersed MFC in DMSO, followed by substitution of DMSO with water. The tensile test of the composite gels revealed that the addition of MFC improved the tensile properties, and the shape of the stress–strain curve of the composite gel became more similar to the typical shape of an elastic material with an increase of MFC content. The rheology measurement showed that the elastic modulus of the composite gel increased with an increase of MFC content. The cell proliferation test on the composite gel showed no toxicity. Full article
(This article belongs to the Special Issue Marine Biomaterials)
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10 pages, 450 KiB  
Article
Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition
by Michio Yamada, Chika I. Someya, Tsukasa Nakahodo, Yutaka Maeda, Takahiro Tsuchiya and Takeshi Akasaka
Molecules 2011, 16(11), 9495-9504; https://doi.org/10.3390/molecules16119495 - 14 Nov 2011
Cited by 18 | Viewed by 6928
Abstract
Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized [...] Read more.
Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized using Vis/NIR absorption spectroscopy and electrochemical measurements. This study demonstrates that glycosylidene carbene is useful to incorporate carbohydrate moieties onto endohedral metallofullerene surfaces. Full article
(This article belongs to the Special Issue Fullerene Chemistry)
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10 pages, 106 KiB  
Article
Isolation of Araguspongine M, a New Stereoisomer of an Araguspongine/Xestospongin alkaloid, and Dopamine from the Marine Sponge Neopetrosia exigua Collected in Palau
by Hongwei Liu, Yuri Mishima, Takeshi Fujiwara, Hiroshi Nagai, Akira Kitazawa, Yuji Mine, Hisayoshi Kobayashi, Xinsheng Yao, Junko Yamada, Taiko Oda and Michio Namikoshi
Mar. Drugs 2004, 2(4), 154-163; https://doi.org/10.3390/md204154 - 25 Nov 2004
Cited by 40 | Viewed by 14589
Abstract
A new stereoisomer of an araguspongine/xestospongin alkaloid, named araguspongine M (1), has been isolated together with 12 known compounds, araguspongines B (2) and D (3), dopamine, three galactosyl diacylglycerols, 24-methyl cholesterol, 5,6-dihydrocholesterol, β-sitosterol, and three 5α,8α-epidioxy sterols (11–13), from the marine sponge Neopetrosia [...] Read more.
A new stereoisomer of an araguspongine/xestospongin alkaloid, named araguspongine M (1), has been isolated together with 12 known compounds, araguspongines B (2) and D (3), dopamine, three galactosyl diacylglycerols, 24-methyl cholesterol, 5,6-dihydrocholesterol, β-sitosterol, and three 5α,8α-epidioxy sterols (11–13), from the marine sponge Neopetrosia exigua (formerly Xestospongia exigua) collected in Palau. The structure of 1 was assigned on the basis of its spectral data analysis. This is the first report on the isolation of dopamine from a marine sponge. This compound may be produced by an endosymbiotic Synechococcus-like cyanobacterium. Compounds 1–3 and 11–13 showed cytotoxicity against HL-60 at IC50’s of 5.5, 5.5, 5.9, 22.4, 9.5, and 9.6 μM, respectively. The possible biosynthesis origin of the isolated metabolites is discussed. Full article
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