Research activity information

• Dec. 2019 JSPS 12th Organocatalyst Simposium, Poster Award, Organic Base-Catalyzed Primary Alcohol-Selective Aroylation For Rapid Access to Complex Unexplored Prodrugs

  Yasuaki Morita, Rubi Nakashima, Bubwoong Kang, Masaki Kuse


• Dec. 2016 日本農芸化学会 関西支部, 日本農芸化学会 関西支部 支部賛助企業特別賞, 高輝度発光基質による発光タンパク質フォラシンの再構成と発光活性

  大西 里佳, KUSE MASAKI, TAKIKAWA HIROSATO

  Japan society


• Mar. 2016 日本農芸化学会, BBB論文賞, A concise synthesis of optically active solanacol, the germination stimulant for seeds of root parasitic weeds

  Hiroshi Kumagai, Mami Fujiwara, Masaki Kuse, Hirosato Takikawa

  Others


• Dec. 2013 日本農芸化学会関西支部, 日本農芸化学会関西支部賛助企業特別賞, 発光波長を改変する生物発光基質アナログの化学合成

  松岡絢香, 南郷成子, 古市卓也, 久世雅樹, TAKIKAWA HIROSATO

  Others


• Mar. 2013 日本農芸化学会, JSBBA Award for Young Scientists, 海洋生物由来の発光タンパク質に関する生物有機化学的研究

  Masaki KUSE


• 2000 天然有機化合物討論会, 第42回天然物有機化合物討論会 奨励賞, 沖縄産トビイカ(Symplectoteuthis oualaniensis L.)の発光タンパク質symplectinとその生物発光の分子機構の研究

  KUSE MASAKI

  International society


• 2000 財団法人サントリー生物有機科学研究所 研究助成金 (SUNBOR GRANT)


• 2000 財団法人サントリー生物有機科学研究所, 財団法人サントリー生物有機科学研究所, 光親和性標識と質量分析を用いた発光タンパクの活性中心に関する生物有機化学的研究

  KUSE MASAKI

  Others

• Bio-guided isolation and bioinformatic studies of cytotoxic phytosterols from Acanthospermum hispidum DC against breast (MCF7) and colorectal (HT29) cancer cells

  Alshaimaa A. Alnoor, Ashraf N. Abdalla, Fatma M. Abdel Bar, Omer Abdalla Ahmed Hamdi, Mohamed E. Elzubier, Hanaa H. A. Mohmed, Ayman A. Salkini, Masaki Kuse, Ehssan Moglad, Amira Mira

  Informa UK Limited, Jun. 2024, Arab Journal of Basic and Applied Sciences, 31(1) (1), 358 - 370, English

  [Refereed]

  Scientific journal


• Phenylpropanoids and neolignans isolated from Myristica fragrans enhance glucose uptake in myotubes

  Yasukiyo Yoshioka, Ryunoshin Kono, Masaki Kuse, Yoko Yamashita, Hitoshi Ashida

  Nutmeg is a promising functional food to prevent post-prandial hyperglycemia and type 2 diabetes mellitus by promoting glucose uptake in muscle.

  Royal Society of Chemistry (RSC), Mar. 2022, Food & Function, 13(7) (7), 3879 - 3893, English, International magazine

  [Refereed]

  Scientific journal


• Formylation Reaction of Amines Using N-Formylcarbazole.

  Bubwoong Kang, Yuki Shimizu, Yusaku Tamura, Eigo Fukuda, Ken-Ichiro Hamamoto, Yuichiro Uchida, Yoko Yasuno, Atsushi Nakayama, Tetsuya Satoh, Masaki Kuse, Tetsuro Shinada

  Formamides are useful starting materials for pharmaceutical syntheses. Although various synthetic methods have been documented in this regard, the use of N-formylcarbazole as a formylation reagent for amines has not yet been reported. We report here the first examples of the use of N-formylcarbazole for the formylation of amines. The characteristic reactivity of N-formylcarbazole enables the selective formylation of sterically less hindered aliphatic primary and secondary amines. In contrast, sterically bulkier amines and weakly nucleophilic amines such as anilines are less reactive under the reaction conditions.

  2022, Chemical & pharmaceutical bulletin, 70(7) (7), 492 - 497, English, Domestic magazine

  Scientific journal


• Anti-allergic property of 4,8-sphingadienine stereoisomers in vivo and in vitro model

  Haruka Shimizu, Masaki Kuse, Ken-ichiro Minato, Masashi Mizuno

  4,8-Sphingadienines (SD), metabolites of glucosylceramides (GlcCer), are sometimes determined as key mediators of the biological activity of dietary GlcCer, and cis/trans geometries of 4,8-SD have been reported to affect its activity. Since regulating excessive activation of mast cells seems an important way to ameliorate allergic diseases, this study was focused on cis/trans stereoisomeric-dependent inhibitory effects of 4,8-SD on mast cell activation. Degranulation of RBL-2H3 was inhibited by treatment of 4-cis-8-trans- and 4-cis-8-cis-SD, and their intradermal administrations ameliorated ear edema in passive cutaneous anaphylaxis reaction, but 4-trans-8-trans- and 4-trans-8-cis-SD did not. Although the activation of mast cells depends on the bound IgE contents, those stereoisomers did not affect IgE contents on RBL-2H3 cells after the sensitization of anti-TNP IgE. These results indicated that 4-cis-8-trans- and 4-cis-8-cis-SD directly inhibit the activation of mast cells. In conclusion, it was assumed that 4,8-SD stereoisomers with cis double bond at C4-position shows anti-allergic activity by inhibiting downstream pathway after activation by the binding of IgE to mast cells.

  Elsevier BV, Nov. 2021, Biochemical and Biophysical Research Communications, 577, 32 - 37, English, International magazine

  [Refereed]

  Scientific journal

  Link to Kobe Univ. Repository (Kernel)


• Isolation and identification of metabolites from ethyl acetate leaf extract of Solenostemma argel

  Hanaa Hassabelrasoul, Maiko Moriguchi, Bubwoong Kang, Awatif Ahmed Siribel, Masaki Kuse

  Corresponding, Oct. 2021, Agriculture and Natural Resources, 55, 757 - 763, English

  [Refereed]

  Scientific journal


• Mild Organic Base-Catalyzed Primary Alcohol-Selective Aroylation Reaction Using N-Aroylcarbazoles for Underexplored Prodrugs

  Yasuaki Morita, Bubwoong Kang, Rubi Nakashima, Yuki Shimizu, Asumi Sakai, Maiko Moriguchi, Yoko Yasuno, Tetsuya Satoh, Tetsuro Shinada, Masaki Kuse

  Jun. 2020, ChemRxiv, English


• N-Acylcarbazole as a selective transamidation reagent

  Bubwoong Kang, Yoko Yasuno, Hironori Okamura, Asumi Sakai, Tetsuya Satoh, Masaki Kuse, Tetsuro Shinada

  The Chemical Society of Japan, May 2020, Bulletin of the Chemical Society of Japan, 93(8) (8), 993 - 999

  [Refereed]

  Scientific journal


• Expression of recombinant apopholasin using a baculovirus–silkworm multigene expression system and activation via dehydrocoelenterazine

  Maiko Moriguchi, Ryo Takahashi, Bubwoong Kang, Masaki Kuse

  Corresponding, Apr. 2020, Bioorganic & Medicinal Chemistry Letters, 30(12) (12), 127177, English

  [Refereed]

  Scientific journal


• Concise synthesis of heliolactone, a non-canonical strigolactone isolated from sunflower

  Shunya Yamamoto, Taiki Atarashi, Masaki Kuse, Yukihiro Sugimoto, Hirosato Takikawa

  Mar. 2020, Bioscience, Biotechnology, and Biochemistry, 84, in press, English

  [Refereed]

  Scientific journal


• Ethyl Acetate Fraction of Solanum nigrum L.: Cytotoxicity, Induction of Apoptosis, Cell Cycle in Breast Cancer Cells, and Gas Chromatography-Mass Spectrometry Analysis

  Ehssan H, O. Moglad, Muddathir S. Alhassan, Eshtiyag A. Abdalkareem, Ashraf N. Abdalla, Masaki Kuse

  Sep. 2019, Asian Journal of Pharmaceutics, 13(3) (3), 246 - 251, English

  [Refereed]

  Scientific journal


• First synthesis and absolute configuration of phorbasin H, a diterpene carboxylic acid isolated from the sponge Phorbas gukulensis

  Kensuke Takahashi, Yusuke Ogura, Masaki Kuse, Hirosato Takikawa

  The first synthesis of phorbasin H, a diterpene carboxylic acid isolated from the sponge Phorbas gukulensis, was achieved using 1,4-trans-cyclohexanedimethanol and (S)-citronellal as starting materials. The data collected in this synthesis indicated the absolute configuration of the naturally occurring phorbasin H to be S.

  Aug. 2019, Bioscience, Biotechnology, and Biochemistry, 83(12) (12), 2198 - 2201, English

  [Refereed]

  Scientific journal


• Enhanced elevations of hypo-osmotic shock-induced cytosolic and nucleic calcium concentrations in tobacco cells by pretreatment with dimethyl sulfoxide

  Hieu T, H. Nguyen, François Bouteau, Christian Mazars, KUSE MASAKI, Tomonori Kawano

  Dimethyl sulfoxide (DMSO) is a dipolar aprotic solvent widely used in biological assays. Here, we observed that DMSO enhanced the hypo-osmotically induced increases in the concentration of Ca 2+ in cytosolic and nucleic compartments in the transgenic cell-lines of tobacco (BY-2) expressing aequorin.

  日本農芸化学会, Feb. 2019, Bioscience, Biotechnology, and Biochemistry, 83(2) (2), 318 - 321, English

  [Refereed]

  Scientific journal


• Natural Products Responsible for Bioluminescence: Synthesis of Coelenterazines and Dehydrocoelenterazines

  MAIKO MORIGUCHI, SAYAKA IBA, KUSE MASAKI

  有機合成化学協会, Oct. 2018, Journal of Synthetic Organic Chemistry, 76(10) (10), 1000 - 1009, Japanese

  [Refereed]

  Scientific journal


• The involvement of calmodulin and protein kinases in the upstream of cytosolic and nucleic calcium signaling induced by hypoosmotic shock in tobacco cells

  H. T, H. Nguyen, F. Bouteau, C. Mazars, KUSE MASAKI, T. Kawano

  Aug. 2018, PLANT SIGNALING & BEHAVIOR, e1494467, 1 - 7, English

  [Refereed]

  Scientific journal


• First synthesis of (S)-(+)-hymenoic acid, a DNA polymerase λ inhibitor isolated from Hymenochaetaceae sp

  Kensuke Takahashi, Miki Matsui, Masaki Kuse, Hirosato Takikawa

  Hymenoic acid, isolated from cultures of the fungus, Hymenochaetaceae sp., is a specific inhibitor of DNA polymerase λ. The first synthesis of (S)-(+)-hymenoic acid was achieved by starting from trans-1,4-cyclohexanedimethanol and methyl (R)-(-)-3-hydroxyisobutyrate, and Julia-Kocienski olefination was employed as the key step.

  Japan Society for Bioscience Biotechnology and Agrochemistry, 2018, Bioscience, Biotechnology and Biochemistry, 82(1) (1), 42 - 45, English

  [Refereed]

  Scientific journal


• Total Synthesis of (+/-)-Ramariolides C and D

  Masaki Kuse, Maiko Moriguchi, Masashi Hachida, Hirosato Takikawa

  Ramariolides A-D (1-4) were isolated from the coral mushroom Ramaria cystidiophora, out of which 1 showed in vitro antimicrobial activity. The structural features of 1-4 are attractive synthetic targets. Here, we report the total synthesis of ramariolides C (3) and D (4). The vinylogous Mukaiyama aldol reaction was employed to construct the carbon skeletons of 3 and 4. The key precursors for the reaction were alpha-hydroxyaldehydes, which were prepared from cyanohydrins via reduction with diisobutylaluminum hydride (DIBAL). Successive acetylation of the aldol adducts and an elimination reaction of the resulting acetates yielded 3 and 4 upon treatment with tetra-n-butylammonium fluoride (TBAF) and acetic acid.

  CHEMICAL SOC JAPAN, Sep. 2017, CHEMISTRY LETTERS, 46(9) (9), 1409 - 1411, English

  [Refereed]

  Scientific journal


• Identification of (Z)-3:(E)-2-Hexenal Isomerases Essential to the Production of the Leaf Aldehyde in Plants

  Mikiko Kunishima, Yasuo Yamauchi, Masaharu Mizutani, Masaki Kuse, Hirosato Takikawa, Yukihiro Sugimoto

  The green odor of plants is characterized by green leaf volatiles (GLVs) composed of C6 compounds. GLVs are biosynthesized from polyunsaturated fatty acids in thylakoid membranes by a series of enzymes. A representative member of GLVs (E)-2-hexenal, known as the leaf aldehyde, has been assumed to be produced by isomerization from (Z)-3-hexenal in the biosynthesis pathway; however, the enzyme has not yet been identified. In this study, we purified the (Z)-3:(E)-2-hexenal isomerase (HI) from paprika fruits and showed that various plant species have homologous HIs. Purified HI is a homotrimeric protein of 110 kDa composed of 35-kDa subunits and shows high activity at acidic and neutral pH values. Phylogenetic analysis showed that HIs belong to the cupin superfamily, and at least three catalytic amino acids (His, Lys, Tyr) are conserved in HIs of various plant species. Enzymatic isomerization of (Z)-3-hexenal in the presence of deuterium oxide resulted in the introduction of deuterium at the C4 position of (E)-2-hexenal, and a suicide substrate 3-hexyn-1-al inhibited HI irreversibly, suggesting that the catalytic mode of HI is a keto-enol tautomerism reaction mode mediated by a catalytic His residue. The gene expression of HIs in Solanaceae plants was enhanced in specific developmental stages and by wounding treatment. Transgenic tomato plants overexpressing paprika HI accumulated (E)-2-hexenal in contrast to wild-type tomato plants mainly accumulating (Z)-3-hexenal, suggesting that HI plays a key role in the production of (E)-2-hexenal in planta.

  AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC, Jul. 2016, JOURNAL OF BIOLOGICAL CHEMISTRY, 291(27) (27), 14023 - 14033, English

  [Refereed]

  Scientific journal


• First synthesis of (+/-)-hostasolide A

  Shun Yamamoto, Masaki Kuse, Hirosato Takikawa

  Hostasolide A is a sesquiterpene lactone isolated from Hosta ensata. The first synthesis of (+/-)-hostasolide A was achieved by employing palladium-catalyzed CO insertion, acid-catalyzed epimerization, and gamma-hydroxylation of alpha,beta-unsaturated lactone as the key steps. (C) 2015 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Oct. 2015, TETRAHEDRON LETTERS, 56(42) (42), 5808 - 5810, English

  [Refereed]

  Scientific journal


• A concise synthesis of optically active solanacol, the germination stimulant for seeds of root parasitic weeds

  Hiroshi Kumagai, Mami Fujiwara, Masaki Kuse, Hirosato Takikawa

  Solanacol, isolated from tobacco (Nicotiana tabacum L.), is a germination stimulant for seeds of root parasitic weeds. A concise synthesis of optically active solanacol has been achieved by employing enzymatic resolution as a key step.

  TAYLOR & FRANCIS LTD, Aug. 2015, BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 79(8) (8), 1240 - 1245, English

  [Refereed]

  Scientific journal


• Chromophores in photoproteins of a glowing squid and mollusk

  Masaki Kuse

  Bioluminescence is a chemical reaction process for light emission in vivo. An organic substance is normally oxidized in the protein to obtain the energy required for the light emission. Determination of the structure of the substance is one of the most important parts of bioluminescent research. Photoproteins of a flying squid and a mollusk contain chromophores that are formed by connecting an apo-protein and dehydrocoelenterazine. The chromophore has a chemical structure that can emit light in a photoprotein. The structural analysis of the chromophores in the photoproteins is described.

  TAYLOR & FRANCIS LTD, May 2014, BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 78(5) (5), 731 - 736, English

  [Refereed][Invited]

  Scientific journal


• Formal synthesis of soybean phytoalexin glyceollin I

  Yuta Kohno, Masatsugu Koso, Masaki Kuse, Hirosato Takikawa

  Glyceollins are well-known phytoalexins isolated from soybean (Glycine max). An efficient three-step synthesis was developed for the preparation of the key intermediate in Khupse's glyceollin I synthesis. Claisen rearrangement-cyclization cascade reaction and Suzuki-Miyaura cross coupling were key steps in this method. (C) 2014 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Mar. 2014, TETRAHEDRON LETTERS, 55(10) (10), 1826 - 1828, English

  [Refereed]

  Scientific journal


• ヒカリカモメガイ由来の発光タンパク質（フォラシン） 小さな発見に至るまでの長い道のり

  KUSE MASAKI

  日本農芸化学会, Mar. 2014, 化学と生物, 52(3) (3), 166 - 171, Japanese

  [Refereed][Invited]

  Scientific journal


• Synthesis of 7-Oxo-5-deoxystrigol, a 7-Oxygenated Strigolactone Analog

  Masashi Tanaka, Yukihiro Sugimoto, Masaki Kuse, Hirosato Takikawa

  A straightforward synthesis of 7-oxo-5-deoxystrigol, a 7-oxygenated strigolactone analog, was achieved by starting from 2,2-dimethylcyclohexane-1,3-dione.

  TAYLOR & FRANCIS LTD, Apr. 2013, BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 77(4) (4), 832 - 835, English

  [Refereed]

  Scientific journal


• First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

  Kimiharu Nakazaki, Kojiro Hayashi, Shintaro Hosoe, Takuya Tashiro, Masaki Kuse, Hirosato Takikawa

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Nov. 2012, TETRAHEDRON, 68(44) (44), 9029 - 9034, English

  [Refereed]

  Scientific journal


• P-66 Luminescent mechanism of a photoprotein, Pholasin(Poster Presentation)

  Kuse Masaki, Tanaka Eiko, Furuichi Takuya, Nango Naruko, Kubo Naohiro, Takikawa Hirosato, Nishikawa Toshio

  Imaging of biological components is a fundamental and important technology in life science. Bioluminescent imaging enables high-sensitive and non-invasive detection of biological components. Green fluorescent protein (GFP) emits light under irradiation of UV light. Static imaging of reporter genes in living cells has been achieved by using GFP. Luciferases and photoproteins require biological components (such as reactive oxygen species (ROS), calcium ion, and ATP) for light emission. These proteins enable dynamic imaging of biological components in living cells. Pholasin is a photoprotein of a common piddock, Pholas dactylus, which emits light in the presence of ROS. Pholasin is commercially available as a ROS indicator. Pholasin has a chromophore for emission of light and its structure has not been determined. Here we report that the chromophore is constituted from apo-Pholasin and dehydrocoelenterazine (DCL). DCL is the organic substance of symplectin, a photoprotein of a luminescent squid (Symplectoteuthis oualaniensis), and is a component of the chromophore of symplectin. Luminescence of symplectin is also initiated by ROS. The similar involvement of ROS in the luminescence of Pholasin and symplectin formulated a hypothesis that DCL might be the organic substance of Pholasin. Actually, addition of DCL resulted in enhancing the activity of Pholasin. The existence of DCL in Pholasin was evidenced by isolating DCL as dithiothreitol adduct from Pholasin. The structure was identified by LC-MS comparing with the synthetic compound. From these results, we concluded that DCL is the organic substance of Pholasin and forms the chromophore for emission of light.

  Symposium on the chemistry of natural products, Sep. 2012, Symposium on the Chemistry of Natural Products, symposium papers, (54) (54), 651 - 656, Japanese


• Dynamic Chirality Determines Critical Roles for Bioluminescence in Symplectin-Dehydrocoelenterazine System

  Vorawan Kongjinda, Yosuke Nakashima, Naoki Tani, Masaki Kuse, Toshio Nishikawa, Chin-Hui Yu, Nobuyuki Harada, Minoru Isobe

  Symplectin is a photoprotein containing the dehydrocoelenterazine (DCL) chromophore, which links to a cysteine residue through a covalent bond with the emission of blue light. This study focuses on the stereochemical process of the emerging stereogenic centers. Two isomeric fluorinated DCL analogs (2,4-diF- and 2,6-diF-DCL) were employed owing to their different bioluminescence activities, these being 200% and 20% compared to natural DCL, respectively. Each of these diF-DCLs was found to exchange with the natural DCL in symplectin at pH 6.0. The emerging stereogenic carbons were racemic at the binding sites. Changing the pH of this storage form to the protein's optimum solubility pH (pH 7.8) resulted in 2,4-diF-DCL-bound symplectin luminescence, and the spent solutions were then analyzed and coelenteramide-390-CGLK-peptide and coelenteramine were detected after a peptidase digestion. The same analysis of the 2,6-diF-DCL-bound symplectin, on the other hand, afforded coelenteramine only but no coelenteramide. When the racemic storage diF-DCLs moved to the active site at pH 7.8, a change in the chirality with the 390-Cys residue resulted. Model experiments using L-cysteine-containing CGLK-peptide supported two diastereoisomers from each diF-DCL. The significant difference in the luminescence from these two chromophores is attributed to a plausible mechanism including the dynamically variable stereogenic center emerging at the storage and then the active site on the symplectin. It is concluded that such dynamic chirality plays a significant role in the symplectoteuthis bioluminescence.

  WILEY-BLACKWELL, Aug. 2011, CHEMISTRY-AN ASIAN JOURNAL, 6(8) (8), 2079 - 2090, English

  [Refereed]

  Scientific journal


• Identification of a Fluorescent Compound in the Cuticle of the Train Millipede Parafontaria laminata armigera

  Masaki Kuse, Miho Yanagi, Eiko Tanaka, Naoki Tani, Toshio Nshikawa

  The train millipede (Parafontaria laminata arinigera) emits a blue fluorescence (lambda(max) = 455 nm) under black light (350 nm). The isolated fluorescent compound from the cuticle of P. laminata armigera was identified as pterin-6-carboxylic acid. The structure of this pound was identified by fluorescent, HPLC, and spectrometric (ESI-ion trap MS) analyses, and compared with an authentic sample.

  TAYLOR & FRANCIS LTD, Nov. 2010, BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 74(11) (11), 2307 - 2309, English

  [Refereed]

  Scientific journal


• Dehydrocoelenterazine is the Organic Substance Constituting the Prosthetic Group of Pholasin

  Eiko Tanaka, Masaki Kuse, Toshio Nishikawa

  WILEY-V C H VERLAG GMBH, Nov. 2009, CHEMBIOCHEM, 10(17) (17), 2725 - 2729, English

  [Refereed]

  Scientific journal


• Substituent Effect of Imino-O-arenesulfonates, a Coupling Partner in Suzuki-Miyaura Reaction for Substitution of the Pyrazine Ring: A Study for the Synthesis of Coelenterazine Analogs

  Arthit Makarasen, Masaki Kuse, Toshio Nishikawa, Minoru Isobe

  Amino(aryl)pyrazines, a key intermediate in the synthesis of coelenterazine and its analogs, can be prepared in excellent yields by utilizing imino-O-tosylates in the Suzuki-Miyaura reaction. These imino-O-tosylates serve as a substitute for the corresponding imino-O-triflates, which are sometimes too unstable to be stored during the optimization of the reaction conditions. Aryltrifluoroborates, a coupling partner, worked well when arylboronic acids or arylboronate esters were less reactive. Aryltrifluoroborates also worked well when containing an electron-donating group attached to the aromatic ring. The study of the substituent effect of imino-O-arenesulfonates demonstrated a major difference in the rate of the reactions when changing from electron-donating groups to electron-withdrawing groups at the para position of arenesulfonates. Imino-O-arenesulfonate containing a para-bromo substituent only gave the desired coupling product leaving the para substituent of arenesulfonate untouched.

  CHEMICAL SOC JAPAN, Jul. 2009, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 82(7) (7), 870 - 878, English

  [Refereed]

  Scientific journal


• H-1 NMR aided elucidation of products derived from photodegradation of ethyl 3-azido-4,6-difluorobenzoate in 2,2,2-trifluoroethanol

  Magne O. Sydnes, Masaki Kuse, Issei Doi, Minoru Isobe

  The major products formed upon photolysis of ethyl 3-azido-4,6-difluorobenzoate in 2,2,2,-tri-fluoroethanol-d(3) has been elucidated by H-1 NMR analysis of the product mixture. Among the products Formed and structurally elucidated was a hitherto unreported product formed during photolysis of aryl azides, namely azoxybenzene 19. The structural assignments of the major components of the reaction mixture were aided by comparison with H-1 NMR data from synthetic reference materials and compound isolation. MS, MS/MS, and HPLC analysis as well as UV spectroscopy was also employed in order to confirm and aid the structural analysis. (C) 2009 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, May 2009, TETRAHEDRON, 65(19) (19), 3863 - 3870, English

  [Refereed]

  Scientific journal


• Selective protein modification by the hydroperoxide intermediate in a photoprotein, aequorin

  Issei Doi, Masaki Kuse, Toshio Nishikawa, Minoru Isobe

  During the course of protein modi. cation program, we employed a recombinant aequorin, the apo-protein reconstituted with coelenterazine, and found out that the photolytic hyperperoxide modified three S-SCH(2)CHOHCHOHCH(2)SH groups to -S-SCH(2)CHOHCH = CH-S = O) H or -S-SCH(2)CHOHCH = CH-S(= O)OH of terminal DTT connected to cysteine residues of the C(145), C(152) and C(180), which turned out to locate near the chromophore. (C) 2009 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, May 2009, BIOORGANIC & MEDICINAL CHEMISTRY, 17(9) (9), 3399 - 3404, English

  [Refereed]

  Scientific journal


• Prevention of Copper-Induced Calcium Influx and Cell Death by Prion-Derived Peptide in Suspension-Cultured Tobacco Cells

  Tomoko Kagenishi, Ken Yokawa, Masaki Kuse, Minoru Isobe, Francois Bouteau, Tomonori Kawano

  Impact of copper on the oxidative and calcium signal transductions leading to cell death in plant cells and the effects of the copper-binding peptide derived from the human prion protein (PrP) as a novel plant-protecting agent were assessed using a cell suspension culture of transgenic tobacco (Nicotiana tabacum L., cell line BY-2) expressing the aequorin gene. Copper induces a series of biological and chemical reactions in plant cells including the oxidative burst reflecting the production of reactive oxygen species (ROS), such as hydroxyl radicals, and stimulation of calcium channel opening, allowing a transient increase in cytosolic calcium concentrations. The former was proven by the action of specific ROS scavengers blocking the calcium responses and the latter was proven by an increase in aequorin luminescence and its inhibition by specific channel blockers. Following these early events completed within 10 min, the development of copper-induced cell death was observed during additional 1 h in a dose-dependent manner. Addition of a synthetic peptide (KTNMKHMA) corresponding to the neurotoxic sequence in human PrP, prior to the addition of copper, effectively blocked both calcium influx and cell death induced by copper. Lastly, a possible mechanism of peptide action and future applications of this peptide in the protection of plant roots from metal toxicity or in favour of phytoremediation processes are discussed.

  VERLAG Z NATURFORSCH, May 2009, ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 64(5-6) (5-6), 411 - 417, English

  [Refereed]

  Scientific journal


• Differentiation of Coelenteramide Sulfates from Phosphates by Hydrogen/Deuterium Exchange Coupled with Ion Trap Mass Spectrometry

  DOI Issei, KUSE Masaki, NAKASHIMA Yosuke, TANI Naoki, ISOBE Minoru

  In general, it is difficult to distinguish between sulfate and phosphate groups in natural products, because these groups are found only in trace amounts in natural products. We have devised a hydrogen/deuterium (H/D) exchange method using the liquid chromatography mass spectrometry technique for establishing a general methodology to distinguish between sulfated and phosphorylated compounds. Sulfate- or phosphate-containing compounds were differentiated by the H/D exchange method based on the number of exchangeable hydrogen in deuterated sulfate (-SO₃D) and phosphate (-PO₃D₂), respectively. In this paper, we describe an application of this method to a natural product and in particular to Watasenia oxyluciferin that is found in the firefly squids (Hotaru-ika in Japanese) for the purpose of identifying coelenteramide disulfate.

  The Mass Spectrometry Society of Japan, 2009, J. Mass Spectrom. Soc. Jpn., 57(2) (2), 89 - 95, English

  [Refereed]


• Cysteine-390 is the binding site of luminous substance with symplectin, a photoprotein from Okinawan squid, Symplectoteuthis oualaniensis

  Minoru Isobe, Masaki Kuse, Naoki Tani, Tatsuya Fujii, Tsukasa Matsuda

  Symplectin is a photoprotein from a luminous squid, Symplectoteuthis oualaniensis. It has a luminous substrate, dehydrocoelenterazine (DCZ); linked through a thioether bond with a cysteine residue. We have proven the binding site of luminous substrate in symplectin by using an artificial analogue of DCZ, ortho-fluoro-DCZ (F-DCZ). F-DCZ-symplectin emitting strong blue light was reconstituted from apo-symplectin and F-DCZ. Proteolytic digestion of the reconstituted F-DCZ-symplectin afforded peptides including C-390 GLK-F-DCZ (amide), which was detected with a house assembled nano-LC-ESI-Q-TOF-MS. The chromo-peptide derived from the F-DCZ-symplectin after luminescence showed the lower molecular mass than that before the luminescence by, 12 mass units, corresponding to the loss of one carbon atom upon emitting light. Thus, we have concluded that F-DCZ analogue binds to Cys390 in symplectin so as to emit light.

  JAPAN ACAD, Nov. 2008, PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 84(9) (9), 386 - 392, English

  [Refereed]

  Scientific journal


• Pholasin luminescence is enhanced by addition of dehydrocoelenterazine

  Masaki Kuse, Eiko Tanaka, Toshio Nishikawa

  Pholasin is a bioluminescent photoprotein of Pholas dactylus. Pholasin is a commercially available photoprotein used to measure intracellular reactive oxygen species. Although extensive efforts have been carried out to determine the chemical structure of the prosthetic (chromophore) group, it still remains unclear to date. Herein, we report the enhancement of pholasin luminescence by the addition of dehydrocoelenterazine, which is organic substance of luminous squids' photoprotein. (C) 2008 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Oct. 2008, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 18(20) (20), 5657 - 5659, English

  [Refereed]

  Scientific journal


• Reductive monoalkylation of nitro aryls in one-pot

  Magne O. Sydnes, Masaki Kuse, Minoru Isobe

  The scope of the serendipitous reductive monoalkylation of ethyl (4-methoxy-3-nitrophenyl) acetate taking place during reduction of the nitro functionality to the corresponding primary amine when treated with hydrogen (I arm) over Pd/C (10%) in ethanol is investigated. Upon prolonged reaction time the reaction conducted in ethanol and methanol yields significant amount of the corresponding secondary amines, while when performed in n-butanol and i-propanol it only resulted in the formation of a small amount of the corresponding secondary amines. Further development of the reductive monoalkylation reaction provided conditions that: facilitate conversion of a range of different nitro aryls in one-pot to the corresponding secondary benzyl amino aryls in mostly good to excellent yields. This is accomplished by using hydrogen (1 arm) over Pd/C (10%) as reducing agent and benzaldehyde as the benzyl source combined with a stepwise reaction sequence. This chemistry was further extended to the formation of substituted benzyl amino aryls. The yields of the latter products varied dramatically depending on the substitution patterns associated with the benzaldehyde. However, by altering the reaction conditions it was possible to improve the yields of the benzylated products. (c) 2008 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Jun. 2008, TETRAHEDRON, 64(27) (27), 6406 - 6414, English

  Scientific journal


• Protein phosphatase inhibitory activity of tautomycin photoaffinity probes evaluated at femto-molar level

  Magne O. Sydnes, Masaki Kuse, Masakuni Kurono, Aya Shimomura, Hiroshi Ohinata, Akira Takai, Minoru Isobe

  Herein we describe the further improvement of our in-house developed firefly bioluminescence assay system for the determination of inhibition of protein phosphatase (PP). The advantage with the new system is higher sensitivity as well as being time and sample efficient. The inhibition activity of tautomycin with PP1 gamma was determined using the upgraded test system and K-i was found to be 4.5 nM, which compare favorably with the activity reported previously by others using different methods. The test system was then used in order to determine the activity of nine tautomycin (TTM) photoaffinity probes. One of the TTM photoaffinity probes (anti-10) was found to possess higher activity than the natural product itself with a K-i of 3.4 nM, while the remaining photoaffinity probes were found to possess K-i in the range of 8.0-213 nM. (C) 2007 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Feb. 2008, BIOORGANIC & MEDICINAL CHEMISTRY, 16(4) (4), 1747 - 1755, English

  [Refereed]

  Scientific journal


• Chemistry for biology of symplectin bioluminescence with fluoro-dehydrocoelenterazine.

  KUSE MASAKI

  2008, Chemiluminescence and Bioluminescence, 51 - 54, English

  [Refereed]

  Scientific journal


• Determination of solvent-trapped products obtained by photolysis of aryl azides in 2,2,2-trifluoroethonol

  Magne O. Sydnes, Issei Doi, Ayako Ohishi, Masaki Kuse, Minoru Isobe

  A series of nonfluorinated and fluorinated aryl azides with varied functionality patterns were irradiated in 2,2,2-trifluoroethanol with either a high-pressure or a low-pressure mercury lamp. Interestingly, one of the major products in these reactions was the result of the recombination of anilino and alkyl radicals to form the corresponding hemiaminal compounds. The structure of the recombination products was assigned unambiguously after proton/deuterium exchange experiments followed by MS and MS/MS analysis.

  WILEY-V C H VERLAG GMBH, 2008, CHEMISTRY-AN ASIAN JOURNAL, 3(1) (1), 102 - 112, English

  [Refereed]

  Scientific journal


• P-464 Photoaffinity Labeling of Aequorin with Nakanishi Protocol

  Doi Issei, Kuse Masaki, Isobe Minoru

  Symposium on the chemistry of natural products, Jul. 2006, International Symposium on the Chemistry of Natural Products, 2006, "P - 464", English


• Action of aluminum, novel TPC1-type channel inhibitor, against salicylate-induced and cold-shock-induced calcium influx in tobacco BY-2 cells

  C Lin, YW Yu, T Kadono, M Iwata, K Umemura, T Furuichi, M Kuse, M Isobe, Y Yamamoto, H Matsumoto, K Yoshizuka, T Kawano

  Previously, effect of A1 ions on calcium signaling was assessed in tobacco cells expressing a Ca2+ -monitoring luminescent protein, aequorin and a newly isolated putative plant Ca2+ channel protein from Arabidopsis thaliana. AtTPC1 (two-pore channel 1). TPC1 channels were shown to be the only channel known to be sensitive to At and they are responsive to reactive oxygen species and cryptogein, a fungal elicitor protein. Thus, involvement of TPC1 channels in calcium signaling leading to development of plant defense mechanism has been suggested. Then, the use of At as a specific inhibitor of TPC1-type plant calcium channels has been proposed. Here, using transgenic tobacco BY-2 cells expressing aequorin, we report on the evidence in support of the involvement of A1-sensitive signaling pathway requiring TPC1-type channel-dependent Ca2+ influx in response to salicylic acid, a key plant defense-inducing agent, but not to an elicitor prepared from the cell wall of rice blast disease fungus Magnaporthe grisea. In addition, involvement of A1-sensitive Ca2+ channels in response to cold shock was also tested. The data suggested that the elicitor used here induces the Ca2+ influx via A1-insensitive path, while salicylic acid and cold-shock-stimulate the influx of Ca2+ via At-sensitive mechanism. (c) 2005 Elsevier Inc. All rights reserved.

  ACADEMIC PRESS INC ELSEVIER SCIENCE, Jul. 2005, BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 332(3) (3), 823 - 830, English

  Scientific journal


• Synthesis of azide-fluoro-dehydrocoelenterazine analog as a photoaffinity-labeling probe and photolysis of azide-fluoro-coelenterazine

  M Kuse, Doi, I, N Kondo, Y Kageyama, M Isobe

  A photosensitive azide-fluoro-dehydrocoelenterazine analog (Az-F-DCT) was synthesized, starting from 4-fluorophenylacetic acid, as a photoaffinity-labeling probe in order to analyze symplectin active site. To examine the photo-reactivity of Az-F-DCT, azide-fluoro-coelenterazine analog (Az-F-CT) was used as a potent symplectin chromophore model. Photolysis of Az-F-CT in 2,2,2-trifluoroethanol afforded nitrene intermediate to give an insertion product. The structure of this product was confirmed through spectroscopic analyses particularly by using a proton/deuterium (H/D) exchange experiments with ESI-Q-TOF-MS and -MS/MS measurement. (c) 2005 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Jun. 2005, TETRAHEDRON, 61(24) (24), 5754 - 5762, English

  Scientific journal


• Novel synthetic route of coelenterazines-2-: Synthesis of various dehydrocoelenterazine analogs

  N Kondo, M Kuse, T Mutarapat, N Thasana, M Isobe

  The novel synthetic route to introduce various substituents into 5-position of coelenteramine is described. Difficulties, however, are observed in the attempted synthesis of some analogs having labile functional groups. This is due to the strong acid conc. H2SO4 after Suzuki-Miyaura coupling, so that the route was limited only to the synthesis for aminopyrazines having acid-stable functional groups. In this report, we describe alternative success in the deprotection of N-tosyl-animopyrazine triflate before the cross coupling; thus, we obtained the aminopyrazine triflate in high yield. This compound enables us to synthesize various coelenterazine analogs. This triflate was proven to be so important intermediate that the versatile synthesis for coelenterazine and dehydrocoelenterazine analogs was established through Suzuki-Miyaura or Sonogashira coupling.

  PERGAMON-ELSEVIER SCIENCE LTD, Apr. 2005, HETEROCYCLES, 65(4) (4), 843 - 856, English

  Scientific journal


• Studies on the bioluminescent mechanism of symplectin photoprotein

  M Isobe, T Matsuda, M Kuse, H Mori, T Fujii, N Kondo, Y Kageyama

  WORLD SCIENTIFIC PUBL CO PTE LTD, 2005, Bioluminescence & Chemiluminescence: Progress and Perspectives, 7 - 10, English

  International conference proceedings


• Aluminium as a specific inhibitor of plant TPC1 Ca2+ channels

  T Kawano, T Kadono, K Fumoto, F Lapeyrie, M Kuse, M Isobe, T Furuichi, S Muto

  In plant cells, Al ion plays dual roles as an inducer and an inhibitor of Ca2+ influx depending on the concentration. Here, the effects of Al on Ca2+ signaling were assessed in tobacco BY-2 cells expressing aequorin and a putative plant Ca2+ channel from Arabidopsis thaliana, AtTPC1 (two-pore channel 1). In wild-type cells (expressing only aequorin), Al treatment induced the generation of superoxide, and Ca2+ influx was secondarily induced by superoxide. Higher Al concentrations inhibited the Al-stimulated and superoxide-mediated Ca2+ influx, indicating that Ca2+ channels responsive to reactive oxygen species (ROS) are blocked by high concentration of Al. H2O2-induced Ca2+ influx was also inhibited by Al. Thus, inhibitory action of Al against ROS-induced Ca2+ influx was confirmed. Similarly, known Ca2+ channel blockers such as ions of La and Gd inhibited the H2O2-induced Ca2+ influx. While La also inhibited the hypoosmotically induced Ca2+ influx, Al showed no inhibitory effect against the hypoosmotic Ca2+ influx. The effects of Al and La on Ca2+ influx were also tested in the cell line overexpressing AtTPC1 and the cell line At TPC1-dependently cosuppressing the endogenous TPC1 equivalents. Notably, responsiveness to H2O2 was lost in the cosuppression cell line, thus TPC1 channels are required for ROS-responsive Ca2+ influx. Data also suggested that hypoosmotic shock induces TPC1-independent Ca2+ influx and Al shows no inhibitory action against the TPC1-independent event. In addition, AtTPC1 overexpression resulted in a marked increase in Al-sensitive Ca2+ influx, indicating that TPC1 channels participate in osmotic Ca2+ influx only when overexpressed. We concluded that members of TPC1 channel family are the only ROS-responsive Ca2+ channels and are the possible targets of Al-dependent inhibition. (C) 2004 Elsevier Inc. All rights reserved.

  ACADEMIC PRESS INC ELSEVIER SCIENCE, Nov. 2004, BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 324(1) (1), 40 - 45, English

  Scientific journal


• Molecular diversity of cereulide detected by means of nano-HPLC-ESI-Q-TOF-MS

  S Pitchayawasin, M Isobe, M Kuse, T Franz, N Agata, M Ohta

  Cereulide is a cyclic dodecadepsipeptide from a pathogenic bacteria Bacillus cereus, which shows the emetic toxicity. Molecular diversity, or variety in homologation was found as a minor constituent of this cyclic peptide. Its molecular weight is 1152 but its homologs were observed as 1138 and 1166, which had 14 mass lower and higher differences from cereulide. This homologation was observed in about 10% of cereulide. It seemed to be difficult to determine the heterogeneous amino acids directly by MS/MS analysis on the intact molecules of cereulide. And hydrolysis of this cyclic peptide gave dipeptides, which were analyzed to determine their heterogeneous components by means of nano-HPLC-ESI-Q-TOF-MS and MS/MS. Among all amino- and oxy-acids, we found that O-Val and O-Leu were the keys of variation in cereulide. These findings will be significant to establish an identification method for pathogenic bacteria on the basis of biosynthetic pathways. (C) 2004 Elsevier B.V. All rights reserved.

  ELSEVIER SCIENCE BV, Jul. 2004, INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 235(2) (2), 123 - 129, English

  Scientific journal


• Studies on the bioluminescent mechanism of the symplectin photoprotein

  KUSE MASAKI

  2004, Luminescence, 19, 157 - 158, English

  International conference proceedings


• Novel synthetic route of aryl-aminopyrazine

  M Kuse, N Kondo, Y Ohyabu, M Isobe

  We report a novel synthetic route of aryl-aminopyrazine through a new cyclization reaction by using a hydroxylamine. Starting from Boc-glycine and aminonitrile, the aminopyrazine ring was prepared in several steps. After trifluoromethane sulfonylation of the aminopyrazinone, the resultant triflate was subjected to Suzuki-Miyaura coupling reaction with aryl boronic acid to afford coelenteramine. (C) 2003 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2004, TETRAHEDRON, 60(4) (4), 835 - 840, English

  Scientific journal


• Complexation of cyclic dodecadepsipeptide, cereulide with ammonium salts

  S Pitchayawasin, M Kuse, K Koga, M Isobe, N Agata, M Ohta

  Cereulide is a principal toxin causing emetic syndrome which is produced by Bacillus cereus and has been known as potassium selective ionophore. This paper deals with its complexation with inorganic and organic ammonium ions to assign the higher structures similar to the complex with potassium ion by means of NMR and ESI-MS spectroscopy. Of particular interest, the detectable ions are not only at m/z 1191.8 as K+ complex but also (or sometimes exclusively) at m/z 1170.8 as NH4+ complex in its LC-MS analyses depending upon the conditions. This difference is due to the sample preparation and measurement condition. (C) 2003 Elsevier Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Oct. 2003, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13(20) (20), 3507 - 3512, English

  Scientific journal


• 「もの」が語るバイオサイエンス-2：発光物質が語るバイオサイエンス

  金久 保暁, 久世 雅樹, 磯部 稔

  日本農芸化学会, Sep. 2003, 化学と生物, 41(9) (9), 605 - 613, Japanese


• A novel photoprotein from oceanic squid (Symplectoteuthis oualaniensis) with sequence similarity to mammalian carbon-nitrogen hydrolase domains

  T Fujii, JY Ahn, M Kuse, H Mori, T Matsuda, M Isobe

  A 60-kDa photoprotein was selectively extracted from squid photogenic organ with 0.6 M KCl solution at pH 6 as luminescence-active forms. The photoprotein with fluorescence chromophore was eluted from size-exclusion HPLC mainly as oligomeric forms (about 200 kDa or more) with a trace amount of monomeric form of about 60 kDa. A limited tryptic digestion of the KCl-extract induced the cleavage into a 40-kDa fragment and a 16-kDa N-terminal fragment and the conversion to the monomeric form which still retained luminescence activity. Under UV light the 60-kDa protein and its 40-kDa fragment emitted fluorescence. Immunoblot analysis using specific antibody showed specific expression of the 60-kDa protein in the photogenic organ. Ammo acid sequences of the 60-kDa photoprotein, its 40- and 16-kDa fragments, and six peptides from the Lys-C digest revealed no sequence similarity to known photoproteins but significant similarity to the carbon-nitrogen hydrolase domain found in mammalian biotinidase and vanin (pantetheinase). (C) 2002 Elsevier Science (USA). All rights reserved.

  ACADEMIC PRESS INC ELSEVIER SCIENCE, May 2002, BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 293(2) (2), 874 - 879, English

  Scientific journal


• F-19-dehydrocoelenterazine as probe to investigate the active site of symplectin

  M Isobe, T Fujii, M Kuse, K Miyamoto, K Koga

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Mar. 2002, TETRAHEDRON, 58(11) (11), 2117 - 2126, English

  Scientific journal


• 7,8-dihydropterin-6-carboxylic acid as light emitter of luminous millipede, Luminodesmus sequoiae

  M Kuse, A Kanakubo, S Suwan, K Koga, M Isobe, O Shimomura

  A luminous millipede, Luminodesmus sequoiae, emits light centered at a wavelength of 500 nm. To determine the light emitter of this bioluminescent system. fluorescent compounds were isolated from pulverized cuticles. NMR and MS spectra of these compounds showed them to be pterin derivatives. Furthermore, proton/deuterium (HD) exchange experiments by ESI-Q-TOF-MS and -MS/MS measurements have proved to be a powerful tool for elucidating these heteroaromatic compounds. Finally? we have concluded that 7,8-dihydropterin-6-carboxylic acid. a new natural product. is the light emitter of Liminodesrmus bioluminescence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Apr. 2001, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 11(8) (8), 1037 - 1040, English

  Scientific journal


• Synthesis of C-13-dehydrocoelenterazine and NMR studies on the bioluminescence of a Symplectoteuthis model

  M Kuse, M Isobe

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Apr. 2000, TETRAHEDRON, 56(17) (17), 2629 - 2639, English

  Scientific journal


• High incorporation of L-amino acids to cereulide, an emetic toxin from Bacillus cereus

  M Kuse, T Franz, K Koga, S Suwan, M Isobe, N Agata, M Ohta

  Cereulide is a principal toxin causing emetic syndrome produced by Bacillus cereus. This paper deals with biosynthetic studies on this unusual cyclic depsipeptide toxin from C-13 labeled L-amino acid precursors (Val, Leu, Ala) upon cultivation in synthetic media. The analyses were made at atomic level of the constituent amino- or oxy-acids through NMR and ESI-MS/MS spectroscopic methods on cereulide and its hydrolysate dipeptides. The incorporation of the C-13 atom was 95% in each O-Val, O-Leu and L-Val, while 40% in D-Ala of cereulide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Apr. 2000, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 10(8) (8), 735 - 739, English

  [Refereed]

  Scientific journal


• 生物発光と化学エネルギー : インテリジェントなシグナルとしての生物発光(化学反応を介して姿を変えるエネルギー)

  磯部 稔, 久世 雅樹

  古来より人々を魅了してきた幻想的に発光する生物達。小さな生物の持つ化学エネルギーは極わずかなものだが, それを効率よく光に変換する精巧な仕組みがそこにある。ここでは, 生物発光の分子機構を分子のサイドから観ることで, 小さな生物でも強力な光を発することができる理由を解説する。また, 生物個体間で用いるシグナルとしての生物発光を, よりインテリジェントなシグナルとして, 分子対分子のシグナルのモニターとして応用した研究例を紹介する。

  社団法人日本化学会, Jan. 2000, 化学と教育, 48(1) (1), 22 - 25, Japanese


• Chemistry of photoproteins as interface between bioactive molecules and protein function

  M Isobe, T Fujii, S Suwan, M Kuse, K Tsuboi, A Miyazaki, MC Feng, JM Li

  Bioluminescence of Okinawan squid includes a photoprotein named "Symplectin" which gives light by addition of Na+ (or K+). The chromophore is covalently bound-imidazopyrazinone analog to protein. Symplectin was extracted with 0.6M KCl and was analyzed to be composed of 3 different molecular-size proteins. Symplectin A, the smallest photoproteins, was purified by gel permeation chromatography to have 15kd by MALDI/TOF mass spectrometry. The molecular mechanism of this luminescence is described. Bioluminescence is also applied for trace analyses and the chromophore in some new fireflies is chemically analyzed. We made a very sensitive detection system of luciferin to a detection limit of 10(-16) mol/10 mu l by using immobilized luciferase and a single photon-counter. An example of the firefly luminescence application is demonstrated in an inhibitory-assay of protein phosphatase activity by inhibitors in the same class of tautomycin/okadaic acid.

  BLACKWELL SCIENCE LTD, Nov. 1998, PURE AND APPLIED CHEMISTRY, 70(11) (11), 2085 - 2092, English

  Scientific journal


• Synthesis of C-13-dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence

  M Isobe, M Kuse, Y Yasuda, H Takahashi

  In the photoprotein of an Okinawan squid bioluminescence of Symplectoteuthis oualaniensis L a dehydrocoelenterazine has been assigned as a chromophoric precursor to its apoprotein. To prove this mechanism, we have established new synthetic route to ca. 100 %C-13 incorporated dehydrocoelenterazine and coelenterazine at the neighboring carbon of the 2-position of 2,3-dihydroimidazo-[1,2a]-pyrazinone skeleton. This C-13 enriched dehydrocoelenterazine readily converted in equilibrium between its adduct forms as a diastereomixture with glutathione (GSH) or dithiothreitol (DTT) compounds having sulfhydryl group. Structures of such adducts were fixed under acidic conditions and then discussed by NMR spectroscopy as well as absorbance and fluorescence spectra. (C) 1998 Elsevier Science Ltd. All rights reserved.

  PERGAMON-ELSEVIER SCIENCE LTD, Oct. 1998, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 8(20) (20), 2919 - 2924, English

  Scientific journal


• Synthesis and Proof of 1,2-Dioxetanone: Low-temperature Photooxygenation of Coelenterate Luciferin Analog

  KUSE MASAKI

  1998, LANDMARKS IN PHOTOBIOLOGY, 149 - 156, English

  International conference proceedings


• Cremiluminescence and Bioluminescence, and its application

  ISOBE MINORU, KUSE MASAKI

  公益社団法人日本薬学会, Jan. 1998, Farumashia, 34(1) (1), 20 - 24, Japanese

  Scientific journal


• Recent advances of chemistry of bioluminescence

  M Isobe, T Fujii, K Usami, M Kuse

  JAPAN BIOCHEMICAL SOC, Nov. 1996, SEIKAGAKU, 68(11) (11), 1683 - 1691, Japanese

  Scientific journal

• Development of primary alcohol-specific aroylation reaction using recyclable aroylating reagents

  森田康明, 中島瑠美, 姜法雄, 久世雅樹

  Mar. 2020, 日本薬学会第140回年会（京都）講演要旨集, Japanese

  Summary national conference


• Asymmetric Total Synthesis of A Benzylic Cyclopropane-Having Cannabinoid, Radulanin J

  大江拓人, 姜法雄, 久世雅樹

  Mar. 2020, 日本農芸化学会2020年度福岡大会講演要旨集, Japanese

  Summary national conference


• Synthesis and luminescent activity of N-Ar-DCL analogs

  森口舞子, KANG Bubwoong, 滝川浩郷, 久世雅樹

  2020, 日本農芸化学会大会講演要旨集(Web), 2020


• Asymmetric Total Synthesis of Radulanin J

  Takuto Oe, Bubwoong Kang, Masaki Kuse

  Jan. 2020, 第16回六甲有機合成研究会, Japanese


• N-アロイルカルバゾールによるアロイル化反応の開発と未開拓プロドラッグの位置特異的合成

  森田康明, 中島瑠美, 姜法雄, 久世雅樹

  Dec. 2019, 若手フロンティア研究会2019

  Summary national conference


• Organic Base-Catalyzed Primary Alcohol-Selective Aroylation For Rapid Access to Complex Unexplored Prodrugs

  Yasuaki Morita, Rubi Nakashima, Bubwoong Kang, Masaki Kuse

  Dec. 2019, 第12回 有機触媒シンポジウム講演要旨集, English

  Summary international conference


• Application of A New Rapid Chromene Construction Catalyzed by DBU to the First Total Synthesis of Radulanin J

  Takuto Oe, Bubwoong Kang, Masaki Kuse

  Dec. 2019, 第12回 有機触媒シンポジウム講演要旨集, English

  Summary international conference


• N-ベンゾイルカルバゾールによる第一級アルコール選択的ベンゾイル化反応の開発

  姜法雄, 森田康明, 中島瑠璃, 久世雅樹

  Oct. 2019, 第69回日本薬学会関西支部総会・大会


• N-ベンゾイルカルバゾールによる第一級アルコール選択的ベンゾイル化法の開発と、複雑分子迅速誘導化への応用

  森田康明, 中島瑠美, 姜法雄, 久世雅樹

  Sep. 2019, 日本農芸化学会関西・中部支部 2019年度合同神戸大会講演要旨集, Japanese

  Summary national conference


• Radulanin I-Kの合成研究

  大江拓人, 姜法雄, 久世雅樹

  Sep. 2019, 日本農芸化学会関西・中部支部 2019年度合同神戸大会講演要旨集


• Cis- / Trans-Selective Synthesis of Sphingadienines

  Ikki Nakamura, Bubwoong Kang, Masashi Mizuno, Masaki Kuse

  Sep. 2019, 日本農芸化学会関西・中部支部 2019年度合同神戸大会講演要旨集


• N, O-アリールデヒドロセレンテラジン誘導体の合成

  森口舞子, 姜法雄, 滝川浩郷, 久世雅樹

  Sep. 2019, 日本農芸化学会関西・中部支部 2019年度合同神戸大会講演要旨集, 510th


• デヒドロセレンテラジン(DCL)およびDCL誘導体の化学合成

  森口舞子, 滝川浩郷, 久世雅樹

  2019, 日本農芸化学会大会講演要旨集(Web), 2019


• ビニロガス向山アルドール反応を利用したブテノリド骨格の構築

  森口舞子, 久世雅樹, 滝川浩郷

  2018, 日本農芸化学会大会講演要旨集(Web), 2018


• ビニロガス向山アルドール反応を利用したブテノリド骨格の構築

  森口舞子, 久世雅樹, 滝川浩郷

  2017, 日本農芸化学会中四国支部講演会講演要旨集(Web), 49th


• Ramariolide類の化学合成

  森口舞子, 久世雅樹, 滝川浩郷

  2017, 日本農芸化学会大会講演要旨集(Web), 2017


• Selective Oxidation by the Hydroperoxide in the Photoprotein, Aequorin

  Doi, I, Kuse, M, Nishikawa, T, Isobe, M

  2009, Bioorg. Med. Chem., 17, 3399-3404, English

  [Refereed]

  Report scientific journal


• Imino-O-Tosylate in Suzuki-Miyaura Reaction for substitution of the Pyrazine Rings: A Study for the Synthesis of Coelenterazine Analogs.

  Makarasen, A, Kuse, M, Nishikawa, T, Isobe, M

  2009, Bull. Chem. Soc. Jpn., 82, 870-878, English

  [Refereed]

  Report scientific journal


• 23 Molecular Mechanism of Luminous Jellyfish Bioluminescence by means of Photolysis of Aequorin(Oral Presentation)

  Doi Issei, Kuse Masaki, Nishikawa Toshio, Isobe Minoru

  Our research has been focusing on the molecular mechanism of a luminous jellyfish, Aequorea aequorea. This jellyfish has a photoprotein (aequorin), which contains coelenterazine (CL) as a chromophore. The chromophore exists as an imidazopyrazinone peroxide as comfirmed by X-ray crystallography studies by Shimomura. We have tried to perform a dynamic analysis of CL, which is only observed on the surface of aequorin. Upon photolysis of the hydroperoxide in aequorin, we found several oxidation points. These modified sites were analyzed by using nano-LC-ESI-ion-trap (IT) -MSn using our pre-pack...

  Symposium on the chemistry of natural products, 01 Sep. 2008, 天然有機化合物討論会講演要旨集, (50) (50), 161 - 166, Japanese


• 17 Molecular Mechanisms of Bioluminescence of Symplectin. a Photoprotein from Okinawan Squid, Symplectoteuthis oualaniensis L.

  Isobe Minoru, Kuse Masaki, Fujii Tatsuya, Takahashi Hiroyuki, Ohshima Kenji, Mori Hitoshi, Ahn J.-Y, Matsuda Tsukasa

  We have been studying on a bioluminescence system of an oceanic luminous squid. Symplectoteuthis oualaniensis L. In 1981, Tsuji and Leisman reported that a homogenate of the luminous organ of this squid gave light in the presence of monocations such as Na^+, K^+ and molecular oxygen at pH 7.8. In 1993, we succeeded in the extraction of a photoprotein. named symplectin, responsible for the bioluminescence in a 0.6M KCl solution from the same squid S. oualaniensis collected in Okinawa, Japan. We reported that this photoprotein includes dehydrocoelenterazine(2) as the chromophore which covalen...

  Symposium on the chemistry of natural products, 01 Oct. 2000, 天然有機化合物討論会講演要旨集, (42) (42), 97 - 102, Japanese


• 化学発光と生物発光及びその利用

  ISOBE MINORU, KUSE MASAKI

  The Pharmaceutical Society of Japan, 01 Jan. 1998, Farumashia, 34(1) (1), 20 - 24, Japanese


• 群選択的ヘテロ共役付加反応の確立 : 有機化学・天然物化学

  久世 雅樹, 磯部 稔

  社団法人日本農芸化学会, 05 Mar. 1996, 日本農藝化學會誌, 70, 1683 - 1691, Japanese


• Cremistry of Bioluminescence ; Recent Progress

  1996, Biochemistry, 68(11) (11), 1683

• Marine Bioluminescence with Dehydrocoelenterazine, an Imidazopyrazinone Compound. In: . Topics in Heterocyclic Chemistry.

  Masaki Kuse

  Single work, Springer, Berlin, Heidelberg, Sep. 2020


• 農芸化学分野における質量分析

  KUSE MASAKI

  Single work, 「農芸化学の事典」, 2003, Japanese

  Scholarly book

• From darkness to light: Investigating the chemical basis of pholasin’s bioluminescent mechanism

  Maiko Moriguchi, Masaki Kuse

  Pure and Applied Chemistry International Conference 2024, Jan. 2024, English

  [Invited]

  Invited oral presentation


• Structural simplification of maytansine and synthesis efficiency for antitumor activity

  Tomomi Uchida, Mayuka Fujimoto, Maina Minamino, Masaki Kuse

  Pure and Applied Chemistry International Conference 2024, Jan. 2024, English

  Oral presentation


• Chemical synthesis research of sea urchin feeding inhibitory substances

  Saki Tanaka, Masaki Kuse

  Pure and Applied Chemistry International Conference 2024, Jan. 2024, English

  Poster presentation


• Bioluminescence for the Assay of Anti-cancer Activity of Natural Products

  Masaki Kuse

  11th International Scientific Conference of National Center for Research, Sudan, Dec. 2022, English

  [Invited]

  Invited oral presentation


• 高輝度発光型デヒドロセレンテラジン（DCL）誘導体の合成と人口フォラシンの創製

  森口舞子, 久世雅樹

  生物発光化学発光研究会 第37回学術講演会, Nov. 2022, Japanese

  Oral presentation


• Bioluminescence for the Assay of Anti-cancer Activity

  The International Conference and Exhibition on Pharmaceutical Sciences and Technology 2022, Jun. 2022, English

  [Invited]

  Invited oral presentation


• ヒカリカモメガイ由来の 発光タンパク質に関する有機化学的研究

  久世雅樹

  日本農芸化学会中四国支部 第32回若手シンポジウム, Jul. 2021, Japanese

  [Invited]

  Invited oral presentation


• Asymmetric Total Synthesis of A Benzylic Cyclopropane-Having Cannabinoid, Radulanin J

  大江 拓人, 姜 法雄, 久世 雅樹

  日本農芸化学会 2020年度大会, Mar. 2020, Japanese

  Oral presentation


• Synthesis and luminescent activity of N-Ar-DCL analogs

  森口 舞子, 姜 法雄, 滝川 浩郷, 久世 雅樹

  日本農芸化学会 2020年度大会, Mar. 2020, Japanese

  Oral presentation


• Isolation and identification of bioactive constituents of Striga hermonthica

  Hanaa Hassab, Masaki Kuse

  JSBBA Kansai 6th Student Forum, Nov. 2019, English

  Oral presentation


• N-ベンゾイルカルバゾールによる第一級アルコール選択的ベンゾイル化法の開発と、複雑分子迅速誘導化への応用

  森田康明, 中島瑠美, 姜 法雄, 久世雅樹

  日本農芸化学会 関西・中部支部 2019年度合同神戸大会, Sep. 2019, Japanese, Domestic conference

  Oral presentation


• Radulanin I-Kの合成研究

  大江拓人, 姜 法雄, 久世雅樹

  日本農芸化学会 関西・中部支部 2019年度合同神戸大会, Sep. 2019, Japanese, Domestic conference

  Oral presentation


• N, O-アリールデヒドロセレンテラジン誘導体の合成

  森口舞子, 姜 法雄, 滝川浩郷, 久世雅樹

  日本農芸化学会 関西・中部支部 2019年度合同神戸大会, Sep. 2019, Japanese, Domestic conference

  Oral presentation


• 幾何選択的なスフィンガジエニン類の合成研究

  中村逸揮, 姜 法雄, 水野雅史, 久世雅樹

  日本農芸化学会 関西・中部支部 2019年度合同神戸大会, Sep. 2019, Japanese, Domestic conference

  Oral presentation


• ヒカリカモメガイの光る仕組みを有機化学で解明する

  KUSE MASAKI

  日本農芸化学会中四国支部 第29回 若手シンポジウム, May 2019, Japanese, 岡山大学農学部, Domestic conference

  [Invited]

  Invited oral presentation


• デヒドロセレンテラジン(DCL)およびDCL 誘導体の化学合成

  MORIGUCHI MAIKO, TAKIKAWA HIROSATO, KUSE MASAKI

  日本農芸化学会 ２０１９年度大会, Mar. 2019, Japanese, 東京, Domestic conference

  Oral presentation


• カーラクトン酸の合成研究

  溝川 孝紀, 大倉 裕貴, 滝川 浩郷, MIYAKE HIDEYOSHI, 新子 大樹, SUGIMOTO YUKIHIRO, KUSE MASAKI

  日本農芸化学会 ２０１９年度大会, Mar. 2019, Japanese, 東京, Domestic conference

  Oral presentation


• Phorbasin H および I の合成研究

  髙橋 健輔, KUSE MASAKI, 森 直紀, 滝川 浩郷

  日本農芸化学会 ２０１９年度大会, Mar. 2019, Japanese, 東京, Domestic conference

  Oral presentation


• 8-Methoxyvestitol の合成研究

  大江 拓人, 滝川 浩郷, KUSE MASAKI

  日本農芸化学会 ２０１９年度大会, Mar. 2019, Japanese, 東京, Domestic conference

  Oral presentation


• Towards Maximum Utilization of the Noxious Invasive Root Parasitic Weeds, Striga spp.

  KUSE MASAKI

  SATREPS SYmposium on Striga Managemnet, Sep. 2018, English, Conference Hall, Ministry of Higher Education, Sudan, International conference

  Oral presentation


• キノリン骨格から誘導されるアライン中間体を利用した環化付加反応

  小玉 彩友美, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会2018年度大会「名古屋」, Mar. 2018, Japanese, 名城大学, Domestic conference

  Oral presentation


• アルキリデンブテノリド骨格の選択的な構築法によるramariolide類の合成

  森口 舞子, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会2018年度大会「名古屋」, Mar. 2018, Japanese, 名城大学, Domestic conference

  Oral presentation


• Synthesis of Ramariolide A, C, and D

  森口 舞子, 八田 雅士, TAKIKAWA HIROSATO, KUSE MASAKI

  JSBBA KANSAI 4th Student Forum, Nov. 2017, English, 神戸大学 瀧川記念学術交流会館, International conference

  Poster presentation


• Sorgomolの光学活性体の合成研究

  HASHIMOTO RINA, KUSE MASAKI, TAKIKAWA HIROSATO

  第32回農薬デザイン研究会, Nov. 2017, Japanese, 大手町サンスカイルーム, Domestic conference

  Poster presentation


• 7-Oxoorobancholの光学活性体合成に関する研究

  NAKAHASHI KAZUYUKI, KUSE MASAKI, TAKIKAWA HIROSATO

  第32回農薬デザイン研究会, Nov. 2017, Japanese, 大手町サンスカイルーム, Domestic conference

  Poster presentation


• 発光タンパク質（フォラシン）阻害剤のデザインと合成

  井庭 早耶香, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 関西・中四国・西日本支部 2017年度合同大阪大会, Sep. 2017, Japanese, 大阪府立大学, Domestic conference

  Oral presentation


• ビニロガス向山アルドール反応を利用したブテノリド骨格の構築

  森口 舞子, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 関西・中四国・西日本支部 2017年度合同大阪大会, Sep. 2017, Japanese, 大阪府立大学, Domestic conference

  Oral presentation


• キノリン骨格から誘導されるアライン中間体を利用した環化付加反応

  小玉 彩友美, 岡 栞里, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 関西・中四国・西日本支部 2017年度合同大阪大会, Sep. 2017, Japanese, 大阪府立大学, Domestic conference

  Oral presentation


• Hymenoic acidの合成研究

  髙橋健輔, KUSE MASAKI, TAKIKAWA HIROSATO

  第61回香料・テルペンおよび精油化学に関する討論会, Sep. 2017, Japanese, 金沢工業大学, Domestic conference

  Oral presentation


• Synthesis of Ramariolide A, C, and D

  森口 舞子, 八田 雅士, TAKIKAWA HIROSATO, KUSE MASAKI

  18th Tetrahedron Symposium Asia Editon, Jul. 2017, English, Melbourne, Australia, International conference

  Poster presentation


• Design and Synthesis of Substrate Analogs for Pholasin Bioluminescence

  KUSE MASAKI, 大西 里佳, 松岡 絢香, TAKIKAWA HIROSATO

  18th Tetrahedron Symposium Asia Editon, Jul. 2017, English, Melbourne, Australia, International conference

  Poster presentation


• 発光タンパクで利用されるヘテロ芳香環化合物の合成と活性評価

  KUSE MASAKI

  近畿化学協会 ヘテロ原子部会 平成２９年度第１回懇話会, May 2017, Japanese, 岩谷産業(株)中央研究所, Domestic conference

  [Invited]

  Invited oral presentation


• 高輝度発光基質による発光タンパク質フォラシンの再構成と発光活性

  大西 里佳, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 ２０１７年度大会, Mar. 2017, Japanese, 京都女子大, Domestic conference

  Oral presentation


• Sorgomol光学活性体の合成

  RIKO YAMADA, DAISUKE HATA, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 ２０１７年度大会, Mar. 2017, Japanese, 京都女子大, Domestic conference

  Oral presentation


• Ramariolide類の化学合成

  森口 舞子, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 ２０１７年度大会, Mar. 2017, Japanese, 京都女子大, Domestic conference

  Oral presentation


• Artemisidiyne Aの合成研究

  KOKI MAEDA, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 ２０１７年度大会, Mar. 2017, Japanese, 京都女子大, Domestic conference

  Oral presentation


• 高輝度発光基質による発光タンパク質フォラシンの再構成と発光活性

  大西 里佳, KUSE MASAKI, TAKIKAWA HIROSATO

  日本農芸化学会 関西支部 第４９７回講演会, Dec. 2016, Japanese, 神戸大学 農学部, Domestic conference

  Oral presentation


• ストリゴラクトン基本骨格の新規合成法開発に関する研究

  熊谷洋, 久世雅樹, 滝川浩郷

  第30回農薬デザイン研究会, Nov. 2015, Japanese, メルパルク京都, Domestic conference

  Poster presentation


• First Synthesis of (+/-)-Hostasolide A

  Shun Yamamoto, Masaki Kuse, Hirosato Takikawa

  The 13th International Kyoto Conference on New Aspects of Organic Chemistry, Nov. 2015, English, Rihga Royal Hotel KYOTO, International conference

  Poster presentation


• 3-フェニルクロマンの新規合成法開発とその天然物合成への展開

  森口正太郎, 河野雄太, 久世雅樹, 滝川浩郷

  第30回農薬デザイン研究会, Nov. 2015, Japanese, メルパルク京都, Domestic conference

  Poster presentation


• 7-Oxoorobancholの光学活性体合成に関する研究

  新子大樹, 田中政志, 久世雅樹, 滝川浩郷

  2015年度日本農芸化学会中部・関西支部合同大会, Sep. 2015, Japanese, 富山県立大学, Domestic conference

  Oral presentation


• 抗マイコバクテリア活性を示すRamariolide Aの化学合成

  八田 雅士, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会 ２０１５年度大会, Mar. 2015, Japanese, 岡山大学, Domestic conference

  Oral presentation


• Soranacolの光学活性体合成

  熊谷 洋, 久世 雅樹, 滝川 浩郷

  日本農薬学会第40回大会, Mar. 2015, Japanese, 玉川大学, Domestic conference

  Oral presentation


• 抗マイコバクテリア活性を示すRamariolide Aの化学合成

  八田 雅士, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会 ４８７回関西支部例会, Dec. 2014, Japanese, 神戸大学, Domestic conference

  Oral presentation


• 4-(2-メチル-1,3-ブタジエニル)ブタノリド構造を有するテルペン類の合成研究

  山本 駿, 久世 雅樹, 滝川 浩郷

  第58回香料・テルペンおよび精油化学に関する討論会, Sep. 2014, Japanese, 和歌山大学, Domestic conference

  Oral presentation


• 発光タンパク質（フォラシン）の発光基質誘導体の合成とその発光活性

  松岡 絢香, 南郷 成子, 古市 卓也, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会大会, Mar. 2014, Japanese, 明治大学, Domestic conference

  Oral presentation


• Hostasolide A の合成研究

  山本 駿, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会大会, Mar. 2014, Japanese, 明治大学, Domestic conference

  Oral presentation


• 発光波長を改変する生物発光基質アナログの化学合成

  松岡 絢香, 南郷 成子, 古市 卓也, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会関西支部会 第482回 講演会, Dec. 2013, Japanese, 神戸：神戸大学, Domestic conference

  Oral presentation


• 海洋生物由来の発光タンパク質に関する生物有機化学的研究

  KUSE MASAKI

  日本農芸化学会関西支部会 第482回 講演会, Dec. 2013, Japanese, 神戸：神戸大学, Domestic conference

  [Invited]

  Invited oral presentation


• Sorgomolの光学活性体の合成研究

  秦 大輔, 北原 彩子, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会関西支部会 第482回 講演会, Dec. 2013, Japanese, 神戸：神戸大学, Domestic conference

  Oral presentation


• Sorgomolの光学活性体の合成研究

  秦 大輔, 北原 彩子, KUSE MASAKI, 滝川 浩郷

  第28回 農薬デザイン研究会, Nov. 2013, Japanese, 京都：メルパルク京都, Domestic conference

  Oral presentation


• トビイカとヒカリカモメガイの生物発光に関する研究

  KUSE MASAKI

  第8回化学生態学研究会, Jun. 2013, Japanese, 湯川プリンスホテル渚亭、函館, Domestic conference

  [Invited]

  Invited oral presentation


• 蛍光性デヒドロセレンテラジン類を用いた発光タンパク質の構築

  南郷 成子, 久保 尚洋, 久世 雅樹, 滝川 浩郷

  日本農芸化学会 2013年度大会, Mar. 2013, Japanese, 東北大学, Domestic conference

  Oral presentation


• 海洋生物由来の発光タンパク質に関する生物有機化学的研究（農芸化学奨励賞 受賞者講演）

  KUSE MASAKI

  日本農芸化学会 2013年度大会, Mar. 2013, Japanese, 仙台：東北大学, Domestic conference

  [Invited]

  Invited oral presentation


• Glyceollin Iの合成研究

  河野 雄太, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会 2013年度大会, Mar. 2013, Japanese, 仙台：東北大学, Domestic conference

  Oral presentation


• 7-Oxoorobancholの合成

  田中 政志, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会 2013年度大会, Mar. 2013, Japanese, 仙台：東北大学, Domestic conference

  Oral presentation


• プテロカルパン骨格の新規構築法に関する研究

  河野 雄太, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会関西支部会 第477回 講演会, Dec. 2012, Japanese, 神戸：神戸大学, Domestic conference

  Oral presentation


• ヒカリカモメガイ発光タンパク質のクロモフォア形成部位に関する研究

  久世 雅樹, 古市 卓也, 南郷 成子, 久保 尚洋, 滝川 浩郷

  日本農芸化学会関西支部会 第477回 講演会, Dec. 2012, Japanese, 神戸大学, Domestic conference

  Oral presentation


• Luminescent mechanism of a photoprotein, Pholasin

  Masaki Kuse, Eiko Tanaka, Takuya Furuichi, Naruko Nango, Naohiro Kubo, Toshio Nishikawa, Hirosato Takikawa

  54th Symposium on the Chemistry of Natural Products, Sep. 2012, Japanese, Tokyo, Domestic conference

  Poster presentation


• ７位が酸素化されたStrigolactone類の合成研究．日本農芸化学会 2012年度大会

  田中 政志, KUSE MASAKI, 滝川 浩郷

  日本農芸化学会 2012年度大会, Mar. 2012, Japanese, 京都：京都女子大学, Domestic conference

  Oral presentation


• 発光タンパク質Pholasinのクロモフォア形成部位に関する研究

  KUSE MASAKI, 田中 瑛子, 西川 俊夫, 滝川 浩郷

  日本農芸化学会2012年度大会, Mar. 2012, Japanese, 京都：京都女子大学, Domestic conference

  Oral presentation


• 両極性炭素を持つイミダゾロン化合物の化学合成研究

  宮田 典明, KUSE MASAKI, 西川 俊夫

  日本農芸化学会関西支部・中部支部合同大会, Oct. 2011, Japanese, 京都：京都大学, Domestic conference

  Oral presentation


• ヒカリカモメガイ発光タンパク質の発光機構に関する研究

  田中 瑛子, KUSE MASAKI, 西川 俊夫

  日本農芸化学会2011年度大会, Mar. 2011, Japanese, 京都, Domestic conference

  Oral presentation


• Identification of a fluorescent compound in a train millipede

  KUSE MASAKI, Miho Yanagi, Eiko Tanaka, Toshio Nishikawa

  The 9th Joint Seminar JSPS-NRCT Core University Program, Dec. 2010, English, Bangkok, International conference

  Oral presentation


• Bioluminescence of a bivalve mollusk, Pholas dactylus

  KUSE MASAKI, Eiko Tanaka, Toshio Nishikawa

  5th International Conference on Cutting-Edge Organic Chemistry in Asia, Nov. 2010, English, Taipei, International conference

  Oral presentation


• 細胞内シグナル伝達機構解明の為の生物発光基質の創出

  KUSE MASAKI, 田中 瑛子, 西川 俊夫

  日本植物学会 第74回大会, Sep. 2010, Japanese, 愛知：中部大学, Domestic conference

  [Invited]

  Invited oral presentation


• ヒカリカモメガイ発光タンパクの発光基質に関する研究

  田中 瑛子, KUSE MASAKI, 西川 俊夫

  日本農芸化学会2010年度大会, Mar. 2010, Japanese, 東京：東京大学, Domestic conference

  Oral presentation


• キシャヤスデの蛍光物質に関する研究

  柳 美帆, 田中 瑛子, 谷 直紀, KUSE MASAKI, 西川 俊夫

  日本農芸化学会2010年度大会, Mar. 2010, Japanese, 東京：東京大学, Domestic conference

  Oral presentation


• 二枚貝発光タンパクの発光機構に関する研究

  田中 瑛子, KUSE MASAKI, 西川 俊夫

  日本農芸化学会 第156回 中部支部例会, Oct. 2009, Japanese, 名古屋：名古屋大学, Domestic conference

  Oral presentation


• キシャヤスデの蛍光物質に関する研究

  柳 美帆, 田中 瑛子, 谷 直紀, KUSE MASAKI, 西川 俊夫

  日本農芸化学会 第156回 中部支部例会, Oct. 2009, Japanese, 名古屋：名古屋大学, Domestic conference

  Oral presentation


• Chemical Biology of the marine bioluminescence with coelenterazines

  KUSE MASAKI

  The Seminar of the JSPS-NRCT Core University Program, Sep. 2009, English, Hat Yai (Thailand), International conference

  [Invited]

  Invited oral presentation


• 二枚貝発光タンパク質に関する生物有機化学的研究

  KUSE MASAKI

  物発光化学発光研究会 第２６回学術講演会, Jun. 2009, Japanese, 東京：東京電気通信大学, Domestic conference

  [Invited]

  Invited oral presentation

• American Chemical Society


• 近畿化学協会


• 生物発光化学発光研究会


• アメリカ化学会


• 有機合成化学協会


• 日本化学会


• 日本農芸化学会

• トビイカ発光タンパクシンプレクチンに関する生物有機化学的研究

  2003 - 2005


• 名古屋大学上海フォーラム

  2005


• 名古屋大学科学研究フォーラム

  2005

• 生物発光の仕組みを利用した活性酸素種の次世代型解析手法の開発

  久世雅樹

  公益財団法人 ひょうご科学技術協会, 学術研究助成金, Apr. 2021 - Mar. 2022, Principal investigator


• 発光タンパク質フォラシンの活性部位の構造解析と高輝度発光系への応用

  久世 雅樹

  日本学術振興会, 学術研究助成基金助成金／基盤研究(C), Apr. 2019 - Mar. 2022, Principal investigator

  Competitive research funding


• 寄生雑草ストライガの２次代謝産物に着目した学際的研究と除草防除の実現

  久世 雅樹

  日本学術振興会, 科学研究費補助金／基盤研究(B)（海外学術調査）, Apr. 2017 - Mar. 2021, Principal investigator

  Competitive research funding


• 発光タンパク質のクロモフォア構造に関する生物有機化学的研究

  久世 雅樹

  日本学術振興会, 学術研究助成基金助成金／基盤研究(C), Apr. 2015 - Mar. 2018, Principal investigator

  Competitive research funding


• Continuous luminescence of photoprotein with substrate analog

  KUSE MASAKI

  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Kobe University, Apr. 2011 - Mar. 2014, Principal investigator

  Attempts have been made to find the condition which enables photoprotein to emit light continuously. A suitable condition for re-generation of photoprotein was obtained by using chemically synthesized oxy-chromophore analog. A florescent substance of photoprotein was also synthesized. A substance analog, in which sulfur and fluorine atoms were incorporated, was finally synthesized. The analog showed high bioluminescent activity as natural substance. From these results, fundamental knowledge was accumulated to obtain continuous luminescence of photoprotein.

  Competitive research funding


• Triggering mechanism on the symplectin bioluminescence by reactive oxygen species

  KUSE Masaki

  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Young Scientists (B), Nagoya University, 2009 - 2010, Principal investigator

  Triggering mechanism of photoproteins has been investigated. The photoproteins have chromophore which is constituted from dehydrocoelenterazine (DCL). It demonstrated that oxo-complex of Fe ion made the luminescence speed fast, on the other hand, peroxide of hypochlorite made the luminescence speed slow. This specific reaction rate was proved to be useful for the identification of reactive oxygen species by using photoproteins. A convenient synthetic method was also established to prepare many kinds of DCLs.

  Competitive research funding


• Dynamic analysis of photoprotein by using photoaffinity labeling and mass spectrometric analysis

  Masaki KUSE

  Ministry of Education, Culture, Sports, Science and Technology, Grants-in-Aid for Scientific Research(若手研究(B)), Grant-in-Aid for Young Scientists (B), Nagoya University, 2007 - 2008, Principal investigator

  発光タンパクが効率よく発光している分子機構を明らかにすることを目的として、イクオリンを光親和性標識した。既に合成したアジド化デヒドロセレンテラジンを用いてイクオリンを再構成し、発光前後において光照射した。トリプシン消化した後、質量分析した結果、システイン残基が特異的に酸化修飾されていることが判明した。この現象はこれまでに報告例が無く、発光前後におけるタンパクの動的変化解析に利用できる手法を確立できた。

  Competitive research funding


• The Innovative Synthesis of Bioactive Molecules based on the Molecular Mechanism of Natural Products Activity

  Minoru ISOBE

  Ministry of Education, Culture, Sports, Science and Technology, Grants-in-Aid for Scientific Research(特別推進研究), Grant-in-Aid for Specially Promoted Research, Nagoya University, 2004 - 2008

  合成化学から生物有機化学までを統一概念とする独創的なところである。本研究で展開されるこれらの手法と結果の解析方法を、合理的分子設計にフィードバックすることは、分子科学においてアフィニティが著しく高い点で毒性物質として取り扱われるものの、活性発現の原理を理解すれば、比活性を下げることで生体系と適当な平衡点を探すことも可能となる。従って、ここで展開している分子科学は、創薬の基礎科学として位置づけることができる。合理的・論理的分子設計に基づく創薬の創製科学の基礎として社会に貢献するという意義も深い。また、純粋に生物有機化学としての価値も高い。

  Competitive research funding


• 光親和性標識法によるトビイカ発光タンパクの活性部位の動的解析

  久世雅樹

  文部科学省, 科学研究費補助金(若手研究(B)), 若手研究(B), 名古屋大学, 2005 - 2006, Principal investigator

  光親和性アジド化デヒドロセレンテラジン(Az-F-DCL)を、活性中心探索プローブとして様々な発光タンパク質でも利用できることを確認するために以下の検討を行った。セレンテラジン系化合物を利用する発光タンパク質として、トビイカ発光タンパク質シンプレクチン、オワンクラゲ発光タンパク質エクオリン、そしてホタルイカルシフェラーゼの3つについて、Az-F-DCLを用いて光標識実験を行った。光照射と、加水分解酵素によるペプチド断片への消化、そして光照射生成物の消化物の質量分析による解析と順次行ったが、光照射部位の特定は容易ではなかった。これは、光照射の効率が高くないことに由来していることが考えられた。そこで、光照射条件を最適化することとした。まず、トリフルオロエタノール(TFE)中で、Az-F-DCLよりも構造をシンプルにした芳香族アジド化合物を数種類合成し、光照射生成物を様々な条件で分析した。生成物を高速液体クロマトグラフィーにて分析したと

  Competitive research funding


• 発光タンパク質の生物有機化学的分子機構解明とその応用

  磯部稔

  文部科学省, 科学研究費補助金(基盤研究(B)), 基盤研究(B), 名古屋大学, 2004 - 2004

  発光タンパク質の中で、トビイカ・ヤスデ・ミミズなどを対象に研究を計画し、特にトビイカ発光タンパク質シンプレクチンは、すでに発光素子の構造と発光タンパクのアミノ酸配列順位の決定や素子の結合システインの位置決定などを完了している。本研究では、この発光タンパク質アポシンプレクチンに組み込むためのアナログの化学合成や標識化合物の化学合成を行い成果を挙げているが、特に新しい第3世代の発光素子を合成するための革新的な方法論を計画している。この計画によれば、390番のシステインに結合したタンパクの周辺部位の様子を解明することができる。実際に、新しい合成ルートでこれまでの方法では不可能と考えられる発光素子を合成し、アポシンプレクチンに組み込み、強い発光を確認する。ヤスデについても、発光タンパク質を精製し、そのアミノ酸配列について部分的な配列順位を決定する。さらに沖縄産の発光ミミズの発光素子を決定し、人工的に発

  Competitive research funding


• 質量分析を用いたトビイカ発光タンパクの動的変化に関する研究

  久世雅樹

  文部科学省, 科学研究費補助金(若手研究(B)), 若手研究(B), 名古屋大学, 2003 - 2004, Principal investigator

  発光タンパク質シンプレクチンをアジド化デヒドロセレンテラジンで光標識しても、標識ペプチドの質量分析による特定は困難であった。これはシンプレクチンの全ペプチド断片を一度に解析していたためと考えられる。そこで、光標識した後、遊離のシステイン残基をすべてアルキル化し、次いでブロモシアンをもちいて大きなフラグメント(数千ダルトン以上)と分解して、電気泳動により蛍光性のフラグメントを特定することとした。アジド基のみならず、ジアゾアセチル基をもつデヒドロセレンテラジンも合成した。これらの光親和性標識化合物について、エクオリンを用いて標識したところ効率よく標識できたことが判明した。光標識されたペプチドのみを簡便に精製できる官能基をもつデヒドロセレンテラジン誘導体も新規に合成することとした。ストレッカー反応を鍵反応として数段階にて効率よく様々な誘導体を合成できる新規ルートの確立に成功した。つぎに、シンプレク

  Competitive research funding


• 複素環化合物の新規合成法

  2001

  Competitive research funding


• 嘔吐毒素の微量検出法の開発

  1999

  Competitive research funding


• Innovative synthesis of probe for dection of emetic toxin

  1999

  Competitive research funding


• 生物発光の分子機構に関する研究

  Competitive research funding


• Study on Molecular Mechanism of Bio luminescence

  Competitive research funding