TOKYO INSTITUTE OF TECHNOLOGY, Chemical Resources Laboratory, Synthetic Organic Division, Nakamura & Okada Laboratory

Papers (2021〜Present)

2024・2023・2022・2021

2024

          1. Y. Shao, K. Miura, Y. Asawa, T. Morita, G. Li, H. Nakamura
            “Discovery of disubstituted carboranes as inhibitors of heat shock protein 90–heat shock factor 1 interaction”, ACS Med. Chem. Lett., accepted (2024). DOI: 10.1021/acsmedchemlett.4c00022

2023

          1. M. Tsuda, T. Morita, Y. Morita, J. Takaya, H. Nakamura
            “Methylene Insertion into Nitrogen-Heteroatom Single Bonds of
            1,2-Azoles via a Zinc Carbenoid: An Alternative Tool for Skeletal Editing”, Adv. Sci.,11, 2307563 (2023). DOI: 10.1002/advs.202307563
          2. T. Morita, K. Makino, M. Tsuda, H. Nakamura
            “Chemoselective α-Trifluoroacetylation of Amides Using Highly Electrophilic Trifluoroacetic Anhydrides and 2,4,6-Colllidine”, Org. Lett., 25, 8901-8905 (2023). DOI: 10.1021/acs.orglett.3c03719
          3. S. Okada, K. Nishimura, Q. Ainaya, K. Shiraishi, S. A. Anufriev, I. B. Sivaev, M. Suzuki, M. Yokoyama, H. Nakamura
            “Development of a gadolinium-boron conjugated albumin for MRI-guided neutron capture therapy”, Mol. Pharm., 20, 6311–6318 (2023). DOI:10.1021/acs.molpharmaceut.3c00726
          4. T. Doi, K. Miura, K. Umedera, T. Morita, H. Nakamura
            “Synthesis of diazatricycloundecane scaffold via gold(I)-catalysed Conia-ene-type 5-exo–dig cyclization and stepwise substituent assembly for construction of sp3-rich compound library”, Org. Biomol. Chem., 21, 8716-87261 (2023). DOI:10.1039/D3OB01534C
          5. H. W. Lai, Y. Tani, U. Sukatta, P. Rugthaworn, A. Thepyos, K. Inoue, H. Yuasa, H. Nakamura, S. Ogura
            “Mangostin enhances efficacy of aminolevulinic acid-photodynamic therapy against cancer through inhibition of ABCG2 activity”, Photodiagnosis Photodyn. Ther., 44, 103798 (2023). DOI:10.1016/j.pdpdt.2023.103798
          6. Y. Fujikawa, Y. Fukuo, K. Nishimura, K. Tsujino, H. Kashiwagi, R. Hiramatsu, N. Nonoguchi, M. Furuse, T. Takami, N. Hu, S. Miyatake, T. Takata, H. Tanaka, T. Watanabe, M. Suzuki, S. Kawabata, H. Nakamura, M. Wanibuchi
            “Evaluation of the effectiveness of boron neutron capture therapy with iodophenyl-conjugated closo-dodecaborate on a rat brain tumor model”, Biology, 12, 1240 (2023). DOI:10.3390/biology12091240
          7. K. Miura, J. Manjusha, T. Morita, H. Nakamura
            “Discovery of three-dimensional bicyclo[3.3.1]nonanols as novel heat shock protein 90 inhibitors”, Booorg. Med. Chem., 93, 117463 (2023). DOI:10.1016/j.bmc.2023.117463
          8. Y. Hattori, T. Andoh, S. Kawabata, N. Hu, H. Michiue, H. Nakamura, T. Nomoto, M. Suzuki, T. Takata, H. Tanaka, T. Watanabe, K. Ono
            “Proposal of recommended experimental protocols for in vitro and in vivo evaluation methods of boron agents for neutron capture therapy”, J. Rad. Res., rrad064 (2023). DOI:10.1093/jrr/rrad064
          9. M. Kaur, R. Meena, K. Nishimura, K. Miura, H. Nakamura, M. Suzuki, R. K. Sharma, A. Kumar
            “Boron Neutron Capture Therapy Anti-Tumor effect of Nanostructured Boron Carbon Nitride: A new potential candidate”, Inorg. Chem. Commun., 157, 111318 (2023). DOI:10.1016/j.inoche.2023.111318
          10. T. Morita, N. Ito, H. Nakamura
            “Asymmetric Synthesis of Bicyclic Isoxazolines via Dearomative Cycloaddition of 4-Nitroisoxazoles with Zwitterionic π-Allyl Palladium Species”, Org. Lett., 25(26), 4787-4791 (2023). DOI:10.1021/acs.orglett.3c01324.
          11. K. Nishimura, H. Kashiwagi, T. Morita, Y. Fukuo, S. Okada, K. Miura, Y. Matsumoto, Y. Sugawara, T. Enomoto, M. Suzuki, K. Nakai, S. Kawabata, H. Nakamura
            “Efficient neutron capture therapy of glioblastoma with pteroyl-closo-dodecaborate-conjugated 4-(p-iodophenyl)butyric acid (PBC-IP)”, J. Control. Release, 360, 249-259 (2023). DOI:10.1021/acs.inorgchem.3c00852 Press Release (Japanese/English)
          12. O. Shamoto, K. Komuro, N. Sugisawa, H. Nakamura, S. Fuse
            “Peptide Cyclization by the Use of Acylammonium Species”,  Angew. Chem. Int. Ed., 62(27), e202300647 (2023). DOI: 10.1002/anie.202300647
          13. D. Loreto, B. Maity, T. Morita, H. Nakamura, A. Merlino, T. Ueno 
            “Cross-linked crystals of dirhodium tetraacetate/RNase A adduct can be used as heterogeneous catalysts. Loreto”,  Inorg. Chem., 62(19), 7515-7524 (2023). DOI:10.1021/acs.inorgchem.3c00852
          14. S. Okada, Y. Muto, B. Zhu, H. Ueda, H. Nakamura
            “Development of a peptide sensor derived from human ACE2 for fluorescence polarization assays of the SARS-CoV-2 receptor binding domain”, Anal. Chem., 95(15), 6198-6202 (2023). DOI: 10.1021/acs.analchem.2c05818
          15. 三浦一輝、WEN Yijin、對馬理彦、中村浩之
            “細胞内分子標的型光線力学療法”、日本レーザー医学会誌「特集 最新光感受性物質」, 44(1), 16-23 (2023). DOI:10.2530/jslsm.jslsm-44_0005
          16. K.Tsujino, H. Kashiwagi, K. Nishimura, R. Kayama, K. Yoshimura, Y. Fukuo, H. Shiba, R. Hiramatsu, N. Nonoguchi, M. Furuse, T. Takami, S.-I. Miyatake, N. Hu, T. Takata, H. Tanaka, M. Suzuki, S. Kawabata, H. Nakamura, M. Wanibuchi
            “Improved Boron Neutron Capture Therapy Using Integrin αvβ3-Targeted Long-Retention-Type Boron Carrier in a F98 Rat Glioma Model”, Biology, 12, 377 (2023). DOI: 10.3390/biology12030377
          17. Y. Orita, S. Shimanuki, S. Okada, K. Nakamura, H. Nakamura, Y. Kitamoto, Y. Shimoyama, Y. Kurashina
            “Acoustic-responsive carbon dioxide-loaded liposomes for efficient drug release”, Ultrason. Sonochem. 94, 106326 (2023). DOI:10.1016/j.ultsonch.2023.106326
          18. 岡田智、Rohmad Yudi Utomo、住吉晃、青木伊知男、中村浩之
            “アミロイドβ線維化を検出・阻害するクルクミン誘導体MRIプローブの開発”、日本分子イメージング学会機関誌、16(1), 26-29 (2023).
          19. 盛田大輝、中村浩之
            “イソオキサゾールの新規官能基化法の開発”、有機合成化学協会 81(3), 244-253 (2023).DOI:10.5059/yukigoseikyokaishi.81.244
          20. 中村浩之
            “中性子捕捉療法の鍵を握る10B薬剤開発”、Precision Medicine「特集 イメージングによる最先端医薬品・医療技術開発」6(1), 28-32 (2023).
          21. K. Umedera, A. Yoshimori, H. Chen, H. Kouji, H. Nakamura, J. Bajorath
            “DeepCubist: Molecular Generator for Designing Peptidomimetics Based on Complex Three-Dimensional Scaffolds”, J. Comput-Aided Mol. Des. 37, 107–115 (2023). DOI:10.1007/s10822-022-00493-y.

2022

          1. K. Umedera, A. Yoshimori, J. Bajorath, H. Nakamura
            “Design of MMP-1 Inhibitors via SAR Transfer and Experimental Validation”, Sci. Rep. 12, 20915 (2022). DOI: 10.1038/s41598-022-25079-4.
          2. K. Umedera, A. Yoshimori, H. Chen, H. Kouji, H. Nakamura, J. Bajorath
            “DeepCubist: Molecular Generator for Designing Peptidomimetics Based on Complex Three-Dimensional Scaffolds”, J. Comput-Aided Mol. Des., online (2022). DOI:10.1007/s10822-022-00493-y.
          3. K. Umedera, T. Morita, H. Nakamura
            “Asymmetric construction of densely functionalized three-dimensional aza-tetracyclic scaffolds for drug discovery”, Chem. Commun., online (2022). DOI:10.1039/D2CC05700J
          4. S. Ogawa, Y. Asawa, M. Iiyama, A. Yoshimori, H. Nakamura, M. Oda
            “Regulation of binding between CD28 cytoplasmic region and SH2 domains of Grb2 and PI3K by carborane compounds for T-cell activation”, Bioorg. Med. Chem. Lett., 78, 129049 (2022). DOI:10.1016/j.bmcl.2022.129049
          5. K. Miura, Y. Wen, M. Tsushima, H. Nakamura
            “Photodynamic therapy by glucose transporter 1–selective light inactivation”, ACS Omega, 7(38), 34685–34692. DOI:10.1021/acsomega.2c05042
          6. A. G. Beck-Sickinger, D. P. Becker, O. Chepurna, B. Das, S. Flieger, E. Hey-Hawkins, N. Hosmane, S. S. Jalisatgi, H. Nakamura, R. Patil, M. da Graça, H. Vicente, C. Viñas
            “New Boron Delivery Agents”, Cancer Biother. Radiopharm., accepted, (2022).
          7. 中村浩之
            “ホウ素の拓く創薬ワールド“、細胞「特集 低分子モダリティの進化―元素・光・分子機能に注目して」54(9), 492-495 (2022).
          8. A. M. Hughes, J. A. Goldfinger, M. A. Palmieri, P. Ramos, I. S. Santa Cruz, L. De Leo, M. A. Garabalino, S. I. Thorp, P. Curotto, E. C. C. Pozzi, K. Kawai, S. Sato, M. E. Itoiz, V. A. Trivillin, J. S. Guidobono, H. Nakamura, A. E. Schwint
            “Boron neutron capture therapy (BNCT) mediated by maleimide-functionalized closo-dodecaborate albumin conjugates (MID:BSA) for oral cancer: Biodistribution studies and in vivo BNCT in the hamster cheek pouch oral cancer model”, Life, 12(7), 1082. DOI:10.3390/life12071082
          9. K. Nishimura, S. Harrison, K. Kawai, T. Morita, K. Miura, S. Okada, H. Nakamura
            Iodophenyl-conjugated closo-dodecaborate as a promising small boron molecule that binds to serum albumin and accumulates in tumor”, Bioorg. Med. Chem. Lett., 72, 128869 (2022). DOI:10.1016/j.bmcl.2022128869
          10. S. Noda, A. Yamada, Y. Asawa, H. Nakamura, T. Matsumura, H. Orimo, and M. Goseki-Sone
            “Characterization and Structure of Alternatively Spliced Transcript Variant of Human Intestinal Alkaline Phosphatase (ALPI) Gene”, J. Nutr. Sci. Vitaminol., 68, 284-293 (2022). DOI:10.3177/jnsv.68.284
          11. H. Kitamura, Y. Otake, N. Sugisawa, H. Sugisawa, T. Ida, H. Nakamura, S. Fuse
            “Sequential Nucleophilic Substitution of Phosphorus Trichloride with Alcohols in a Continuous-Flow Reactor and Consideration of a Mechanism for Reduced Over-reaction through the Addition of Imidazole”,             Chem. Eur. J., 28(37), e202200932. DOI:10.1002/chem.202200932
          12. 盛田大輝、中村浩之
            “光反応を利用したタンパク質の化学修飾”, カレントレビュー, 43, 71-77 (2022).
          13. S. Koyama, H. Sato, H. Sugai, M. Murakoshi, T. Kobayashi, S. Usami, K. Ikeda, Y. Haga, K. Tsumoto, H. Nakamura, N. Hirasawa, K. Ishihara, H. Wada
            “Effects of Salicylate Derivatives on Changes in Localization of H723R Pendrin Mutant Expressed in HEK293 Cells”, Auris Nasus Larynx., 49(6), 928-937 (2022). DOI: 10.1016/j.anl.2022.03.009
          14.  K. Nakane, T. Niwa, M. Tsushima, S. Tomoshige, H. Taguchi, H. Nakamura, M. Ishikawa, S. Sato
            “BODIPY Catalyzes Proximity‐Dependent Histidine Labelling”,
             ChemCatChem., 14(9), e202200077 (2022). DOI:10.1002/cctc.202200077
          15. R. Y. Utomo, S. Okada, A. Sumiyoshi, I. Aoki, H. Nakamura
            “Detoxification by curcumin derivative via dissociation of amyloid β fibrils and its verification in Drosophila Alzheimer’s model”, RSC Adv., 12, 5027-5030 (2022). DOI:10.1039/D2RA00614F
          16. R. Y. Utomo, A. Sugie, S. Okada, K. Miura, H. Nakamura
            “Detoxification by curcumin derivative via dissociation of amyloid β fibrils and its verification in Drosophila Alzheimer’s model”, Chem. Commun., 58, 2576-2579 (2022). DOI:10.1039/D1CC07000B
          17. M. Tsuda, T. Morita, H. Nakamura
            “Synthesis of isoxazoloazaborines via Gold(I)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade”, Chem. Commun., 58, 1942-1945(2022). DOI:10.1039/D1CC07002A
             Highlighted in Synfacts Issue 05/Volume 18/2022
          18. M. Tsushima, S. Sato, K. Miura, T. Niwa, H. Taguchi, H. Nakamura
            “Intracellular Photocatalytic-Proximity Labeling for Profiling Protein–Protein Interactions in Microenvironments”, Chem. Commun., 58, 1926-1929 (2022). DOI:10.1039/D1CC05764B
          19. A. R Jalilian, A. Shahi, I. P. Swainson, H. Nakamura, M. Venkatesh, J. A. Osso Jr
            “Potential theranostic BNCT agents as multimodal radiopharmaceuticals”, Cancer Biother. Radiopharm., 37(5), 342-354 (2022). DOI:10.1089/cbr.2021.0276
          20. T. Morita, H. Murakami, Y. Asawa, H. Nakamura
            “Enantioselective Synthesis of Oxazaborolidines by Palladium-Catalyzed N–H/B–H Double Activation of 1,2-Azaborines”, Angew. Chem. Int. Ed., 61, e202113558 (2022). DOI:10.1002/anie.202113558
             Highlighted in Synfacts Issue 03/Volume 18/2022
          21. H. Ueda, P. Wipf, H. Nakamura
            “Synthesis of sp3-rich chiral bicyclo[3.3.1]nonanes for chemical space expansion and study of biological activities”, Bioorg. Med. Chem., 54, 116561 (2022). DOI:10.1016/j.bmc.2021.116561
          22. T.-H. Han, M. K. Park, H. Nakamura, H. S. Ban
            “Capsaicin inhibits HIF-1α accumulation through suppression of mitochondrial respiration in lung cancer cells”, Biomed. Pharm., 146, 112500 (2022). DOI:10.1016/j.biopha.2021.112500
          23. G. Li, G. Yu, C. Wang, T. Morita X. Zhang, H. Nakamura
            “Copper(I)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with phosphites”, Org. Biomol. Chem., 20, 113-116 (2022). DOI:10.1039/D1OB02091A
          24. H. Kashiwagi, S. Kawabata, K. Yoshimura, Y. Fukuo, T. Kanemitsu, K. Takeuchi, R. Hiramatsu, K. Nishimura, K. Kawai, T. Takata, H. Tanaka, T. Watanabe, M. Suzuki, S. Miyatake, H. Nakamura, M. Wanibuchi
            “Boron neutron capture therapy using dodecaborated albumin conjugates with maleimide is effective in a rat glioma model”, Investigational New Drugs, 40, 255–264 (2022). DOI:10.1007/s10637-021-01201-7

2021

          1. Yanagie, M. Yanagawa, Y. Sakurai, K. Mouri, Y. Morishita, A. Shinohara, N. Dewi, Y. Nonaka, Y. Furuya, R. Mizumachi, Y. Murata, H. Nakamura, M. Suzuki, Y. Sakurai, H. Tanaka, S. Masunaga, K. Ono, T. Sugihara, M. Nashimoto, H. Yamauchi, M. Ono, J. Nakajima, H. Terada, H. Takahashi
            “Tumour Growth Suppression in Rabbit Hepatic Cancer Model by Boron Neutron Capture Therapy with Liposomal Boron Delivery Systems”, In Vivo, 35(6), 3125-3135 (2021). DOI: 10.21873/invivo.12607
          2. Y. Asawa, S. Hatsuzawa, A. Yoshimori, K. Yamada, A. Katoh, H. Kouji, H. Nakamura
            “Comprehensive Exploration of Chemical Space Using Trisubstituted Carboranes”, Sci. Rep., 11, 24101 (2021). DOI: 10.1038/s41598-021-03459-6
          3. Y. Tsuji, N. Nonoguchi, D. Okuzaki, Y. Wada, D. Motooka, Y. Hirota, T. Toho, N. Yoshikawa, M. Furuse, S. Kawabata, S.-I. Miyatake, H. Nakamura, R. Yamamoto, S. Nakamura, T. Kuroiwa, M. Wanibuchi
            “Chronic pathophysiological changes in the normal brain parenchyma caused by radiotherapy accelerate glioma progression”, Sci. Rep., 11, 22110 (2021). DOI: 10.1038/s41598-021-01475-0
          4. Y. Asawa, K. Nishida, K. Domae, K. Kawai, H. S. Ban, H. Asami, J.-Y. Kohno, S. Okada, H. Tokuma, D. Sakano, S. Kume, M. Tanaka, H. Nakamura
            “Carborane as an Alternative Efficient Hydrophobic Tag for Protein Degradation”,
            Bioconjugate Chem., 32(11), 2377–2385 (2021). DOI: 10.1021/acs.bioconjchem.1c00431
          5. S. Okada, S. Takayasu, A. Sumiyoshi, I. Aoki, H. Nakamura
            “MRI-based Glucose Assay Using Magnetic Nanoparticle Sensors”, Anal. Sci. 37, 12, 1765-1769 (2021) DOI: 10.2116/analsci.21P082
          6. S. Sato, M. Matsumura, H. Ueda, H. Nakamura
            “Preparation of an antigen-responsive fluorogenic immunosensor by tyrosine chemical modification of the antibody complementarity determining region”, Chem. Commun., 57, 9760-9763 (2021).  DOI: 10.1039/d1cc03231c
          7. G. Li, Y. Shao, Y. Pan, Y. Li, Y. Wang, L. Wan, K. Shao, S. Wang, H. Dong, X. W, X. Guo, W. Zhao, H. Nakamura
            “Total synthesis and biological evaluation of 7-Hydroxyneolamellarin A as hypoxia-inducible factor-1α inhibitor for cancer therapy”, Bioorg. Med. Chem. Lett., 50, 128338 (2021). DOI:10.1016/j.bmcl.2021.128338
          8. R. Yudi Utomo, Y. Asawa, S. Okada, H. S. Ban, A. Yoshimori, J. Bajorath, H. Nakamura
            “Development of curcumin-based amyloid β aggregation inhibitors for Alzheimer’s disease using the SAR matrix approach”, Bioorg. Med. Chem., 46, 116357 (2021).  DOI:10.1016/j.bmc.2021.116357
          9. N. Sugisawa, H. Sugisawa, Y. Otake, R. V. Krems, H. Nakamura, S. Fuse
            “Rapid and Mild One-Flow Synthetic Approach to Unsymmetrical Sulfamides Guided by Bayesian Optimization”, Chemistry Methods, 1(11), 484-490 (2021).　DOI:10.1002/cmtd.202100053
          10. K. Umedera, T. Morita, A. Yoshimori, K. Yamada, A. Katoh, H. Koji, H. Nakamura
            “Synthesis of Three-Dimensional (3D) (Di)azatricyclododecene Scaffold and its Application to Peptidomimetics”, Chem. Eur. J., 27(46), 11888-11894 (2021). DOI:10.1002/chem.202101440
          11. M. Tsuda, T. Morita, H. Nakamura
            “Suzuki-Miyaura Cross-coupling of 3,4-disubstituted 5-bromoisoxazoles: An efficient access to trisubstituted isoxazoles”, Tetrahedron Lett., 75, 153185 (2021). DOI:10.1016/j.tetlet.2021.153185
          12. K. Nakane, S. Sato, T. Niwa, M. Tsushima, S. Tomoshige, H. Taguchi, M. Ishikawa, H. Nakamura
            “Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen”, J. Am. Chem. Soc., 143(20), 7726–7731 (2021). DOI:10.1021/jacs.1c01626
          13. P. Singh, M. Kaur, K. Singh, G. Kaur, R. Meena, M. Kaur, B. Singh, A. Thakur, J. Sharma, A. Singh, M. Kumar, J. H. Yun, F. Nakagawa, M. Suzuki, H. Nakamura, A. Kumar
            “Fluorescent Boron Carbide Quantum dots synthesized with a low-temperature solvothermal approach for boron neutron capture therapy”, Phys. E: Low-Dimens. Syst. Nanostructures, 132, 114766 (2021). DOI:10.1016/j.physe.2021.114766
          14. S. Fuse, K. Komuro, Y. Otake, H. Masui, H. Nakamura
            “Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Micro-Flow Reactor”, Chem. Eur. J., 27(27), 7525-7532 (2021). DOI:10.1002/chem.202100059
          15. Y. Asawa, A. V. Arsent’eva, S. A. Anufriev, A. A. Anisimov, K. Y. Suponitsky, O. A. Filippov, H. Nakamura, I. B. Sivaev
            “Synthesis of Bis(Carboranyl)amides 1,1’-μ-(CH2NH(O)C(CH2)n– 1,2-C2B10H11)2 (n = 0, 1) and Attempt of Synthesis of Gadolinium Bis(Dicarbollide)”, Molecules, 26(5), 1321 (2021). DOI:10.3390/molecules26051321
          16. 中村 浩之
            “BNCTの薬剤と中性子の反応”、月刊インナービジョン特集号、36(2), 40-42 (2021).
          17. M. Tsuda, S. Fukuhara, T. Morita, H. Nakamura
            “Synthesis of 4-Amino-5-allenylisoxazoles via Gold(I)-Catalyzed Propargyl Aza-Claisen Rearrangement”, Org. Biomol. Chem.,19, 1358 (2021). DOI:10.1039/D0OB02544E
          18. S. Ban, Y. Uto, H. Nakamura
            “Hypoxia-inducible factor (HIF) inhibitors: a patent survey (2016-2020)”, Expert Opin. Ther. Pat., 31(5), 387-397 (2021). DOI:10.1080/13543776.2021.1874345
          19. T. Shimizu, N. Takahashi, V. J. Huber, Y. Asawa, H. Ueda, A. Yoshimori, Y. Muramatsu, H. Seimiya, H. Kouji, H. Nakamura, H. Oguri 
            “Design and synthesis of 14 and 15-membered macrocyclic scaffolds exhibiting inhibitory activities of hypoxia-inducible factor 1α”,
            Bioorg. Med. Chem., 30, 115949 (2021). DOI:10.1016/j.bmc.2020.115949

           

             

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