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

Papers (2021〜Present)



          1. K. Umedera, T. Morita, H. Nakamura
            “Asymmetric construction of densely functionalized three-dimensional aza-tetracyclic scaffolds for drug discovery”, Chem. Commun., accepted (2022). DOI:10.1039/D2CC05700J
          2. 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
          3. 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
          4. 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).
          5. 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).
          6. 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
          7. 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
          8. 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
          9. 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
          10. 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).
          11. 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
          12.  K. Nakane, T. Niwa, M. Tsushima, S. Tomoshige, H. Taguchi, H. Nakamura, M. Ishikawa, S. Sato
            “BODIPY Catalyzes ProximityDependent Histidine Labelling”,
             ChemCatChem., 14(9), e202200077 (2022). DOI:10.1002/cctc.202200077
          13. 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
          14. 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
          15. 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
          16. 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
          17. 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
          18. 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
          19. 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
          20. 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
          21. 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
          22. 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



          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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