京都大学大学院農学研究科食品生物科学専攻食品生命科学講座 生命有機化学分室

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原著論文

*corresponding author

  1. Irie, K., Hirota, M., Hagiwara, N., *Koshimizu, K., Hayashi, H., Murao, S., Tokuda, H. and Ito, Y.: The Epstein-Barr virus early antigen-inducing indole alkaloids, (-)-indolactam V and its related compounds, produced by Actinomycetes. Agric. Biol. Chem., 48 (5), 1269-1274 (1984).
  2. Irie, K., Hagiwara, N., *Koshimizu, K., Hayashi, H., Murao, S., Tokuda, H. and Ito, Y.: Isolation and the Epstein-Barr virus early antigen-inducing activity of olivoretins from Streptoverticillium blastmyceticum. Agric. Biol. Chem., 49 (1), 221-223 (1985).
  3. Irie, K., Hagiwara, N., *Koshimizu, K., Hayashi, H., Murao, S. and Ito, Y.: Identification of the microorganism which produces Epstein-Barr virus early antigen-inducing indole alkaloids. Agric. Biol. Chem., 49 (3), 845-847 (1985).
  4. *Fujiki, H., Suganuma, M., Hakii, H., Nakayasu, M., Endo, Y., Shudo, K., Irie, K., Koshimizu, K. and Sugimura, T.: Tumor promoting activities of new synthetic analogues of teleocidin. Proc. Japan Acad. Ser. B, 61, 45-47 (1985).
  5. Irie, K., Hagiwara, N., *Koshimizu, K., Tokuda, H., Ito, Y., Hayashi, H. and Murao, S.: Epstein-Barr virus early antigen inducing activity of 14-O-derivatives of (-)-indolactam V. Agric. Biol. Chem., 49 (5), 1441-1446 (1985).
  6. Hagiwara, N., Irie, K., *Koshimizu, K., Hayashi, H., Murao, S., Tokuda, H. and Ito, Y.: New teleocidin metabolites from Streptoverticillium blastmyceticum. Agric. Biol. Chem., 49 (8), 2529-2530 (1985).
  7. Irie, K., Tokuda, H., Hagiwara, N., *Koshimizu, K., Hayashi, H., Murao, S. and Ito, Y.: Structure-activity relationship in the induction of Epstein-Barr virus by teleocidin derivatives. Int. J. Cancer, 36 (4), 485-488 (1985).
  8. Irie, K., Hayashi, H., Arai, M. and *Koshimizu, K.: Substitution reaction on the indole ring of (-)-indolactam V, the fundamental structure of teleocidins. Agric. Biol. Chem., 50 (10), 2679-2680 (1986).
  9. Irie, K., Hagiwara, N., Kurome, T., Hayashi, H., Arai, M. and *Koshimizu, K.: New teleocidin-related metabolites from Streptoverticillium blastmyceticum producing tumor-promoting indole alkaloids. Agric. Biol. Chem., 51 (1), 285-287 (1987).
  10. Irie, K., Hagiwara, N., Tokuda, H. and *Koshimizu, K.: Structure-activity studies of the indole alkaloid tumor promoter teleocidins. Carcinogenesis, 8 (4), 547-552 (1987).
  11. Irie, K., Hagiwara, N., Funaki, A., Hayashi, H., Arai, M. and *Koshimizu, K.: Isolation of blastmycetin D, a possible precursor of teleocidins, from Streptoverticillium blastmyceticum. Agric. Biol. Chem.,51 (6), 1733-1735 (1987).
  12. Irie, K., Hagiwara, N. and *Koshimizu, K.: Synthesis of a biologically active fluorescent indolactam derivative; a method of preparing new probes for receptor analysis of tumor promoters. Tetrahedron Lett., 28 (28), 3267-3270 (1987).
  13. Hagiwara, N., Irie, K., Tokuda, H. and *Koshimizu, K.: The metabolism of indole alkaloid tumor promoter, (-)-indolactam V, which has the fundamental structure of teleocidins, by rat liver microsomes. Carcinogenesis, 8 (7), 963-965 (1987).
  14. Irie, K., Hagiwara, N. and *Koshimizu, K.: New probes for receptor analysis of tumor promoters; synthesis of fluorescent derivatives of (-)-indolactam V, the basic ring-structure of teleocidins. Tetrahedron, 43 (22), 5251-5260 (1987).
  15. *Nakagawa, Y., Sotomatsu, T., Irie, K., Kitahara, K., Iwamura, H. and Fujita, T.: Quantitative structure-activity studies of benzoylphenylurea larvicides. Pestic. Biochem. Pysiol., 27, 143-155 (1987).
  16. Hagiwara, N., Irie, K., Funaki, A., Hayashi, H., Arai, M. and *Koshimizu, K.: Structure and tumor-promoting activity of new teleocidin-related metabolites (blastmycetins) from Streptoverticillium blastmyceticum. Agric. Biol. Chem., 52 (3), 641-648 (1988).
  17. Irie, K. and *Koshimizu, K.: Structure-activity studies of indole alkaloid tumor promoters. Mem. Coll. Agric., Kyoto Univ., 132, 1-59 (1988).
  18. Irie, K., Hagiwara, N., Funaki, A., Hayashi, H., Arai, M., Tokuda, H. and *Koshimizu, K.: Isolation and biological activities of N13-desmethyl analogues of tumor promoter teleocidin from Streptoverticillium blastmyceticum. Agric. Biol. Chem., 52 (12), 3193-3195 (1988).
  19. Irie, K., Okuno, S., *Koshimizu, K., Tokuda, H., Nishino, H. and Iwashima, A.: Biological activities and cellular uptake studies of fluorescent derivatives of indole alkaloid tumor promoter teleocidin. Int. J. Cancer, 43 (3), 513-519 (1989).
  20. Irie, K., Funaki, A., *Koshimizu, K., Hayashi, H. and Arai, M.: Structure of blastmycetin E, a new teleocidin-related compound, from Streptoverticillium blastmyceticum. Tetrahedron Lett., 30 (16), 2113-2116 (1989).
  21. Irie, K., Kajiyama, S., Funaki, A., *Koshimizu, K., Hayashi, H. and Arai, M.: Biosynthesis of (-)-indolactam V, the basic ring-structure of tumor promoters teleocidins.  Tetrahedron Lett., 31 (1), 101-104 (1990).
  22. Irie, K., Kajiyama, S., Funaki, A., *Koshimizu, K., Hayashi, H. and Arai, M.: Biosynthesis of indole alkaloid tumor promoters teleocidins (I); possible biosynthetic pathway of the monoterpenoid moieties of teleocidins.  Tetrahedron, 46 (8), 2773-2788 (1990).
  23. Okuno, S., *Irie, K., Nishino, H., Iwashima, A. and Koshimizu, K.: Syntheses and biological activities of photolabile indolactam derivatives; new probes for the receptor analysis of tumor promoters.  Agric. Biol. Chem., 54 (7), 1885-1887 (1990).
  24. Kinoshita, T., Takahashi, I., Kobayashi, E., Tamaoki, T., Irie, K., Koshimizu, K. and *Osato, T.: Suppression by protein kinase C inhibitors of tumor promoter enhancement of Epstein-Barr virus-induced growth transformation.  Anticancer Res., 10 (4), 1051-1054 (1990).
  25. *Irie, K., Kajiyama, S., Koshimizu, K., Hayashi, H. and Arai, M.: Isolation and biosynthesis of (-)-indolactam I, a new congener of indole alkaloid tumor promoter teleocidins.  Tetrahedron Lett., 31 (50), 7337-7340 (1990).
  26. Ando, T., *Irie, K., Koshimizu, K., Takemura, T., Nishino, H., Iwashima, A., Nakajima, S. and Sakata, I.: Synthesis, physicochemical properties and photocytotoxicity of five new δ-substituted chlorin e6 derivatives.  Tetrahedron, 46 (17), 5921-5930 (1990).
  27. Kajiyama, S., *Irie, K., Kido, T., Koshimizu, K., Hayashi, H. and Arai, M.: Synthesis of new indolactam analogues by microbial conversion.  Tetrahedron, 47 (29), 5453-5462 (1991).
  28. *Irie, K., Okuno, S., Kajiyama, S., Koshimizu, K., Nishino, H. and Iwashima, A.: Quantitative structure-activity studies on indole alkaloid tumor promoter indolactam congeners.   Carcinogenesis, 12 (10), 1883-1886 (1991).
  29. Ando, T., *Irie, K., Koshimizu, K., Shingu, T., Takeda, N., Takemura, T., Nakajima, S. and Sakata, I.: New photosensitizers for photodynamic therapy: syntheses of chlorin e6 dimer and trimer.  Agric. Biol. Chem., 55 (9), 2441-2443 (1991).
  30. Ando, T., Suzuki, Y., Geka, R., *Irie, K., Koshimizu, K., Takemura, T., Nakajima, S. and Sakata, I.: New water-soluble pyropheophorbide a derivatives as possible agents for photodynamic therapy of cancer.  Tetrahedron Lett., 32 (38), 5107-5110 (1991).
  31. *Irie, K., Okuno, S., Koizumi, F., Koshimizu, K., Nishino, H. and Iwashima, A.: Photolabile derivatives of indole alkaloid tumor promoter teleocidins: synthesis, biological activities and photoaffinity labeling studies.  Tetrahedron, 49 (47), 10817-10830 (1993).
  32. Ando, T., *Irie, K., Koshimizu, K., Takemura, T., Nishino, H., Iwashima, A., Takeda, N., Nakajima, S. and Sakata, I.: Photocytotoxicity of water-soluble metalloporphyrin derivatives. Photochem. Photobiol., 57 (4), 629-633 (1993).
  33. *Wender, P. A., Irie, K. and Miller, B. L.: Synthesis and binding of photoaffinity ligand candidates for protein kinase C.  J. Org. Chem., 58 (16), 4179-4181 (1993).
  34. Okuno, S., *Irie, K., Suzuki, Y., Koshimizu, K., Nishino, H. and Iwashima, A.: Synthesis and biological activities of fluorine-substituted (-)-indolactam-V, the core structure of tumor promoter teleocidins.  Bioorg. Med. Chem. Lett., 4 (3), 431-434 (1994).
  35. *Irie, K., Kajiyama, S., Okuno, S., Kondo, M., Koshimizu, K., Hayashi, H., Arai, M., Nishino, H. and Iwashima, A.: New teleocidin-related metabolites, (-)-7-geranylindolactam-V and blastmycetin F, from Streptoverticillium blastmyceticum.  J. Nat. Prod., 57 (3), 363-368 (1994).
  36. *Wender, P. A., Irie, K. and Miller, B. L.: Identification, activity, and structural studies of peptides incorporating the phorbol ester binding domain of protein kinase C.  Proc. Natl. Acad. Sci. USA, 92 (1), 239-243 (1995).
  37. *Irie, K., Iguchi, M., Oda, T., Suzuki, Y., Okuno, S., Ohigashi, H., Koshimizu, K., Hayashi, H., Arai, M., Nishino, H. and Iwashima, A.: Synthesis of 6-substituted indolactams by microbial conversion.  Tetrahedron, 51 (22), 6255-6266 (1995).
  38. *Irie, K., Koizumi, F., Iwata, Y., Ishii, T., Yanai, Y., Nakamura, Y., Ohigashi, H. and Wender, P. A.: Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins.  Bioorg. Med. Chem. Lett., 5 (5), 453-458 (1995).
  39. *Irie, K., Isaka, T., Iwata, Y., Yanai, Y., Nakamura, Y., Koizumi, F., Ohigashi, H., *Wender, P. A., Satomi, Y. and Nishino, H.: Synthesis and biological activities of new conformationally restricted analogues of (-)-indolactam-V: elucidation of the biologically active conformation of the tumor-promoting teleocidins.  J. Am. Chem. Soc., 118 (44), 10733-10743 (1996).
  40. *Irie, K., Ishii, T., Ohigashi, H., *Wender, P. A., Miller, B. L. and Takeda, N.: Synthesis and characterization of new photolabile phorbol esters for affinity labeling of protein kinase C.  J. Org. Chem., 61 (6), 2164-2173 (1996).
  41. *Irie, K., Yanai, Y., Ohigashi, H., *Wender, P. A. and Miller, B. L.: Synthesis and characterization of the second cysteine-rich region of mouse skin PKCη.  Bioorg. Med. Chem. Lett., 6 (4), 353-356 (1996).
  42. *Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S. and Nakamura, E.: Photocytotoxicity of water-soluble fullerene derivatives.  Biosci. Biotech. Biochem., 60 (8), 1359-1361 (1996).
  43. Nakagawa, Y., *Irie, K., Nakamura, Y., Ohigashi, H. and Hayashi, H.: Synthesis and biological activities of indolactone-V, the lactone analogue of the tumor promoter (-)-indolactam-V.  Biosci. Biotech. Biochem., 61 (8), 1415-1417 (1997).
  44. *Irie, K., Yanai, Y., Oie, K., Ohigashi, H. and *Wender, P. A.: Protein kinase C regulatory domain surrogate peptides: effects of metal ions on folding, phorbol ester-binding, and selectivity.  Bioorg. Med. Chem. Lett., 7 (8), 965-970 (1997).
  45. Yanai, Y., *Irie, K., Ohigashi, H. and *Wender, P. A.: Synthesis and characterization of the first cysteine-rich domain of novel protein kinase C.  Bioorg. Med. Chem. Lett., 7 (2), 117-122 (1997).
  46. *Irie, K., Yanai, Y., Oie, K., Ishizawa, J., Nakagawa, Y., Ohigashi, H., *Wender, P. A. and Kikkawa, U.: Comparison of chemical characteristics of the first and the second cysteine-rich domains of protein kinase Cγ.  Bioorg. Med. Chem., 5 (8), 1725-1737 (1997).
  47. Nakagawa, Y., *Irie, K., Nakamura, Y., Ohigashi, H. and Hayashi, H.: Synthesis and biological activities of (-)-6-n-octyl-indolactam-V, a new potent analogue of the tumor promoter (-)-indolactam-V.  Biosci. Biotech. Biochem., 62 (8), 1568-1573 (1998).
  48. *Irie, K., Oie, K., Nakahara, A., Yanai, Y., Ohigashi, H., *Wender, P. A., Fukuda, H., Konishi, H. and Kikkawa, U.: Molecular basis for protein kinase C isozyme-selective binding: the synthesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes.  J. Am. Chem. Soc., 120 (36), 9159-9167 (1998).
  49. Fukuda, H., *Irie, K., Nakahara, A., Oie, K., Ohigashi, H. and Wender, P. A.: Synthesis and binding studies of the 116-mer peptide containing the double cysteine-rich motifs of protein kinase C gamma.  Tetrahedron Lett.,39 (43), 7943-7946 (1998).
  50. *Irie, K., Nakagawa, Y., Tomimatsu, S. and Ohigashi, H.: Biosynthesis of the monoterpenoid moiety of teleocidins via the non-mevalonate pathway in Streptomyces.  Tetrahedron Lett., 39 (43), 7929-7930 (1998).
  51. Fukuda, H., *Irie, K., Nakahara, A., Ohigashi, H. and Wender, P. A.: Solid-phase synthesis, mass spectrometric analysis of the zinc-folding, and phorbol ester-binding studies of the 116-mer peptide containing the tandem cysteine-rich C1 domains of protein kinase C gamma.  Bioorg. Med. Chem., 7 (6), 1213-1221 (1999).
  52. *Wender, P. A., Lippa, B. L., Park, C.-M., Irie, K., Nakahara, A. and Ohigashi, H.: Selective binding of bryostatin analogues to the cysteine rich domains of protein kinase C isozymes.  Bioorg. Med. Chem. Lett., 9 (12), 1687-1690 (1999).
  53. *Irie, K., Nakahara, A., Ohigashi, H., Fukuda, H., Wender, P. A., Konishi, H. and Kikkawa, U.: Synthesis and phorbol ester-binding studies of the individual cysteine-rich motifs of protein kinase D.  Bioorg. Med. Chem. Lett., 9 (17), 2487-2490 (1999).
  54. *Wender, P. A., Koehler, M. F. T., Wright, D. L. and Irie, K.: Mapping phorbol ester binding domains of protein kinase C (PKC): the design, synthesis and biological activity of novel phorbol ester dimmers.  Synthesis, 1401-1406 (1999).
  55. *Irie, K., Tomimatsu, S., Nakagawa, Y., Ohigashi, H. and Hayashi, H.: Isolation of (-)-14-O-malonylindolactam-V as a possible precursor of (-)-indolactam-V and (-)-14-O-acetylindolactam-V from Streptomyces blastmyceticumBiosci. Biotechnol. Biochem., 63 (9), 1669-1670 (1999).
  56. *Wender, P. A., Kirschberg, T. A., Williams, P. D., Bastiaans, H. M. M. and Irie, K.: A new class of simplified phorbol ester analogues: synthesis and binding to PKC and ηPKC-C1B (ηPKC-CRD2).  Org. Lett., 1 (7), 1009-1012 (1999).
  57. Nakagawa, Y., *Irie, K., Ohigashi, H., Hayashi, H. and Wender, P. A.: Synthesis and PKC isozyme surrogate binding of indothiolactam-V, a new thioamide analogue of tumor promoting indolactam-V.  Bioorg. Med. Chem. Lett., 10 (18), 2087-2090 (2000).
  58. *Irie, K., Nakahara, A., Ikawa, Y., Tanaka, M., Nakagawa, Y., Nakamura, Y., Ohigashi, H. and Wender, P. A.: Synthesis and tumor-promoting activities of 12-epi-phorbol-12,13-dibutyrate.  Biosci. Biotechnol. Biochem., 64 (11), 2429-2436 (2000).
  59. Tanaka, M., *Irie, K., Nakagawa, Y., Nakamura, Y., Ohigashi, H. and Wender, P. A.: The C4 hydroxyl group of phorbol esters is not necessary for protein kinase C binding.  Bioorg. Med. Chem. Lett., 11 (5), 719-722 (2001).
  60. Nakagawa, Y., *Irie, K., Nakamura, Y. and Ohigashi, H.: The amide hydrogen of (-)-indolactam- V and benzolactam-V8’s plays a critical role in protein kinase C binding and tumor-promoting activities.  Bioorg. Med. Chem. Lett., 11 (5), 723-728 (2001).
  61. Shindo, M., *Irie, K., Nakahara, A., Ohigashi, H., Konishi, H., Kikkawa, U., Fukuda, H. and Wender, P. A.: Toward the identification of selective modulators of protein kinase C (PKC) isozymes: establishment of a binding assay for PKC isozymes using synthetic C1 peptide receptors and identification of the critical residues involved in the phorbol ester binding.  Bioorg. Med. Chem., 9 (8), 2073-2081 (2001).
  62. Shindo, M., *Irie, K., Ohigashi, H., Kuriyama, M. and Saito, N.: Diacylglycerol kinase γ is one of the specific receptors of tumor-promoting phorbol esters.  Biochem. Biophys. Res. Commun. 289 (2), 451-456 (2001).
  63. Nakagawa, Y., *Irie, K., Masuda, A. and Ohigashi, H.: Synthesis, conformation and PKC isozyme surrogate binding of new lactone analogues of benzolactam-V8s.  Tetrahedron, 58 (5), 2101-2115 (2002).
  64. Murakami, K., *Irie, K., Morimoto, A., Ohigashi, H., Shindo, M., Nagao, M., Shimizu, T. and Shirasawa, T.: Synthesis, aggregation, neurotoxicity, and secondary structure of various Aβ1-42 mutants of familial Alzheimer’s disease at positions 21-23.  Biochem. Biophys. Res. Commun., 294 (1), 5-10 (2002).
  65. Masuda, A., *Irie, K., Nakagawa, Y. and Ohigashi, H.: Binding selectivity of conformationally restricted analogues of (-)-indoalctam-V to the C1 domains of protein kinase C isozymes.  Biosci. Biotechnol. Biochem., 66 (7), 1615-1617 (2002).
  66. Morimoto, A., *Irie, K., Murakami, A., Ohigashi, H., Shindo, M., Nagao, M., Shimizu, T. and Shirasawa, T.: Aggregation and neurotoxicity of mutant amyloid β (Aβ) peptides with proline replacement: importance of turn formation at positions 22 and 23.  Biochem. Biophys. Res. Commun., 295 (2), 306-311 (2002).
  67. Shindo, M., *Irie, K., Masuda, A., Ohigashi, H., Shirai, Y., Miyasaka, K. and Saito, N.: Synthesis and phorbol ester binding of the cysteine-rich domains of diacylglycerol kinase (DGK) isozymes: DGKγ and DGKβ are new targets of tumor-promoting phorbol esters.  J. Biol. Chem., 278 (20), 18448-18454 (2003).
  68. Nakagawa, Y., *Irie, K., Yamanaka, N., Ohigashi, H. and Tsuda, K.-i.: Synthesis and binding selectivity of 7- and 15-decylbenzolactone-V8 for the C1 domains of protein kinase C isozymes.  Bioorg. Med. Chem. Lett., 13 (18), 3015-3019 (2003).
  69. Murakami, K., *Irie, K., Morimoto, A., Ohigashi, H., Shindo, M., Nagao, M., Shimizu, T. and Shirasawa, T.: Neurotoxicity and physicochemical properties of Aβ mutant peptides from cerebral amyloid angiopathy: implication for the pathogenesis of cerebral amyloid angiopathy and Alzheimer’s disease.  J. Biol. Chem., 278 (46), 46179-46187 (2003).
  70. Shindo, M., *Irie, K., Fukuda, H. and Ohigashi, H.: Analysis of the non-covalent interaction between metal ions and the cysteine-rich domain of protein kinase C eta by electrospray ionization mass spectrometry.  Bioorg. Med. Chem., 11 (23), 5075-5082 (2003).
  71. Nakagawa, Y., *Irie, K., Komiya, Y., Ohigashi, H. and Tsuda, K.-i.: Synthesis, conformation and PKC isozyme surrogate binding of indolinelactam-Vs, new conformationally restricted analogues of (-)-indolactam-V.  Tetrahedron, 60 (33), 7077-7084 (2004).
  72. *Irie, K., Masuda, A., Shindo, M., Nakagawa, Y. and Ohigashi, H.: Tumor promoter binding of the protein kinase C C1 homology domain peptides of RasGRPs, chimaerins, and Unc13s.  Bioorg. Med. Chem., 12 (17), 4575-4583 (2004).
  73. Morimoto, A., *Irie, K., Murakami, K., Masuda, Y., Ohigashi, H., Nagao, M., Fukuda, H., Shimizu, T. and Shirasawa, T.: Analysis of the secondary structure of β-amyloid (Aβ42) fibrils by systematic proline replacement.  J. Biol. Chem., 279 (50), 52781-52788 (2004).
  74. Nakagawa, Y., *Irie, K., Yanagita, R. C., Ohigashi, H. and Tsuda, K.-i.: Indolactam-V is involved in the CH/π interaction with Pro-11 of the PKCδ C1B domain: application for the structural optimization of the PKCδ ligand.  J. Am. Chem. Soc., 127 (16), 5746-5747 (2005).
  75. Murakami, K., *Irie, K., Ohigashi, H., Hara, H., Nagao, M., Shimizu, T. and Shirasawa, T.: Formation and stabilization model of the 42-mer Aβ radical: implications for the long-lasting oxidative stress in Alzheimer’s disease.  J. Am. Chem. Soc., 127 (43), 15168-15174 (2005).
  76. *Nagao, M., Wen, T. C., Okamoto, M., Irie, K., Takaku, T. and Sakanaka, M.: In vivo neuroprotective activity of epopeptide AB against ischemic damage.  Cytotechnol., 47 (1-3), 139-144 (2005).
  77. Masuda, Y., *Irie, K., Murakami, K., Ohigashi, H., Ohashi, R., Takegoshi, K., Shimizu, T. and Shirasawa, T.: Verification of the turn at positions 22 and 23 of the β-amyloid fibrils with Italian mutation using solid-state NMR.  Bioorg. Med. Chem., 13 (24), 6803-6809 (2005).
  78. Nakagawa, Y., *Irie, K., Yanagita, R. C., Ohigashi, H., Tsuda, K.-i., Kashiwagi, K. and Saito, N.: Design and synthesis of 8-octyl-benzolactam-V9, a selective activator for protein kinase Cε and η.  J. Med. Chem., 49 (9), 2681-2688 (2006).
  79. Yanagita, C. R., Torii, K., Nakagawa, Y. and *Irie, K.: Binding selectivity of 1- or 12-substituted indolactam derivatives for protein kinase C isozymes.  Heterocycles, 73, 289-302 (2007).
  80. Murakami, K., Hara, H., Masuda, Y., Ohigashi, H. and *Irie, K.: Distance measurement between Tyr10 and Met35 in Amyloid β by site-directed spin-labeling ESR spectroscopy: implications for the stronger neurotoxicity of Aβ42 than Aβ40.  ChemBioChem, 8 (18), 2308-2314 (2007).
  81. Murakami, K., Uno, M., Masuda, Y., Shimizu, T., Shirasawa, T. and *Irie, K.: Isomerization and/or racemization at Asp23 of Aβ42 do not increase its aggregative ability, neurotoxicity, and radical productivity in vitroBiochem. Biophys. Res. Commun., 366 (3), 745-751 (2008).
  82. Yanagita, C. R., Nakagawa, Y., Yamanaka, N., Kashiwagi, K., Saito, N. and *Irie, K.: Synthesis, conformational analysis, and biological evaluation of 1-hexylindolactam-V10 as a selective activator for novel protein kinase C isoymes.  J. Med. Chem., 51 (1), 46-56 (2008).
  83. Sugimoto, T., Itagaki, K. and *Irie, K.: Design and physicochemical properties of new fluorescent ligands of protein kinase C isozymes focused on CH/π interaction.  Bioorg. Med. Chem., 16 (2), 650-657 (2008).
  84. Masuda, Y., Uemura, S., Nakanishi, A., Ohashi, R., Takegoshi, K., Shimizu, T., Shirasawa, T. and *Irie, K.: Verification of the C-terminal intramolecular β-sheet in Aβ42 aggregates using solid-state NMR: implications for potent neurotoxicity through the formation of radicals.  Bioorg. Med. Chem. Lett., 18 (11), 3206-3210 (2008).
  85. Masuda, Y., Nakanishi, A., Ohashi, R., Takegoshi, K., Shimizu, T., Shirasawa, T. and *Irie, K.: Verification of the intermolecular parallel β-sheet in E22K-Aβ42 aggregates by solid-state NMR using rotational resonance: implications for the supramolecular arrangement of the toxic conformer of Aβ42.  Biosci. Biotechnol. Biochem., 72 (8), 2170-2175 (2008).
  86. Masuda, Y., Uemura, S., Ohashi, R., Nakanishi, A., Takegoshi, K., Shimizu, T., Shirasawa, T. and *Irie, K.: Identification of physiological and toxic conformations in Aβ42 aggregates.  ChemBioChem, 10 (2), 287-295 (2009).
  87. Nakagawa, Y., Yanagita, R. C., Hamada, N., Murakami, A., Takahashi, H., Saito, N., Nagai, H. and *Irie, K.: A simple analogue of tumor-promoting aplysiatoxin is an antineoplastic agent rather than a tumor promoter: development of a synthetically accessible protein kinase C activator with bryostatin-like activity.  J. Am. Chem. Soc., 131 (22), 7573-7579 (2009).
  88. Ohnishi, K., Irie, K. and *Murakami, A.: In vitro covalent binding proteins of zerumbone, a chemopreventive food factor.  Biosci. Biotechnol. Biochem., 73 (8), 1905–1907 (2009). 
  89. Huynh, M. U., Elston, M. C., Hernandez, N. M., Ball, D. B., Kajiyama, S.-i., Irie, K., Gerwick, W. H. and *Edwards, D. J.: Enzymatic production of (-)-indolactamV by LtxB, a cytochrome P450 monooxygenase.  J. Nat. Prod., 73 (1), 71–74 (2010).
  90. Kondo, T., Kajita, R., Miyazaki, A., Hokoyama, M., Nakamura-Miura, T., Mizuno, S., Masuda, Y., Irie, K., Tanaka, Y., Takada, S., Kakimoto, T. and *Sakagami, Y.: Stomatal density is controlled by a mesophyll-derived signaling molecule.  Plant Cell Physol., 51 (1), 1–8 (2010).
  91. Sekiguchi, H., Irie, K. and *Murakami, A.: Suppression of CD74 expression and Helicobacter pylori adhesion by auraptene targeting serum starvation-activated ERK1/2 in NCI-N87 gastric carcinoma cells.  Biosci. Biotechnol. Biochem., 74 (5), 1018–1024 (2010).
  92. Yasuda, M., Irie, K. and *Murakami, A.: Inhibition by genistein of the lipopolysaccharide-induced down-regulation of programmed cell death 4 in RAW 264.7 mouse macrophages.  Biosci. Biotechnol. Biochem., 74 (5), 1095–1097 (2010).
  93. Yasuda, M., Schmid, T., Rübsamen, D., Colburn, N. H., Irie, K. and *Murakami, A.: Downregulation of programmed cell death 4 by inflammatory conditions contributes to the generation of the tumor promoting microenvironment.  Mol. Carcinog., 49 (9), 837–848 (2010).
  94. Yanagita, R. C., Kamachi, H., Tanaka, K., Murakami, A., Nakagawa, Y., Tokuda, H., Nagai, H. and *Irie, K.: Role of the phenolic hydroxyl group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity.  Bioorg. Med. Chem. Lett., 20 (20), 6064-6066 (2010).
  95. Murakami, K., Horikoshi-Sakuraba, Y., Murata, N., Noda, Y., Masuda, Y., Kinoshita, N., Hatsuta, H., Murayama, S., Shirasawa, T., *Shimizu, T. and *Irie, K.: Monoclonal antibody against the turn of the 42-residue amyloid β-protein at positions 22 and 23.  ACS Chem. Neurosci., 1 (11), 747-756 (2010).
  96. Murata, N., Murakami, K., Ozawa, Y., Kinoshita, N., Irie, K., Shirasawa, T. and *Shimizu T.: Silymarin attenuated the amyloid β plaque burden and improved behavioral abnormalities in an Alzheimer’s disease mouse model.  Biosci. Biotechnol. Biochem., 74 (11), 2299-2306 (2010).
  97. Suzuki, T., Murakami, K., Izuo, N., Kume, T., Akaike, A., Nagata, T., Nishizaki, T., Tomiyama, T., Mori, H. and *Irie, K.: E22Δ mutation in amyloid β-protein promotes β-sheet transformation, radical production, and synaptotoxicity, but not neurotoxicity.  Int. J. Alzheimers Dis., ID 431320 (8 pages) (2010).
  98. Nakagawa, Y., Kikumori, M., Yanagita, R. C., Murakami, A., Tokuda, H., Nagai, H. and *Irie, K.: Synthesis and biological evaluation of the 12,12-dimethyl derivative of aplog-1, an antiproliferative analogue of tumor-promoting aplysiatoxin.  Biosci. Biotechnol. Biochem., 75 (6), 1167-1173 (2011).
  99. Murakami, K., Murata, N., Ozawa, Y., Kinoshita, N., Irie, K., Shirasawa, T. and *Shimizu, T.: Vitamin C restores behavioral deficits and Aβ oligomerization without affecting plaque formation in a mouse model of Alzheimer’s disease.  J. Alzheimers Dis., 26 (1), 7-18 (2011).
  100. Murakami, K., Yokoyama, S.-i., Murata, N., Ozawa, Y., Irie, K., Shirasawa, T. and *Shimizu, T.: Insulin receptor mutation results in insulin resistance and hyperinsulinemia but does not exacerbate Alzheimer’s-like phenotypes in mice.  Biochem. Biophys. Res. Commun., 409 (1), 34-39 (2011).
  101. Kawamura, T., Matsubara, K., Otaka, H., Tashiro, E., Shindo, K., Yanagita, R. C., Irie, K. and *Imoto, M.: Generation of “Unnatural Natural Product” library and identification of a small molecule inhibitor of XIAP.  Bioorg. Med. Chem., 19 (14), 4377-4385 (2011).
  102. *Takahashi, M., Sugiyama, Y., Kawabata, K., Takahashi, Y., Irie, K., Murakami, A., Kubo, Y., Kobayashi, K. and Ohigashi, H.: 1,2-Di-O-α-linolenoyl-3-O-β-galactosyl-sn-glycerol as a superoxide generation inhibitor from Perilla frutescens var. crispaBiosci. Biotechnol. Biochem., 75 (11), 2240-2242 (2011).
  103. *Masuda, Y., Fukuchi, M., Yatagawa, T., Tada, M., Takeda, K., Irie, K., Akagi, K.-i., Monobe, Y., Imazawa, T. and Takegoshi K.: Analysis of interaction sites of curcumin with the fibrils of 42-residue amyloid β protein (Aβ42) using solid-state NMR.  Bioorg. Med. Chem., 19 (20), 5967-5974 (2011).
  104. Murakami, K., Murata, N., Noda, Y., Tahara S., Kaneko, T., Kinoshita, N., Hatsuta, H., Murayama, S., Barnham, K. J., Irie, K., Shirasawa, T. and *Shimizu, T.: SOD1 (cupper/zinc superoxide dismutase) deficiency drives amyloid β protein oligomerization and memory loss in mouse model of Alzheimer’s disease.  J. Biol. Chem., 286 (52), 44557-44568 (2011).
  105. Tsuji, F., Ishihara, A., Kurata, K., Nakagawa, A., Okada, M., Kitamura, S., Kanamaru, K., Masuda, Y., Murakami, K., Irie, K. and *Sakagami, Y.: Geranyl modification on the tryptophan residue of ComXRO-E-2 pheromone by a cell-free system.  FEBS Lett., 586 (2), 174-179 (2012).
  106. Ueno, S., Yanagita, R. C., Murakami, K., Murakami, A., Tokuda, H., Suzuki, N., Fujiwara, T. and *Irie, K.: Identification and biological activities of bryostatins from Japanese bryozoan.  Biosci. Biotechnol. Biochem., 76 (5), 1041-1043 (2012).
  107. Murakami, K., Murata, N., Noda, Y., Irie, K., Shirasawa, T. and *Shimizu, T.: Stimulation of the amyloidogenic pathway by cytoplasmic superoxide radicals in an Alzheimer’s disease mouse model.  Biosci. Biotechnol. Biochem., 76 (6), 1098-1103 (2012).
  108. Shu, Y., Yanagita, R. C., Tokuda, H., Suzuki, N. and *Irie, K.: Synthesis of antineoplastic analogs of aplysiatoxin with various side chain structures.  Heterocycles, 86 (1), 281-303 (2012).
  109. *Tsuji, F., Ishihara, A. Nakagawa, A., Okada, M., Kitamura, S., Kanamaru, K., Masuda, Y., Murakami, K., Irie, K. and Sakagami, Y.: Lack of the consensus sequence necessary for tryptophan prenylation in the ComX pheromone precursor.  Biosci. Biotechnol. Biochem., 76 (8), 1492-1496 (2012).
  110. Kikumori, M., Yanagita, R. C., Tokuda, H., Suzuki, N., Nagai, H., Suenaga, K. and *Irie, K.: Structure-activity studies on the spiroketal moiety of a simplified analog of debromoaplysiatoxin with antiproliferative activity.  J. Med. Chem., 55 (11), 5614-5626 (2012).
  111. Izuo, N., Kume, T., Sato, M., Murakami, K., *Irie, K., Izumi, Y. and *Akaike, A.: Toxicity in rat primary neuron through the cellular oxidative stress induced by the turn formation at positions 22 and 23 of Aβ42.  ACS Chem. Neurosci., 3 (9), 674-681 (2012).
  112. Izumi, Y., Matsumura, A., Wakita, S., Akagi, K.-i., Fukuda, H., Kume, T., Irie, K., Sugimoto, H., Hashimoto, T. and *Akaike, A.: Isolation, identification, and biological evaluation of Nrf2-ARE activator from the leaves of green perilla (Perilla frutescencs var. crispa f. viridis).  Free Radc. Biol. Med., 53 (4), 669-679 (2012).
  113. Miyamae, Y., Kurisu, M., Murakami, K., Han, J., Isoda, H., Irie, K. and *Shigemori, H.: Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein.  Bioorg. Med. Chem., 20 (19), 5844-5849 (2012).
  114. Sekiguchi, H., Takabayashi, F., Irie, K. and *Murakami, A.: Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice.  J. Med. Food, 15 (7), 658-663 (2012).
  115. Ikeda, Y., Yamaji, R., Irie, K., Kioka, N. and *Murakami, A.: Glyceraldehyde 3-phosphate dehydrogenase regulates cyclooxygenase-2 expression by targeting mRNA stabiliy.  Arch. Biochem. Biophys., 528 (2), 141-147 (2012).
  116. *Kulic, L., McAfoose, J., Welt, T., Tackenberg, C., Späni, C., Wirth, F., Finder, V., Konietzko, U., Giese, M., Eckert, A., Kinoshita, N., Shimizu, T., Murakami, K., Irie, K., Rasool, S., Glabe, C., Hock, C. and Nitsch, R. M.: Early accumulation of intracellular fibrillar oligomers and late congophilic amyloid angiopathy in mice expressing the Osaka intra-Aβ APP mutation.  Transl. Psychiatry, 2, e183 (2012).
  117. Doi, T., *Masuda, Y., Irie, K., Akagi, K., Monobe, Y., Imazawa, T. and Takegoshi, K.: Solid-state NMR analysis of the β-strand orientation of the protofibrils of amyloid β-protein.  Biochem. Biophys. Res. Commun., 428 (4), 458-462 (2012).
  118. Soejima, N., *Ohyagi, Y., Nakamura, N., Himeno, E., Iimura, K. M., Sakae, N., Yamasaki, R., Tabira, T., Murakami, K., Irie, K., Kinoshita, N., Laferla, F. M., Kiyohara, Y., Iwaki, T. and Kira, J.-i.: Intracellular accumulation of toxic turn amyloid-β is associated with endoplasmic reticulum stress in Alzheimer’s disease.  Curr. Alzheimer Res., 10 (1), 11-20 (2013).
  119. Ohnishi, K., Nakahata, E., Irie, K. and *Murakami, A.: Zerumbone, an electrophilic sesquiterpene, induces cellular proteo-stress leading to activation of ubiquitin-proteasome system and autophagy.  Biochem. Biophys. Res. Commun., 430 (2), 616-622 (2013).
  120. Hanaki, Y., Kikumori, M., Ueno, S., Tokuda, H., Suzuki, K. and *Irie, K.: Structure-activity studies at position 27 of aplog-1, a simplified analog of debromoaplysiatoxin with anti-proliferative activity.  Tetrahedron, 69 (36), 7636-7645 (2013).
  121. Sato, M., Murakami, K., Uno, M., Ikubo, H., Nakagawa, Y., Katayama, S., Akagi, K.-i. and *Irie, K.: Structure–activity relationship of (+)-taxifolin isolated from silymarin as an inhibitor of amyloid β aggregation.  Biosci. Biotechnol. Biochem., 77 (5), 1100-1103 (2013).
  122. Kondo, T., Asai, M., Tsukita, K., Kutoku, Y., Ohsawa, Y., Sunada, Y., Imamura, K., Okita, K., Takahashi, K., Asaka, I., Aoi, T., Watanabe, A., Watanabe, K., Kadoya, C., Nakano, R., Watanabe, D., Maruyama, K., Hori, O., Hibino, S., Choshi, T., Nakahata, T., Hioki, H., Kaneko, T., Kobayashi, K., Toda, T., Murakami, K., Irie, K., Klein, W. L., Mori, H., Asada, T., Takahashi, R., *Iwata, N., Yamanaka, S. and *Inoue, H.: A drug screening platform for Alzheimer’s disease with intracellular Aβ oligomers using patient-specific iPSCs.  Cell Stem Cell, 12 (4), 487-489 (2013).
  123. Kurisu, M., Miyamae, Y., Murakami, K., Han, J., Isoda, H., Irie, K. and *Shigemori, H.: Inhibition of amyloid β aggregation by acteoside, a phenylethanoid glycoside.  Biosci. Biotechnol. Biochem., 77 (6), 1329-1332 (2013).
  124. Ohnishi, K., Ohkura, S., Nakahata, E., Ishisaka, A., Kawai, Y., Terao, J., Mori, T., Ishii, T., Nakayama, T., Kioka, N., Matsumoto, S., Ikeda, Y., Akiyama, M., Irie, K. and *Murakami, A.: Non-specific protein modifications by a phytochemical induce heat shock response for self-defense.  PLoS ONE, 8 (3), e58641 (2013).
  125. Kamachi, H., Tanaka, K., Yanagita, R. C., Murakami, A., Murakami, K., Tokuda, H., Suzuki, N., Nakagawa, Y. and *Irie, K.: Structure–activity studies on the side chain of a simplified analog of aplysiatoxin (aplog-1) with anti-proliferative activity.  Bioorg. Med. Chem., 21 (10), 2695-2702 (2013).
  126. Izuo, N., Murakami, K., Sato, M., Iwasaki, M., Izumi, Y., Kinoshita, N., Akaike, A., *Irie, K. and *Kume, T.: Non-toxic conformer of Aβ42 may suppress Aβ42-induced toxicity in rat primary neurons: implications for the novel therapeutic strategy of Alzheimer’s disease.  Biochem. Biophys. Res. Commun., 438 (1), 1-5 (2013).
  127. Yanagita, R. C., Kamachi, H., Kikumori, M., Tokuda, H., Suzuki, N., Suenaga, K., Nagai, H., and *Irie, K.: Effects of the methoxy group in the side chain of debromoaplysiatoxin on its tumor-promoting and anti-proliferative activities.  Bioorg. Med. Chem. Lett., 23 (15), 4319-4323 (2013).
  128. Sato, M., Murakami, K., Ikubo, H., Uno, M., Nakagawa, Y., Katayama, S., Akagi, K.-i. and *Irie, K.: Site-specific inhibitory mechanism for amyloid-β42 aggregation by catechol-type flavonoids targeting the Lys-residues.  J. Biol. Chem., 288 (32), 23212-23224 (2013).
  129. Ohtera, A., Miyamae, Y., Nakai, N., Kawachi, A., Kawada, K., Han, J., Isoda, H., Neffati, M., Akita, T., Maejima, K., Masuda, S., Kambe, T., Mori, N., Irie, K. and *Nagao, M.: Identification of 6-octadecynoic acid from a methanol extract of Marrubium vulgare L. as a peroxisome proliferator-activated receptor γ agonist.  Biochem. Biophys. Res. Commun., 440 (2), 204-209 (2013).
  130. Jiang, W., Zhou, W., Uchida, H., Kikumori, M., Irie, K., Watanabe, R., Suzuki, T., Sakamoto, B., Kamio, M. and *Nagai, H.: A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producensMar. Drugs, 12, 2748-2759 (2014).
  131. Kikumori, M., Yanagita, R. C. and *Irie, K.: Improved and large-scale synthesis of 10-methyl-aplog-1, a potential lead for an anticancer drug.  Tetrahedron, 70 (52), 9776-9782 (2014).
  132. Jiang, W., Tan, S., Hanaki, Y., Irie, K., Uchida, H., Watanabe, R., Suzuki, T., Sakamoto, B., Kamio, M. and *Nagai, H.: Two new lyngbyatoxin derivatives from the cyanobacterium Moorea producensMar. Drugs, 12, 5788-5800 (2014).
  133. Takahashi, H., Adachi, N., Shirafuji, T., Danno, S., Ueyama, T., Vendruscolo, M., Shuvaev, A. N., Sugimoto, T., Seki, T., Hamada, D., Irie, K., Hirai, H., Sakai, N. and *Saito, N.: Identification and characterization of PKCγ, implicated in SCA14, as an amyloidogenic protein.  Human Mol. Genet., 24 (2), 525-539 (2015).
  134. Hanaki, Y., Yanagita, R. C., Sugahara, T., Aida, M., Tokuda, H., Suzuki, N. and *Irie, K.: Synthesis and biological activities of the amide derivative of aplog-1, a simplified analog of aplysiatoxin with anti-proliferative and cytotoxic activities.  Biosci. Biotechnol. Biochem., 79 (6), 888-895 (2015).
  135. Murakami, K., Suzuki, T., Hanaki, M., Monobe, Y., Akagi, K.-i. and *Irie, K.: Synthesis and characterization of the amyloid β40 dimer model with a linker at position 30 adjacent to the intermolecular β-sheet region.  Biochem. Biophys. Res. Commun., 466 (3), 463-467 (2015).
  136. Hashimoto, A., Ohkura, K., Takahashi, M., Kizu, K., Narita, H., Enomoto, S., Miyamae, Y., Masuda, S., Nagao, M., Irie, K., Ohigashi, H., Andrews, G. K. and *Kambe, T.: Soybean extracts increase cell surface ZIP4 abundance and cellular zinc levels: a potential novel strategy to enhance zinc absorption by ZIP4-targeting.  Biochem. J., 472 (2), 183-193 (2015).
  137. Ohtera, A., *Miyamae, Y., Yoshida, K., Mejima, K., Akita, T., Kakizuka, A., Irie, K., Masuda, S., Kambe, T. and Nagao, M.: Identification of a new type of covalent PPARγ agonist using a ligand-linking strategy.  ACS Chem. Biol., 10 (12), 2794-2804 (2015).
  138. Hanaki, M., Murakami, K., Akagi, K.-i. and *Irie, K.: Structural insights into mechanisms for inhibiting amyloid β42 aggregation by non-catechol-type flavonoids.  Bioorg. Med. Chem., 24 (2), 304-313 (2016).
  139. Kikumori, M., Yanagita, R. C., Tokuda, H., Suenaga, K., Nagai, H. and *Irie, K.: Structural optimization of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, as an anticancer lead.  Biosci. Biotechnol. Biochem., 80 (2), 221-231 (2016).
  140. Murakami, K., Tokuda, M., Suzuki, T., Irie, Y., Hanaki, M., Izuo, N., Monobe, Y., Akagi, K.-i., Ishii, R., Tatebe, H., Tokuda, T., Maeda, M., Kume, T., Shimizu, T. and *Irie, K.: Monoclonal antibody with conformational specificity for a toxic conformer of amyloid β42 and its application toward the Alzheimer’s disease diagnosis.  Sci. Rep., 6, 29038 (2016).
  141. Ashida, Y., *Yanagita, R. C., Takahashi, C., Kawanami, Y. and Irie, K.: Binding mode prediction of aplysiatoxin, a potent agonist of protein kinase C, through molecular simulation and structure-activity study on simplified analogs of the receptor-recognition domain.  Bioorg. Med. Chem., 24 (18), 4218-4227 (2016).
  142. Igarashi, Y., Onishi, K., Irie, K. and *Murakami, A.: Possible contribution of zerumbone-induced proteo-stress to its anti-inflammatory functions via the activation of heat shock factor 1.  PLoS ONE, 11 (8), e0161282 (2016).
  143. Yoshioka, T., Murakami, K., Ido, K., Hanaki, M., Yamaguchi, K., Midorikawa, S., Taniwaki, S., Gunji, H. and *Irie, K.: Semisynthesis and structure-activity studies of Uncarinic acid C isolated from Uncaria rhynchophilla as a specific inhibitor of the nucleation phase in amyloid β42 aggregation.  J. Nat. Prod., 79 (10), 2521-2529 (2016). 
  144. Kidachi, E., Kurisu, M., Miyamae, Y., Hanaki, M., Murakami, K., Irie, K. and *Shigemori, H.: Structure-activity relationship of phenylethanoid glycosides on the inhibition of amyloid β aggregation.  Heterocycles, 92 (11), 1976-1982 (2016).
  145. Himidene, A. B., Hanaki, M., Murakami, K., Irie, K., Isoda, H. and *Shigemori, H.: Inhibitory activities of antioxidant flavonoids from Tamarix gallica on amyloid aggregation related to Alzheimer’s and type 2 diabetes diseases.  Biol. Pharm. Bull., 40 (2), 238-241 (2017).
  146. Irie, Y., Murakami, K., Hanaki, M., Hanaki, Y., Suzuki, T., Monobe, Y., Takai, T., Akagi, K.-i., Kawase, T., Hirose, K. and *Irie, K.: Synthetic models of quasi-stable amyloid β40 oligomers with significant neurotoxicity.  ACS Chem. Neurosci., 8 (4), 807-816 (2017).
  147. Hanaki, Y., Kikumori, M., Tokuda, H., Okamura, M., Dan, S., Adachi, N., Saito, N., Yanagita, R. C. and *Irie, K.: Loss of the phenolic hydroxyl group and aromaticity from the side chain of anti-proliferative 10-methyl-aplog-1, a simplified analog of aplysiatoxin, enhances its tumor-promoting and proinflammatory activities.  Molecules, 22 (4), 631 (2017).
  148. Oku, Y., Murakami, K., Irie, K., Hoseki, J. and *Sakai, Y.: Synthesized Aβ42 caused intracellular oxidative damage, leading to cell death, via lysosome rupture.  Cell Struct. Funct., 42 (1), 71-79 (2017).
  149. Aihara, Y., Kawaguchi, A., Hanaki, M., Murakami, K., Irie, K. and *Shigemori, H.: Inhibitory activity of hispidin derivatives isolated from inonotus obliquus on amyloid β aggregation.  Heterocycles, 94 (7), 1280-1287 (2017).
  150. Kawabata, K., Kitamura, K., Irie, K., Naruse, S., Matsuura, T., Uemae, T., Taira, S., Ohigashi, H., Murakami, S., Takahashi, M., Kaido and Kawakami, B.: Triterpenoids isolated from Ziziphus jujuba enhance glucose uptake activity in skeletal muscle cells.  J. Nutr. Sci. Vitaminol., 63 (3), 193-199 (2017).
  151. Izuo, N., Kasahara, C., Murakami, K., Kume, T., Maeda, M., Irie, K., Yokote, K. and *Shimizu, T.: A toxic conformer of Aβ42 with a turn at 22-23 is a novel therapeutic target for Alzheimer’s disease.  Sci. Rep., 7, 11811 (2017).
  152. Hanaki, Y., Shikata, Y., Kikumori, M., Hotta, N., Imoto, M. and *Irie, K.: Identification of protein kinase C isozymes involved in the anti-proliferative and pro-apoptotic activities of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, in several cancer cell lines.  Biochem. Biophys. Res. Commun., in press. 

総説・著書など

  1. 入江一浩*小清水弘一:微生物の生産する発癌プロモーター. 日本放線菌学会会誌, 49, 3-9 (1986).
  2. 入江一浩:Teleocidin 類の構造活性相関と蛍光標識化. 日本農芸化学会誌, 61 (7), 830-833 (1987).
  3. *Koshimizu, K. and Irie, K.: Structure-activity studies in the induction of Epstein-Barr virus by the indole alkaloid tumor promoter teleocidins.  In Hokkaido University Medical Library Series, Vol. 24, Ed. Osato, T., pp.111-134 (1989).
  4. *入江一浩,小清水弘一:発癌プロモーターの作用機作解明への有機化学的アプローチ. 有機合成化学協会誌, 49 (11), 1070-1079 (1991).
  5. *Irie, K. and Koshimizu, K.: The indole alkaloid tumor promoter teleocidins as Epstein-Barr virus inducers: structure, biosynthesis and structure-activity relationship.  In Natural products as antiviral agents, Eds. Chu, C. K. and Cutler, H. G., Plenum, New York, pp.257-273 (1992).
  6. Ando, T., Irie, K., *Koshimizu, K., Nakajima, S., Takemura, T. and Sakata, I.: A convenient synthesis of chlorin e6 dimer and trimer.  In Photodynamic Therapy and Biomedical Lasers, Eds. Spinelli, P., Dal Fante, M. and Marchesini, R., Elsevier Science Publishers B. V., Amsterdam, pp.764-768 (1992).
  7. *入江一浩,小清水弘一:腫瘍親和性光増感剤ヘマトポルフィリン誘導体の活性成分は? 化学, 47 (2), 142 (1992).
  8. Irie, K. and *Koshimizu, K.: Chemistry of indole alkaloid tumor promoter teleocidins.  Comments Agric. & Food Chemistry, 3 (1), 1-25 (1993).
  9. 入江一浩:発癌プロモーター・テレオシジンの作用機構に関する有機化学的研究. 日本農芸化学会誌, 68 (9), 1289-1296 (1994).
  10. 入江一浩:プロテインキナーゼCのホルボールエステル結合部位の光アフィニティーラベリングによる構造解析.生化学, 68 (2), 129-132 (1996).
  11. *入江一浩,大東 肇:プロテインキナーゼCのホルボールエステル結合部位の合成と化学的特性.有機合成化学協会誌, 54 (12), 1024-1033 (1996).
  12. 入江一浩:プロテインキナーゼCの2つの zinc finger モチーフの機能と役割. 化学と生物, 35 (9), 638-639 (1997).
  13. *Irie, K., Yanai, Y., Ohigashi, H. and Wender, P. A.: Synthesis and characterization of model peptides incorporating the phorbol ester-binding domain of protein kinase C.  In Peptide Chemistry 1996, Ed. Kitada, C., Protein Research Foundation, Osaka, pp.209-212 (1997).
  14. 入江一浩:プロテインキナーゼ機能ドメインの化学合成. バイオサイエンスとインダストリー, 56 (8), 541-544 (1998).
  15. 入江一浩:ビオチンを用いた新しい光アフィニティーラベリング法の開発と応用. 化学と工業, 51 (10), 1634 (1998).
  16. *Wender, P. A., Martin-Cantalejo, Y., Carpenter, A. J., Chiu, A., Brabander, J. D., Harran, P. G., Jimenez, J.-M., Koehler, M. F. T., Lippa, B., Morrison, J. A., Müller, S. G., Müller, S. N., Park, C.-M., Shiozaki, M., Siedenbiedel, C., Skalitzky, D. J., Tanaka, M. and Irie, K.: The chemistry-medicine continuum: synthetic, computer, spectroscopic and biological studies on new chemotherapeutic leads.  Pure & Appl. Chem., 70 (3), 539-546 (1998).
  17. *Irie, K., Oie, K., Nakahara, A., Yanai, Y., Ohigashi, H., Fukuda, H. and Wender, P. A.: Synthesis and phorbol ester binding of the zinc-finger like sequences of all protein kinase C isozymes.  In Peptide Science 1998, Ed. Kondo, M., Protein Research Foundation, Osaka, pp.65-68 (1999).
  18. 中川 優,*入江一浩:発がんプロモーターのnPKC C1Bドメインへの選択的結合. バイオサイエンスとインダストリー, 58 (8), 570-571 (2000).
  19. *Irie, K., Nakahara, A., Nakagawa, Y., Ohigashi, H., Shindo, M., Fukuda, H., Konishi, H. and Kikkawa, U.: Selective binding of tumor promoters to the novel PKC C1B domains.  In Peptide Science 2000, Ed. Shioiri, T., The Japanese Peptide Society, pp.197-200 (2001).
  20. Shindo, M., *Irie, K., Ohigashi, H., Kuriyama, M. and Saito, N.: Tumor-promoting phorbol esters bind directly to the regulatory domain of diacylglycerol kinase gamma.  In Peptide Science 2001, Ed. Aoyagi, H., The Japanese Peptide Society, pp.207-210 (2002).
  21. *入江一浩,大東 肇:プロテインキナーゼCのシステインリッチドメインの化学合成,機能解析とドラッグデザイン.有機合成化学協会誌, 60 (6), 563-572 (2002).
  22. *Irie, K., Nakahara, A., Nakagawa, Y., Ohigashi, H., Shindo, M., Fukuda, H., Konishi, H., Kikkawa, U., Kashiwagi, K. and Saito, N.: Establishment of a binding assay for protein kianse C isozymes using synthetic C1 peptides and development of new medicinal leads with protein kinase C isozyme and C1 domain selectivity.  Pharmacol. Ther., 93 (2-3), 271-281 (2002).
  23. *入江一浩,大東 肇:ペプチド合成によるホルボールエステル受容体の機能解析. 化学と生物, 42 (1), 54-62 (2004).
  24. *Irie, K., Nakagawa, Y. and Ohigashi, H.: Indolactam and benzolactam compounds as new medicinal leads with binding selectivity for C1 domains of protein kinase C isozymes.  Curr. Pharm. Design, 10 (12), 1371-1385 (2004).
  25. Murakami, K., *Irie, K., Morimoto, A., Masuda, Y., Ohigashi, H., Nagao, M., Fukuda, H., Shimizu, T. and Shirasawa, T.: New aggregation model of amyloid β by the systematic proline replacement.  In Peptide Science 2004, Shimohigashi, Y. (Ed.), The Japanese Peptide Society, pp.179-182 (2005).
  26. *Irie, K., Murakami, K., Masuda, Y., Morimoto, A., Ohigashi, H., Ohashi, R., Takegoshi, K., Nagao, M., Shimizu, T. and Shirasawa, T.: Structure of β-amyloid fibrils and its relevance to their neurotoxicity: implications for the pathogenesis of Alzheimer’s disease.  J. Biosci. Bioeng., 99 (5), 437-447 (2005).
  27. *Irie, K., Nakagawa, Y. and Ohigashi, H.: Toward the development of new medicinal leads with selectivity for protein kinase C isozymes.  Chem. Rec., 5 (4), 185-195 (2005).
  28. 入江一浩:CH/π 相互作用を利用した薬剤開発.ファルマシア, 42 (5), 427-430 (2006).
  29. Murakami, K., *Irie, K., Ohigashi, H., Hara, H., Nagao, M., Shimizu, T. and Shirasawa, T.: ‘Malignant’ conformation of Alzheimer’s β peptide (Aβ42) through radical formation.  In Peptide Science 2006, H. Ishida and H. Mihara (Eds.), The Japanese Peptide Society, pp.19-20 (2006).
  30. *Irie, K., Murakami, K., Masuda, Y., Morimoto, A., Ohigashi, H., Hara, H., Ohashi, R., Takegoshi, K., Fukuda, H., Nagao, M., Shimizu, T. and Shirasawa, T.: The toxic conformation of the 42-residue amyloid β peptide and its relevance to oxidative stress in Alzheimer’s disease.  Mini-Rev. Med. Chem., 7 (10), 1001-1008 (2007).
  31. *入江一浩, 増田裕一:βアミロイドの毒性コンホメーション:化学と生物, 46 (6), 431-434 (2008).
  32. *村上一馬, 清水孝彦, 白澤卓二, 入江一浩:アミロイドβ (Aβ42) の毒性コンホメーションの提唱.基礎老化研究, 32 (3), 25-29 (2008).
  33. Masuda, Y., Uemura, S., Ohashi, R., Nakanishi, A., Takegoshi, K. and *Irie, K.: Identification of toxic conformation in Aβ42 aggregates using solid-state NMR.  In Peptide Science 2008, M. Nomizu (Eds.), The Japanese Peptide Society, pp.25-28 (2009).
  34. 増田裕一, *入江一浩:ポリフェノールによるアルツハイマー病予防の可能性.FFIジャーナル, 215 (1), 53–59 (2010).
  35. Murakami, K., Masuda, Y., Shirasawa, T., *Shimizu, T. and *Irie, K.: The turn formation at positions 22 and 23 in the 42-mer a myloid β peptide: The emerging role in the pathogenesis of Alzheimer’s disease.  Geriatr. Gerontol. Int., 10 (Suppl. 1), S169-S179 (2010).
  36. *Murakami, K., Shimizu, T. and Irie, K.: Formation of the 42-mer amyloid β radical and the therapeutic role of superoxide dismutase in Alzheimer’s disease.  J. Amino Acids, ID 654207 (10 pages) (2011).
  37. *Irie, K., Yanagita, C. R. and Nakagawa, Y.: Challenges to develop bryostatin-type anticancer drugs based on the activation mechanism of protein kinase Cδ.  Med. Res. Rev., 32 (3), 518-535 (2012).
  38. *Irie, K., Kikumori, M., Kamachi, H., Tanaka, K., Murakami, A., Yanagita, R. C., Tokuda, H., Suzuki, N., Nagai, H. and Nakagawa, Y.: Synthesis and structure–activity studies of simplified analogs of aplysiatoxin with anti-proliferative activity like bryostatin 1.  Pure Appl. Chem., 84 (6), 1341-1351 (2012).
  39. 村上一馬,増田裕一,*入江一浩:固体NMRおよびESRによるアミロイド β の立体構造解析と毒性ターン構造特異抗体の開発.遺伝子医学MOOK21号「最新ペプチド合成技術とその創薬研究への応用」,メディカル ドゥ,第6章6-4, p211-216 (2012).
  40. 大西康太,入江一浩*村上 明:ハナショウガ含有テルペノイドzerumboneの発がん抑制機構.Vitamins (Japan), 86 (3), 133-141 (2012).
  41. 村上一馬,佐藤瑞穂,鈴木啓之,泉尾直孝,久米利明,赤池昭紀,永田 徹,西崎知之,富山貴美,森 啓,*入江一浩:アミロイド β の「毒性コンホマー」形成とGlu22位における遺伝性変異.Dementia Japan, 26 (3), 311-318 (2012).
  42. 村上一馬,*入江一浩:アミロイド β の毒性ターン構造を認識する抗体の開発.神経内科, 77 (2), 179-184 (2012).
  43. 大西康太,入江一浩*村上 明:発がん抑制物質ゼルンボンのタンパク質変性ストレスに起因した生理作用.バイオサイエンスとインダストリー, 71 (5), 400-406 (2013).
  44. Ohnishi, K., Irie, K. and *Murakami, A.: Modulation of protein quality control systems as novel mechanisms underlying functionality of food phytochemicals.  Funct. Foods Health Dis., 3 (10), 400-415 (2013).
  45. *Irie, K. and R. C. Yanagita: Synthesis and biological activities of the simplified analogs of natural PKC ligands, bryostatin-1 and aplysiatoxin.  Chem. Rec., 14 (2), 251-267 (2014).
  46. *Murakami, K., Irie, K. and Shimizu, T.: Potential role of vitamin C in the prevention of Alzheimer’s disease. In Diet and Nutrition in Dementia and Cognitive Decline, C. R. Martin and V. R. Preedy (Eds.), Elsevier, pp.663-668 (2015).
  47. 入江一浩:アプリシアトキシンの骨格を利用した抗がん剤シーズの開発研究.CSJ Current Rev. 19, 生物活性分子のケミカルバイオロジー, 日本化学会編, Chapter 12, p127-133 (2015).
  48. 入江一浩,津江広人編著,高野俊幸,加納太一,松原誠二郎,板東俊和,藤田健一著:有機化学要論、学術図書出版社 (2015).
  49. *泉尾直孝,村上一馬,久米利明,前田雅弘,入江一浩,清水孝彦:アルツハイマー病様神経毒性におけるアミロイドβコンホマーの役割,基礎老化研究39 (3), 29-34 (2015).
  50. 入江一浩:アルツハイマー病の正確な早期診断の実現に向けて.化学, 71 (11), 41-44 (2016).
  51. *入江一浩,村上一馬: アミロイドβタンパク質の構造解析と診断への応用.「認知症」,実験医学35 (12) 増刊,p52-59 (2017).
  52. 村上一馬,*入江一浩:食品・生薬成分によるアミロイドβ42の凝集抑制機構の系統的解析.日本認知症学会誌, 31 (3), 351-360 (2017).

特許登録

  1. *Irie, K., Murakami, K., Masuda, Y., Shimizu, T., Shirasawa, T. and Seito, T.: Antibody recognizing turn structure in amyloid β.  United States Patent, US 8,710,193, Apr. 29, 2014.
  2. *Irie, K., Murakami, K., Masuda, Y., Shimizu, T., Shirasawa, T. and Seito, T.: Antibody recognizing turn structure in amyloid β.  China Patent, ZL201080046483.9, Dec. 24, 2014.
  3. *入江一浩,菊森将之,蒲池弘明,柳田 亮,中川 優:新規アプリシアトキシン誘導体及びそれを含有する抗がん剤,特許第6170908号,平成29年7月7日.