Previous publications (-2004)


　
(アセトゲニン類の合成と阻害機構)

　
(ユビキノン類縁体の生物有機化学)

　
(その他の呼吸鎖酵素阻害剤)





・ Miyoshi, H., Ohshima, M., Shimada, H., Akagi, T., Iwamura, H. and McLaughlin, J.L.(1998) Essential structural factors of annonaceous acetogenins as potent inhibitors of mitochondrial complex I. Biochim. Biophys. Acta (Bioenergetics) 1365, 443-452.


・ Ichimaru, N., Murai, M., Abe, M.,Hamada, T., Yamada, Y.,Makino, S., Nishioka, T., Makabe, H., Makino, A., Kobayashi, T. and Miyoshi, H. (2004) Synthesis and inhibition mechanism of Δlac-acetogenins, a novel type of inhibitor of bovine heart mitochondrial complex I. Biochemistry, 44, 816-825.


・ Makabe, H., Hattori, Y., Kimura, Y., Konno, H., Abe, M., Miyoshi, H., Tanaka, A. and Oritani, T. (2004) Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I. Tetrahedron, 60, 10651-10657.


・ Hamada, T., Ichimaru, N., Abe, M., Fujita, D., Kenmochi, A., Nishioka, T., Zwicker, K., Brandt, U. and Miyoshi, H. (2004) Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I. Biochemistry 43, 3651-3658.


・ Ichimaru, N., Abe, M., Kenmochi, A., Hamada, T., Nishioka, T. and Miyoshi, H. (2004) Synthesis of 13C-Labeled Ubiquinone-Acetogenin Hybrid Inhibitors of Mitochondrial Complex I. J. Pesticide Sci. 29, 127-129.


・ Abe, M., Kenmochi, A., Ichimaru, N., Hamada, T., Nishioka, T. and Miyoshi, H. (2004) Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings. Bioorg. Med. Chem. Lett. 14, 779-782.


・ Konno, H., Hiura N., Makabe, H., Abe, M. and Miyoshi, H. (2004) Synthesis and mitochondrial complex I inhibition of dihydroxy-cohibin A, non-THF annonaceous acetogenin analogue. Bioorg. Med. Chem. Lett. 14, 629-632.


・ Makabe, H., Miyawaki, A., Takahashi, R., Hattori, Y., Konno, H., Abe, M. and Miyoshi, H. (2004) Synthesis of two possible diastereomers of reticulatain-1. Tetrahedron Lett. 45, 973-977


・ Yabunaka, H., Abe, M., Kenmochi, A., Hamada, T., Nishioka T. and Miyoshi, H. (2003) Synthesis and inhibitory activity of ubiquinone-acetogenin hybrid inhibitor with bovine mitochondrial complex I. Bioorg. Med. Chem. Lett. 13, 2385-2388.


・ Motoyama, T., Yabunaka, H. and Miyoshi, H. (2002) Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I. Bioorg. Med. Chem. Lett. 12, 2089-2092.


・ Takada, M., Kuwabara, K., Nakato, H., Tanaka, A., Iwamura, H., and Miyoshi, H. (2000) Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I. Biochim. Biophys. Acta (Bioenergetics) 1460, 302-310.


・ Kuwabara, K., Takada, M., Iwata, J., Tatsumoto, K., Sakamoto, K., Iwamura, H. and Miyoshi, H. (2000) Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics. Eur. J. Biochem. 267, 2538-2546.









・ Elias, M.D., Nakamura, S., Migita, C. T., Miyoshi, H., Toyama, H., Matsushita, K., Adachi, O. and Yamada, M. (2004) Occurrence of a bound ubiquinone and its function in Escherichia coli membrane-bound quinoprotein glucose dehydrogenase. J. Biol. Chem. 279, 3078-3083.


・ Grimaldi S., Ostermann, T., Weiden, N., Mogi, T., Miyoshi, H., Lidwig, B., Michel, H., Prinsner, T. F. and MacMillan, F. (2003) Asymmetric binding of the high-affinity QH ubisemiquinone in quinol oxidase (bo3) from Escherichia coli studied by multifrequency electron paramagnetic resonance spectroscopy. Biochemistry 42, 5632-5639.


・ Yankovskaya, V., Horsefield, R., Tornroth, S., Luna-Chavez, C., Miyoshi, H., Leger, C., Byrne, B., Cecchini, G. and Iwata, S. (2003) Architecture of succinate dehydrogenase and reactive oxygen species generation. Science 299, 700-704.


・ Sakamoto, K., Nomura, K. and Miyoshi, H. (2002) Synthesis and electron-transfer activity of azido ubiquinone-2. J. Pesticide Sci. 27, 147-149.


・ Miyoshi, H. (2001) Probing the ubiquinone reduction site in bovine mitochondrial complex I using a series of synthetic ubiquinones and inhibitors. J. Bioenerg. Biomembr. 33, 223-231.


・ Miyadera, H., Amino, H., Hiraishi, A., Taka, H., Murayama, K., Miyoshi, H., Sakamoto, K., Ishii, N., Hekimi, S. and Kita, K. (2001) Altered quinone biosynthesis in the long-lived clk-1 mutants of Caenorhabditis. elegans. J. Biol. Chem. 276, 7713-7716.


・ Hellwig, P., Mogi, T., Tomson, F. L., Gennis, R. B., Iwata, J., Miyoshi, H. and Matele, W. (1999) The vibrational modes of ubiquinone in cytochrome bo3 from Escherichia coli identified by Fourier transform infrared difference spectroscopy and specific 13C labeling. Biochemistry 38, 14683-14689


・ Sakamoto, K., Miyoshi, H., Ohshima, M., Kuwabara, K., Kano, K., Akagi, T., Mogi, T. and Iwamura, H. (1998) Role of isoprenyl tail of ubiquinone in reaction with respiratory enzymes: Studies with bovine heart mitochondrial complex I and Escherichia coli bo-type ubiquinol oxidase. Biochemistry 37, 15106-15113.


・ Sato-Watanabe, M., Mogi, T., Sakamoto, K., Miyoshi, H. and Anraku, Y. (1998) Isolation and characterization of quinone analogue-resistant mutants of bo-type ubiquinol oxidase from Escherichia coli. Biochemistry 37, 12744-12752.


・ Ohshima, M., Miyoshi, H., Sakamoto, K., Takegami, K., Iwata, J., Kuwabara, K., Iwamura, H. and Yagi, T. (1998) Characterization of the ubiquinone reduction site of mitochondrial complex I using bulky synthetic ubiquinones. Biochemistry 37, 6436-6445.


・ Sato-Watanabe, M., Mogi, T., Miyoshi, H. and Anraku, Y. (1998) Characterization and functional role of the QH site of bo-type ubiquinol oxidase from Escherichia coli. Biochemistry 37, 5356-5361.


・ Sakamoto, K., Miyoshi, H., Takegami, K., Mogi, T., Anraku, Y. and Iwamura, H. (1996) Probing substrate binding site of the Escherichia coli quinol oxidases using synthetic ubiquinol analogues. J. Biol. Chem. 271, 29897-29902.


・ Sato-Watanabe, M., Mogi, T., Ogura, T., Kitagawa, T., Miyoshi, H., Iwamura, H. and Anraku, Y. (1994) Identification of a novel quinone binding site in the cytochrome bo complex from Escherichia coli. J. Biol. Chem. 269, 28908-28912.


・ Sato-Watanabe, M., Mogi, T., Miyoshi, H., Iwamura, H., Matsushita, K., Adachi, O. and Anraku, Y. (1994) Structure-function studies of the ubiquinol oxidation site of cytochrome bo complex from Escherichia coli using p-benzoquinones and substituted phenols. J. Biol. Chem. 269, 28899-28907.







・ Ritter, M., Palsdottir, H., Abe, M., Mantele, W., Hunte, C., Miyoshi, H. and Hellwig, P. (2004) Direct evidence for the interaction of stigmatellin with a protonated acidic group in the bc1 complex from S. cerevisiae as monitored by FTIR difference spectroscopy and 13C specific labeling. Biochemistry 43, 8439-8446.


・ Ino, T., Nishioka, T. and Miyoshi, H. (2003) Characterization of inhibitor binding sites of mitochondrial complex I using fluorescent inhibitor. Biochim. Biophys. Acta (Bioenergetics) 1605, 15-20.


・ Miyadera, H., Shiomi, K., Ui, H., Yamaguchi Y., Masuma, R., Tomoda, H., Miyoshi, H., Osanai, A., Kita, K. and Ohmura, S. (2003) Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase). Proc. Natl. Acad. Sci. USA 100, 473-477.


・ Nakamaru-Ogiso, E., Sakamoto, K., Matsuno-Yagi, A., Miyoshi, H. and Yagi, T. (2003) The ND5 subunit was labeled by a photoaffinity analogue of fenpyroximate in bovine mitochondrial complex I. Biochemistry 42, 746-754.


・ Yabunaka, H., Kenmochi, A., Nakatogawa, A., Sakamoto, K. and Miyoshi, H. (2002) Hybrid ubiquinone; novel inhibitor of mitochondrial complex I. Biochim. Biophys. Acta (Bioenergetics) 1556, 106-112.


・ Ohmura, S., Miyadera, H., Ui, H., Shiomi, K., Yamaguchi, Y., Masuma, R., Nagamitsu, T., Takano, D., Sunazuka, T., Harder, A., Kolbl, H., Namikoshi, M., Miyoshi H., Sakamoto, K. and Kita, K. (2001) Anthelmintic compound, nafuredin, shows selective inhibition of complex I in helminth mitochondria. Proc. Natl. Acad. Sci. USA 98, 60-62.
・ Iwata, J., Miyoshi, H. and Iwamura, H. (1999) Origin of selective inhibition of mitochondrial complex I by pyridinium-type inhibitor MP-24. Biochim. Biophys. Acta (Bioenergetics) 1413, 63-69.


・ Miyoshi, H. (1998) Structure-activity relationships of some complex I inhibitors. Biochim. Biophys. Acta (Bioenergetics) 1364, 236-244.


・ Miyoshi, H., Iwata, J., Sakamoto, K., Furukawa, H., Takada, M., Iwamura, H., Watanabe, T. and Kodama, Y. (1998) Specificity of pyridinium inhibitors of the ubiquinone reduction sites in mitochondrial complex I. J. Biol. Chem. 273, 17368-17374.


・ Miyoshi, H., Inoue, M., Okamoto, S., Ohshima, M., Sakamoto, K. and Iwamura, H. (1997) Probing the ubiquinone reduction site of mitochondrial complex I using novel cationic inhibitors. J. Biol. Chem. 272, 16176-16183.


・ Miyoshi, H., Tokutake, N., Imaeda, Y., Akagi, T. and Iwamura, H. (1995) A model of antimycin A binding based on structure-activity studies of synthetic antimycin A analogues. Biochim. Biophys. Acta (Bioenergetics) 1229, 149-154.