RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines |
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| Authors: | Takuya Tashiro Ryusuke Nakagawa Takatsugu Hirokawa Sayo Inoue Hiroshi Watarai Masaru Taniguchi Kenji Mori |
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| Institution: | 1. Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan;2. Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN Yokohama Institute, Suehiro-cho 1-7-22, Tsurumi-ku, Yokohama-shi, Kanagawa 230-0045, Japan;3. Molecular Modeling and Design Team, Computational Biology Research Center, National Institute of Advanced Industrial Science and Technology (AIST), Aomi 2-42, Koto-ku, Tokyo 135-0064, Japan |
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| Abstract: | Cyclitol RCAI-37 (1), 59 (5), 92 (7), and 102 (2)] and carbasugar analogs RCAI-56 (3), 60 (4), and 101 (6)] of KRN7000 were synthesized through coupling reactions of the corresponding cyclitol or carbasugar derivatives with a cyclic sulfamidate (9) as the key step. Bioassay showed RCAI-56 (3, carbagalactose analog of KRN7000), 59 (5, 1-deoxy-neo-inositol analog), and 92 (7, 1-O-methylated 5) to be remarkably potent stimulants of mouse lymphocytes to produce Th1-biased cytokines, such as interferon-γ, in vivo. RCAI-60 (4, carbafucose analog) and RCAI-101 (6, 6-O-methylated 3) showed strong bioactivity, on the other hands, RCAI-37 (1, myo-inositol analog) and 102 (2, neo-inositol analog) induced little cytokine production. |
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| Keywords: | Carbasugar Cyclitol α -GalCer KRN7000 NKT cell |
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