RCAI-37、56、59、60、92、101和102，KRN7000的环糖醇和碳环糖类似物：它们的合成及其对小鼠淋巴细胞产生Th1偏向性细胞因子的生物活性。
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.
作者信息
Tashiro Takuya, Nakagawa Ryusuke, Hirokawa Takatsugu, Inoue Sayo, Watarai Hiroshi, Taniguchi Masaru, Mori Kenji
机构信息
Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan.
出版信息
Bioorg Med Chem. 2009 Sep 1;17(17):6360-73. doi: 10.1016/j.bmc.2009.07.025. Epub 2009 Jul 18.
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-gamma, 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.
通过相应的环醇或碳环糖衍生物与环氨基磺酸酯（9）的偶联反应作为关键步骤，合成了KRN7000的环醇[RCAI - 37（1）、59（5）、92（7）和102（2）]和碳环糖类似物[RCAI - 56（3）、60（4）和101（6）]。生物测定表明，RCAI - 56（3，KRN7000的碳环半乳糖类似物）、59（5，1 - 脱氧新肌醇类似物）和92（7，1 - O - 甲基化的5）在体内是小鼠淋巴细胞产生Th1偏向性细胞因子（如干扰素 - γ）的显著有效刺激物。另一方面，RCAI - 60（4，碳环岩藻糖类似物）和RCAI - 101（6，6 - O - 甲基化的3）表现出较强的生物活性，而RCAI - 37（1，肌醇类似物）和102（2，新肌醇类似物）诱导的细胞因子产生很少。
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