RCAI-85 | 1092684-41-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: RCAI-85
• 英文别名: (2S,3S,4R)-1-O-(6-O-ethyl-α-D-galactopyranosyl)-2-(hexacosanamido)octadecane-1,3,4-triol；N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-(ethoxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
• CAS: 1092684-41-7
• 化学式: C₅₂H₁₀₃NO₉
• 分子量: 886.391
• InChiKey: MFERRQBPRXDUME-OEUZROOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  62
• 可旋转键数：
  46
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-O-ethyl-α-D-galactopyranosyl)octadecane-1,3,4-triol 在 Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 生成 RCAI-85
  参考文献：
  名称：

  RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.074

文献信息

• RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2013.03.028

  日期：2013.6

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.
• TECHNOLOGY FOR EFFICIENT ACTIVATION OF NKT CELLS
  申请人：RIKEN

  公开号：US20190134094A1

  公开（公告）日：2019-05-09

  The present invention relates to a method for producing en NKT cell ligand-pulsed human CD14 positive cell that activates NKT cells and strongly induces proliferation, IFN-γ production, and/or cytotoxic activity of NKT cells. More specifically, the method is characterized in that the isolated CD14 positive cell is cultured in a medium containing an NKT cell ligand and GM-CSF and substantially free of IL-4. In addition, the present invention relates to a method for producing an NKT cell ligand-pulsed human CD14 positive cell line and, specifically, the method is characterized in that the isolated CD14 positive cell is cultured in a medium containing an NKT cell ligand and substantially free of GM-CSF and IL-4. The present invention also relates to a cell preparation containing an NKT cell ligand-pulsed human CD14 positive cell or an NKT cell ligand-pulsed human CD14 positive cell line and pharmaceutical use thereof.