RCAI-58 | 1092684-43-9

• 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-58
• 英文别名: (2S,3S,4R)-1-O-(α-D-fucopyranosyl)-2-(hexacosanamido)octadecane-1,3,4-triol；1-O-(6-deoxy-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1092684-43-9
• 化学式: C₅₀H₉₉NO₈
• 分子量: 842.338
• InChiKey: KKOZCUQTUVXSML-XNIGCKSUSA-N

物化性质

• 沸点：
  913.7±65.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  59
• 可旋转键数：
  43
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-3,4-二[(叔-丁基二甲基硅烷基)氧基]-2-二十六烷酰基氨基-4-十八烷醇 在 10 wt% Pd(OH)2 on carbon 、 四丁基氟化铵 、 氢气 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 RCAI-58
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.03.028

文献信息

• Divergent synthetic approach to 6′′-modified α-GalCer analogues
  作者：Nora Pauwels、Sandrine Aspeslagh、Gerd Vanhoenacker、Koen Sandra、Esther D. Yu、Dirk M. Zajonc、Dirk Elewaut、Bruno Linclau、Serge Van Calenbergh

  DOI：10.1039/c1ob06235b

  日期：——

  A synthetic approach is presented for the synthesis of galacturonic acid and D-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6′′-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6′′-modified KRN7000 analogues.

  提出了一种合成半乳糖醛酸和D-岩藻糖修饰的KRN7000的合成方法。该方法允许对糖的6′′-OH和神经氨酸氨基组进行后期功能化，从而便于合成有前景的6′′修饰的KRN7000类似物。
• NOVEL PSEUDOGLYCOLIPID AND USE THEREOF
  申请人：Riken

  公开号：EP2133326A1

  公开（公告）日：2009-12-16

  The present invention provides a novel pseudoglycolipid effective for cancer treatment and the like and a novel synthesis intermediate therefor, as well as a medicament containing the novel pseudoglycolipid and the like. A compound represented by the following formula (1) or a salt thereof. wherein each symbol is as defined in the specification.

  本发明提供了一种对癌症治疗等有效的新型假糖脂及其新型合成中间体，以及一种含有该新型假糖脂的药物等。 由下式（1）代表的化合物或其盐。 其中各符号如说明书中所定义。
• TECHNOLOGY FOR EFFICIENT ACTIVATION OF NKT CELLS
  申请人：Riken

  公开号：EP3453755A1

  公开（公告）日：2019-03-13

  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.

  本发明涉及一种生产 NKT 细胞配体脉冲人 CD14 阳性细胞的方法，该细胞可激活 NKT 细胞并强烈诱导 NKT 细胞的增殖、IFN-γ 的产生和/或细胞毒性活性。更具体地说，该方法的特征在于，分离出的 CD14 阳性细胞是在含有 NKT 细胞配体和 GM-CSF 且基本上不含 IL-4 的培养基中培养的。此外，本发明还涉及一种生产 NKT 细胞配体脉冲人 CD14 阳性细胞系的方法，具体而言，该方法的特征在于分离的 CD14 阳性细胞在含有 NKT 细胞配体且基本不含 GM-CSF 和 IL-4 的培养基中培养。本发明还涉及一种含有 NKT 细胞配体的人 CD14 阳性细胞或 NKT 细胞配体的人 CD14 阳性细胞系的细胞制剂及其药物用途。
• RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tetlet.2008.09.074

  日期：2008.11

  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.
• US8299223B2
  申请人：——

  公开号：US8299223B2

  公开（公告）日：2012-10-30