N-Acetylpsychosine | 35823-61-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-Acetylpsychosine
• 英文别名: C2 Galactosylceramide (d18:1/2:0)；N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]acetamide
• CAS: 35823-61-1
• 化学式: C₂₆H₄₉NO₈
• 分子量: 503.677
• InChiKey: HJFSOLRPKRHPEE-VIEJJRQOSA-N

物化性质

• 沸点：
  741.0±60.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

制备方法与用途

生物活性

N-乙酰-psichizin（C2-半乳糖基鞘氨脂（d18:1/2:0）），也称为α-半乳糖化C2-鞘氨脂，具有免疫刺激活性。N-乙酰-psichizin 是研究凋亡机制和树突状细胞 (DCs) 诱导的免疫应答的有效工具。

体外研究

在浓度为80 ng/mL 到 2 µg/mL 范围内，N-乙酰-psichizin 呈浓度依赖性地刺激混合淋巴细胞反应（MLR）响应。

反应信息

• 作为产物：
  描述：

  神经鞘氨醇半乳糖苷 、 乙酰氯 在 吡啶 作用下， 以 N-甲基吡咯烷酮 、 四氢呋喃 为溶剂， 生成 N-Acetylpsychosine
  参考文献：
  名称：

  The Synthesis and Biological Characterization of a Ceramide Library

  摘要：

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.

  DOI：

  10.1021/ja017576o

文献信息

• Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells
  作者：Jin Park、Qian Li、Young-Tae Chang、Tae Sung Kim

  DOI：10.1016/j.bmc.2005.01.027

  日期：2005.4

  Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we investigated the inhibitory activity of IL-4 production in activated T cells by screening ceramide derivatives prepared by solid phase combinatorial chemistry. Many ceramide derivatives significantly inhibited IL-4 production in T cells. In particular, ceramide derivatives with a lauroyl group showed strong inhibitory activities on IL-4 production in both phorbol 12-myristate 13-acetate (PMA)-activated EL4 T cells and antigen-primed cells, suggesting that they can be used as compounds for the development of anti-allergic agents. (c) 2005 Elsevier Ltd. All rights reserved.
• The Synthesis and Biological Characterization of a Ceramide Library
  作者：Young-Tae Chang、Jaehwa Choi、Sheng Ding、Eva E. Prieschl、Thomas Baumruker、Jae-Mok Lee、Sung-Kee Chung、Peter G. Schultz

  DOI：10.1021/ja017576o

  日期：2002.3.1

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.