1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-D-xylo-phytosphingosine | 1057620-49-1

• 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: 1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-D-xylo-phytosphingosine
• 英文别名: N-[(2S,3R,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1057620-49-1
• 化学式: C₅₀H₉₉NO₉
• 分子量: 858.337
• InChiKey: VQFKFAKEUMHBLV-HKCHYWKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  60
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Sodium N-{3-[acetyl(methyl)amino]-5-carboxy-2,4,6-triiodophenyl}ethanimidate--hex-2-ulofuranosyl hexopyranoside (1/1/1) 、 1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-D-xylo-phytosphingosine 以 二甲基亚砜 为溶剂， 反应 72.33h， 以CD1c+ cells were obtained from the suspension的产率得到11-[4-[2-(2-羟基乙氧基)乙基]-1-哌嗪基]二苯并[b,f][1,4]硫氮杂卓半富马酸盐
  参考文献：
  名称：

  Method for activating human antigen presenting cells, activated human antigen - presenting cells, and use thereof

  摘要：

  本发明涉及一种通过与式（A）或其盐中的至少一种糖苷化合物的体外培养来激活人源性抗原呈递细胞的方法[优选示例：（2S，3S，4R）-1-（α-D-半乳糖苷基）-2-己二十六酸酰胺基-3,4-十八碳二醇]，以及通过该方法激活的人源性抗原呈递细胞的方法。本发明还涉及一种使用激活的人源性抗原呈递细胞治疗癌症和包括艾滋病在内的传染病的方法，以及使用激活的人源性抗原呈递细胞制备治疗这些疾病的药物的用途。该发明可以在不需要脉冲肿瘤抗原的情况下，对癌症和包括艾滋病在内的传染病提供满意的治疗效果。

  公开号：

  US20060073122A1
• 作为产物：
  描述：

  在 Pd(OH)2/C 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 以88%的产率得到1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-D-xylo-phytosphingosine
  参考文献：
  名称：

  Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

  摘要：

  KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.036

文献信息

• Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand
  作者：Jeong-Ju Park、Ji Hyung Lee、Subhash C. Ghosh、Gabriel Bricard、Manjunatha M. Venkataswamy、Steven A. Porcelli、Sung-Kee Chung

  DOI：10.1016/j.bmcl.2008.06.036

  日期：2008.7

  KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• Method for activating human antigen presenting cells, activated human antigen - presenting cells, and use thereof
  申请人：Koezuka Yasuhiko

  公开号：US20060073122A1

  公开（公告）日：2006-04-06

  The invention relates to a method for activating human-derived antigen-presenting cells by in vitro cultivation with at least one of the glycoside compounds represented by formula (A) or salts thereof [preferred example: (2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecanediol], and to human antigen-presenting cells activated by the method. The invention also relates to a method for treatment of cancer and infectious diseases including AIDS with the activated human antigen-presenting cells, and to a use of the activated human antigen-presenting cells in the preparation of medicines for treating such diseases. The invention can provide a satisfactory therapeutic effect on cancer and infectious diseases including AIDS without the need to pulse the human antigen-presenting cells with tumor antigens.

  本发明涉及一种通过与式（A）或其盐中的至少一种糖苷化合物的体外培养来激活人源性抗原呈递细胞的方法[优选示例：（2S，3S，4R）-1-（α-D-半乳糖苷基）-2-己二十六酸酰胺基-3,4-十八碳二醇]，以及通过该方法激活的人源性抗原呈递细胞的方法。本发明还涉及一种使用激活的人源性抗原呈递细胞治疗癌症和包括艾滋病在内的传染病的方法，以及使用激活的人源性抗原呈递细胞制备治疗这些疾病的药物的用途。该发明可以在不需要脉冲肿瘤抗原的情况下，对癌症和包括艾滋病在内的传染病提供满意的治疗效果。