cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-deoxy-6-morpholinio-β-D-glucopyranoside | 1258840-09-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-deoxy-6-morpholinio-β-D-glucopyranoside
• CAS: 1258840-09-3
• 化学式: C₄₃H₆₉NO₉
• 分子量: 744.022
• InChiKey: GVQSQCYICQYPCP-UGCFKKQLSA-N

反应信息

• 作为反应物：
  描述：

  cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-deoxy-6-morpholinio-β-D-glucopyranoside 、 碘甲烷 反应 3.0h， 以82%的产率得到cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-deoxy-6-(N-methylmorpholinio)-β-D-glucopyranoside iodide
  参考文献：
  名称：

  Synthesis and delivery activity of new cationic cholesteryl glucosides

  摘要：

  Cholesterol amphiphiles containing positively charged groups (pyridinium, N-methylimidazolium, N-methylmorpholinium, and N-methylpiperidinium) linked via beta-glucosyl spacer were prepared by alkylation of the corresponding bases with 6-O-mesyl-beta-D-cholesteryl glucopyranoside. IC50 values were in the range 20-35 mu M for the series of compounds and liposomal formulations with DOPE (1:1) were significantly less toxic. The liposomal formulations provided the accumulation of FITC-labeled oligonucleotide in cells, and the efficiency of this process was comparable to that of Lipofectamine (R) 2000. Cationic liposomes were able to deliver siRNA into the cells, and the liposomal formulation 7d/DOPE provided the most pronounced down-regulation of EGFP expression both in the presence and in the absence of serum (up to 30%). 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.012
• 作为产物：
  描述：

  吗啉 、 cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-O-methanesulfonyl-β-D-glucopyranoside 、 乙酸酐 反应 12.0h， 以52%的产率得到cholest-5-en-3β-yl 2,3,4-tri-O-acetyl-6-deoxy-6-morpholinio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and delivery activity of new cationic cholesteryl glucosides

  摘要：

  Cholesterol amphiphiles containing positively charged groups (pyridinium, N-methylimidazolium, N-methylmorpholinium, and N-methylpiperidinium) linked via beta-glucosyl spacer were prepared by alkylation of the corresponding bases with 6-O-mesyl-beta-D-cholesteryl glucopyranoside. IC50 values were in the range 20-35 mu M for the series of compounds and liposomal formulations with DOPE (1:1) were significantly less toxic. The liposomal formulations provided the accumulation of FITC-labeled oligonucleotide in cells, and the efficiency of this process was comparable to that of Lipofectamine (R) 2000. Cationic liposomes were able to deliver siRNA into the cells, and the liposomal formulation 7d/DOPE provided the most pronounced down-regulation of EGFP expression both in the presence and in the absence of serum (up to 30%). 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.012