His-Cys-OMe | 1232513-87-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: His-Cys-OMe
• CAS: 1232513-87-9
• 化学式: C₁₀H₁₆N₄O₃S
• 分子量: 272.328
• InChiKey: ZAGWUGQZIVKCHC-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.13
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110.1
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Boc-His(Boc)-Cys(Acm)-OMe 在 mercury(II) acetate 、 溶剂黄146 、 三氟乙酸 作用下， 反应 3.0h， 生成 His-Cys-OMe
  参考文献：
  名称：

  Efficient Gene Transfection by Histidine-Modified Chitosan through Enhancement of Endosomal Escape

  摘要：

  Chitosan has the potential to be a biocompatible gene carrier. However, the transfection efficiency of chitosan is low because of the slow endosomal escape rate. The buffering capacity of histidine in the endosomal range would help the escape of plasmid DNA (pDNA) from endosomes. In this study, histidine was introduced into chitosan to improve the transfection efficiency. Chitosan and histidine were linked by disulfide bonds provided by 2-iminothiolane and cysteine. The complexes were prepared by mixing chitosan or histidine-modified chitosan with plasmid DNA. A broader buffering range of histidine-modified chitosan was observed, and the cellular uptake of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. Although chitosan/tetramethylrhodamine (TMR)-pDNA complexes were trapped in the vesicles in cytosol, TMR-pDNA carried by histidine-modified chitosan was more widely distributed in the cytosol. This result suggests that histidine can help pDNA escape from endosomes with the help of the high buffering capacity. The gene expression of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. These results suggest that histidine modification improves the transfection efficiency of chitosan.

  DOI：

  10.1021/bc1000609