N-acetyl-L-seryl-L-seryl-L-alanyl-L-tryptophyl-L-tryptophyl-L-seryl-L-tyrosyl-L-tryptophyl-L-prolyl-L-prolyl-L-valyl-L-alaninamide | 1039089-33-2

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: N-acetyl-L-seryl-L-seryl-L-alanyl-L-tryptophyl-L-tryptophyl-L-seryl-L-tyrosyl-L-tryptophyl-L-prolyl-L-prolyl-L-valyl-L-alaninamide
• 英文别名: Ac-Ser-Ser-Ala-Trp-Trp-Ser-Tyr-Trp-Pro-Pro-Val-Ala-NH2；(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carbonyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]pyrrolidine-2-carboxamide
• CAS: 1039089-33-2
• 化学式: C₇₄H₉₂N₁₆O₁₇
• 分子量: 1477.64
• InChiKey: MXYGBLLHCNXWRR-DHOCSQBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  107
• 可旋转键数：
  34
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  503
• 氢给体数：
  18
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  在 三异丙基硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 以8.3 mg的产率得到N-acetyl-L-seryl-L-seryl-L-alanyl-L-tryptophyl-L-tryptophyl-L-seryl-L-tyrosyl-L-tryptophyl-L-prolyl-L-prolyl-L-valyl-L-alaninamide
  参考文献：
  名称：

  Selective Disruption of Early/Recycling Endosomes: Release of Disulfide-Linked Cargo Mediated by a N-Alkyl-3β-Cholesterylamine-Capped Peptide

  摘要：

  The use of endocytic uptake pathways to deliver poorly permeable molecules into mammalian cells is often plagued by entrapment and degradation of material in late endosomes and lysosomes. As a strategy to prevent the exposure of cargo to these highly hydrolytic membrane-sealed compartments, we synthesized derivatives of the membrane anchor N-alkyl-3 beta-cholesterylamine that selectively target linked compounds to less hydrolytic early/recycling endosomes. By targeting a pH-dependent membrane-lytic dodecapeptide and dislufide-linked flurophore to these compartments in Chinese hamster ovary cells or Jurkat lymphocytes, membranes of early-recycling endosomes were selectively disrupted, resulting in cleavage of the disulphide and escape of the fluorophore into cytosol and nucleus with low toxicity. The ability os appropriately designed N-alkyl-3 beta-cholesterylamines to deliver cargo into and release dislufide-linked cargo from relatively nonhydrolytic early/recycling endosomes may be useful for the delivery of a variety of sensitive molecules into living mammalian cells.

  DOI：

  10.1021/ja803380a

文献信息

• DISRUPTORS OF EARLY/RECYCLING ENDOSOMES
  申请人：Peterson Blake R.

  公开号：US20100041773A1

  公开（公告）日：2010-02-18

  A delivery system for introducing a cargo molecule into cytosol of a living cell can include: a first membrane binding element linked to an endosomal compartment disrupting element through a first linker having one or more anionic moieties; and a second membrane binding element linked to an exogenous cargo molecule through a second linker having one or more anionic moieties, the second linker having a region that is selectively cleavable, wherein the first and second membrane binding elements both induce endocytosis into an early/recycling endosome and the endosomal compartment disrupting element destabilizes the early/recycling endosome such that the exogenous cargo molecule is released from the second membrane binding element and into the cytosol of the living cell.

  一种将货物分子引入生物细胞细胞质的传递系统可以包括：第一膜结合元素通过具有一个或多个阴离子基团的第一连接物与内体区域破坏元素相连；第二膜结合元素通过具有一个或多个阴离子基团的第二连接物与外源货物分子相连，第二连接物具有可选择裂解的区域，其中第一和第二膜结合元素均诱导内吞作用进入早期/循环内体，内体区域破坏元素破坏早期/循环内体，使外源货物分子从第二膜结合元素中释放并进入生物细胞细胞质。
• US8889631B2
  申请人：——

  公开号：US8889631B2

  公开（公告）日：2014-11-18