cell-penetrating peptide Tat (AA 48-60) | 337516-13-9

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: cell-penetrating peptide Tat (AA 48-60)
• 英文别名: GRKKRRQRRRPPQ-NH₂；CPP Tat (AA 48-60)；GRKKRRQRRRPPQ；H-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg-Pro-Pro-Gln-NH2；(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]pentanediamide
• CAS: 337516-13-9
• 化学式: C₇₀H₁₃₂N₃₆O₁₅
• 分子量: 1718.05
• InChiKey: YOORDWDVSBGORK-XNHKUAGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.2
• 重原子数：
  121
• 可旋转键数：
  61
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  925
• 氢给体数：
  28
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  、 Fmoc-甘氨酸 、 Fmoc-L-脯氨酸 、 FMOC-赖氨酸 、 Fmoc-L-谷氨酰胺 、 FMOC-L-精氨酸 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 N,N-二异丙基乙胺 、 哌啶 作用下， 反应 0.22h， 生成 cell-penetrating peptide Tat (AA 48-60)
  参考文献：
  名称：

  Cell penetrating peptide-mediated transport enables the regulated secretion of accumulated cargoes from mast cells

  摘要：

  The in vivo utility of technologies employing cell penetrating peptides and bioportides may be compromised by the general capacity of polycationic peptides to activate mast cell secretion. Moreover, the same technologies could be exploited in a clinical setting either to directly modulate intrinsic exocytotic mechanisms or to load mast cells with bioactive cargoes. Comparative investigations identified two cell penetrating vectors, Tat and C105Y, which readily translocate into mast cells without inducing receptor-independent exocytosis. Efficient Tat transduction also enabled the intracellular delivery and accumulation of cargoes within discrete intracellular compartments. A tetramethylrhodamine-Tat conjugate is effectively translocated into the secretory lysosomes of RBL-2H3 cells. In contract, the intracellular delivery of avidin, as a non-covalent complex with a biotinylated Tat vector, is also efficient but the protein is predominantly accumulated outside of secretory lysosomes. Significantly, both cargoes can be subsequently released following mast cell stimulation either by mastoparan, a wasp venom secretagogue, or by the physiological mechanism of antigen-induced aggregation of high affinity IgE receptors. These studies indicate that mast cells could be exploited to direct the delivery of bioactive agents to disease sites as an innovative cell-mediated therapy. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2015.02.005