5-氧代-L-脯氨酰-L-苯丙氨酰-L-苯丙氨酰-L-脯氨酰-亮氨酰-L-蛋氨酰胺 | 79775-19-2

• 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
• 中文名称: 5-氧代-L-脯氨酰-L-苯丙氨酰-L-苯丙氨酰-L-脯氨酰-亮氨酰-L-蛋氨酰胺
• 英文名称: Septide
• 英文别名: [pGlu⁶,Pro⁹]substance P-(6-11)；(2S)-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-5-oxopyrrolidine-2-carboxamide
• CAS: 79775-19-2
• 化学式: C₃₉H₅₃N₇O₇S
• 分子量: 763.959
• InChiKey: UUZURPUIMYJOIL-JNRWAQIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  234
• 氢给体数：
  6
• 氢受体数：
  8

制备方法与用途

septide((Pyr6,Pro9)-P物质)是一种有效的NK1受体激动剂，其Kd值为0.55纳摩尔。

反应信息

• 作为产物：
  描述：

  L-焦谷氨酸 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 生成 5-氧代-L-脯氨酰-L-苯丙氨酰-L-苯丙氨酰-L-脯氨酰-亮氨酰-L-蛋氨酰胺
  参考文献：
  名称：

  [pGlu6, Pro9]SP6-11, a selective agonist for the substance P P-receptor subtype

  摘要：

  Substitution of a single amino acid residue, proline for glycine-9 in [pGlu6]SP6-11, a hexapeptide analogue of substance P, confers on the peptide selective agonist activity toward the SP-P receptor subtype. [pGlu6,Pro9]SP6-11 had 20% and 75% of the activity of [pGlu6]SP6-11 in stimulating, respectively, K+ release from rat parotid slices and contraction of the isolated guinea pig ileum, via the SP-P receptor subtype. In contrast, [pGlu6,Pro9]SP6-11 had substantially reduced activity on SP-E systems such as the hamster urinary bladder and rat duodenum, being about 20-fold less potent than [pGlu6]SP6-11 and 200-670-fold less potent than neurokinin B. In the guinea pig ileum [pGlu6,Pro9]SP6-11 had very low activity on the neuronal tachykinin receptor, being 325 times less potent than [pGlu6]SP6-11 and 1000 times less potent than neurokinin B. Because of its discrimination between the muscular and neuronal receptors in the guinea pig ileum (muscular/neuronal potency ratio = 600), [pGlu6,Pro9]SP6-11 can be used to specifically desensitize the muscular receptor of this tissue. This procedure enables a selective and sensitive bioassay of the neuronal receptor.

  DOI：

  10.1021/jm00157a029

文献信息

• COMPOSITIONS AND METHODS FOR IMMUNE CELL MODULATION IN ADOPTIVE IMMUNOTHERAPIES
  申请人：Fate Therapeutics, Inc.

  公开号：US20200179451A1

  公开（公告）日：2020-06-11

  Compounds that either produce a higher proportion or greater absolute number of phenotypically identified naive, stem cell memory, central memory T cells, adaptive NK cells, and type I NKT cells are identified. Compositions and methods for modulating immune cells including T, NK, and NKT cells for adoptive cell therapies, such as those providing improvements in one or more therapeutic outcomes, are provided.
• [pGlu6, Pro9]SP6-11, a selective agonist for the substance P P-receptor subtype
  作者：Ralph Laufer、Chaim Gilon、Michael Chorev、Zvi Selinger

  DOI：10.1021/jm00157a029

  日期：1986.7

  Substitution of a single amino acid residue, proline for glycine-9 in [pGlu6]SP6-11, a hexapeptide analogue of substance P, confers on the peptide selective agonist activity toward the SP-P receptor subtype. [pGlu6,Pro9]SP6-11 had 20% and 75% of the activity of [pGlu6]SP6-11 in stimulating, respectively, K+ release from rat parotid slices and contraction of the isolated guinea pig ileum, via the SP-P receptor subtype. In contrast, [pGlu6,Pro9]SP6-11 had substantially reduced activity on SP-E systems such as the hamster urinary bladder and rat duodenum, being about 20-fold less potent than [pGlu6]SP6-11 and 200-670-fold less potent than neurokinin B. In the guinea pig ileum [pGlu6,Pro9]SP6-11 had very low activity on the neuronal tachykinin receptor, being 325 times less potent than [pGlu6]SP6-11 and 1000 times less potent than neurokinin B. Because of its discrimination between the muscular and neuronal receptors in the guinea pig ileum (muscular/neuronal potency ratio = 600), [pGlu6,Pro9]SP6-11 can be used to specifically desensitize the muscular receptor of this tissue. This procedure enables a selective and sensitive bioassay of the neuronal receptor.