(S)-4-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-3-((S)-2-((S)-2-(2-azidoacetamido)-3-(1H-indol-3-yl)propanamido)hexanamido)-4-oxobutanoic acid

• 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: (S)-4-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-3-((S)-2-((S)-2-(2-azidoacetamido)-3-(1H-indol-3-yl)propanamido)hexanamido)-4-oxobutanoic acid
• 英文别名: deamino-Gly(N3)-Trp-Nle-Asp-Phe-NH2；(3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-2-[(2-azidoacetyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-4-oxobutanoic acid
• 化学式: C₃₂H₃₉N₉O₇
• 分子量: 661.718
• InChiKey: BLZUTIDYYAIHMY-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  227
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  三炔丙基胺 、 (S)-4-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-3-((S)-2-((S)-2-(2-azidoacetamido)-3-(1H-indol-3-yl)propanamido)hexanamido)-4-oxobutanoic acid 在 2,6-二甲基吡啶 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以12%的产率得到(3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-2-[[2-[4-[[bis[[1-[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]triazol-4-yl]methyl]amino]methyl]triazol-1-yl]acetyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-4-oxobutanoic acid
  参考文献：
  名称：

  Development of a time-resolved fluorescence probe for evaluation of competitive binding to the cholecystokinin 2 receptor

  摘要：

  The synthesis, characterization, and use of Eu-DTPA-PEGO-Trp-Nle-Asp-Phe-NH2 (Eu-DTPA-PEGO-CCK4), a luminescent probe targeted to cholecystokinin 2 receptor (CCK2R, aka CCKBR), are described. The probe was prepared by solid phase synthesis. A K-d value of 17 +/- 2 nM was determined by means of saturation binding assays using HEK-293 cells that overexpress CCK2R. The probe was then used in competitive binding assays against Ac-CCK4 and three new trivalent CCK4 compounds. Repeatable and reproducible binding assay results were obtained. Given its ease of synthesis, purification, receptor binding properties, and utility in competitive binding assays, Eu-DTPA-PEGO-CCK4 could become a standard tool for high-throughput screening of compounds in development targeted to cholecystokinin receptors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.028

文献信息

• Development of a time-resolved fluorescence probe for evaluation of competitive binding to the cholecystokinin 2 receptor
  作者：N.G.R. Dayan Elshan、Thanuja Jayasundera、Craig S. Weber、Ronald M. Lynch、Eugene A. Mash

  DOI：10.1016/j.bmc.2015.02.028

  日期：2015.4

  The synthesis, characterization, and use of Eu-DTPA-PEGO-Trp-Nle-Asp-Phe-NH2 (Eu-DTPA-PEGO-CCK4), a luminescent probe targeted to cholecystokinin 2 receptor (CCK2R, aka CCKBR), are described. The probe was prepared by solid phase synthesis. A K-d value of 17 +/- 2 nM was determined by means of saturation binding assays using HEK-293 cells that overexpress CCK2R. The probe was then used in competitive binding assays against Ac-CCK4 and three new trivalent CCK4 compounds. Repeatable and reproducible binding assay results were obtained. Given its ease of synthesis, purification, receptor binding properties, and utility in competitive binding assays, Eu-DTPA-PEGO-CCK4 could become a standard tool for high-throughput screening of compounds in development targeted to cholecystokinin receptors. (C) 2015 Elsevier Ltd. All rights reserved.