[2-[4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrole-2-carbonyl]phenyl] 2-[[2-[7-(dimethylamino)-2-oxochromen-4-yl]acetyl]amino]acetate | 1186308-34-8

• 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: [2-[4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrole-2-carbonyl]phenyl] 2-[[2-[7-(dimethylamino)-2-oxochromen-4-yl]acetyl]amino]acetate
• CAS: 1186308-34-8
• 化学式: C₃₇H₂₆Cl₄N₄O₈
• 分子量: 796.447
• InChiKey: OMAYXLLCKPSOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,5-dioxopyrrolidin-1-yl 2-(2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetamido)acetate 、 marinopyrrole A 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到[2-[4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrole-2-carbonyl]phenyl] 2-[[2-[7-(dimethylamino)-2-oxochromen-4-yl]acetyl]amino]acetate
  参考文献：
  名称：

  Marinopyrrole A Target Elucidation by Acyl Dye Transfer

  摘要：

  The targeting of marinopyrrole A to actin was identified using a fluorescent dye transfer strategy. The process began by appending a carboxylic acid terminal tag to a phenol in the natural product. The resulting probe was then studied in live cells to verify that it maintained activity comparable to marinopyrrole A. Two-color fluorescence microscopy confirmed that both unlabeled and labeled materials share comparable uptake and subcellular Localization in HCT-116 cells. Subsequent immunoprecipitation studies identified actin as a putative target in HCT-116 cells, a result that was validated by mass spectral, affinity, and activity analyses on purified samples of actin. Further data analyses indicated that the dye in the marinopyrrole probe was selectively transferred to a single residue K,15, an event that did not occur with related acyl phenols and reactive labels. In this study, the combination of cell, protein, and amino acid analysis arose from a single sample of material, thereby, suggesting a means to streamline and reduce material requirements involved in mode of action studies.

  DOI：

  10.1021/ja903149u

文献信息

• Marinopyrrole A Target Elucidation by Acyl Dye Transfer
  作者：Chambers C. Hughes、Yu-Liang Yang、Wei-Ting Liu、Pieter C. Dorrestein、James J. La Clair、William Fenical

  DOI：10.1021/ja903149u

  日期：2009.9.2

  The targeting of marinopyrrole A to actin was identified using a fluorescent dye transfer strategy. The process began by appending a carboxylic acid terminal tag to a phenol in the natural product. The resulting probe was then studied in live cells to verify that it maintained activity comparable to marinopyrrole A. Two-color fluorescence microscopy confirmed that both unlabeled and labeled materials share comparable uptake and subcellular Localization in HCT-116 cells. Subsequent immunoprecipitation studies identified actin as a putative target in HCT-116 cells, a result that was validated by mass spectral, affinity, and activity analyses on purified samples of actin. Further data analyses indicated that the dye in the marinopyrrole probe was selectively transferred to a single residue K,15, an event that did not occur with related acyl phenols and reactive labels. In this study, the combination of cell, protein, and amino acid analysis arose from a single sample of material, thereby, suggesting a means to streamline and reduce material requirements involved in mode of action studies.