| 1416080-93-7

• 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
• CAS: 1416080-93-7
• 化学式: C₄₁H₆₃N₅O₁₂
• 分子量: 817.978
• InChiKey: LZTGVQNCUXNUQG-AWCRTANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  58.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  238.83
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  QSY21-NHS 、 在 N,N-二异丙基乙胺 作用下， 以60%的产率得到
  参考文献：
  名称：

  Functional Imaging of Legumain in Cancer Using a New Quenched Activity-Based Probe

  摘要：

  Legumain is a lysosomal cysteine protease whose biological function remains poorly defined. Legumain activity is up-regulated in most human cancers and inflammatory diseases most likely as the result of high expression in populations of activated macrophages. Within the tumor microenvironment, legumain activity is thought to promote tumorigenesis. To obtain a greater understanding of the role of legumain activity during cancer progression and inflammation, we developed an activity-based probe that becomes fluorescent only upon binding active legumain. This probe is highly selective for legumain, even in the context of whole cells and tissues, and is also a more effective label of legumain than previously reported probes. Here we present the synthesis and application of our probe to the analysis of legumain activity in primary macrophages and in two mouse models of cancer. We find that legumain activity is highly correlated with macrophage activation and furthermore that it is an ideal marker for primary tumor inflammation and early stage metastatic lesions.

  DOI：

  10.1021/ja307083b
• 作为产物：
  描述：

  (4S)-5-[(2S)-2-[[(2S)-4-[4-[3-[[1-[2-[3,6-bis(2,3-dihydroindol-1-yl)xanthen-10-ium-9-yl]phenyl]sulfonylpiperidine-4-carbonyl]amino]propylcarbamoyl]-2,6-dimethylbenzoyl]oxy-1-carboxy-3-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-4-[6-[2-[(1E,3E,5Z)-5-(1-ethyl-3,3-dimethyl-5-sulfoindol-2-ylidene)penta-1,3-dienyl]-3,3-dimethyl-5-sulfoindol-1-ium-1-yl]hexanoylamino]-5-oxopentanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以14 mg的产率得到
  参考文献：
  名称：

  Functional Imaging of Legumain in Cancer Using a New Quenched Activity-Based Probe

  摘要：

  Legumain is a lysosomal cysteine protease whose biological function remains poorly defined. Legumain activity is up-regulated in most human cancers and inflammatory diseases most likely as the result of high expression in populations of activated macrophages. Within the tumor microenvironment, legumain activity is thought to promote tumorigenesis. To obtain a greater understanding of the role of legumain activity during cancer progression and inflammation, we developed an activity-based probe that becomes fluorescent only upon binding active legumain. This probe is highly selective for legumain, even in the context of whole cells and tissues, and is also a more effective label of legumain than previously reported probes. Here we present the synthesis and application of our probe to the analysis of legumain activity in primary macrophages and in two mouse models of cancer. We find that legumain activity is highly correlated with macrophage activation and furthermore that it is an ideal marker for primary tumor inflammation and early stage metastatic lesions.

  DOI：

  10.1021/ja307083b