[(hydrazinylcarbonothioyl)amino]acetic 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: [(hydrazinylcarbonothioyl)amino]acetic acid
• 英文别名: 2-(Aminocarbamothioylamino)acetic acid；2-(aminocarbamothioylamino)acetic acid
• 化学式: C₃H₇N₃O₂S
• 分子量: 149.173
• InChiKey: HCOLAWHKVDGNIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(hydrazinylcarbonothioyl)amino]acetic acid 、 3-氨基吡啶-2-醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以51%的产率得到[({2-[(3-aminopyridin-2-yl)methylidene]hydrazinyl}carbonothioyl)amino]acetic acid
  参考文献：
  名称：

  Impact of thiosemicarbazones on the accumulation of PpIX and the expression of the associated genes

  摘要：

  Thiosemicarbazone derivatives are known for their broad biological activity including their antitumor potency. The aim of the current study was to examine the effect of a novel series of non-toxic iron chelators on the accumulation of protoporphyrin IX after external 5-aminolevulonic acid administration. From this series we selected one the most promising derivative which causes a pronounced increase in the concentration of protoporphyrin IX. The increase of the photosensitizer concentration is necessary for the trigger the efficient therapeutic effect of the photodynamic reaction. For selected compound 2 we performed an examination of a panel of the genes that are involved in the heme biosynthesis and degradation. Results indicated the crucial roles of ferrochelatase and heme oxygenase in the described processes. Surprisingly, there was a strict dependence on the type of the tested cell line. A decrease in the expression of the two aforementioned enzymes after incubation with compound 2 and 5-aminolevulonic acid is a commonly known fact and we detected this trend for the MCF-7 and HCT 116 cell lines. However, we noticed the upregulation of the tested targets for the Hs683 cells. These unconventional results prompted us to do a more in-depth analysis of the described processes. In conclusion, we found that compound 2 is a novel, highly effective booster of photodynamic therapy that has prospective applications.

  DOI：

  10.1016/j.jphotobiol.2019.111585
• 作为产物：
  描述：

  N,N'-硫羰基二咪唑 、 聚甘氨酸 在 hydrazine hydrate 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以85%的产率得到[(hydrazinylcarbonothioyl)amino]acetic acid
  参考文献：
  名称：

  Impact of thiosemicarbazones on the accumulation of PpIX and the expression of the associated genes

  摘要：

  Thiosemicarbazone derivatives are known for their broad biological activity including their antitumor potency. The aim of the current study was to examine the effect of a novel series of non-toxic iron chelators on the accumulation of protoporphyrin IX after external 5-aminolevulonic acid administration. From this series we selected one the most promising derivative which causes a pronounced increase in the concentration of protoporphyrin IX. The increase of the photosensitizer concentration is necessary for the trigger the efficient therapeutic effect of the photodynamic reaction. For selected compound 2 we performed an examination of a panel of the genes that are involved in the heme biosynthesis and degradation. Results indicated the crucial roles of ferrochelatase and heme oxygenase in the described processes. Surprisingly, there was a strict dependence on the type of the tested cell line. A decrease in the expression of the two aforementioned enzymes after incubation with compound 2 and 5-aminolevulonic acid is a commonly known fact and we detected this trend for the MCF-7 and HCT 116 cell lines. However, we noticed the upregulation of the tested targets for the Hs683 cells. These unconventional results prompted us to do a more in-depth analysis of the described processes. In conclusion, we found that compound 2 is a novel, highly effective booster of photodynamic therapy that has prospective applications.

  DOI：

  10.1016/j.jphotobiol.2019.111585