1-hydroxy-3-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy}-9,10-anthraquinone | 1338001-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-3-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy}-9,10-anthraquinone
• 英文别名: 1-Hydroxy-3-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]anthracene-9,10-dione
• CAS: 1338001-95-8
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: TYOOOGPAUVYGJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-二羥蒽醌 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 1-hydroxy-3-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy}-9,10-anthraquinone
  参考文献：
  名称：

  Anthraquinone derivatives induce G2/M cell cycle arrest and apoptosis in NTUB1 cells

  摘要：

  Thirteen anthraquinone derivatives 5-17 including two 3-(3-alkylaminopropoxy)-9,10-anthraquinone (NHA) derivatives 5 and 6, and 11 1-hydroxy-3-(3-alkylaminopropoxy)-9,10-anthraquinone (MHA) derivatives 7-17 were synthesized, evaluated for cytotoxicities against two cancer cell lines, and assayed the generation of reactive oxygen species (ROS) in NTUB1 cells (a human bladder carcinoma cell line). Compound 9 bearing a pyrrolidinyl group induced the stronger cytotoxic effect than those of other synthesized NHA and MHA derivatives. Exposure of NTUB1 cells to, 9, 13, and 17 for 24 h significantly increased the production of ROS, respectively. Flow cytometric analysis exhibited that the exposure of NTUB1 cells to the selective 9 led to the G2/M phase arrest accompanied by an increase of apoptotic cell death after the incubation for 24 h. Compound 9 induced up-regulation of cyclinB1 and p21 expressions. Biological results suggested that the induction of G2/M arrest, apoptosis, and cell death by 9 may associate with increased expression of p21 and cyclin B1, elevation of Bax and p53 levels, and generation of ROS in the cell. In conclusion, these series of compounds may be used as anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.021

文献信息

• Anthraquinone derivatives induce G2/M cell cycle arrest and apoptosis in NTUB1 cells
  作者：Huang-Yao Tu、A-Mei Huang、Chi-Huang Teng、Tzyh-Chyuan Hour、Shyh-Chyun Yang、Yeong-Shiau Pu、Chun-Nan Lin

  DOI：10.1016/j.bmc.2011.07.021

  日期：2011.9

  Thirteen anthraquinone derivatives 5-17 including two 3-(3-alkylaminopropoxy)-9,10-anthraquinone (NHA) derivatives 5 and 6, and 11 1-hydroxy-3-(3-alkylaminopropoxy)-9,10-anthraquinone (MHA) derivatives 7-17 were synthesized, evaluated for cytotoxicities against two cancer cell lines, and assayed the generation of reactive oxygen species (ROS) in NTUB1 cells (a human bladder carcinoma cell line). Compound 9 bearing a pyrrolidinyl group induced the stronger cytotoxic effect than those of other synthesized NHA and MHA derivatives. Exposure of NTUB1 cells to, 9, 13, and 17 for 24 h significantly increased the production of ROS, respectively. Flow cytometric analysis exhibited that the exposure of NTUB1 cells to the selective 9 led to the G2/M phase arrest accompanied by an increase of apoptotic cell death after the incubation for 24 h. Compound 9 induced up-regulation of cyclinB1 and p21 expressions. Biological results suggested that the induction of G2/M arrest, apoptosis, and cell death by 9 may associate with increased expression of p21 and cyclin B1, elevation of Bax and p53 levels, and generation of ROS in the cell. In conclusion, these series of compounds may be used as anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.