7-ethoxyresorufin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-ethoxyresorufin
• 英文别名: ethoxyresorufin；ETRR；7-ethoxy-5a,10a-dihydrophenoxazin-3-one
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: IEUCHHWCXSAMRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-ethoxyresorufin 在 金圣草(黄)素 、 还原型辅酶II(NADPH)四钠盐 、 还原型辅酶Ⅰ 、 magnesium chloride 作用下， 反应 0.17h， 生成 试卤灵
  参考文献：
  名称：

  A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells

  摘要：

  A 17 beta-estradiol (E-2) is hydrolyzed to 2-hydroxy-E-2 (2-OHE2) and 4-hydroxy-E-2 (4-OHE2 ) via cytochrome P450 (CYP) 1A1 and 1B1, respectively. In estrogen target tissues including the mammary gland, ovaries, and uterus, CYP1B1 is highly expressed, and 4-OHE2 is predominantly formed in cancerous tissues. In this study, we investigated the inhibitory effects of chrysoeriol (luteorin-3'-methoxy ether), which is a natural methoxyflavonoid, against activity of CYP1A1 and 1B1 using in vitro and cultured cell techniques. Chrysoeriol selectively inhibited human recombinant CYP1B1-mediated 7-ethoxyresorufin-O-deethylation (EROD) activity 5-fold more than that of CYP1A1-mediated activity in a competitive manner. Additionally, chrysoeriol inhibited E-2 hydroxylation was catalyzed by CYP1B1, but not by CYP1A1. Methylation of 4-OHE2, which is thought to be a detoxification process, was not affected by the presence of chrysoeriol. In human breast cancer MCF-7 cells, chrysoeriol did not affect the gene expression of CYP1A1 and 1B1, but significantly inhibited the formation of 4-methoxy E-2 without any effects on the formation of 2-methoxy E-2. In conclusion, we present the first report to show that chrysoeriol is a chemopreventive natural ingredient that can selectively inhibit CYP1B1 activity and prevent the formation of carcinogenic 4-OHE2 from E-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2009.10.002

文献信息

• A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells
  作者：Hitomi Takemura、Harue Uchiyama、Takeshi Ohura、Hiroyuki Sakakibara、Ryoko Kuruto、Takashi Amagai、Kayoko Shimoi

  DOI：10.1016/j.jsbmb.2009.10.002

  日期：2010.1

  A 17 beta-estradiol (E-2) is hydrolyzed to 2-hydroxy-E-2 (2-OHE2) and 4-hydroxy-E-2 (4-OHE2 ) via cytochrome P450 (CYP) 1A1 and 1B1, respectively. In estrogen target tissues including the mammary gland, ovaries, and uterus, CYP1B1 is highly expressed, and 4-OHE2 is predominantly formed in cancerous tissues. In this study, we investigated the inhibitory effects of chrysoeriol (luteorin-3'-methoxy ether), which is a natural methoxyflavonoid, against activity of CYP1A1 and 1B1 using in vitro and cultured cell techniques. Chrysoeriol selectively inhibited human recombinant CYP1B1-mediated 7-ethoxyresorufin-O-deethylation (EROD) activity 5-fold more than that of CYP1A1-mediated activity in a competitive manner. Additionally, chrysoeriol inhibited E-2 hydroxylation was catalyzed by CYP1B1, but not by CYP1A1. Methylation of 4-OHE2, which is thought to be a detoxification process, was not affected by the presence of chrysoeriol. In human breast cancer MCF-7 cells, chrysoeriol did not affect the gene expression of CYP1A1 and 1B1, but significantly inhibited the formation of 4-methoxy E-2 without any effects on the formation of 2-methoxy E-2. In conclusion, we present the first report to show that chrysoeriol is a chemopreventive natural ingredient that can selectively inhibit CYP1B1 activity and prevent the formation of carcinogenic 4-OHE2 from E-2. (C) 2009 Elsevier Ltd. All rights reserved.