5,12-Naphthacenedione, 7,8,9,10-tetrahydro-8-(hydroxyacetyl)-1-methoxy-10-((2,3,6-trideoxy-3-((((4-(beta-D-glucopyranosyloxy)-3-nitrophenyl)methoxy)carbonyl)amino)-alpha-L-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-, (8S-cis)- | 160065-76-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-8-(hydroxyacetyl)-1-methoxy-10-((2,3,6-trideoxy-3-((((4-(beta-D-glucopyranosyloxy)-3-nitrophenyl)methoxy)carbonyl)amino)-alpha-L-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-, (8S-cis)-
• 英文别名: [3-nitro-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl N-[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]carbamate
• CAS: 160065-76-9
• 化学式: C₄₁H₄₄N₂O₂₁
• 分子量: 900.801
• InChiKey: OMFTUPWGMZJWDV-YZUCLQJOSA-N

物化性质

• 沸点：
  1161.6±65.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  364
• 氢给体数：
  10
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  5,12-Naphthacenedione, 7,8,9,10-tetrahydro-8-(hydroxyacetyl)-1-methoxy-10-((2,3,6-trideoxy-3-((((4-(beta-D-glucopyranosyloxy)-3-nitrophenyl)methoxy)carbonyl)amino)-alpha-L-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-, (8S-cis)- 在 β-galactosidase 作用下， 反应 2.0h， 生成 阿霉素
  参考文献：
  名称：

  Development of a theranostic prodrug for colon cancer therapy by combining ligand-targeted delivery and enzyme-stimulated activation

  摘要：

  The high incidence of colorectal cancer worldwide is currently a major health concern. Although conventional chemotherapy and surgery are effective to some extent, there is always a risk of relapse due to associated side effects, including post-surgical complications and non-discrimination between cancer and normal cells. In this study, we developed a small molecule-based theranostic system, Gal-Dox, which is preferentially taken up by colon cancer cells through receptor-mediated endocytosis. After cancer specific activation, the active drug Dox (doxorubicin) is released with a fluorescence turn-on response, allowing both drug localization and site of action to be monitored. The therapeutic potency of Gal-Dox was also evaluated, both in vivo and ex vivo, thus illustrating the potential of Gal-Dox as a colorectal cancer theranostic with great specificity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.biomaterials.2017.11.019

文献信息

• Development of a theranostic prodrug for colon cancer therapy by combining ligand-targeted delivery and enzyme-stimulated activation
  作者：Amit Sharma、Eun-Joong Kim、Hu Shi、Jin Yong Lee、Bong Geun Chung、Jong Seung Kim

  DOI：10.1016/j.biomaterials.2017.11.019

  日期：2018.2

  The high incidence of colorectal cancer worldwide is currently a major health concern. Although conventional chemotherapy and surgery are effective to some extent, there is always a risk of relapse due to associated side effects, including post-surgical complications and non-discrimination between cancer and normal cells. In this study, we developed a small molecule-based theranostic system, Gal-Dox, which is preferentially taken up by colon cancer cells through receptor-mediated endocytosis. After cancer specific activation, the active drug Dox (doxorubicin) is released with a fluorescence turn-on response, allowing both drug localization and site of action to be monitored. The therapeutic potency of Gal-Dox was also evaluated, both in vivo and ex vivo, thus illustrating the potential of Gal-Dox as a colorectal cancer theranostic with great specificity. (C) 2017 Elsevier Ltd. All rights reserved.