11,11'-((13-acetyl-2,9-dihydroxy-1,5,6,10-tetramethoxy-12-methyl-3,8-dioxo-8,11-dihydro-3H-cyclohepta[ghi]perylene-4,7-diyl)bis(sulfanediyl))diundecanoic acid | 1242410-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 11,11'-((13-acetyl-2,9-dihydroxy-1,5,6,10-tetramethoxy-12-methyl-3,8-dioxo-8,11-dihydro-3H-cyclohepta[ghi]perylene-4,7-diyl)bis(sulfanediyl))diundecanoic acid
• CAS: 1242410-98-5
• 化学式: C₅₂H₆₄O₁₃S₂
• 分子量: 961.204
• InChiKey: ZFLDOMTWAMSITG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.63
• 重原子数：
  67.0
• 可旋转键数：
  29.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  203.19
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  11,11'-((13-acetyl-2,9-dihydroxy-1,5,6,10-tetramethoxy-12-methyl-3,8-dioxo-8,11-dihydro-3H-cyclohepta[ghi]perylene-4,7-diyl)bis(sulfanediyl))diundecanoic acid 在 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Novel Surfactant-like Hypocrellin Derivatives to Achieve Simultaneous Drug Delivery in Blood Plasma and Cell Uptake

  摘要：

  AbstractWater‐soluble derivatives of hypocrellins can be safely delivered in blood plasma but lose their photodynamic activity in vivo due to poor cell uptake, while hydrophobic derivatives retaining their activity may aggregate in the blood plasma and block vascular networks. Considering both drug delivery and biological activity, surfactant‐like hypocrellin B (HB) derivatives, sodium 12‐2‐HB‐aminododecanoate (SAHB) and sodium 11,11′‐5,8‐HB‐dimercaptoundecanoate (DMHB), were first designed and then synthesized in the current work. Both SAHB and DMHB were photoactive, generating free radicals and reactive oxygen species, as confirmed by EPR and chemical measurements. Most importantly, DMHB was not only readily soluble, allowing preparation of an intravenous injection solution at a clinically acceptable concentration, but it was also more photodynamic therapy (PDT) active to human breast carcinoma MCF‐7 cells than its parent HB under irradiation. The photodynamic activity was exactly identical to the 1O2 quantum yield and was not reduced by the improved water solubility, suggesting an independent hydrophilicity or lipophilicity. To our knowledge, this is a new strategy that possesses general significance for converting hydrophobic photosensitizers into clinically usable PDT drugs.

  DOI：

  10.1111/j.1751-1097.2010.00711.x
• 作为产物：
  描述：

  11-巯基十一烷酸 、 hypocrellin B 在 三乙胺 、 盐酸 作用下， 以 二甲基亚砜 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以60%的产率得到11,11'-((13-acetyl-2,9-dihydroxy-1,5,6,10-tetramethoxy-12-methyl-3,8-dioxo-8,11-dihydro-3H-cyclohepta[ghi]perylene-4,7-diyl)bis(sulfanediyl))diundecanoic acid
  参考文献：
  名称：

  Novel Surfactant-like Hypocrellin Derivatives to Achieve Simultaneous Drug Delivery in Blood Plasma and Cell Uptake

  摘要：

  AbstractWater‐soluble derivatives of hypocrellins can be safely delivered in blood plasma but lose their photodynamic activity in vivo due to poor cell uptake, while hydrophobic derivatives retaining their activity may aggregate in the blood plasma and block vascular networks. Considering both drug delivery and biological activity, surfactant‐like hypocrellin B (HB) derivatives, sodium 12‐2‐HB‐aminododecanoate (SAHB) and sodium 11,11′‐5,8‐HB‐dimercaptoundecanoate (DMHB), were first designed and then synthesized in the current work. Both SAHB and DMHB were photoactive, generating free radicals and reactive oxygen species, as confirmed by EPR and chemical measurements. Most importantly, DMHB was not only readily soluble, allowing preparation of an intravenous injection solution at a clinically acceptable concentration, but it was also more photodynamic therapy (PDT) active to human breast carcinoma MCF‐7 cells than its parent HB under irradiation. The photodynamic activity was exactly identical to the 1O2 quantum yield and was not reduced by the improved water solubility, suggesting an independent hydrophilicity or lipophilicity. To our knowledge, this is a new strategy that possesses general significance for converting hydrophobic photosensitizers into clinically usable PDT drugs.

  DOI：

  10.1111/j.1751-1097.2010.00711.x