5-[1-(9,17-Dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxo-12-hexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaenyl)ethylideneamino]pentane-1-sulfonic acid | 1364083-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苝醌类
• 英文名称: 5-[1-(9,17-Dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxo-12-hexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaenyl)ethylideneamino]pentane-1-sulfonic acid
• CAS: 1364083-80-6
• 化学式: C₃₅H₃₅NO₁₁S
• 分子量: 677.729
• InChiKey: OBISVZVCKSZQMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 potassium carbonate 、 sodium sulfite 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 5-[1-(9,17-Dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxo-12-hexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaenyl)ethylideneamino]pentane-1-sulfonic acid
  参考文献：
  名称：

  Quantitative and Site-Directed Chemical Modification of Hypocrellins toward Direct Drug Delivery and Effective Photodynamic Activity

  摘要：

  For photodynamic therapy (PDT) treatment of microvascular diseases, drugs are delivered via blood circulation and the targets are vasculature endothelial cells, for which the contradictory requirements of hydrophilicity and lipophilicity of the drugs have been achieved by liposome preparations. Herein, it is demonstrated that the drug delivery and target affinity are achieved by a single chemical compound, hypocrellin B (HB) derivative 6 selected from three novel aminoalkanesulfonic acid HB derivatives, 5-7. 6 exhibits a much higher PDT activity (IC50 = 22 nM) on human gastric carcinoma BGC823 cells than HB, while it has no cellular toxicity in the dark. On the basis of estimation of the clinically required concentration according to relative PDT activity and clinical criteria, it can be predicted that 6 is directly deliverable to and PDT effective on target cells. The enhanced red absorption and superhigh photoactivity suggest that 6 is more powerful for PDT of tumors than HB.

  DOI：

  10.1021/jm2017368

文献信息

• Quantitative and Site-Directed Chemical Modification of Hypocrellins toward Direct Drug Delivery and Effective Photodynamic Activity
  作者：Hong Deng、Xin Liu、Jie Xie、Rong Yin、Naiyan Huang、Ying Gu、Jingquan Zhao

  DOI：10.1021/jm2017368

  日期：2012.3.8

  For photodynamic therapy (PDT) treatment of microvascular diseases, drugs are delivered via blood circulation and the targets are vasculature endothelial cells, for which the contradictory requirements of hydrophilicity and lipophilicity of the drugs have been achieved by liposome preparations. Herein, it is demonstrated that the drug delivery and target affinity are achieved by a single chemical compound, hypocrellin B (HB) derivative 6 selected from three novel aminoalkanesulfonic acid HB derivatives, 5-7. 6 exhibits a much higher PDT activity (IC50 = 22 nM) on human gastric carcinoma BGC823 cells than HB, while it has no cellular toxicity in the dark. On the basis of estimation of the clinically required concentration according to relative PDT activity and clinical criteria, it can be predicted that 6 is directly deliverable to and PDT effective on target cells. The enhanced red absorption and superhigh photoactivity suggest that 6 is more powerful for PDT of tumors than HB.