N-(3,4-dibenzyloxybenzyl)daunorubicin

• 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: N-(3,4-dibenzyloxybenzyl)daunorubicin
• 英文别名: (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-[[3,4-bis(phenylmethoxy)phenyl]methylamino]-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 化学式: C₄₈H₄₇NO₁₂
• 分子量: 829.901
• InChiKey: YLDNUHMDLSNOEM-KMQKJLQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  61
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  190
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 、 柔红霉素 盐酸盐 在 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 N-(3,4-dibenzyloxybenzyl)daunorubicin
  参考文献：
  名称：

  Plasma stability and cytotoxicity of lipophilic daunorubicin derivatives incorporated into low density lipoproteins

  摘要：

  The selective targeting of antineoplastic drugs to tumours by incorporation in low density lipoproteins (LDL) is an attractive possibility if the drug-LDL complex remains stable in the circulation and is taken up by the tumour. In previous studies we have shown that vincristine- and N-trifluoroacetyladriamycin-14-valerate-LDL complexes were unstable in vivo. We synthesized five N-substituted lipophilic derivatives of daunorubicin and studied their incorporation into LDL. Three out of five daunorubicin derivatives incorporated successfully into LDL. In vitro these complexes were more cytotoxic towards LDL receptor positive Chinese hamster ovary cells than LDL receptor negative cells. Non-specific cytotoxicity was explained by slow dissociation of the drug-LDL complex in plasma. Our results underline the importance of careful studies of plasma stability when investigating lipoproteins and other carriers in drug targeting. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00139-2

文献信息

• Plasma stability and cytotoxicity of lipophilic daunorubicin derivatives incorporated into low density lipoproteins
  作者：M Masquelier

  DOI：10.1016/s0223-5234(00)00139-2

  日期：2000.4

  The selective targeting of antineoplastic drugs to tumours by incorporation in low density lipoproteins (LDL) is an attractive possibility if the drug-LDL complex remains stable in the circulation and is taken up by the tumour. In previous studies we have shown that vincristine- and N-trifluoroacetyladriamycin-14-valerate-LDL complexes were unstable in vivo. We synthesized five N-substituted lipophilic derivatives of daunorubicin and studied their incorporation into LDL. Three out of five daunorubicin derivatives incorporated successfully into LDL. In vitro these complexes were more cytotoxic towards LDL receptor positive Chinese hamster ovary cells than LDL receptor negative cells. Non-specific cytotoxicity was explained by slow dissociation of the drug-LDL complex in plasma. Our results underline the importance of careful studies of plasma stability when investigating lipoproteins and other carriers in drug targeting. (C) 2000 Editions scientifiques et medicales Elsevier SAS.