| 1493681-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1493681-55-2
• 化学式: C₁₀₂H₁₈₀N₁₂O₄₂
• 分子量: 2246.61
• InChiKey: YISHYTHBHFPOHN-AQHGZQGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  156.0
• 可旋转键数：
  48.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  758.1
• 氢给体数：
  24.0
• 氢受体数：
  42.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design and Evaluation of Folate-Appended α-, β-, and γ-Cyclodextrins Having a Caproic Acid as a Tumor Selective Antitumor Drug Carrier in Vitro and in Vivo

  摘要：

  We reported that per-6-folic acid (FA)-appended beta-cyclodextrin (beta-CyD) possessing two caproic acids between FA and a beta-CyD molecule as a spacer (Fol-c(2)-beta-CyD) could be useful as a promising antitumor drug carrier. However, the effects of the cavity size and the spacer length on the carrier ability are not still known. In this study, we designed and evaluated the FA-appended three kinds of CyDs possessing a caproic acid as a spacer between FA and a CyD molecule (Fol-c(1)-CyDs) as a tumor targeting carrier for antitumor drugs. The stability constant of the Fol-c(1)-beta-CyD/doxorubicin (DOX) complex was much higher than those of Fol-c(1)-alpha-CyD and Fol-c(1)-gamma-CyD at pH 7.3. Antitumor activity of DOX was increased by the complexation with Fol-c(1)-beta-CyD, but not with Fol-c(1)-alpha-CyD or Fol-c(1)-gamma-CyD in KB cells, a folate receptor-alpha-positive cell line. Also, Fol-c(1)-beta-CyD increased antitumor activities of paclitaxel and vinblastine, but not 5-fluorouracil. Furthermore, Fol-c(1)-beta-CyD accelerated cellular uptake of DOX and inhibited its efflux from KB cells. The Fol-c(1)-beta-CyD/DOX complex showed much higher antitumor activity than DOX alone after intratumoral and intravenous administrations to tumor-bearing mice with a negligible change of the blood chemistry values. These findings suggest that Fol-c(1)-beta-CyD could be useful as a tumor-selective carrier for antitumor drugs.

  DOI：

  10.1021/bm401340g
• 作为产物：
  描述：

  氨基-Α-环糊精 、 叔丁氧羰酰基6-氨基己酸 在 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 甲醇 、 水 为溶剂， 反应 42.0h， 生成
  参考文献：
  名称：

  Design and Evaluation of Folate-Appended α-, β-, and γ-Cyclodextrins Having a Caproic Acid as a Tumor Selective Antitumor Drug Carrier in Vitro and in Vivo

  摘要：

  We reported that per-6-folic acid (FA)-appended beta-cyclodextrin (beta-CyD) possessing two caproic acids between FA and a beta-CyD molecule as a spacer (Fol-c(2)-beta-CyD) could be useful as a promising antitumor drug carrier. However, the effects of the cavity size and the spacer length on the carrier ability are not still known. In this study, we designed and evaluated the FA-appended three kinds of CyDs possessing a caproic acid as a spacer between FA and a CyD molecule (Fol-c(1)-CyDs) as a tumor targeting carrier for antitumor drugs. The stability constant of the Fol-c(1)-beta-CyD/doxorubicin (DOX) complex was much higher than those of Fol-c(1)-alpha-CyD and Fol-c(1)-gamma-CyD at pH 7.3. Antitumor activity of DOX was increased by the complexation with Fol-c(1)-beta-CyD, but not with Fol-c(1)-alpha-CyD or Fol-c(1)-gamma-CyD in KB cells, a folate receptor-alpha-positive cell line. Also, Fol-c(1)-beta-CyD increased antitumor activities of paclitaxel and vinblastine, but not 5-fluorouracil. Furthermore, Fol-c(1)-beta-CyD accelerated cellular uptake of DOX and inhibited its efflux from KB cells. The Fol-c(1)-beta-CyD/DOX complex showed much higher antitumor activity than DOX alone after intratumoral and intravenous administrations to tumor-bearing mice with a negligible change of the blood chemistry values. These findings suggest that Fol-c(1)-beta-CyD could be useful as a tumor-selective carrier for antitumor drugs.

  DOI：

  10.1021/bm401340g