喜树碱-20-O-甲基碳酸酯 | 56581-35-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 中文名称: 喜树碱-20-O-甲基碳酸酯
• 英文名称: camtothecin-20-O-methyl carbonate
• 英文别名: (S)-4-ethoxycarbonyloxy-4-ethyl-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione；O-ethoxycarbonyl-camptothecin；[(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] methyl carbonate
• CAS: 56581-35-2
• 化学式: C₂₂H₁₈N₂O₆
• 分子量: 406.395
• InChiKey: YJKRDQZBWXMKNO-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  喜树碱-20-O-甲基碳酸酯 在 sulfanyl-lithium 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 喜树碱
  参考文献：
  名称：

  信函：天然20（S）-喜树碱的全合成。

  摘要：

  DOI：

  10.1021/jo00902a034
• 作为产物：
  描述：

  喜树碱 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 喜树碱-20-O-甲基碳酸酯
  参考文献：
  名称：

  20-O-Acylcamptothecin Derivatives:  Evidence for Lactone Stabilization

  摘要：

  Convincing UV and NMR spectrophotometric evidence is presented which demonstrates that at physiological pH, 7.4, 20-O-acyl derivatives of camptothecin (CPT) are substantially more stable in the lactone form than the 20-OH parent. Additionally, it was determined by HPLC analysis that the lactone ring of a 20-O-ether derivative of CPT underwent endocyclic ring opening at pR greater than or equal to 8.5, while the lactone ring of 20-O-acyl CPT derivatives remained unaffected. PEG (and other smaller alkyl) 20-O-acyl-CPT derivatives released native CPT at pH > 9.5, which arises from exocyclic cleavage, thus precluding isolation of any open CPT acyl PEG (or alkyl) carboxylate forms.

  DOI：

  10.1021/jo000221n

文献信息

• Drug carrier and preparation method thereof
  申请人：HAINAN POLY PHARM CO., LTD.

  公开号：US11534435B2

  公开（公告）日：2022-12-27

  This present invention relates to a drug carrier comprising a polymer of γ-glutamyl transpeptidase catalyzing hydrolysis-induced charge reversal, and a method for preparing the same. It can have a long circulation time in the blood, and can realize a charge reversal from negatively charged or the neutral to positively charged around the tumor blood vessel region, so that the positively charged polymer effectively penetrates deep into the tumor tissue, fast entering into the tumor cells, and greatly improves the therapeutic effect of the drug on the tumor. This overcomes the problems of slow diffusion of traditional polymer drug carriers in tumors and weak interaction with tumor cells, and has great significance in the field of anticancer treatment in the medical field.

  本发明涉及一种由γ-谷氨酰转肽酶催化水解诱导电荷反转的聚合物组成的药物载体及其制备方法。γ-谷氨酰转肽酶催化水解诱导电荷反转的聚合物及其制备方法，在血液中的循环时间长，能在肿瘤血管区域周围实现从带负电荷或中性到带正电荷的电荷反转，使带正电荷的聚合物有效渗透到肿瘤组织深处，快速进入肿瘤细胞，大大提高了药物对肿瘤的治疗效果。这克服了传统高分子药物载体在肿瘤中扩散慢、与肿瘤细胞相互作用弱等问题，在医学领域的抗癌治疗领域具有重要意义。