4-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate | 126900-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate
• 英文别名: [4-(pyridin-2-yldisulfanyl)phenyl]methyl (4S,6S,7R,8S)-11-amino-8-(carbamoyloxymethyl)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-diene-5-carboxylate
• CAS: 126900-80-9
• 化学式: C₂₈H₂₇N₅O₇S₂
• 分子量: 609.684
• InChiKey: QILVYPPLXBWDBI-TTXBDRSASA-N

物化性质

• 熔点：
  99 °C (decomp)
• 沸点：
  814.6±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  218
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  mPEG5000-SH 、 4-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以61%的产率得到
  参考文献：
  名称：

  An oral redox-sensitive self-immolating prodrug strategy

  摘要：

  我们报告了一种新颖的口服前药方法，其中与药物结合的增溶聚合物被设计为在肠道中由外源性给药剂作用下释放。

  DOI：

  10.1039/c5cc00405e
• 作为产物：
  描述：

  (4-(pyridin-2-yldisulfanyl)phenyl)methanol 在 吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate
  参考文献：
  名称：

  Development of a drug-release strategy based on the reductive fragmentation of benzyl carbamate disulfides

  摘要：

  DOI：

  10.1021/jo00296a082

文献信息

• Conjugating Aptamer and Mitomycin C with Reductant-Responsive Linker Leading to Synergistically Enhanced Anticancer Effect
  作者：Qiuxia Yang、Zhengyu Deng、Dan Wang、Jiaxuan He、Dailiang Zhang、Yan Tan、Tianhuan Peng、Xue-Qiang Wang、Weihong Tan

  DOI：10.1021/jacs.9b12409

  日期：2020.2.5

  Mitomycin C (MMC) has been using for the treatment of a variety of digestive tract cancers. However, its nonspecific DNA-alkylating ability usually causes severe side effects, thus largely limiting its clinical applications. The utilization of an efficient active targeted drug delivery technique would address this issue. Accordingly, we report the design and development of aptamer-mitomycin C conjugates that use different cross-linking chemistry. The targeted delivery ability and cytotoxicity of these conjugates were carefully studied. It is worth noting that a linker-dependent cytotoxicity effect was observed for these conjugates. The use of a reductant-sensitive disulfide bond cross-linking strategy resulted in significantly enhanced cytotoxicity of MMC against the target cancer cell lines. Importantly, this cytotoxicity enhancement was suited to different types of aptamers, demonstrating the success of our design. Mechanistic studies of the enhanced cytotoxicity effect indicated that the target recognition, specific binding, and receptor-mediated internalization of aptamer were also critical for the observed effect.
• SENTER, PETER D.;PEARCE, WALTER E.;GREENFIELD, ROBERT S., J. ORG. CHEM., 55,(1990) N, C. 2975-2978
  作者：SENTER, PETER D.、PEARCE, WALTER E.、GREENFIELD, ROBERT S.

  DOI：——

  日期：——