1-ethyl-2-(2-(2-(ethyl((2-((2-hydroxyethyl)disulfaneyl)ethoxy)carbonyl)amino)-3-(2-(1-ethyl-3,3-dimethylindolin-2-ylidene)ethylidene)-5-(prop-2-yn-1-yloxy)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium chloride | 1447817-79-9

• 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: 1-ethyl-2-(2-(2-(ethyl((2-((2-hydroxyethyl)disulfaneyl)ethoxy)carbonyl)amino)-3-(2-(1-ethyl-3,3-dimethylindolin-2-ylidene)ethylidene)-5-(prop-2-yn-1-yloxy)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium chloride
• CAS: 1447817-79-9
• 化学式: C₄₄H₅₆N₃O₄S₂*Cl
• 分子量: 790.531
• InChiKey: KIYMYNMWDHCEAF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.25
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-ethyl-2-(2-(2-(ethyl((2-((2-hydroxyethyl)disulfaneyl)ethoxy)carbonyl)amino)-3-(2-(1-ethyl-3,3-dimethylindolin-2-ylidene)ethylidene)-5-(prop-2-yn-1-yloxy)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium chloride 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl 2-[2-[ethyl-[(6E)-2-[(E)-2-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-6-[(2E)-2-(1-ethyl-3,3-dimethylindol-2-ylidene)ethylidene]-4-prop-2-ynoxycyclohexen-1-yl]carbamoyl]oxyethyldisulfanyl]ethyl carbonate;chloride
  参考文献：
  名称：

  Folate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery

  摘要：

  A series of heptamethine cyanine (1-3) derivatives bearing a carbamate ethyl disulfide group and gemcitabine, an anticancer drug, have been newly synthesized. Their disulfide bonds are readily cleaved by various thiols including glutathione, to result in a subsequent decomposition of the carbamate into amine followed by release of the active gemcitabine, which can be monitored by the fluorescence changes. In the biological experiment, prodrug 1 is preferentially up-taken by folate-positive KB cells over folate-negative A549 cells via receptor-mediated endocytosis to release gemcitabine causing cell death and to emit fluorescence in endoplasmic reticulum. Moreover, it is selectively accumulated in the KB cells which were treated to mice by dorsal subcutaneous injection. This drug delivery system is a new theranostic agent, wherein both therapeutic effect and drug uptake can be easily monitored at the subcellular level, by in vivo and in vitro fluorescence imaging.

  DOI：

  10.1021/ja405372k
• 作为产物：
  描述：

  1-乙基-2,3,3-三甲基吲哚鎓碘化物 在 4-二甲氨基吡啶 、 sodium acetate 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 1-ethyl-2-(2-(2-(ethyl((2-((2-hydroxyethyl)disulfaneyl)ethoxy)carbonyl)amino)-3-(2-(1-ethyl-3,3-dimethylindolin-2-ylidene)ethylidene)-5-(prop-2-yn-1-yloxy)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium chloride
  参考文献：
  名称：

  Folate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery

  摘要：

  A series of heptamethine cyanine (1-3) derivatives bearing a carbamate ethyl disulfide group and gemcitabine, an anticancer drug, have been newly synthesized. Their disulfide bonds are readily cleaved by various thiols including glutathione, to result in a subsequent decomposition of the carbamate into amine followed by release of the active gemcitabine, which can be monitored by the fluorescence changes. In the biological experiment, prodrug 1 is preferentially up-taken by folate-positive KB cells over folate-negative A549 cells via receptor-mediated endocytosis to release gemcitabine causing cell death and to emit fluorescence in endoplasmic reticulum. Moreover, it is selectively accumulated in the KB cells which were treated to mice by dorsal subcutaneous injection. This drug delivery system is a new theranostic agent, wherein both therapeutic effect and drug uptake can be easily monitored at the subcellular level, by in vivo and in vitro fluorescence imaging.

  DOI：

  10.1021/ja405372k