1-(5-methoxy-2-nitro-4-(4-oxo-4-(prop-2-yn-1-ylamino)butoxy)phenyl)ethyl(4-nitrophenyl)carbonate | 1375413-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-methoxy-2-nitro-4-(4-oxo-4-(prop-2-yn-1-ylamino)butoxy)phenyl)ethyl(4-nitrophenyl)carbonate
• 英文别名: 1-(5-Methoxy-2-nitro-4-(4-oxo-4-(prop-2-yn-1-ylamino)butoxy)phenyl)ethyl (4-nitrophenyl) carbonate；1-[5-methoxy-2-nitro-4-[4-oxo-4-(prop-2-ynylamino)butoxy]phenyl]ethyl (4-nitrophenyl) carbonate
• CAS: 1375413-68-5
• 化学式: C₂₃H₂₃N₃O₁₀
• 分子量: 501.45
• InChiKey: WEGVQDNGMBJRHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  阿霉素 、 1-(5-methoxy-2-nitro-4-(4-oxo-4-(prop-2-yn-1-ylamino)butoxy)phenyl)ethyl(4-nitrophenyl)carbonate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  LIGHT-ENABLED DRUG DELIVERY

  摘要：

  提供了一种缀合物，该缀合物包括与一个不可透过细胞膜的基团相连的可透过细胞膜的药物。不可透过细胞膜的基团的附着阻止了药物穿过细胞膜并进入细胞。然而，光照要么i）断裂这种连接，释放药物并允许其进入细胞；要么ii）将不可透过细胞膜的基团转化为可透过细胞膜的形式，允许整个缀合物进入细胞，在细胞中药物通过裂解从缀合物中释放。因此，可透过细胞膜的药物以时间和空间可控的方式被递送到感兴趣的位置，例如肿瘤中的癌细胞。

  公开号：

  US20140236071A1
• 作为产物：
  描述：

  4-(4-(1-羟基乙基)-2-甲氧基-5-硝基苯氧基)丁酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-(5-methoxy-2-nitro-4-(4-oxo-4-(prop-2-yn-1-ylamino)butoxy)phenyl)ethyl(4-nitrophenyl)carbonate
  参考文献：
  名称：

  Photocaged permeability: a new strategy for controlled drug release

  摘要：

  光被用来从细胞非通透性小分子中释放药物，揭开其对癌细胞的细胞毒性效应。

  DOI：

  10.1039/c2cc30819c

文献信息

• Molecular Glue that Spatiotemporally Turns on Protein–Protein Interactions
  作者：Rina Mogaki、Kou Okuro、Ryosuke Ueki、Shinsuke Sando、Takuzo Aida

  DOI：10.1021/jacs.9b02427

  日期：2019.5.22

  We developed a dendritic molecular glue (PC)Glue-NBD that can serve universally to "turn on" protein-protein interactions (PPIs) spatiotemporally. (PC)Glue-NBD carrying multiple guanidinium ion (Gu(+)) pendants can adhere strongly to target proteins and cover their surfaces including the PPI interface regions, thereby suppressing PPIs with their receptor proteins. Upon irradiation with UV light, (PC)Glue-NBD on a target protein is photocleaved at butyrate-substituted nitroveratryloxycarbonyl linkages in the dendrimer framework, so that the multivalency for the adhesion is reduced. Consequently, the guest protein is liberated and becomes eligible for a PPI. We found that hepatocyte growth factor HGF, when mixed with (PC)Glue-NBD, lost the affinity toward its receptor c-Met. However, upon exposure of the (PC)Glue-NBD/HGF hybrid to light-emitting diode light (365 nm), the (PC)Glue-NBD molecules on HGF were photocleaved as described above, so that HGF was liberated and retrieved its intrinsic PPI affinity toward c-Met. The turn-on PPI, thus achieved for HGF and c-Met, leads to cell migration, which can be made spatiotemporally with a millimeter-scale resolution by pointwise irradiation with UV light.
• US9364551B2
  申请人：——

  公开号：US9364551B2

  公开（公告）日：2016-06-14
• LIGHT-ENABLED DRUG DELIVERY
  申请人：Virginia Commonwealth University

  公开号：US20140236071A1

  公开（公告）日：2014-08-21

  Conjugates are provided which comprise a membrane permeable drug linked to a moiety that is not membrane permeable. Attachment of the moiety that is not membrane permeable prevents the drug from crossing cell membranes and entering cells. However, exposure to light either i) breaks the linkage, releasing the drug and allowing it to enter cells; or ii) converts the non-membrane permeable moiety to a membrane permeable form, allowing the entire conjugate to enter the cell, where the drug is released from the conjugate by cleavage. The membrane permeable drugs are thus delivered to cells at locations of interest, e.g. cancer cells in a tumor, in a temporally and spatially controlled manner.

  提供了一种缀合物，该缀合物包括与一个不可透过细胞膜的基团相连的可透过细胞膜的药物。不可透过细胞膜的基团的附着阻止了药物穿过细胞膜并进入细胞。然而，光照要么i）断裂这种连接，释放药物并允许其进入细胞；要么ii）将不可透过细胞膜的基团转化为可透过细胞膜的形式，允许整个缀合物进入细胞，在细胞中药物通过裂解从缀合物中释放。因此，可透过细胞膜的药物以时间和空间可控的方式被递送到感兴趣的位置，例如肿瘤中的癌细胞。
• Photocaged permeability: a new strategy for controlled drug release
  作者：M. Michael Dcona、Deboleena Mitra、Rachel W. Goehe、David A. Gewirtz、Deborah A. Lebman、Matthew C. T. Hartman

  DOI：10.1039/c2cc30819c

  日期：——

  Light is used to release a drug from a cell impermeable small molecule, uncloaking its cytotoxic effect on cancer cells.

  光被用来从细胞非通透性小分子中释放药物，揭开其对癌细胞的细胞毒性效应。