EF-31 | 342808-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: EF-31
• 英文别名: 3,5-bis(2-pyridinylmethylidene)-4-piperidone；3,5-Bis(2-pyridylmethylene)-4-piperidone；3,5-bis(pyridin-2-ylmethylidene)piperidin-4-one
• CAS: 342808-24-6
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: GXFKPANENAOEOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  EF-31 、 H-Cys-Phe-OH 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Curcumin analog cytotoxicity against breast cancer cells: exploitation of a redox-dependent mechanism

  摘要：

  A series of novel curcumin analogs, symmetrical dienones, were previously shown to possess cytotoxic, anti-angiogenic and anti-tumor activities. Analogs 1 (EF24) and 2 (EF31) share the dienone scaffold and serve as Michael acceptors. We propose that the anti-cancer effects of 1 and 2 are mediated in part by redox-mediated induction of apoptosis. In order to support this concept, 1 and 2 were treated with L-glutathione (GSH) and cysteine-containing dipeptides under mild conditions to form colorless water-soluble adducts, which were identified by LC/MS. Comparison of the cytotoxic action of 1, 2 and the corresponding conjugates, 1-(GSH)(2) and 2-(GSH)(2), illustrated that the two classes of compounds exhibit essentially identical cell killing capabilities. Compared with the yellow, somewhat light sensitive and nearly water insoluble compounds 1 and 2, the glutathione conjugates represent a promising new series of stable and soluble anti-tumor pro-drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.023

文献信息

• DELIVERY SYSTEMS AND METHODS FOR REACTIVE HYDROXYL-CONTAINING COMPOUNDS
  申请人：University of Kentucky Research Foundation

  公开号：US20190314512A1

  公开（公告）日：2019-10-17

  Disclosed are methods for delivering a reactive hydroxyl compound, systems comprising a delivery composition comprising a reactive hydroxyl compound and a trigger, and kits which incorporate a reactive hydroxyl compound and a trigger.

  本发明涉及一种传递反应性羟基化合物的方法，包括一种传递组合物，该组合物包括反应性羟基化合物和触发剂，以及包含反应性羟基化合物和触发剂的工具箱。
• POLYMERIC NANOPARTICLES THAT TARGET LIVER SINUSOIDAL ENDOTHELIAL CELLS TO INDUCE ANTIGEN-SPECIFIC IMMUNE TOLERANCE
  申请人：The Regents of the University of California

  公开号：US20220395563A1

  公开（公告）日：2022-12-15

  In various embodiments tolerogenic nanoparticles are provided that induce immune tolerance to one or more desired antigen(s) and/or that reduce an immune response to those antigen(s). In certain embodiments the tolerogenic nanoparticle comprises a nanoparticle comprising a biocompatible polymer; an antigen disposed within or attached to said biocompatible polymer where said antigen comprises an antigen to which immune tolerance is to be induced by administration of said tolerogenic nanoparticle to a mammal; and a first targeting moiety that binds to a scavenger receptor in the liver, and/or a second targeting moiety that binds to a mannose receptor in the liver, and/or a third targeting moiety that binds to hepatocytes, wherein said first and/or second and/or third targeting moiety are attached to the surface of said nanoparticle.
• [EN] POLYMERIC NANOPARTICLES THAT TARGET LIVER SINUSOIDAL ENDOTHELIAL CELLS TO INDUCE ANTIGEN-SPECIFIC IMMUNE TOLERANCE<br/>[FR] NANOPARTICULES POLYMÈRES CIBLANT DES CELLULES ENDOTHÉLIALES SINUSOÏDALES DU FOIE POUR INDUIRE UNE TOLÉRANCE IMMUNITAIRE SPÉCIFIQUE À L'ANTIGÈNE
  申请人：UNIV CALIFORNIA

  公开号：WO2021096972A1

  公开（公告）日：2021-05-20

  In various embodiments tolerogenic nanoparticles are provided that induce immune tolerance to one or more desired antigen(s) and/or that reduce an immune response to those antigen(s). In certain embodiments the tolerogenic nanoparticle comprises a nanoparticle comprising a biocompatible polymer; an antigen disposed within or attached to said biocompatible polymer where said antigen comprises an antigen to which immune tolerance is to be induced by administration of said tolerogenic nanoparticle to a mammal; and a first targeting moiety that binds to a scavenger receptor in the liver, and/or a second targeting moiety that binds to a mannose receptor in the liver, and/or a third targeting moiety that binds to hepatocytes, wherein said first and/or second and/or third targeting moiety are attached to the surface of said nanoparticle.
• Curcumin analog cytotoxicity against breast cancer cells: exploitation of a redox-dependent mechanism
  作者：Aiming Sun、Yang J. Lu、Haipeng Hu、Mamoru Shoji、Dennis C. Liotta、James P. Snyder

  DOI：10.1016/j.bmcl.2009.10.023

  日期：2009.12

  A series of novel curcumin analogs, symmetrical dienones, were previously shown to possess cytotoxic, anti-angiogenic and anti-tumor activities. Analogs 1 (EF24) and 2 (EF31) share the dienone scaffold and serve as Michael acceptors. We propose that the anti-cancer effects of 1 and 2 are mediated in part by redox-mediated induction of apoptosis. In order to support this concept, 1 and 2 were treated with L-glutathione (GSH) and cysteine-containing dipeptides under mild conditions to form colorless water-soluble adducts, which were identified by LC/MS. Comparison of the cytotoxic action of 1, 2 and the corresponding conjugates, 1-(GSH)(2) and 2-(GSH)(2), illustrated that the two classes of compounds exhibit essentially identical cell killing capabilities. Compared with the yellow, somewhat light sensitive and nearly water insoluble compounds 1 and 2, the glutathione conjugates represent a promising new series of stable and soluble anti-tumor pro-drugs. (C) 2009 Elsevier Ltd. All rights reserved.