N1,N2,N3,N4-tetra(trifluoroacetyl)spermine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N1,N2,N3,N4-tetra(trifluoroacetyl)spermine
• 英文别名: 2,2,2-trifluoro-N-[3-(2,2,2-trifluoroacetylamino)propyl]-N-(4-{trifluoroacetyl-[3-(2,2.2-trifluoroacetylamino)propyl]amino}-butyl)acetamide；2,2,2-trifluoro-N-[3-[(2,2,2-trifluoroacetyl)-[4-[(2,2,2-trifluoroacetyl)-[3-[(2,2,2-trifluoroacetyl)amino]propyl]amino]butyl]amino]propyl]acetamide
• 化学式: C₁₈H₂₂F₁₂N₄O₄
• 分子量: 586.378
• InChiKey: RWNSCJLFKPQCKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N1,N2,N3,N4-tetra(trifluoroacetyl)spermine 在 甲醇 、 4-二甲氨基吡啶 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 di-tert-butyl ((butane-1,4-diylbis(azanediyl))bis(propane-3,1-diyl))dicarbamate
  参考文献：
  名称：

  MMT, Npeoc-protected spermine, a valuable synthon for the solid phase synthesis of oligonucleotide oligospermine conjugates via guanidine linkers

  摘要：

  Solid phase spermine oligomerization via guanidine linkers was achieved using activated thiourea coupling reaction with primary amino group. Disymmetric spermine synthon was efficiently synthesised in eight steps from spermine. MMT group was used as coupling monitor and resulting oligomeric spermines were conjugated to oligonucleotides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.061
• 作为产物：
  描述：

  精胺 、 三氟乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 N1,N2,N3,N4-tetra(trifluoroacetyl)spermine
  参考文献：
  名称：

  MMT, Npeoc-protected spermine, a valuable synthon for the solid phase synthesis of oligonucleotide oligospermine conjugates via guanidine linkers

  摘要：

  Solid phase spermine oligomerization via guanidine linkers was achieved using activated thiourea coupling reaction with primary amino group. Disymmetric spermine synthon was efficiently synthesised in eight steps from spermine. MMT group was used as coupling monitor and resulting oligomeric spermines were conjugated to oligonucleotides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.061

文献信息

• Acid-sensitive compounds, their preparation and uses
  申请人：——

  公开号：US20020091242A1

  公开（公告）日：2002-07-11

  Novel acid-sensitive compounds comprising a cyclic ortho-ester that is acid-sensitive, and their salts, and comprising at least one hydrophilic substituent. These compounds are useful, for example, for forming conjugates (liposomes, complexes, nanoparticles and the like) with biologically active substances and releasing them into cellular tissues or compartments whose pH is acidic, or as nonionic surfactant for stabilizing particles encapsulating a biologically active substance and then destabilizing them in acid medium, or alternatively as a vector covalently linked to a therapeutic molecule so as to release said therapeutic molecule into the cellular tissues or compartments whose pH is acidic.

  包含一种对酸敏感的环状邻酯化合物及其盐的新型酸敏感化合物，其中至少包含一个亲水性取代基。这些化合物可用于与生物活性物质形成共轭物（如脂质体、复合物、纳米粒子等），并将其释放到pH值为酸性的细胞组织或区室中，或作为非离子表面活性剂用于稳定封装生物活性物质的粒子，然后在酸性介质中使其变得不稳定，或作为共价连接到治疗分子的载体，以便将所述治疗分子释放到pH值为酸性的细胞组织或区室中。
• Acid-sensitive compounds, preparation and use thereof
  申请人：Bessodes Michel

  公开号：US20050085426A1

  公开（公告）日：2005-04-21

  Novel acid-sensitive compounds comprising at least one hydrophilic substituent and a cyclic ortho-ester which is acid-sensitive, and their salts. These compounds are useful for forming conjugates (liposomes, complexes, nanoparticles and the like) with biologically active substances and releasing them into cellular tissues or compartments whose pH is acidic, or as nonionic surfactant for stabilizing particles encapsulating a biologically active substance and then destabilizing them in acid medium, or alternatively as a vector covalently linked to a therapeutic molecule so as to release said therapeutic molecule into the cellular tissues or compartments whose pH is acidic.

  本发明涉及一种酸敏感的新型化合物，其中包括至少一个亲水性取代基和一个酸敏感的环状正交酯，以及它们的盐。这些化合物可用于与生物活性物质形成共轭物（脂质体、复合物、纳米粒子等），并将它们释放到pH值为酸性的细胞组织或区域中，或作为非离子表面活性剂，用于稳定包含生物活性物质的粒子，然后在酸性介质中使其不稳定，或作为与治疗分子共价连接的载体，以便将所述治疗分子释放到pH值为酸性的细胞组织或区域中。
• Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability
  作者：Junsuke Hayashi、Tomoko Hamada、Ikumi Sasaki、Osamu Nakagawa、Shun-ichi Wada、Hidehito Urata

  DOI：10.1016/j.bmcl.2015.06.071

  日期：2015.9

  A spermine-conjugated ethyl phosphotriester oligonucleotide was obtained by solid-phase synthesis based on phosphoramidite chemistry. The ethyl phosphotriester linkage was robust to exonuclease digestion and stable in fetal bovine serum. Cell membrane permeability of the spermine-conjugated ethyl phosphotriester oligonucleotide was studied by fluorescence experiments. The effective cell penetrating potency of the spermine-conjugated ethyl phosphotriester oligonucleotide was determined by confocal laser scanning microscopy and measurement of intracellular fluorescence intensity. (C) 2015 Elsevier Ltd. All rights reserved.
• COMPOSES ACIDOSENSIBLES, LEUR PREPARATION ET UTILISATIONS
  申请人：CENTELION

  公开号：EP1317439B1

  公开（公告）日：2005-12-07
• US7641914B2
  申请人：——

  公开号：US7641914B2

  公开（公告）日：2010-01-05