N-dodecyl-4-(hydroxymethyl)-3-nitrobenzamide | 1018856-54-6

• 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: N-dodecyl-4-(hydroxymethyl)-3-nitrobenzamide
• CAS: 1018856-54-6
• 化学式: C₂₀H₃₂N₂O₄
• 分子量: 364.485
• InChiKey: OSOGRGCMATYHAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  N-dodecyl-4-(hydroxymethyl)-3-nitrobenzamide 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以81%的产率得到4-(dodecylcarbamoyl)-2-nitrobenzyl (4-nitrophenyl) carbonate
  参考文献：
  名称：

  Constrained and UV-activatable cell-penetrating peptides for intracellular delivery of liposomes

  摘要：

  Herein we report on the development of a novel method of constraining a cell-penetrating peptide, which can be used to trigger transport of liposomes into cells upon in this case radiation with UV-light. A cell-penetrating peptide, which was modified on both termini with an alkyl chain, was anchored to the liposomal surface in a constrained and deactivated form. Since one of the two alkyl chains was connected to the peptide via a UV-cleavable linker, disconnection of this alkyl chain upon irradiation led to the exposure of the cell-penetrating peptide, and mediated the transport of the entire liposome particle into cells. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2012.10.008
• 作为产物：
  描述：

  4-溴甲基-3-硝基苯甲酸 在 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 N-dodecyl-4-(hydroxymethyl)-3-nitrobenzamide
  参考文献：
  名称：

  Constrained and UV-activatable cell-penetrating peptides for intracellular delivery of liposomes

  摘要：

  Herein we report on the development of a novel method of constraining a cell-penetrating peptide, which can be used to trigger transport of liposomes into cells upon in this case radiation with UV-light. A cell-penetrating peptide, which was modified on both termini with an alkyl chain, was anchored to the liposomal surface in a constrained and deactivated form. Since one of the two alkyl chains was connected to the peptide via a UV-cleavable linker, disconnection of this alkyl chain upon irradiation led to the exposure of the cell-penetrating peptide, and mediated the transport of the entire liposome particle into cells. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2012.10.008

文献信息

• Photo-Cleavable Surfactants
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20210253519A1

  公开（公告）日：2021-08-19

  The present invention provides photo-cleavable anionic surfactants, particularly 4-hexylphenylazosulfonate (Azo) and sodium 4-hexylphenylazosulfonate derivatives, which can be rapidly degraded upon UV irradiation, for top-down and bottom-up proteomics. These surfactants can effectively solubilize proteins and peptide fragments with performance comparable to sodium dodecyl sulfate (SDS) and are compatible with mass spectrometry analysis of the solubilized proteins and peptide fragments. Top-down proteomic studies using the present photo-cleavable anionic surfactants has allowed the detection of 100-fold more unique proteoforms as compared to controls and has enabled the solubilization of membrane proteins for comprehensive characterization of protein post-trans-modifications. In addition, the present photo-cleavable anionic surfactants are also suitable for dissolving polypeptides in bottom-up proteomic experiments including extracellular matrix proteomics, and are suitable as a substitute for SDS in gel electrophoresis.

  本发明提供了光解离的阴离子表面活性剂，特别是4-己基苯基偶氮磺酸盐（Azo）和钠4-己基苯基偶氮磺酸盐衍生物，可以在紫外辐射下迅速降解，用于自顶向下和自底向上的蛋白质组学研究。这些表面活性剂可以有效溶解蛋白质和肽段，性能可与十二烷基硫酸钠（SDS）相媲美，并且与质谱分析兼容，可对溶解的蛋白质和肽段进行分析。利用本发明的光解离的阴离子表面活性剂进行自顶向下蛋白质组学研究，相比对照组，已实现了检测100倍更多独特的蛋白质形式，并实现了膜蛋白的溶解，以全面表征蛋白质后转录修饰。此外，本发明的光解离的阴离子表面活性剂还适用于溶解多肽在自底向上的蛋白质组学实验中，包括细胞外基质蛋白质组学，并可作为凝胶电泳中SDS的替代品。