1-azido-11-(triphenylmethyloxy)-3,6,9-undecane | 868594-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-azido-11-(triphenylmethyloxy)-3,6,9-undecane
• 英文别名: [2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethoxy-diphenylmethyl]benzene
• CAS: 868594-38-1
• 化学式: C₂₇H₃₁N₃O₄
• 分子量: 461.561
• InChiKey: FSNSDRLQUPIGKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-azido-11-(triphenylmethyloxy)-3,6,9-undecane 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 1-氨基-3,6,9-三噁-11-十一醇
  参考文献：
  名称：

  Ligand–Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

  摘要：

  We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug target complex. Thus, we designed ligand phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

  DOI：

  10.1021/acs.jmedchem.8b00041
• 作为产物：
  描述：

  2-<2-(triphenylmethoxy)ethoxy>ethyl methanesulfonate 在 sodium azide 、 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 30.5h， 生成 1-azido-11-(triphenylmethyloxy)-3,6,9-undecane
  参考文献：
  名称：

  Ligand–Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

  摘要：

  We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug target complex. Thus, we designed ligand phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

  DOI：

  10.1021/acs.jmedchem.8b00041

文献信息

• Synthesis of Bifunctional Integrin-Binding Peptides Containing PEG Spacers of Defined Length for Non-Viral Gene Delivery
  作者：Michael A. Pilkington-Miksa、Supti Sarkar、Michele J. Writer、Susie E. Barker、Parviz Ayazi Shamlou、Stephen L. Hart、Helen C. Hailes、Alethea B. Tabor

  DOI：10.1002/ejoc.200701188

  日期：2008.6

  series of bifunctional peptides bearing short PEG spacers of defined structure as components of lipopolyplex gene delivery vectors. Short, high-yielding routes to a series of PEG-amino acids are described: these PEG-amino acids can be used in varying combinations to afford bifunctional peptides with varying lengths of PEG spacers by using standard solid-phase synthesis techniques. A series of lipopolyplexes

  提高非病毒基因递送载体的缓冲液和血清稳定性，增加其体内循环时间，是当前基因治疗研究的一个重要焦点。迄今为止最成功的策略包括用大的多分散 PEG 加合物屏蔽复合物。然而，这种方法伴随着转染效率的下降。在本文中，我们描述了一系列双功能肽的固相合成，这些肽带有定义结构的短 PEG 间隔物，作为 lipopolyplex 基因递送载体的组分。描述了一系列 PEG-氨基酸的短、高产路线：这些 PEG-氨基酸可以以不同的组合使用，通过使用标准固相合成技术提供具有不同长度 PEG 间隔物的双功能肽。使用这些双功能肽配制了一系列 lipopolyplexes，并评估了它们的转染特性。对具有最佳转染特性的复合物的动态光散射测量表明，在磷酸盐缓冲盐水中，该复合物比使用缺乏短 PEG 间隔物的类似肽配制的复合物要稳定得多，并且聚集得更慢。© Wiley-VCH Verlag GmbH & Co. KGaA，2008
• Materials for the delivery of biologically-active material to cells
  申请人：Hailes Claire Helen

  公开号：US20050245446A1

  公开（公告）日：2005-11-03

  The invention provides a lipid of general formula (I) or (II): wherein X 1 , X 2 and R 1 to R 5 are as defined herein. Such lipids are used to form complexes with a biologically-active material such as a nucleic acid, peptide or small molecule for delivering the biologically-active material to cells. The complexes may incorporate an integrin-binding peptide and, when the biologically-active material is DNA, thereby constitute a LID complex.

  该发明提供了一种通式为(I)或(II)的脂质：其中，X1、X2和R1至R5的定义如本文所述。这些脂质用于与生物活性物质，如核酸、肽或小分子形成复合物，以将生物活性物质传递到细胞内。这些复合物可以包含整合素结合肽，并且当生物活性物质为DNA时，因此构成LID复合物。
• Synthesis and ligation ability of mono-aminooxy-functionalized dendrigraft poly-l-lysine (DGL)
  作者：Andrea Molero Bondia、Nicolas Larcher、Laurent Garrelly、Jean Christophe Rossi、Robert Pascal

  DOI：10.1016/j.tetlet.2010.04.078

  日期：2010.6

  A bifunctional tetraethylene glycol (TEG) linker was prepared and used as an initiator for the synthesis of the first two generations of dendrigraft poly-L-lysines (DGL). The key steps involved the desymmetrization of TEG by introduction of an amine group after activation of a terminal hydroxyl group and of a conveniently protected aminooxy functionality at the other end. Initiation of L-lysine N-carboxyanhydride polymerization by the terminal amine yielded generations 1 and 2 of DGL in which a subsequent functionalization of the aminooxy group by ligation with entities bearing an aldehyde group turned out to be feasible. (C) 2010 Elsevier Ltd. All rights reserved.
• US7598421B2
  申请人：——

  公开号：US7598421B2

  公开（公告）日：2009-10-06
• [EN] MATERIALS FOR THE DELIVERY OF BIOLOGICALLY-ACTIVE MATERIAL TO CELLS<br/>[FR] MATIERE DESTINEE A L'ADMINISTRATION D'UNE MATIERE BIOACTIVE A DES CELLULES
  申请人：UCL BIOMEDICA PLC

  公开号：WO2005117985A2

  公开（公告）日：2005-12-15

  The invention provides a complex suitable for delivery of a biologically-active material to a cell, which complex comprises: (a) a lipid of formula: (III); wherein RI, R2, R3, B, Q and m are as defined herein; (b) a biologically-active material; and (c) an integrin-binding peptide. The invention also provides a complex suitable for delivery of a biologically-active material to a cell, which complex comprises: (a) a lipid of formula: (I); wherein R1, R2, X1, X2 and R5,are as defined herein; (b) a biologically-active material; and (c) an integrin-binding peptide of formula: [DNA-Binding]-[Spacer]k-[Ligand] wherein DNA-Binding, Spacer, k and Ligand are as defined herein.