乙酰硫基-PEG3-C2-叠氮 | 1310827-26-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 乙酰硫基-PEG3-C2-叠氮
• 英文名称: azidetetraethylene glycolthioacetate
• 英文别名: S-2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl ethanethioate；S-11-azido-3,6,9-trioxaundecyl ethanethioate；S-Acetyl-PEG3-azide；S-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl] ethanethioate
• CAS: 1310827-26-9
• 化学式: C₁₀H₁₉N₃O₄S
• 分子量: 277.345
• InChiKey: PIXCCFAIMVRUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 储存条件：
  -20°C下存储在惰性气体中，并且要避免光照、潮湿和加热，以防止分解。

制备方法与用途

S-Acetyl-PEG3- azide是一种PROTAC连接子，属于PEG类化合物，可用于合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  乙酰硫基-PEG3-C2-叠氮 在 sodium methylate 、 二甲基亚砜 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以93%的产率得到Azido-PEG3-SS-PEG3-azide
  参考文献：
  名称：

  Synthesis of a new potential biodegradable disulfide containing poly(ethylene imine)–poly(ethylene glycol) copolymer cross-linked with click cluster for gene delivery

  摘要：

  Poly(ethylene glycol)-grafted-polyethylenimine (PEG-PEI) are promising non-viral gene delivery systems. Herein, we aimed to synthesize a biodegradable disulfide containing PEGylated PEI to attempt to reduce its cytotoxicity and enhance the gene transfer activity. Using click chemistry, low Mw PEI (br. 2 kDa) and short chain length PEG (tetraethylene glycol, TEG) were cross-linked to a high Mw PEG-PEI copolymer (similar to 22 kDa). The chemical structure of the copolymer was characterized using H-1 NMR and GPC The degradation behavior was investigated under in vitro conditions in the presence of 1,4-dithiothreitol (DTT). The gel retardation assay, dynamic light scattering and atomic force microscopy showed good DNA condensation ability by forming polyplexes with small particle size and positive zeta potential. In particular, MTT assay indicated that this PEG-PEI polymer is about 22-fold less toxic than PEI 25k and only 2-fold more toxic than PEI 2k in L929 cell line. After coupling of small PEG chains and cross-linking by disulfide bridges, the transfection efficiency is increased approximately 6-fold in comparison to PEI 2k and still reaches approximately 17% of PEI 25k. Hence, this click cluster cross-linked disulfide containing PEG-PEI copolymer could be an attractive cationic polymer for non-viral gene delivery. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.03.038
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 在 sodium azide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 乙酰硫基-PEG3-C2-叠氮
  参考文献：
  名称：

  Interfacial strain-promoted alkyne–azide cycloaddition (I-SPAAC) for the synthesis of nanomaterial hybrids

  摘要：

  本文介绍了一种界面应变促进叠氮烷烃环加成（I-SPACC）的方法，用于制备稳健的纳米材料混合物。新型二苯并环辛炔改性单壁碳纳米管（DBCO-SWCNT）与多功能水溶性叠氮改性金纳米粒子（N3-EG4-AuNP）之间的反应证明了这一点。

  DOI：

  10.1039/c3cc41634h

文献信息

• Miktoarm star conjugated multifunctional gold nanoshells: synthesis and an evaluation of biocompatibility and cellular uptake
  作者：Vanessa W. K. Ng、Pramod K. Avti、Mathieu Bédard、Tina Lam、Léonie Rouleau、Jean-Claude Tardif、Éric Rhéaume、Frédéric Lesage、Ashok Kakkar

  DOI：10.1039/c4tb00722k

  日期：——

  multifunctional GNS contain lipoic acid (LA) as a model therapeutic agent, poly(ethylene glycol) (PEG350) as a solubilizing and stealth agent, and tetraethylene glycol (TEG) with a terminally conjugated thiol moiety. These GNS have an average size of 40 nm, a shell thickness of 6 nm, a well-defined crystal structure lattice (111), and a surface absorption plasmon band in the near infrared (NIR) region

  报道了一种简单且高度通用的基于点击化学的合成策略，用于开发与金纳米壳（GNS）结合的ABC型miktoarm星型配体。表面官能化的多功能GNS包含硫辛酸（LA）作为模型治疗剂，聚（乙二醇）（PEG 350）作为增溶剂和隐形剂，以及带有末端共轭硫醇部分的四甘醇（TEG）。这些GNS具有40 nm的平均大小，6 nm的壳厚度，清晰的晶体结构晶格（111）和近红外（NIR）区域中的表面吸收等离子体激元带。用该配体功能化的miktoarm星和GNS对高达5μgmL -1无细胞毒性在浓度为5μgmL -1时，人脐静脉内皮细胞将这些GNS的85％内在化。我们的研究结果表明，生物相容的拟臂星型配体提供了一个有用的平台，可以将多种功能合成地表达到GNS上，并通过将其固有的成像功能与有效治疗剂的有效传递和蓄积相结合来扩大其范围。
• Development of a Hypoxia-Selective Near-Infrared Fluorescent Probe for Non-invasive Tumor Imaging
  作者：Bahaa Gamal Mohamed Youssif、Kensuke Okuda、Tetsuya Kadonosono、Ola Ibrahim Abdel Razek Salem、Alaa Arafat Mohamed Hayallah、Mostafa Ahmed Hussein、Shinae Kizaka-Kondoh、Hideko Nagasawa

  DOI：10.1248/cpb.60.402

  日期：——

  A near-infrared fluorochrome, GPU-311, was designed, synthesized and evaluated for its application in non-invasive imaging of tumor hypoxia. Efficient synthesis was achieved by nucleophilic substitution and click chemistry ring using the bifunctional tetraethylene glycol linker 2 containing thiol and azide groups for the conjugation of the propargylated nitroimidazole 1 and the heptamethine cyanine

  设计，合成和评估了近红外荧光染料GPU-311在肿瘤缺氧的非侵入性成像中的应用。通过使用含有硫醇和叠氮基团的双功能四乙二醇接头2进行亲核取代和点击化学环，可实现高效合成，以使炔丙基化的硝基咪唑1和带有2-氯-1-环己烯基环的七甲基花青染料3缀合。GPU-311表现出长激发和发射波长（Ex / Em = 785/802 nm）和适度的量子产率（0.05）。GPU-311的水溶性和亲水性增加。用GPU-311体外处理SUIT-2 / HRE-Luc胰腺癌细胞后，在缺氧条件下选择性观察到的荧光水平高于在常氧条件下。然而，
• HETEROBIFUNCTIONAL LINKER
  申请人：THE GOVERNORS OF THE UNIVERSITY OF ALBERTA

  公开号：US20180086724A1

  公开（公告）日：2018-03-29

  The present disclosure relates generally to heterobifunctional linkers.

  本公开涉及异双功能连接剂。
• Synthesis of a new potential biodegradable disulfide containing poly(ethylene imine)–poly(ethylene glycol) copolymer cross-linked with click cluster for gene delivery
  作者：Nan Zhao、Susanne Roesler、Thomas Kissel

  DOI：10.1016/j.ijpharm.2011.03.038

  日期：2011.6

  Poly(ethylene glycol)-grafted-polyethylenimine (PEG-PEI) are promising non-viral gene delivery systems. Herein, we aimed to synthesize a biodegradable disulfide containing PEGylated PEI to attempt to reduce its cytotoxicity and enhance the gene transfer activity. Using click chemistry, low Mw PEI (br. 2 kDa) and short chain length PEG (tetraethylene glycol, TEG) were cross-linked to a high Mw PEG-PEI copolymer (similar to 22 kDa). The chemical structure of the copolymer was characterized using H-1 NMR and GPC The degradation behavior was investigated under in vitro conditions in the presence of 1,4-dithiothreitol (DTT). The gel retardation assay, dynamic light scattering and atomic force microscopy showed good DNA condensation ability by forming polyplexes with small particle size and positive zeta potential. In particular, MTT assay indicated that this PEG-PEI polymer is about 22-fold less toxic than PEI 25k and only 2-fold more toxic than PEI 2k in L929 cell line. After coupling of small PEG chains and cross-linking by disulfide bridges, the transfection efficiency is increased approximately 6-fold in comparison to PEI 2k and still reaches approximately 17% of PEI 25k. Hence, this click cluster cross-linked disulfide containing PEG-PEI copolymer could be an attractive cationic polymer for non-viral gene delivery. (C) 2011 Elsevier B.V. All rights reserved.
• Interfacial strain-promoted alkyne–azide cycloaddition (I-SPAAC) for the synthesis of nanomaterial hybrids
  作者：Pierangelo Gobbo、Samantha Novoa、Mark C. Biesinger、Mark S. Workentin

  DOI：10.1039/c3cc41634h

  日期：——

  An interfacial strain promoted azide–alkyne cycloaddition (I-SPACC) is introduced as a method to prepare robust nanomaterial hybrids. This is demonstrated with a reaction between a novel dibenzocyclooctyne-modified single walled carbon nanotubes (DBCO-SWCNT) and a versatile water-soluble azide modified gold nanoparticle (N3-EG4-AuNP).

  本文介绍了一种界面应变促进叠氮烷烃环加成（I-SPACC）的方法，用于制备稳健的纳米材料混合物。新型二苯并环辛炔改性单壁碳纳米管（DBCO-SWCNT）与多功能水溶性叠氮改性金纳米粒子（N3-EG4-AuNP）之间的反应证明了这一点。