(E)-2-(4-(phenyldiazenyl)phenoxy)acetic acid | 1422464-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (E)-2-(4-(phenyldiazenyl)phenoxy)acetic acid
• 英文别名: (trans)-4-phenylazophenoxyacetic acid；trans-4-phenylazophenoxyacetic acid；2-[4-(phenylazo)phenoxy]-ethanoic acid
• CAS: 1422464-41-2
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: JGKOBEFQCFRUSF-FOCLMDBBSA-N

物化性质

• 沸点：
  445.6±20.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-(phenyldiazenyl)phenoxy)acetic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (E)-(2-(4-(phenyldiazenyl)phenoxy)acetyl)-L-tyrosine
  参考文献：
  名称：

  Biocatalytic amide condensation and gelation controlled by light

  摘要：

  我们报道了一个超分子自组装系统，它展示了耦合的光开关、生物催化缩合/水解和凝胶化。

  DOI：

  10.1039/c4cc01431f
• 作为产物：
  描述：

  (E)-4-Phenylazophenol 在 甲醇 、 potassium carbonate 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (E)-2-(4-(phenyldiazenyl)phenoxy)acetic acid
  参考文献：
  名称：

  Biocatalytic amide condensation and gelation controlled by light

  摘要：

  我们报道了一个超分子自组装系统，它展示了耦合的光开关、生物催化缩合/水解和凝胶化。

  DOI：

  10.1039/c4cc01431f

文献信息

• Arylazopyrazoles as Light-Responsive Molecular Switches in Cyclodextrin-Based Supramolecular Systems
  作者：Lucas Stricker、Eva-Corinna Fritz、Martin Peterlechner、Nikos L. Doltsinis、Bart Jan Ravoo

  DOI：10.1021/jacs.6b00484

  日期：2016.4.6

  most efficient AAP shows binding affinities comparable to azobenzenes, but more effective switching and higher thermal stability of the Z-isomer. As a proof-of-principle, we investigated two CD-based supramolecular systems, containing either cyclodextrin vesicles (CDVs) or cyclodextrin-functionalized gold nanoparticles (CDAuNPs), which revealed excellent reversible, light-responsive aggregation and

  报道了具有优异光物理特性的水溶性芳基并吡唑 (AAP) 的简单和高产率合成。羧酸的引入允许 AAP 的多样化功能化。基于开关单元的结构修改，可以调整 AAP 的光物理特性以获得具有有利光静止状态的分子开关。此外，AAP 与 β-环糊精 (β-CD) 形成稳定且光响应的主客体复合物。我们最高效的 AAP 显示出与偶氮苯相当的结合亲和力，但 Z 异构体的转换效率更高，热稳定性更高。作为原理证明，我们研究了两种基于 CD 的超分子系统，包含环糊精囊泡 (CDV) 或环糊精功能化金纳米粒子 (CDAuNP)，这显示出优异的可逆、光响应聚集和分散行为。总而言之，AAP 具有在高要求和多价光响应系统中作为分子开关的巨大潜力。
• Light‐Triggered Capture and Release of DNA and Proteins by Host–Guest Binding and Electrostatic Interaction
  作者：Johanna Moratz、Avik Samanta、Jens Voskuhl、Siva Krishna Mohan Nalluri、Bart Jan Ravoo

  DOI：10.1002/chem.201405936

  日期：2015.2.16

  dynamic trapping and light‐stimulated release of both DNA and proteins. Self‐assembled ternary complexes act as nanoscale carriers, comprising vesicles of amphiphilic cyclodextrin, the target biomolecules and linker molecules with an azobenzene unit and a charged functionality. The non‐covalent linker binds to the cyclodextrin by host–guest complexation with the azobenzene. Proteins or DNA are then bound

  可以应用于多种结构多样的生物分子的有效且通用的递送方法的开发仍然是现代药物治疗中的瓶颈。在此，我们提出了一种超分子系统，用于动态捕获和光刺激释放DNA和蛋白质。自组装的三元复合物充当纳米级载体，包括两亲性环糊精的囊泡，目标生物分子和具有偶氮苯单元和带电功能的连接分子。非共价接头通过主客体与偶氮苯的络合与环糊精结合。然后，蛋白质或DNA通过多价静电吸引与功能化囊泡结合。客体-客体复合体的光响应允许光从多价状态转换，该状态可使生物分子与游离接头的低亲和力状态结合，从而提供了对货物释放的外部控制。这种递送方法的主要优点是可以通过多价静电相互作用解决多种靶标，我们在四种类型的DNA和六种不同的蛋白质上进行了证明。
• Photoresponsive vesicle permeability based on intramolecular host–guest inclusion
  作者：Ulrike Kauscher、Avik Samanta、Bart Jan Ravoo

  DOI：10.1039/c3ob41893f

  日期：——

  This article describes light-responsive vesicles that can release their contents in response to a light-sensitive molecular trigger. To this end, liposomes were equipped with amphiphilic β-cyclodextrin that was covalently labeled with azobenzene. Using dye encapsulation and confocal laser scanning microscopy, we show that the permeability of these vesicles strongly increases upon UV irradiation (λ = 350 nm) with concomitant isomerization of apolar trans-azobenzene to polar cis-azobenzene on the liposome surface.

  本文介绍了光响应囊泡，这种囊泡能在光敏分子触发下释放其内容物。为此，我们在脂质体中加入了用偶氮苯共价标记的两性δ-环糊精。利用染料封装和激光共聚焦扫描显微镜，我们发现在紫外线照射（δ" = 350 nm）下，这些囊泡的渗透性强烈增加，同时脂质体表面的无极性反式偶氮苯异构化为极性顺式偶氮苯。
• Delivery system in micellar form having modular spectral response based on enzyme-responsive amphiphilic PEG-dendron hybrid polymers
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：US10869939B2

  公开（公告）日：2020-12-22

  The present invention relates to new molecular design that allows micelles to report their activation and disassembly by an enzymatic trigger. The molecular design is based on introduction of a labeling moiety selected from a fluorescent dye, a dark quencher, combinations of dyes or dyes/quenchers, and a fluorinated moiety (a 19F-magenetic resonance (MR) probe for turn ON/OFF of a 19F-MR signal) through covalent binding to the focal point of amphiphilic polymer-dendron hybrids with the labeling moiety. At the assembled micellar state, the dyes are closely packed and hence the probability for intermolecular interactions increases significantly, leading to alteration of the fluorescent properties (signal quench or shift) or the 19F-MR signal (OFF state) of the micelles. Upon enzymatic cleavage of the hydrophobic end-groups from enzyme-responsive dendron, the polymers become hydrophilic and disassemble. This structural change is then translated into a spectral change as dye-dye interactions are halted and the dyes regain their intrinsic fluorescent properties, or alternatively by turn ON the 19F-MR signal. The high modularity of the design allows the introduction of various types of dyes and thus enables rational adjustment of the spectral response. Two major types of responses are described: Turn-On/Off and spectral shift, depending on the type of labeling dye. The present invention further provides methods of use of the hybrid delivery system and to a kit comprising the same.

  本发明涉及一种新的分子设计，可使胶束在酶触发下报告其活化和分解情况。分子设计的基础是通过与两亲性聚合物-树枝杂交体的焦点共价结合，从荧光染料、暗淬火剂、染料或染料/淬火剂的组合以及含氟分子（用于打开/关闭 19F-MR 信号的 19F 遗传共振（MR）探针）中引入标记分子。在组装胶束状态下，染料紧密排列，因此分子间相互作用的概率大大增加，从而导致胶束的荧光特性（信号淬灭或偏移）或 19F-MR 信号（关闭状态）发生变化。当酶反应树枝状突起的疏水末端基团被酶裂解时，聚合物就会变得亲水并分解。这种结构变化会转化为光谱变化，因为染料与染料之间的相互作用会停止，染料会恢复其固有的荧光特性，或者打开 19F-MR 信号。设计的高度模块化允许引入各种类型的染料，从而对光谱响应进行合理调整。下面介绍两种主要的响应类型：开启/关闭和光谱偏移，取决于标记染料的类型。本发明进一步提供了混合投递系统的使用方法以及包含该系统的试剂盒。
• Ocular device delivery methods and systems
  申请人：LayerBio, Inc.

  公开号：US11185441B2

  公开（公告）日：2021-11-30

  The present disclosure provides an ophthalmic article. The ophthalmic article may comprise a biocompatible matrix comprising a copolymer derived from a caprolactone monomer and at least one other monomer. The ophthalmic article may also comprise an active agent or a diagnostic agent. The ophthalmic article may be configured to associate to a haptic of an intraocular lens (IOL).

  本公开提供了一种眼科用品。该眼科用品可包括生物相容性基质，该基质包含由己内酰胺单体和至少一种其他单体衍生的共聚物。眼科用品还可包括活性剂或诊断剂。眼科用品可配置为与眼内晶状体（IOL）的触觉连接。