| 1570112-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• CAS: 1570112-02-5
• 化学式: C₁₆H₁₅N₅O
• 分子量: 293.328
• InChiKey: HMPHWOBZMGHWNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  以 aq. phosphate buffer 、 氯仿 、 乙腈 为溶剂， 反应 12.0h， 生成 4-oxo-4-((2-phenyl-3a,4-dihydro-3H-benzo[b]pyrazolo[1,5-d][1,4]oxazin-7-yl)amino)butanoic acid
  参考文献：
  名称：

  Photodegradable Supramolecular Hydrogels with Fluorescence Turn-On Reporter for Photomodulation of Cellular Microenvironments

  摘要：

  Photodegradable hydrogels that allow 3D encapsulation of cells are important biomaterials to modulate cellular microenvironments with temporal and spatial resolution. Herein we report a photodegradable hydrogel formed by the self-assembly of short peptides modified with a novel phototrigger. The phototrigger is a biaryl-substituted tetrazole moiety that, upon mild light irradiation, undergoes rapid intramolecular photoclick ligation to form a highly fluorescent pyrazoline moiety. Short peptides linked with a tetrazole-containing moiety, Tet(I) or Tet(II), are able to self-assemble into hydrogels, among which the Tet(I)-GFF and Tet(II)-GFRGD gels show good mechanical strength and biocompatibility for 3D encapsulation and prolonged culture of live cells. The phototriggered tetrazole-to-pyrazoline transformation generates a highly fluorescent reporter and induces the disassembly of the hydrogel matrix by disturbing the balance between hydrophilic interaction and it-if stacking of the self-assembled system. Photomodulation of cellular microenvironments was demonstrated not only for the cells grown on top of the gel but also for stem cells encapsulated inside the hydrogels.

  DOI：

  10.1021/ja409000b
• 作为产物：
  描述：

  2-(allyloxy)-4-nitroaniline 在 盐酸 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Photodegradable Supramolecular Hydrogels with Fluorescence Turn-On Reporter for Photomodulation of Cellular Microenvironments

  摘要：

  Photodegradable hydrogels that allow 3D encapsulation of cells are important biomaterials to modulate cellular microenvironments with temporal and spatial resolution. Herein we report a photodegradable hydrogel formed by the self-assembly of short peptides modified with a novel phototrigger. The phototrigger is a biaryl-substituted tetrazole moiety that, upon mild light irradiation, undergoes rapid intramolecular photoclick ligation to form a highly fluorescent pyrazoline moiety. Short peptides linked with a tetrazole-containing moiety, Tet(I) or Tet(II), are able to self-assemble into hydrogels, among which the Tet(I)-GFF and Tet(II)-GFRGD gels show good mechanical strength and biocompatibility for 3D encapsulation and prolonged culture of live cells. The phototriggered tetrazole-to-pyrazoline transformation generates a highly fluorescent reporter and induces the disassembly of the hydrogel matrix by disturbing the balance between hydrophilic interaction and it-if stacking of the self-assembled system. Photomodulation of cellular microenvironments was demonstrated not only for the cells grown on top of the gel but also for stem cells encapsulated inside the hydrogels.

  DOI：

  10.1021/ja409000b