4-(3-acrloyloxymethyl)-4-nitrophenoxybutanoic acid | 1392043-89-8

• 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: 4-(3-acrloyloxymethyl)-4-nitrophenoxybutanoic acid
• 英文别名: 4-[4-Nitro-3-(prop-2-enoyloxymethyl)phenoxy]butanoic acid；4-[4-nitro-3-(prop-2-enoyloxymethyl)phenoxy]butanoic acid
• CAS: 1392043-89-8
• 化学式: C₁₄H₁₅NO₇
• 分子量: 309.276
• InChiKey: QWLLFOFBPQGREJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-((3-甲酰基-4-硝基苯基)氧基)丁酸乙酯 在 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 40.0h， 生成 4-(3-acrloyloxymethyl)-4-nitrophenoxybutanoic acid
  参考文献：
  名称：

  Photodegradable Macromers and Hydrogels for Live Cell Encapsulation and Release

  摘要：

  Hydrogel scaffolds are commonly used as 3D carriers for cells because their properties can be tailored to match natural extracellular matrix. Hydrogels may be used in tissue engineering and regenerative medicine to deliver therapeutic cells to injured or diseased tissue through controlled degradation. Hydrolysis and enzymolysis are the two most common mechanisms employed for hydrogel degradation, but neither allows sequential or staged release of cells. In contrast, photodegradation allows external real-time spatial and temporal control over hydrogel degradation, and allows for staged and sequential release of cells. We synthesized and characterized a series of macromers incorporating photodegradbale ortho-nitrobenzyl (o-NB) groups in the macromer backbone. We formed hydrogels from these macromers via redox polymerization and quantified the apparent rate constants of degradation (k(app)) of each via photorheology at 370 nm, 10 mW/cm(2). Decreasing the number of aryl ethers on the o-NB group increases k(app), and changing the functionality from primary to seconday at the benzylic site dramatically increases k(app). Human mesenchymal stem cells (hMSCs) survive encapsulation in the hydrogels (90% viability postencapsulation). By exploiting the differences in reactivity of two different o-NB linkers, we quantitatively demonstrate the biased release of one stem cell population (green-fluoroescent protein expressing hMSCs) over another (red-fluorescent protein expressing hMSCs).

  DOI：

  10.1021/ja305280w

文献信息

• Photodegradable Macromers and Hydrogels for Live Cell Encapsulation and Release
  作者：Donald R. Griffin、Andrea M. Kasko

  DOI：10.1021/ja305280w

  日期：2012.8.8

  Hydrogel scaffolds are commonly used as 3D carriers for cells because their properties can be tailored to match natural extracellular matrix. Hydrogels may be used in tissue engineering and regenerative medicine to deliver therapeutic cells to injured or diseased tissue through controlled degradation. Hydrolysis and enzymolysis are the two most common mechanisms employed for hydrogel degradation, but neither allows sequential or staged release of cells. In contrast, photodegradation allows external real-time spatial and temporal control over hydrogel degradation, and allows for staged and sequential release of cells. We synthesized and characterized a series of macromers incorporating photodegradbale ortho-nitrobenzyl (o-NB) groups in the macromer backbone. We formed hydrogels from these macromers via redox polymerization and quantified the apparent rate constants of degradation (k(app)) of each via photorheology at 370 nm, 10 mW/cm(2). Decreasing the number of aryl ethers on the o-NB group increases k(app), and changing the functionality from primary to seconday at the benzylic site dramatically increases k(app). Human mesenchymal stem cells (hMSCs) survive encapsulation in the hydrogels (90% viability postencapsulation). By exploiting the differences in reactivity of two different o-NB linkers, we quantitatively demonstrate the biased release of one stem cell population (green-fluoroescent protein expressing hMSCs) over another (red-fluorescent protein expressing hMSCs).