4-(4-(1-(methacryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid | 1352127-36-6

• 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-(4-(1-(methacryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid
• 英文别名: 4-[2-methoxy-4-[1-(2-methylprop-2-enoyloxy)ethyl]-5-nitrophenoxy]butanoic acid
• CAS: 1352127-36-6
• 化学式: C₁₇H₂₁NO₈
• 分子量: 367.356
• InChiKey: KVVBWUJBMOUCOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(4-(1-(methacryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Dual Stimuli-Responsive Poly(2-hydroxyethyl methacrylate-co-methacrylic acid) Microgels Based on Photo-Cleavable Cross-Linkers: pH-Dependent Swelling and Light-Induced Degradation

  摘要：

  Dual stimuli-responsive p(HEMA-co-MAA) microgels were prepared in a facile way by inverse miniemulsion copolymerization of 2-hydroxyethyl methacrylate (HEMA) with methacrylic acid (MAA) and two kinds of newly synthesized photodegradable cross-linkers. The pH-dependent swelling behavior induced by the protonation/deprotonation of the methacrylic acid groups in the network-forming polymer was investigated by means of the particle volume change as determined by DLS measurements. Photolytic degradation experiments were conducted by irradiation with UV light which led to particle disintegration caused by cleavage of the photolabile cross-linking points. The degradation behavior of the microgels was investigated with respect to degradation rates and changes in the degree of swelling. Those parameters were found to depend on the pH value of the solvent, the light intensities, and the irradiation wavelengths applied. For similar conditions, the degradation profile was demonstrated to strongly depend not only on the molecular structure of the cross-linking molecule but also on the molecular weight of the network-forming copolymers. The particular combination of the stimuli described is designed as a new strategy to two different swelling/degradation profiles. This dual stimuli-responsiveness was shown to enable the efficient loading and subsequent release of myoglobin as a model protein. Here a slow diffusion controlled release (induced by changes of the pH) was combined with a fast degradation controlled (induced by irradiation) on-demand release. This novel two-step release profile is proposed to bear great potential for delivery applications.

  DOI：

  10.1021/ma201706r
• 作为产物：
  描述：

  methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-(4-(1-(methacryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid
  参考文献：
  名称：

  Dual Stimuli-Responsive Poly(2-hydroxyethyl methacrylate-co-methacrylic acid) Microgels Based on Photo-Cleavable Cross-Linkers: pH-Dependent Swelling and Light-Induced Degradation

  摘要：

  Dual stimuli-responsive p(HEMA-co-MAA) microgels were prepared in a facile way by inverse miniemulsion copolymerization of 2-hydroxyethyl methacrylate (HEMA) with methacrylic acid (MAA) and two kinds of newly synthesized photodegradable cross-linkers. The pH-dependent swelling behavior induced by the protonation/deprotonation of the methacrylic acid groups in the network-forming polymer was investigated by means of the particle volume change as determined by DLS measurements. Photolytic degradation experiments were conducted by irradiation with UV light which led to particle disintegration caused by cleavage of the photolabile cross-linking points. The degradation behavior of the microgels was investigated with respect to degradation rates and changes in the degree of swelling. Those parameters were found to depend on the pH value of the solvent, the light intensities, and the irradiation wavelengths applied. For similar conditions, the degradation profile was demonstrated to strongly depend not only on the molecular structure of the cross-linking molecule but also on the molecular weight of the network-forming copolymers. The particular combination of the stimuli described is designed as a new strategy to two different swelling/degradation profiles. This dual stimuli-responsiveness was shown to enable the efficient loading and subsequent release of myoglobin as a model protein. Here a slow diffusion controlled release (induced by changes of the pH) was combined with a fast degradation controlled (induced by irradiation) on-demand release. This novel two-step release profile is proposed to bear great potential for delivery applications.

  DOI：

  10.1021/ma201706r

文献信息

• NanoPARCEL: a method for controlling cellular behavior with external light
  作者：Shuhei Murayama、Baowei Su、Kohki Okabe、Akihiro Kishimura、Kensuke Osada、Masayuki Miura、Takashi Funatsu、Kazunori Kataoka、Masaru Kato

  DOI：10.1039/c2cc32718j

  日期：——

  We developed a simple preparation procedure for the protein encapsulated nanoparticle and used the nanoparticle for spatiotemporal activity control of various proteins. We succeeded in the local protein activation within cells by light using the nanoparticle.

  我们开发了一种简单的蛋白质封装纳米粒子的制备方法，并利用这种纳米粒子对各种蛋白质进行时空活性控制。我们成功地利用这种纳米粒子在光照下激活了细胞内的局部蛋白质。