2-(succinimidyl carbonate)ethyl acrylamide | 1394033-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(succinimidyl carbonate)ethyl acrylamide
• CAS: 1394033-15-8
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: QDVIWQCCNULITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 N-羟乙基丙烯酰胺 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 以80%的产率得到2-(succinimidyl carbonate)ethyl acrylamide
  参考文献：
  名称：

  [EN] NANOPARTICLE, LIPOSOMES, POLYMERS, AGENTS AND PROTEINS MODIFIED WITH REVERSIBLE LINKERS
  [FR] NANOPARTICULES, LIPOSOMES, POLYMÈRES, AGENTS ET PROTÉINES MODIFIÉS AVEC DES LIEURS RÉVERSIBLES

  摘要：

  描述了含有可逆二硫键的药物、化学物质和生物制剂。这些制剂也可以共价结合或包含在传递载体中，以将制剂传递到所需的靶标或区域。还描述了含有可逆二硫键的制剂的传递载体，以及与含有可逆二硫键的制剂共价结合的载体。本文描述的修饰可以改变制剂和载体的性质，从而提供所需的溶解性、稳定性、疏水性和靶向性，而连接物的可逆性可以使其附着的制剂在还原后不受残留化学基团的影响。

  公开号：

  WO2012112689A1

文献信息

• Reductively Responsive siRNA-Conjugated Hydrogel Nanoparticles for Gene Silencing
  作者：Stuart S. Dunn、Shaomin Tian、Steven Blake、Jin Wang、Ashley L. Galloway、Andrew Murphy、Patrick D. Pohlhaus、Jason P. Rolland、Mary E. Napier、Joseph M. DeSimone

  DOI：10.1021/ja300174v

  日期：2012.5.2

  A critical need still remains for effective delivery of RNA interference (RNAi) therapeutics to target tissues and cells. Self assembled lipid- and polymer based systems have been most extensively explored for transfection with small interfering RNA (siRNA) in liver and cancer therapies. Safety and compatibility of materials implemented in delivery systems must be ensured to maximize therapeutic indices. Hydrogel nanoparticles of defined dimensions and compositions, prepared via a particle molding process that is a unique off shoot of soft lithography known as Particle replication in nonwetting templates (PRINT), were explored in these studies as delivery vectors. Initially, siRNA was encapsulated in particles through electrostatic association and physical entrapment Dose dependent gene silencing was elicited by PEGylated hydrogels at low siRNA doses without cytotoxicity. To prevent disassociation of cargo from particles after systemic administration or during postfabrication processing for surface functionalization, a polymerizable siRNA pro-drug conjugate with a degradable, disulfide linkage was prepared. Triggered release of siRNA from the pro-drug hydrogels was observed under a reducing environment while cargo retention and integrity were maintained under physiological conditions. Gene silencing efficiency and cytocompatibility were optimized by screening the amine content. of the particles. When appropriate control siRNA cargos were loaded into hydrogels, gene knockdown was only encountered for hydrogels containing releasable, target specific siRNAs, accompanied by minimal cell death Further investigation into shape, size, and surface decoration of siRNA-conjugated hydrogels should enable efficacious targeted in vivo RNAi therapies.