2-cyano-5-((3,4-dihydroxyphenethyl)amino)-5-oxopentan-2-yl benzodithioate | 1146697-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-cyano-5-((3,4-dihydroxyphenethyl)amino)-5-oxopentan-2-yl benzodithioate
• CAS: 1146697-76-8
• 化学式: C₂₁H₂₂N₂O₃S₂
• 分子量: 414.549
• InChiKey: FZVXLKZVXGJFSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.35
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  pentafluorophenyl (4-phenylthiocarbonylthio-4-cyanovalerate) 、 盐酸多巴胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以87%的产率得到2-cyano-5-((3,4-dihydroxyphenethyl)amino)-5-oxopentan-2-yl benzodithioate
  参考文献：
  名称：

  Boronic acid ester with dopamine as a tool for bioconjugation and for visualization of cell apoptosis

  摘要：

  1,2-苯二醇与硼酸之间的硼酯是一种生物偶联的有效方式。该酯在生理条件下是稳定的，但在内体器官和溶酶体中发现的酸性pH值下裂解速度非常缓慢。在细胞凋亡过程中，硼酯酯被裂解，很可能是由于Ca²⁺离子的流入和1,2-苯二醇的氧化。

  DOI：

  10.1039/c3cc49100e

文献信息

• Folate Conjugation to Polymeric Micelles via Boronic Acid Ester to Deliver Platinum Drugs to Ovarian Cancer Cell Lines
  作者：Wei Scarano、Hien T. T. Duong、Hongxu Lu、Paul L. De Souza、Martina H. Stenzel

  DOI：10.1021/bm400121q

  日期：2013.4.8

  In this study, a novel technique was used for the reversible attachment of folic acid on the surface of polymeric micelles for a tumor-specific drug delivery system. The reversible conjugation is based on the interaction between phenylboronic acid (PBA) and dopamine to form a borate ester. The conjugation is fast and efficient and in vitro experiments via confocal fluorescent microscopy show that the linker is stable in for several hours. Reversible addition fragmentation chain transfer (RAFT) polymerization was used to synthesize two various sized water-soluble block copolymer of oligoethylene glycol methylether methacylate and methyl acrylic acid (POEGMEMA(35)-b-PMAA(200) and POEGMEMA(26)-b-PMAA(90)). The platinum drug, oxoplatin, was then subsequently attached to the polymer via ester formation leading to platinum loading of 12 wt % as determined by TGA. The platinum-induced amphiphilic block copolymers that consequently led to the formation of micelles of sizes 150 and 20 nm in an aqueous environment with the longer PMAA block forming larger micelles. The small micelles were in addition cross linked using 1,8-diaminooctane to further stabilize their structure. The targeting ability of folate conjugated polymeric micelles was investigated against two types of tumor cell lines: A549 (-FR) and OVCAR-3 (+FR). The cell line growth inhibitory efficacy of material synthesized was evaluated by using SRB method. The results revealed that folate conjugated micelles showed higher activity in FR + OVCAR-3 cells but not in FR A549 cells. Similar results were obtained for both small and large micelles without the conjugation of folate. Comparing large and small micelles it can be observed that larger micelles are more efficient, which has been attributed to the lower stability of the smaller micelles. Micelle stabilization via cross-linking could indeed increase the toxicity of the drug carrier.