2-(tert-butoxycarbonylamino)ethoxy-2-oxo-1,3,2-dioxaphospholane | 1075701-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧磷杂环戊烷
• 英文名称: 2-(tert-butoxycarbonylamino)ethoxy-2-oxo-1,3,2-dioxaphospholane
• 英文别名: tert-butyl N-[2-[(2-oxo-1,3,2lambda5-dioxaphospholan-2-yl)oxy]ethyl]carbamate；tert-butyl N-[2-[(2-oxo-1,3,2λ5-dioxaphospholan-2-yl)oxy]ethyl]carbamate
• CAS: 1075701-44-8
• 化学式: C₉H₁₈NO₆P
• 分子量: 267.219
• InChiKey: OPSDIJXXVJFEOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonylamino)ethoxy-2-oxo-1,3,2-dioxaphospholane 、 sodium methacrylate 在 18-冠醚-6 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以0.99 g的产率得到MPE(Boc)
  参考文献：
  名称：

  Synthesis of biomembrane-mimic polymers with various phospholipid head groups

  摘要：

  Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2-methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MU) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.12.020
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 9.0h， 生成 2-(tert-butoxycarbonylamino)ethoxy-2-oxo-1,3,2-dioxaphospholane
  参考文献：
  名称：

  Synthesis of biomembrane-mimic polymers with various phospholipid head groups

  摘要：

  Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2-methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MU) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.12.020

文献信息

• BLOCK COPOLYMER, LIQUID COMPOSITE THEREOF, NUCLEIC ACID PREPARATION, PREPARATION METHODS THEREFOR, AND USE THEREOF
  申请人：Suzhou Ribo Life Science Co., Ltd.

  公开号：US20150093444A1

  公开（公告）日：2015-04-02

  Provided are a polycaprolactone-polyphosphate block copolymer, a liquid composite formed by the block copolymer, a nucleic acid preparation, preparation methods for the copolymer and the liquid composite, and the use of the copolymer and the liquid composite in a nucleic acid medicine delivery system. The block copolymer prepared using the present invention has good biocompatibility, low cytotoxicity, and good biodegradability. The micelles provided in the present invention self-assemble into nano-particles in an aqueous solution, and have good stability, biocompatibility, and biodegradability, and low cytotoxicity. The preparation method is simple, has high repeatability, as a vector can protect small nucleic acids such as siRNA from biodegradation, can combine with the scale effect of nano-particles, and can be used for treating different diseases. Additionally, bonding targeting groups enable specificity recognition of different cancer cells.

  提供了一种聚己内酯-聚磷酸酯嵌段共聚物，由该嵌段共聚物形成的液体复合物，核酸制剂，以及该共聚物和液体复合物在核酸药物传递系统中的使用。利用本发明制备的嵌段共聚物具有良好的生物相容性，低细胞毒性和良好的生物降解性。本发明提供的胶束在水溶液中自组装成纳米粒子，并具有良好的稳定性，生物相容性，生物降解性和低细胞毒性。该制备方法简单，具有高重复性，作为载体可以保护小核酸如siRNA免受生物降解，可以与纳米粒子的规模效应结合，并可用于治疗不同疾病。此外，结合靶向基团使得能够特异识别不同癌细胞。
• US9549986B2
  申请人：——

  公开号：US9549986B2

  公开（公告）日：2017-01-24
• Ursolic acid loaded tri-block copolymer nanoparticles based on triphenylphosphine for mitochondria-targeted cancer therapy
  作者：Jieqiong Ding、Jie Tan、Xiaohang Peng、Liyuan Cheng、Weiling Huang、Binhua Luo

  DOI：10.1088/1748-605x/ad2ecf

  日期：2024.5.1

  A novel biodegradable amphiphilic triblock copolymer, polyphosphate, polyethylene glycol, and polylactic acid (PAEEP-PEG-PLLA), was synthesized by twice ring-opening polymerization and triphenylphosphine (TPP) was grafted onto the block copolymer to synthesize a carrier material TPP-PAEEP-PEG-PLLA, which was identified by ¹H-nuclear magnetic resonance (¹H-NMR) spectroscopy. The TPP-PAEEP-PEG-PLLA nanoparticles encapsulated with ursolic acid (UA) were prepared by the emulsion-solvent evaporation method and characterized by dynamic light scattering. The mitochondrial targeting ability of fluorescently labeled nanoparticles was evaluated by laser confocal microscopy. The average particle size and surface charge of the UA -loaded nanoparticle solution were 180.07 ± 1.67 nm and +15.57 ± 1.33 mV, respectively. The biocompatibility of nanoparticles was briefly evaluated by erythrocyte hemolysis assay. In vitro cell proliferation assay and scratch migration assay were performed to compare the difference in anti-tumor effect between UA and UA nanoparticles. The results showed that TPP-modified triblock copolymers had good mitochondrial targeting and improved the low bioavailability of UA, and UA nanoparticles exhibited more pronounced anti-tumor capabilities. In summary, the results suggested that our UA nanoparticles were a promising drug-targeted delivery system for the treatment of tumors.
• Synthesis of biomembrane-mimic polymers with various phospholipid head groups
  作者：Heejin Kim、Wonmin Choi、Seonju Lee、Sooyeol Kim、Jiyeon Ham、Ji-Hun Seo、Sangmok Jang、Yan Lee

  DOI：10.1016/j.polymer.2013.12.020

  日期：2014.1

  Lipid bilayers in biomembranes consist of diverse phospholipids, including phosphatidic acid (PA), phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS) with various compositions according to the cell and tissue types. We synthesized biomembrane-mimic polymers, poly(2-methacryloyloxyethyl phosphoric acid) (PMPA), poly(2-methacryloyloxyethyl phosphorylethanolamine) (PMPE), and poly(2-methacryloyloxyethyl phosphorylserine) (PMPS), with PA, PE, and PS head groups, respectively. PA monomer was synthesized from 2-hydroxyethyl methacrylate (HEMA) and dimethyl chlorophosphate (DCP). PE and PS monomers were synthesized from N-tert-butoxycarbonyl (tBoc) protected ethanolamine and serine through the reaction with 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP). Each biomembrane-mimic polymer was successfully synthesized by atom transfer radical polymerization (ATRP) from the monomer. The molecular weight distributions of PMPA, PMPE, and PMPS were analyzed by gel permeation chromatography (GPC) and in vitro cytotoxicity was also examined by 3[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MU) and lactate dehydrogenase (LDH) assay. The new biomembrane-mimic polymers could be used to prepare a polymeric platform that mimic a cell- or tissue-specific membrane for future applications in biomedical fields such as tissue engineering or bioimplants. (C) 2013 Elsevier Ltd. All rights reserved.