DOAP

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: DOAP
• 英文别名: [3-amino-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• 化学式: C₃₉H₇₃NO₄
• 分子量: 620.013
• InChiKey: UKMPCZJUVBJMDS-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  44
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DOAP 、 (4,7,10-三叔丁氧羰基-1,4,7,10-四氮杂环癸-1-基)乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以29.1%的产率得到
  参考文献：
  名称：

  用于DNA传递的基于Cyclenn的双尾脂质：合成及其连接基团结构的影响

  摘要：

  阳离子脂质的基因转染效率（TE）在很大程度上受脂质结构的影响。六种新颖的1、4、7、10-四氮杂十二烷基（环素）基阳离子脂质L1 - L6设计并合成了含有双油基作为疏水尾基的化合物。这些脂质之间的区别是它们的不同骨架。由脂质和DOPE制备的脂质体显示出良好的DNA亲和力，并且可以在N / P为4时实现完全的DNA缩合，形成具有适当大小和Zeta电位的脂质复合体，用于基因转染。研究了这些脂质作为非病毒基因传递载体的构效关系。研究发现，较小的骨架结构变化（包括连接基团和结构对称性）会影响TE。二亚乙基三胺衍生的脂质L4含有酰胺连接键的TE效果最好，比市售转染试剂lipofectamine 2000高出几倍。此外，这些脂质显示出低细胞毒性，表明它们具有良好的生物相容性。结果表明，这种类型的阳离子脂质可能是有前途的非病毒基因载体，也为设计具有更高TE和生物相容性的新型载体提供了线索。

  DOI：

  10.1016/j.bmc.2015.07.005
• 作为产物：
  描述：

  3-([tert-butoxycarbonyl]amino)propane-1,2-diyl dioleate 在 三氟乙酸 作用下， 反应 3.0h， 以50.2%的产率得到DOAP
  参考文献：
  名称：

  用于长循环和膜融合的不对称二疏水链聚乙二醇脂质的合成

  摘要：

  脂质体是制药行业广泛使用的主要药物递送系统，但快速清除和内体降解是提高脂质体递送效率的主要障碍，尤其是对蛋白质或基因的递送效率。模拟病毒膜融合肽，设计并合成了四种具有长循环和膜融合特性的不对称二疏水链聚乙二醇 (PEG) 脂质。合成 PEG 脂质的结构特点为1H NMR和质谱。与传统的表面活性剂如SDBS或SDS相比，PEG脂质的临界胶束浓度降低了一个或两个数量级，表现出优异的脂质自组装性能。由中性脂质DOPC和PEG脂质构成的脂质体的大小和形态通过动态光散射（DLS）和透射电子显微镜（TEM）来表征。在 50% 乙醇和 5-25 mmol L -1 Ca 2+的条件下，包裹 pEGFP 的 PEG 中性脂质复合物几乎是中性的，直径低于 300 nm。

  DOI：

  10.1002/jsde.12598

文献信息

• Interfacial cationization to quicken redox-responsive drug release
  作者：Yaxin Zheng、Jie Lei、Qi Li、Xuan Jin、Qingyuan Li、Yang Li

  DOI：10.1039/d1cc00156f

  日期：——

  Interfacial cationization increases redox-responsiveness of nanocarriers to accelerate intracellular drug release by generating and adsorbing ionized thiols at interfaces.

  界面阳离子化增加了纳米载体的氧化还原响应性，通过在界面生成和吸附离子化巯基来加速细胞内药物释放。
• Cyclen-based double-tailed lipids for DNA delivery: Synthesis and the effect of linking group structures
  作者：Yi-Mei Zhang、De-Chun Chang、Ji Zhang、Yan-Hong Liu、Xiao-Qi Yu

  DOI：10.1016/j.bmc.2015.07.005

  日期：2015.9

  The gene transfection efficiency (TE) of cationic lipids is largely influenced by the lipid structure. Six novel 1, 4, 7, 10-tetraazacyclododecane (cyclen)-based cationic lipids L1–L6, which contain double oleyl as hydrophobic tails, were designed and synthesized. The difference between these lipids is their diverse backbone. Liposomes prepared by the lipids and DOPE showed good DNA affinity, and full

  阳离子脂质的基因转染效率（TE）在很大程度上受脂质结构的影响。六种新颖的1、4、7、10-四氮杂十二烷基（环素）基阳离子脂质L1 - L6设计并合成了含有双油基作为疏水尾基的化合物。这些脂质之间的区别是它们的不同骨架。由脂质和DOPE制备的脂质体显示出良好的DNA亲和力，并且可以在N / P为4时实现完全的DNA缩合，形成具有适当大小和Zeta电位的脂质复合体，用于基因转染。研究了这些脂质作为非病毒基因传递载体的构效关系。研究发现，较小的骨架结构变化（包括连接基团和结构对称性）会影响TE。二亚乙基三胺衍生的脂质L4含有酰胺连接键的TE效果最好，比市售转染试剂lipofectamine 2000高出几倍。此外，这些脂质显示出低细胞毒性，表明它们具有良好的生物相容性。结果表明，这种类型的阳离子脂质可能是有前途的非病毒基因载体，也为设计具有更高TE和生物相容性的新型载体提供了线索。
• Methods and compositions for the efficient delivery of therapeutic agents to cells and animals
  申请人：Rana M. Tariq

  公开号：US20070260055A1

  公开（公告）日：2007-11-08

  The present invention provides methods of carrying out the safe and reliable preparation of lipids comprising quaternary amines. Such lipids are especially suited for introducing therapeutic agents into cells or organisms. In particular, the lipids of the invention are suitable for the efficient transfer of gene therapy agents into mammalian cells or organisms in a cell type specific or tissue specific manner.

  本发明提供了一种安全可靠的制备含季铵盐脂质的方法。这种脂质特别适合将治疗剂介入细胞或生物体中。特别是，本发明的脂质适用于以细胞类型特异性或组织特异性的方式高效地将基因治疗剂转移到哺乳动物细胞或生物体中。
• Inorganic kernel - Supported asymmetric hybrid vesicles for targeting delivery of STAT3-decoy oligonucleotides to overcome anti-HER2 therapeutic resistance of BT474R
  作者：Kai Shi、Yan Fang、Shan Gao、Dongjuan Yang、Hongshu Bi、Jianxiu Xue、Anqi Lu、Yuai Li、Liyuan Ke、Xiaojie Lin、Xuechao Jin、Min Li

  DOI：10.1016/j.jconrel.2018.04.023

  日期：2018.6

  As a recombinant humanized monoclonal antibody that targets the extracellular region of HER2 tyrosine kinase receptor, trastuzumab (TRAZ) has demonstrated comparable clinical efficacy and improved survival in patients with HER2-positive breast cancer. Nevertheless, the therapeutic potential of TRAZ is often limited due to its frequent resistance to anti-HER2 therapy. Therefore, we investigate the reversal effect of STAT3-specific decoy oligonucleotides (STAT3-decoy ODNs) on TRAZ resistance, which contain the consensus sequence within the targeted gene promoter of STAT3. Considering the shortcomings of poor cellular permeability and rapid degradation in vivo limit the further clinical applications of ODNs, we report here an asymmetric hybrid lipid/polymer vesicles with calcium phosphate as the solid kernel (CaP@HA). Through hyaluronan-mediated CD44 targeting, the constructed vesicles can specifically carry STAT3-decoy ODNs into TRAZ-resistant breast cancer cells and then regulate TRAZ-induced apoptosis. In comparison with the native ones, ODNs packaged with CaP@ HA showed significantly increased serum stability, cellular transfection, synergistic cytotoxicity and apoptosis in vitro. The improved TRAZ sensitization is attributed to the blockade of STAT3 signaling as well as the expression of downstream target genes associated with TRAZ resistance. With the synergistic action of STAT3-decoy ODNs loaded CaP@HA, TRAZ inhibited the growth of its resistant breast cancer xenograft dramatically and induced significant tumor cell apoptosis in vivo. These results suggested that CaP@HA mediated targeted delivery of STAT3-decoy ODNs might be a promising new strategy to overcome anti-HER2 resistance in breast cancer therapy.
• Polymeric Metformin And Its Use As A Therapeutic Agent And As A Delivery Vehicle
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20180055792A1

  公开（公告）日：2018-03-01

  Provided herein are polymers comprising Metformin residues (“PolyMet”) as useful therapeutic agents, delivery vehicles and transfection agents for nucleotides. Also provided herein are methods for the treatment of a disease or an unwanted condition in a subject, wherein the methods comprise administering PolyMet as a therapeutic agent to combat the disease or condition. Also provided herein are methods for the treatment of a disease or an unwanted condition in a subject, wherein the methods comprise administering a therapeutic agent in a delivery vehicle that comprises PolyMet. Further provided herein are methods for making PolyMet.