dioleyloxybenzaldehyde | 926652-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dioleyloxybenzaldehyde
• 英文别名: 3,4-Dioleyloxybenzaldehyde；3,4-bis[(Z)-octadec-9-enoxy]benzaldehyde
• CAS: 926652-61-1
• 化学式: C₄₃H₇₄O₃
• 分子量: 639.059
• InChiKey: QNYWFLYGFPKFRU-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  46
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dioleyloxybenzaldehyde 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and Transfection Efficiencies of New Lipophilic Polyamines

  摘要：

  A homologous series of lipophilic polyamines was synthesized and evaluated for DNA delivery and transfection efficiency. The series contained 1,4-butanediamine, 1,8-octanediamine, 2-[2-(2-amino-ethoxy)-ethoxy]-ethylamine, homospermidine, and homospermine covalently attached via their N-1 terminus to a 3,4-bis(oleyloxy)-benzyl motif. In addition, homospermidine and homospermine were also attached via amide linkers. The homospermidine derivatives (i.e., benzyl tether 25 and benzamide tether 27) showed a 3-fold and 4-fold respective enhancement in delivery of AlexaFluor-488-labeled DNA over the butanediamine analogue 22. Homospermine derivative 26 was shown to inhibit C-14-spermine uptake (IC50 similar to 10 mu M), which implied that 26 is able to compete effectively for polyamine recognition sites on the cell surface. This study demonstrated that the number and position of the positive charges along the polyamine scaffold plays a key role in DNA delivery and in determining the transfection efficiency.

  DOI：

  10.1021/jm0607101
• 作为产物：
  描述：

  油醇 在 四溴化碳 、 potassium carbonate 、 三苯基膦 、 potassium iodide 作用下， 以 二氯甲烷 、 环己酮 为溶剂， 反应 18.67h， 生成 dioleyloxybenzaldehyde
  参考文献：
  名称：

  用于 A549/ADR 治疗中阿霉素递送的酸敏感 PEG 可去除纳米级脂质体

  摘要：

  聚乙二醇（PEG）可以赋予药物载体长循环性能，常用于药物载体修饰。然而，PEG修饰阻碍了细胞对药物载体的摄取和药物在细胞内的释放，这一问题被称为“PEG困境”，限制了其应用。在本研究中，我们设计并合成了具有酸敏感腙键合的 mPEG-N CH-DOB 分子，用于响应性去除 PEG。用于阿霉素（DOX）递送的载药脂质 PHDGX 是通过将 mPEG-N CH-DOB 与脂质 DOPG 复合而获得的，其具有长循环能力和酸敏感的 PEG 去除能力，可加速药物释放并增强细胞摄取。聚乙二醇-NCH-DOB在pH 5.0下24小时后断裂率可达到50%。细胞毒性试验和流式细胞术（FCM）结果表明，在低DOX浓度下，PHDGX比游离DOX更容易进入A549/ADR细胞，并具有更强的抗癌能力。通过共聚焦激光扫描显微镜（CLSM）研究，发现PHDGX在同一时间点比游离DOX更容易进入A549/ADR细胞核，这表

  DOI：

  10.1039/d3nj01764h

文献信息

• Lipid nanoparticle based compositions and methods for the delivery of biologically active molecules
  申请人：Chen Tongqian

  公开号：US20060240554A1

  公开（公告）日：2006-10-26

  The present invention relates to novel cationic lipids, transfection agents, microparticles, nanoparticles, and short interfering nucleic acid (siNA) molecules. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism. Specifically, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules, such as antibodies (e.g., monoclonal, chimeric, humanized etc.), cholesterol, hormones, antivirals, peptides, proteins, chemotherapeutics, small molecules, vitamins, co-factors, nucleosides, nucleotides, oligonucleotides, enzymatic nucleic acids, antisense nucleic acids, triplex forming oligonucleotides, 2,5-A chimeras, dsRNA, allozymes, aptamers, decoys and analogs thereof, and small nucleic acid molecules, such as short interfering nucleic acid (siNA), short interfering RNA (siRNA), double-stranded RNA (dsRNA), micro-RNA (miRNA), and short hairpin RNA (shRNA) molecules, to relevant cells and/or tissues, such as in a subject or organism. Such novel cationic lipids, microparticles, nanoparticles and transfection agents are useful, for example, in providing compositions to prevent, inhibit, or treat diseases, conditions, or traits in a cell, subject or organism. The compositions described herein are generally referred to as formulated molecular compositions (FMC) or lipid nanoparticles (LNP).

  本发明涉及新型阳离子脂质体、转染剂、微粒子、纳米粒子和短干扰核酸（siNA）分子。本发明还涉及用于研究、诊断和治疗对基因表达和/或活性调节有反应的特征、疾病和状况的组合物和使用方法。具体而言，本发明涉及能够有效转染或传递生物活性分子的新型阳离子脂质体、微粒子、纳米粒子和转染剂，例如抗体（例如单克隆、嵌合、人源化等）、胆固醇、激素、抗病毒药物、肽、蛋白质、化学治疗药物、小分子、维生素、辅因子、核苷、核苷酸、寡核苷酸、酶性核酸、反义核酸、三链形成寡核苷酸、2,5-A嵌合体、双链RNA、等位酶、适配体、诱饵和其类似物以及小的核酸分子，例如短干扰核酸（siNA）、短干扰RNA（siRNA）、双链RNA（dsRNA）、微小RNA（miRNA）和短发夹RNA（shRNA）分子，传递到相关的细胞和/或组织中，例如在主体或生物体中。这些新型阳离子脂质体、微粒子、纳米粒子和转染剂在提供用于预防、抑制或治疗细胞、主体或生物体中的疾病、状况或特征的组合物方面是有用的。本文所描述的组合物通常被称为配制分子组合物（FMC）或脂质纳米粒子（LNP）。
• LIPID NANOPARTICLE BASED COMPOSITIONS AND METHODS FOR THE DELIVERY OF BIOLOGICALLY ACTIVE MOLECULES
  申请人：Chen Tongqian

  公开号：US20080188675A1

  公开（公告）日：2008-08-07

  The present invention relates to novel cationic lipids, transfection agents, microparticles, nanoparticles, and short interfering nucleic acid (siNA) molecules. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism. Specifically, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules, such as antibodies (e.g., monoclonal, chimeric, humanized etc.), cholesterol, hormones, antivirals, peptides, proteins, chemotherapeutics, small molecules, vitamins, co-factors, nucleosides, nucleotides, oligonucleotides, enzymatic nucleic acids, antisense nucleic acids, triplex forming oligonucleotides, 2,5-A chimeras, dsRNA, allozymes, aptamers, decoys and analogs thereof, and small nucleic acid molecules, such as short interfering nucleic acid (siNA), short interfering RNA (siRNA), double-stranded RNA (dsRNA), micro-RNA (miRNA), and short hairpin RNA (shRNA) molecules, to relevant cells and/or tissues, such as in a subject or organism. Such novel cationic lipids, microparticles, nanoparticles and transfection agents are useful, for example, in providing compositions to prevent, inhibit, or treat diseases, conditions, or traits in a cell, subject or organism. The compositions described herein are generally referred to as formulated molecular compositions (FMC) or lipid nanoparticles (LNP).

  本发明涉及新型阳离子脂质体、转染剂、微粒、纳米粒子和短干扰核酸（siNA）分子。本发明还涉及用于研究、诊断和治疗对基因表达和/或活性调节有反应的特征、疾病和状况的组合物和使用方法。具体而言，本发明涉及新型阳离子脂质体、微粒、纳米粒子和转染剂，它们能有效地转染或传递生物活性分子，例如抗体（例如单克隆、嵌合、人源化等）、胆固醇、激素、抗病毒药物、肽、蛋白质、化疗药物、小分子、维生素、辅因子、核苷、核苷酸、寡核苷酸、酶性核酸、反义核酸、三股形成寡核苷酸、2,5-A嵌合体、dsRNA、等位酶、适配体、诱饵和类似物以及小核酸分子，例如短干扰核酸（siNA）、短干扰RNA（siRNA）、双链RNA（dsRNA）、微RNA（miRNA）和短发夹RNA（shRNA）分子，传递到相关的细胞和/或组织中，例如在主体或生物体中。这些新型阳离子脂质体、微粒、纳米粒子和转染剂在提供组合物以预防、抑制或治疗细胞、主体或生物体的疾病、状况或特征方面是有用的。本文所描述的组合物通常被称为配制的分子组合物（FMC）或脂质纳米粒子（LNP）。
• Lipid Nanoparticle Based Compositions and Methods for the Delivery of Biologically Active Molecules
  申请人：Chen Tongqian

  公开号：US20090048197A1

  公开（公告）日：2009-02-19

  The present invention relates to novel cationic lipids, transfection agents, microparticles, nanoparticles, and short interfering nucleic acid (siNA) molecules. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism. Specifically, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules, such as antibodies (e.g., monoclonal, chimeric, humanized etc.), cholesterol, hormones, antivirals, peptides, proteins, chemotherapeutics, small molecules, vitamins, co-factors, nucleosides, nucleotides, oligonucleotides, enzymatic nucleic acids, antisense nucleic acids, triplex forming oligonucleotides, 2,5-A chimeras, dsRNA, allozymes, aptamers, decoys and analogs thereof, and small nucleic acid molecules, such as short interfering nucleic acid (siNA), short interfering RNA (siRNA), double-stranded RNA (dsRNA), micro-RNA (miRNA), short hairpin RNA (shRNA), and RNAi inhibitor molecules, to relevant cells and/or tissues, such as in a subject or organism. Such novel cationic lipids, microparticles, nanoparticles and transfection agents are useful, for example, in providing compositions to prevent, inhibit, or treat diseases, conditions, or traits in a cell, subject or organism. The compositions described herein are generally referred to as formulated molecular compositions (FMC) or lipid nanoparticles (LNP).

  本发明涉及新型阳离子脂质、转染剂、微粒、纳米粒子和短干扰核酸（siNA）分子。本发明还涉及组合物和使用方法，用于研究、诊断和治疗对基因表达和/或活性调节有反应的个体或生物的特征、疾病和状况。具体而言，本发明涉及新型阳离子脂质、微粒、纳米粒子和转染剂，可以有效地转染或传递生物活性分子，如抗体（例如单克隆、嵌合、人源化等）、胆固醇、激素、抗病毒药物、肽、蛋白质、化学治疗药物、小分子、维生素、辅因子、核苷、核苷酸、寡核苷酸、酶性核酸、反义核酸、三链体寡核苷酸、2,5-A嵌合体、dsRNA、异构酶、aptamers、诱饵和其类似物，以及小的核酸分子，如短干扰核酸（siNA）、短干扰RNA（siRNA）、双链RNA（dsRNA）、微RNA（miRNA）、短发夹RNA（shRNA）和RNAi抑制分子，传递到相关的细胞和/或组织中，例如在个体或生物中。这种新型阳离子脂质、微粒、纳米粒子和转染剂在提供组合物以预防、抑制或治疗细胞、个体或生物的疾病、状况或特征方面是有用的。本文所描述的组合物通常称为配方分子组合物（FMC）或脂质纳米粒子（LNP）。
• COMPOSITIONS AND METHODS FOR POTENTIATED ACTIVITY OF BIOLOGICALLY ACTIVE MOLECULES
  申请人：Jadhav Vasant

  公开号：US20100015218A1

  公开（公告）日：2010-01-21

  The present invention relates to novel compositions and methods for potentiating the activity of biologically active molecules in conjunction with one or more delivery vehicles and one or more carrier molecules. Specifically, the invention features the use of a carrier molecule in combination with a delivery vehicle and a biologically active molecule of interest to potentiate the activity of the biologically active molecule. The carrier molecule can be biologically inert, inactive, or attenuated; or can alternately be biologically active in the same or different manner than the biologically active molecule of interest. Specifically, the invention features novel particle forming delivery agents including cationic lipids, microparticles, and nanoparticles that are useful for delivering various biologically active molecules to cells in conjunction with a carrier molecule. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism that are delivered intracellularly in conjunction with a carrier molecule. In various embodiments, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules, such as antibodies (e.g., monoclonal, chimeric, humanized etc.), cholesterol, hormones, antivirals, peptides, proteins, chemotherapeutics, small molecules, vitamins, co-factors, nucleosides, nucleotides, oligonucleotides, enzymatic nucleic acids, antisense nucleic acids, triplex forming oligonucleotides, 2,5-A chimeras, allozymes, aptamers, decoys and analogs thereof, and small nucleic acid molecules, such as short interfering nucleic acid (siNA), short interfering RNA (siRNA), double-stranded RNA (dsRNA), micro-RNA (miRNA), and short hairpin RNA (shRNA) molecules, to relevant cells and/or tissues, such as in a subject or organism, in conjunction with one or more carrier molecules. Such novel cationic lipids, microparticles, nanoparticles and transfection agents that are used in conjunction with one or more carrier molecules are useful, for example, in providing compositions to prevent, inhibit, or treat diseases, conditions, or traits in a cell, subject or organism.

  本发明涉及一种新型组合物和方法，用于增强生物活性分子的活性，结合一个或多个传递载体和一个或多个载体分子。具体而言，本发明涉及使用载体分子与传递载体和感兴趣的生物活性分子结合，以增强生物活性分子的活性。载体分子可以是生物惰性、不活跃或减弱的；或者可以是与生物活性分子以相同或不同的方式活跃的。具体而言，本发明涉及新型形成颗粒的传递剂，包括阳离子脂质、微粒和纳米粒子，它们对于传递各种生物活性分子到细胞中与载体分子结合是有用的。本发明还涉及组合物和使用方法，用于研究、诊断和治疗在主体或有机体中对基因表达和/或活性调节有反应的特征、疾病和情况，这些组合物和方法是与载体分子一起递送到细胞内的。在各种实施例中，本发明涉及新型阳离子脂质、微粒、纳米粒子和转染剂，它们有效地转染或递送生物活性分子，如抗体（例如单克隆、嵌合、人源化等）、胆固醇、激素、抗病毒药物、肽、蛋白质、化学治疗药物、小分子、维生素、辅因子、核苷、核苷酸、寡核苷酸、酶核酸、反义核酸、三链体寡核苷酸、2,5-A嵌合体、异构酶、适配体、诱饵和其类似物以及小核酸分子，如短干扰核酸（siNA）、短干扰RNA（siRNA）、双链RNA（dsRNA）、微RNA（miRNA）和短发夹RNA（shRNA）分子，递送到相关的细胞和/或组织中，例如在主体或有机体中，与一个或多个载体分子结合。这种与一个或多个载体分子一起使用的新型阳离子脂质、微粒、纳米粒子和转染剂是有用的，例如提供组合物以预防、抑制或治疗细胞、主体或有机体中的疾病、情况或特征。
• Lipophilic polyamines providing enhanced intracellular delivery of agents by a polyamine transport system
  申请人：University of Central Florida Research Foundation, Inc.

  公开号：US07910363B1

  公开（公告）日：2011-03-22

  Polyamine cationic lipids have been synthesized that have the ability to be transported into cells having an active polyamine transport system. Accordingly, these lipids may be conjugated with various agents and, thereby, act as vectors for transporting the agent into the cell aided by the cell's own polyamine transport system. A method of delivering an agent into a cell includes associating the agent with a polyamine cationic lipid selected from compounds 25, 26, 27, 28, their pharmaceutically acceptable salts and combinations thereof and contacting the cell therewith.

  合成了具有运输到具有活性多胺转运系统的细胞的能力的聚胺阳离子脂质。因此，这些脂质可以与各种药剂结合，并作为向细胞运输药剂的载体，利用细胞自身的多胺转运系统。将药剂与从化合物25、26、27、28及其药学上可接受的盐和其组合物中选择的多胺阳离子脂质关联，并与细胞接触的方法可将药剂传递到细胞中。