N,N-dioctadecylsuccinamic acid | 37519-63-4

• 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: N,N-dioctadecylsuccinamic acid
• 英文别名: 4-(dioctadecylamino)-4-oxobutanoic acid；N-succinyl-dioctadecylamine；N,N-dioctadecylsuccinamide；Butanoic acid, 4-(dioctadecylamino)-4-oxo-
• CAS: 37519-63-4
• 化学式: C₄₀H₇₉NO₃
• 分子量: 622.072
• InChiKey: CQUJVIROQGZGMC-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  696.8±38.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  44
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dioctadecylsuccinamic acid 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 4-(dioctadecylamino)butan-1-ol
  参考文献：
  名称：

  功能化脂质的合成及其在可调节的核苷和核酸疏水化中的应用

  摘要：

  制备了两个功能化的单侧链和双侧链脂质分子（方案1和2）。该化合物带有末端COOH，OH或卤素取代基。此外，双侧链脂质18带有内部炔烃官能团。后一种化合物通过碱催化的烷基化作用在N（3）处使胸苷疏水化。此外，完全保护的胸苷，32，是N（3）烷基化与所述双面链醇9施加光延反应条件。

  DOI：

  10.1002/hlca.201100410
• 作为产物：
  描述：

  十八胺 在 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.0h， 生成 N,N-dioctadecylsuccinamic acid
  参考文献：
  名称：

  Molecular Recognition of Nucleotides by the Guanidinium Unit at the Surface of Aqueous Micelles and Bilayers. A Comparison of Microscopic and Macroscopic Interfaces

  摘要：

  Molecular recognition of the guanidinium/phosphate pair was investigated at microscopic interfaces of aqueous micelles and bilayers. Monoalkyl and dialkyl amphiphiles with guanidinium head groups were synthesized and dispersed in water to form micelles and bilayers having guanidinium groups at the aggregate surface. Binding of nucleotides such as AMP to these functionalized aggregates was evaluated by using an equilibrium dialysis (ultrafiltration) method. The observed binding constants of 10(2)-10(4) M(-1) are much larger than the corresponding binding constant reported for a monomerically dispersed pair in the aqueous phase (1.4 M(-1)) but are smaller than those found at the macroscopic air-water interface (10(6)-10(7) M(-1)). Therefore, the macroscopic interface promotes guanidinium-phosphate interaction more effectively than the microscopic interface. The present finding indicates that the microscopic interface can strengthen hydrogen bonding and/or electrostatic interaction even in the presence of water. Saturation binding phenomena were different between micelles and bilayers. All of the guanidinium groups in fluid micelles are effective for phosphate binding, but part of the guanidinium group in bilayers are not effective probably because of steric restriction.

  DOI：

  10.1021/ja960991+

文献信息

• REACTIVE, LIPOPHILIC NUCLEOSIDE BUILDING BLOCKS FOR THE SYNTHESIS OF HYDROPHOBIC NUCLEIC ACIDS
  申请人：Ionovation GmbH

  公开号：US20190175633A1

  公开（公告）日：2019-06-13

  The present invention relates to a method for the isolation and/or identification of known or unknown sequences of nucleic acids (target sequences) optionally marked with reporter groups by base specific hybridation with complementary sequences using nucleolipids. The nucleolipids are prepared by lipophilizing nucleosides of formula (Ia) wherein Q represents a group having a substituted tetrahydrofuran ring and Bas represents a group having one or more heterocyclic rings having one or more heterocyclic nitrogen atoms.

  本发明涉及一种方法，用于通过碱特异性杂交与互补序列使用核苷酸脂质来分离和/或识别带有报告基团的已知或未知核酸序列（目标序列）。所述核苷酸脂质是通过使式（Ia）的核苷的亲脂化制备的， 其中，Q代表具有取代四氢呋喃环的基团，Bas代表具有一个或多个含有一个或多个杂环氮原子的杂环环的基团。
• Design of Ionizable Lipids To Overcome the Limiting Step of Endosomal Escape: Application in the Intracellular Delivery of mRNA, DNA, and siRNA
  作者：Damien Habrant、Pauline Peuziat、Thibault Colombani、Laurence Dallet、Johan Gehin、Emilie Goudeau、Bérangère Evrard、Olivier Lambert、Thomas Haudebourg、Bruno Pitard

  DOI：10.1021/acs.jmedchem.5b01679

  日期：2016.4.14

  The intracellular delivery of nucleic acid molecules is a complex process involving several distinct steps; among these the endosomal escape appeared to be of particular importance for an efficient protein production (or inhibition) into host cells. In the present study, a new series of ionizable vectors, derived from naturally occurring aminoglycoside tobramycin, was prepared using improved synthetic

  核酸分子的细胞内递送是一个复杂的过程，涉及几个不同的步骤。其中，对于有效地向宿主细胞中产生蛋白质（或抑制），内体逃逸似乎尤为重要。在本研究中，使用改良的合成程序制备了一系列新的可离子化的载体，这些载体均来自天然存在的氨基糖苷妥布霉素，可在接头和疏水域上进行结构变化。新的可电离脂质与mRNA，DNA或siRNA之间形成的复合物通过冷冻TEM实验进行了表征，并使用不同的细胞类型评估了它们的转染能力。我们证明了铅分子30，带有可生物降解的二酯连接子，与核酸形成小的复合物，并且对所有测试的核酸和细胞类型均具有非常高的转染效率。获得的结果表明，通过脂质混合机制优化的内体逃逸，可改善30种“通用”递送特性。
• Drug‐Sponge Lipid Nanocarrier for in Situ Cargo Loading and Release Using Dynamic Covalent Chemistry
  作者：Fei Liu、Yosuke Niko、Redouane Bouchaala、Luc Mercier、Olivier Lefebvre、Bohdan Andreiuk、Thierry Vandamme、Jacky G. Goetz、Nicolas Anton、Andrey Klymchenko

  DOI：10.1002/anie.202014259

  日期：2021.3.15

  Currently, drug‐delivery strategies using nanocarriers (NCs) deal with encapsulation of cargo or its covalently modified prodrug. Herein, we propose a concept of reversible pH‐controlled capture and delivery of active cargo based on dynamic covalent chemistry inside lipid nano‐droplets (nanoemulsions), coined as “drug sponge”. We designed a highly lipophilic hydrazide (LipoHD) capable of reacting with

  当前，使用纳米载体（NCs）的药物输送策略涉及货物或其共价修饰前药的封装。本文中，我们提出了一种基于脂质纳米液滴（纳米乳剂）内部动态共价化学的可逆pH值控制的活性货物捕获和输送的概念，被称为“药物海绵”。我们设计了一种高度亲脂性的酰肼（LipoHD），它可以直接与脂质NC内部的游离货物酮（荧光染料和阿霉素药物）反应，从而产生有效捕获在油芯中的亲脂性pro前药。装载LipoHD的NCs自发地积累了货物酮，产生了在pH 7.4时对货物泄漏稳定的制剂，并在溶液和活细胞中在低pH范围（5.0–6.8）下释放了它们的染料/药物货物。载有阿霉素的药物海绵NC表现出对四种癌细胞系的细胞毒性，并具有抑制小鼠皮下异种移植物中肿瘤生长的能力。最终，药物海绵NC可以实现前所未有的直接从细胞和组织中提取染料/药物货物（即解毒）的作用。
• [EN] NANOEMULSIONS ENCAPSULATING PRODRUGS<br/>[FR] NANOÉMULSIONS ENCAPSULANT DES PROMÉDICAMENTS
  申请人：UNIV STRASBOURG

  公开号：WO2020144297A1

  公开（公告）日：2020-07-16

  The present invention concerns nanoemulsions encapsulating a prodrug and bearing a targeting ligand, said nanoemulsion being formed by a natural oil and/or a synthetic oil and an amphiphilic surfactant, the methods for preparing these nanoemulsion, and the applications of these nanoemulsion.

  本发明涉及一种封装前药并带有靶向配体的纳米乳液，所述纳米乳液由天然油和/或合成油以及一种两亲性表面活性剂形成，本发明还涉及这些纳米乳液的制备方法以及这些纳米乳液的应用。
• CHELATE NANOEMULSION FOR MRI
  申请人：Port Marc

  公开号：US20130309176A1

  公开（公告）日：2013-11-21

  The present invention relates to an oil-in-water nanoemulsion composition for MRI, comprising: an aqueous phase, representing 70% to 90% by weight of the composition, advantageously 75% to 85% and more advantageously from 78% to 82% a lipid phase comprising an oil, representing 9.5% to 29.5% by weight of the composition, advantageously 14% to 25% and more advantageously 17% to 21%, a surfactant at the interface between the aqueous and lipid phases, the surfactant comprising at least one amphiphilic paramagnetic metal chelate and optionally an amphiphilic lipid; the total content of surfactant by weight relative to the oil being between 4% and 10% and advantageously between 5% and 8%; the total content of surfactant by weight relative to the composition being between 0.35% and 2.95% and advantageously between 0.5% and 2%; the oil comprising at least 70%, advantageously at least 80%, advantageously at least 95% by weight and especially at least 97% of saturated C6-C18, advantageously C6-C14 and more advantageously C6-C10 fatty acids.

  本发明涉及一种用于磁共振成像的油包水纳米乳液组合物，包括： 水相，表示组合物重量的70%至90%，优选75%至85%，更优选78%至82%； 脂相包括一种油，表示组合物重量的9.5%至29.5%，优选14%至25%，更优选17%至21%； 表面活性剂位于水相和脂相之间的界面上，表面活性剂包括至少一种两性磁性金属螯合物和可选的两性脂质； 相对于油的重量，表面活性剂的总含量在4%至10%之间，优选在5%至8%之间； 相对于组合物的重量，表面活性剂的总含量在0.35%至2.95%之间，优选在0.5%至2%之间； 油包括至少70%，优选至少80%，优选至少95%的饱和C6-C18，优选C6-C14，更优选C6-C10脂肪酸。