N,N-di-n-dodecylglycine | 65527-68-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-di-n-dodecylglycine
• 英文别名: didodecyiglycine；2-(didodecylamino)acetic acid；Glycine, N,N-didodecyl-
• CAS: 65527-68-6
• 化学式: C₂₆H₅₃NO₂
• 分子量: 411.712
• InChiKey: MVYRCGLBWXZUFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-di-n-dodecylglycine 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 3.05h， 生成 2-[[2-(Didodecylamino)acetyl]amino]acetic acid
  参考文献：
  名称：

  Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides

  摘要：

  Several structurally simple N-monoalkylated and -dialkylated dipeptides made of alpha-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's Lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 x 10(3) and > 10(4), respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions Can form neutral complexes at the pH value of the source phase.

  DOI：

  10.1021/jo9703257
• 作为产物：
  描述：

  Ethyl 2-(didodecylamino)acetate 在 乙醇 、 potassium hydroxide 作用下， 以65 %的产率得到N,N-di-n-dodecylglycine
  参考文献：
  名称：

  阳离子脂质共轭双亚芳基羟吲哚衍生物作为广谱乳腺癌选择性治疗剂

  摘要：

  乳腺癌是一种异质性恶性肿瘤，在治疗反应、总生存期等方面存在广泛差异。可用化学治疗剂实现临床成功的主要挑战是维持全身生物分布和避免非特异性不良反应。双亚芳基羟吲哚是具有中等效力的雌激素受体 (ER) 选择性生物活性分子。在这里，我们设计、合成和评估了一系列双脂肪链阳离子脂质共轭双亚芳基羟吲哚分子，这些分子具有不同的接头性质、碳间隔基长度和疏水双链。我们观察到，在各种结构类似物中，含有 C8 双链的分子PGC8、S2C8和S3C8在不同的癌细胞系中显示出有效的癌细胞选择性细胞毒性，IC 50范围为 4 至 7 µM。这些分子在 ER + 乳腺癌细胞而非非癌细胞中选择性地诱导细胞凋亡、ROS 产生和 G1/S 期细胞周期抑制。此外，这些分子形成了同质的自组装体，显示出具有正表面电荷的有效流体动力学直径。自组装还显示出突出的癌细胞选择性摄取和 DNA 结合能力。因此，我们已经证明成功地将地塞米松掺入自组装体中，并且即使在

  DOI：

  10.1016/j.bioorg.2023.106395

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR L'ADMINISTRATION INTRACELLULAIRE D'AGENTS THÉRAPEUTIQUES ET/OU PROPHYLACTIQUES
  申请人：MODERNATX INC

  公开号：WO2017112865A1

  公开（公告）日：2017-06-29

  The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

  该披露涉及氨基脂质和相关组合物。纳米粒子组合物包括氨基脂质以及额外的脂质，如磷脂、结构脂质、PEG脂质或二者的组合。纳米粒子组合物还包括治疗和/或预防剂，如RNA，可用于将治疗和/或预防剂传递至哺乳动物细胞或器官，例如，调节多肽、蛋白质或基因表达。
• [EN] N-ALKYLATED AMINO ACIDS AND OLIGOPEPTIDES, USES THEREOF AND METHODS FOR PROVIDING THEM.<br/>[FR] ACIDES AMINÉS N-ALKYLÉS ET OLIGOPEPTIDES, LEURS UTILISATIONS ET LEURS PROCÉDÉS DE PRODUCTION
  申请人：UNIV GRONINGEN

  公开号：WO2018178397A1

  公开（公告）日：2018-10-04

  The invention relates to the synthesis of amphiphilic amino acid derivatives, in particular to a method for the N-alkylation of an unprotected amino acid or the N-terminus of an oligopeptide substrate, comprising reacting said unprotected amino acid or oligopeptide substrate with an alcohol, e.g. a fatty alcohol, in the presence of a homogeneous transition metal catalyst.

  该发明涉及两性氨基酸衍生物的合成，特别涉及一种用于对未保护的氨基酸或寡肽底物的N-烷基化的方法，包括将所述未保护的氨基酸或寡肽底物与醇（例如脂肪醇）在均相过渡金属催化剂的存在下反应。
• [EN] LIPIDS SUITABLE FOR NUCLEIC ACID DELIVERY<br/>[FR] LIPIDES APPROPRIÉS POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES
  申请人：UNIV RAMOT

  公开号：WO2022168085A1

  公开（公告）日：2022-08-11

  The present invention provides lipids and lipid nanoparticle formulations comprising these lipids, alone or in combination with other lipids. These lipid nanoparticles may be formulated with nucleic acids to facilitate their intracellular delivery both in vitro and for therapeutic applications. The present invention also provides methods of chemical synthesis of these lipids, lipid nanoparticle preparation and formulation with nucleic acids.

  本发明提供了脂质和脂质纳米粒子配方，包括这些脂质，单独或与其他脂质结合。这些脂质纳米粒子可以与核酸配方，以促进它们在体外和治疗应用中的细胞内传递。本发明还提供了这些脂质的化学合成方法、脂质纳米粒子制备和核酸配方的制备方法。
• COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS
  申请人：Modernatx, Inc.

  公开号：EP3394030A1

  公开（公告）日：2018-10-31
• US4067890A
  申请人：——

  公开号：US4067890A

  公开（公告）日：1978-01-10