N(2),N(6)-二棕榈酰赖氨酸 | 20257-67-4

• 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
• 中文名称: N(2),N(6)-二棕榈酰赖氨酸
• 英文名称: N^α,N^ε-bis(hexadecanoyl)-L-lysine
• 英文别名: dipalmitoyl lysine；bis-palmitoyl-L-Lys；N^α,N^ε-dihexadecanoyl-L-lysine；N,N'-di-nexadecanoyl-Lys；N²,N⁶-dipalmitoyl-L-lysine；N²,N⁶-Dipalmitoyl-L-lysin；α-N,ε-N-Dipalmitoyl-lysin；N,N'-Dipalmitoyl-L-lysin；N,N'-dipalmitoyllysine；Dipalmitoyllysine；(2S)-2,6-bis(hexadecanoylamino)hexanoic acid
• CAS: 20257-67-4
• 化学式: C₃₈H₇₄N₂O₄
• 分子量: 623.017
• InChiKey: VKCGSTZAZMNTRV-DHUJRADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  44
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  N(2),N(6)-二棕榈酰赖氨酸 在 钯 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 31.0h， 生成 N^α,N^ε-bis(hexadecanoyl)-N-(2-carboxyethyl)-L-lysinamide
  参考文献：
  名称：

  来自α-氨基酸的脂质的超分子受体

  摘要：

  制备了衍生自L-，D-，DL-谷氨酸，L-天冬氨酸，L-赖氨酸，L-鸟氨酸和L -2,4-二氨基丁酸的阴离子脂质，以及与结构相关的溶剂化阳离子苯乙烯基苯乙烯的方法研究了将染料掺入这些脂质聚集体中的方法。的大号-或d具有戊二酸头基的β-谷氨酸衍生的脂质聚集形成特定的疏水腔，其主要基于平面性识别而表现出对苯乙烯基染料的包涵能力。这样的特定疏水腔的形成不仅可以通过在聚集体中引入能够与相邻脂质之间互补的氢键结合的酰胺基，而且可以通过将适当的间隔基亚甲基引入例如戊二酸酯头基来实现。还发现氨基酸残基的侧链亚甲基在特定的疏水腔以及间隔基亚甲基的形成中起重要作用。还为适当设计的L-赖氨酸和L形成了此类腔-鸟氨酸来源的脂质。这些结果表明，特异性掺入不是谷氨酸来源的脂质所特有的，而是来自适当设计的L-氨基酸来源的脂质的聚集体的普遍现象。在组装的方式的差异大号之间谷氨酸残基大号- ， - d -异构体，和DL

  DOI：

  10.1039/a903956b
• 作为产物：
  描述：

  L-赖氨酸 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 氯仿 、 苯 为溶剂， 反应 27.0h， 生成 N(2),N(6)-二棕榈酰赖氨酸
  参考文献：
  名称：

  Synthesis and Assembly of Poly(ethylene glycol)−Lipids with Mono-, Di-, and Tetraacyl Chains and a Poly(ethylene glycol) Chain of Various Molecular Weights

  摘要：

  We synthesized a series of amphiphiles with poly(ethylene glycol) [MW 2000 (PEG20), 5000 (PEG50), 12 500 (PEG125)] as a headgroup and one, two, or four palmitoyl chains (1C16, 2C16, or 4C16), using a lysine monodendron as a connector. The relationship between the hydrophilic-hydrophobic balance of the multiacyl PEG-lipids and the physicochemical characteristics in self- or co-assembly with phospholipids were studied. The PEG-lipids were easily synthesized by combination of a general liquid-phase peptide synthesis and the acylation of an amino acid. The PEG part of the PEG-lipid films was crystallized to show a typical spherulite pattern. The thermal properties and microscopic observation revealed the phase separation of PEG and acyl chain parts. The critical micelle concentrations (cmcs) mainly depend on the number of acyl chains rather than the molecular weight of the PEG chain, although the area per molecule is dependent on the molecular weight of the PEG chain rather than the number of the acyl chains. The gel-to-liquid crystalline phase transition temperature was increased with the increasing number of acyl chains and the decreasing molecular weight of the PEG chain. The PEG-lipids in the aqueous dispersions assemble to take fibrous structures with bimolecular thickness because of the intermolecular hydrogen bonding. The PEG-lipids were immobilized onto the surface of the phospholipid vesicles by simply adding their aqueous dispersions to the vesicle dispersion; however, they dissociated from the vesicles on dilution of the mixed dispersion because they were incorporated into the vesicles in an equilibrium state. To prevent the dissociation of the PEG-lipids, at least two and four acyl chains were required for PEG with M-W 5000 and 12 500, respectively. The aggregation of the vesicles by the addition of water-soluble polymers was significantly inhibited with the increasing molecular weight of the PEG chain. For the tight immobilization of the PEG-lipids with the long PEG chain onto the vesicular surface, an increased number of acyl chains is necessary, and the surface modification with the long PEG chains significantly increases the dispersion stability of the vesicles.

  DOI：

  10.1021/ja000835+

文献信息

• Molecular structural requirements, dye specificity, and application of anionic peptide amphiphiles that induce intense fluorescence in cationic dyes
  作者：Hiroshi Hachisako、Naoya Ryu、Ryoichi Murakami

  DOI：10.1039/b818206j

  日期：——

  acid with relatively shorter side-chain methylenes. The dye specificity in terms of induction of the intense fluorescence was also investigated using hemicyanines (stilbazoliumetc.), cyanine, carbocyanine, thiacarbocyanines, and azo dye. The amphiphile with the shortest octanoyl-β-alanyl double-chain alkyl groups, longer side-chain, and shorter spacer was found to show increased sensitivity to alkali

  我们以前曾报道过，能够在分子间形成三氢键的双链阴离子两亲物可能在水中形成极疏水的位点。 水特别是掺入了基于噻唑鎓的紧凑型半花青染料作为单体物质，从而导致染料中强烈的荧光发射。本文研究了强荧光诱导两亲物的结构要求。注意到将β-Ala残基引入两个长链烷基基团对于衍生自的两亲物最有效L-谷氨酸具有相对较短的侧链亚甲基。还使用半花菁（stilbazolium等），花菁，碳花菁，硫代碳菁和偶氮染料研究了染料在诱导强荧光方面的特异性。发现具有最短的辛酰基-β-丙氨酰基双链烷基，侧链较长和间隔基较短的两亲物显示出对碱金属离子，特别是Li +的敏感性增加。这可能是Li +的潜在OFF-ON型荧光传感器。
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：DTX PHARMA INC

  公开号：WO2021108640A1

  公开（公告）日：2021-06-03

  Disclosed herein are compounds including a single-stranded oligonucleotide (A) having a nucleobase sequence complementary to a portion of the dystrophin pre-mRNA, their preparation, and uses thereof for the treatment of Duchenne muscular dystrophy.

  本文披露了一种化合物，包括一种单链寡核苷酸（A），其具有与肌营养不良前体mRNA的部分互补的核碱基序列，以及它们的制备方法和用途，用于治疗杜兴氏肌肉营养不良。
• Application of synthetic liposomes based on acyl amino acids or acyl peptides as drug carriers. I. Their preparation and transport of glutathione into the liver.
  作者：HIROSHI KIWADA、MASAMI AKIMOTO、MICHIYO ARAKI、MITSUKO TSUJI、YURIKO KATO

  DOI：10.1248/cpb.35.2935

  日期：——

  Palmitoyl amino acids and palmitoyl glutathione were synthesized. Liposome-like vesicles based on these compounds were prepared and their barrier functions were examined. These vesicles showed encapsulation efficiencies for aqueous solute comparable to that of conventional phosphatidylcholine liposomes (PC-liposomes). They were also stable in fresh rat plasma at 37°C. The biological behavior (blood clearance, urinary excretion and tissue distribution) of the vesicles based on palmitoyl serine (PSer-liposomes) or palmitoyl glutathione (PGSH-liposomes) was examined after intravenous injection in rats. The synthetic liposomes were cleared very rapidly from the blood compared with PC-liposomes. PSer-Liposomes showed a large amount of urinary excretion of aqueous marker ([3H] inulin), suggesting that the mechanisms of vesicle degradation in vivo and in vitro are different. These synthetic liposomes showed low affinity to the spleen and high affinity to the liver in the tissue distribution study, and thus they may be expected to be a useful drug carrier which is targetable to the liver. A suppressing effect of PGSH-liposomes on the increase of plasma glutamate oxaloacetate transaminase (GOT) induced by a high dose of acetaminophen in mice was observed, and transport of glutathione into the liver cells apparently occurred. The suppressing effect was greater than that of free glutathione or PC-liposomes containing free glutathione. However, the effect was not observed in the case of PGSH-liposomes without phosphatidylcholine, which appears to have an important role in the liposome-cell interaction.

  合成了棕榈酰氨基酸和棕榈酰谷胱甘肽。基于这些化合物的脂质体样囊泡被制备出来，并检测了它们的屏障功能。这些囊泡对水溶性溶质的包封效率与传统磷脂酰胆碱脂质体（PC-脂质体）相当。它们在37°C的新鲜大鼠血浆中也表现稳定。基于棕榈酰丝氨酸（PSer-脂质体）或棕榈酰谷胱甘肽（PGSH-脂质体）的囊泡在大鼠静脉注射后的生物行为（血液清除、尿液排泄和组织分布）被研究。合成脂质体相比PC-脂质体从血液中清除得非常迅速。PSer-脂质体显示出大量的水溶性标记物（[3H]菊粉）的尿液排泄，表明囊泡在体内和体外的降解机制是不同的。这些合成脂质体在组织分布研究中对脾脏的亲和力低，而对肝脏的亲和力高，因此它们可能成为肝脏靶向的有用药物载体。观察到PGSH-脂质体对小鼠因高剂量扑热息痛引起的血浆谷氨酸草酰乙酸转氨酶（GOT）升高的抑制作用，并且明显发生了谷胱甘肽向肝细胞的转运。抑制效果大于游离谷胱甘肽或含有游离谷胱甘肽的PC-脂质体。然而，在没有磷脂酰胆碱的PGSH-脂质体中并未观察到这种效果，这表明磷脂酰胆碱在脂质体-细胞相互作用中起着重要作用。
• [EN] COMPOUND COMPRISING A NUCLEIC ACID AND A HALF-LIFE EXTENSION MOTIF<br/>[FR] COMPOSÉ COMPRENANT UN ACIDE NUCLÉIQUE ET UN MOTIF D'EXTENSION DE DEMI-VIE
  申请人：DTX PHARMA INC

  公开号：WO2021108662A1

  公开（公告）日：2021-06-03

  Disclosed herein are compounds including a nucleic acid (A), their preparation, and their use.

  本文披露了包括核酸（A）的化合物，它们的制备以及它们的用途。
• Synthesis and Antibacterial Activities of Amphiphilic Neomycin B-based Bilipid Conjugates and Fluorinated Neomycin B-based Lipids
  作者：Smritilekha Bera、Ramesh Dhondikubeer、Brandon Findlay、George G. Zhanel、Frank Schweizer

  DOI：10.3390/molecules17089129

  日期：——

  compounds incorporated either palmitic or arachidic di-lipid lysine tails, while two had single fluorinated undecanoic acid tails. The basicity of half of the compounds was increased through the incorporation of six guanidine moieties, in order to assess the effect of base strength on antimicrobial activity. A panel of ten bacteria was used for the testing, with seven strains obtained from the American Type

  研究脂质疏水性对两亲性新霉素 B 偶联物活性的影响，创建了六种聚阳离子两亲物 (PA)。四种新化合物包含棕榈酸或花生二脂赖氨酸尾，而两种具有单一氟化十一酸尾。一半化合物的碱性通过加入六个胍部分而增加，以评估碱强度对抗菌活性的影响。一组十种细菌用于测试，其中七株来自美国典型培养物保藏中心，三株临床分离株来自加拿大重症监护病房。与之前使用烃类单脂的结果相比，发现所有化合物的活性都降低，