18-aminooctadecanoic acid | 17437-24-0

• 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: 18-aminooctadecanoic acid
• CAS: 17437-24-0
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: ACQSOZZSYSEKHC-UHFFFAOYSA-N

物化性质

• 沸点：
  434.1±18.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  将保存条件设定为2-8°C，需保持干燥并密封储存。

反应信息

• 作为反应物：
  描述：

  18-aminooctadecanoic acid 在 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Direct interaction, instrumental for signaling processes, between LacCer and Lyn in the lipid rafts of neutrophil-like cells

  摘要：

  Lactosylceramide [LacCer; beta-Gal-(1-4)-beta-Glc-(1-1)-Cer] has been shown to contain very long fatty acids that specifically modulate neutrophil properties. The interactions between LacCer and proteins and their role in cell signaling processes were assessed by synthesizing two molecular species of azide-photoactivable tritium-labeled LacCer having acyl chains of different lengths. The lengths of the two acyl chains corresponded to those of a short/medium and very long fatty acid, comparable to the lengths of stearic and lignoceric acids, respectively. These derivatives, designated C18-[H-3] LacCer-(N-3) and C24-[H-3]LacCer-(N-3), were incorporated into the lipid rafts of plasma membranes of neutrophilic differentiated HL-60 (D-HL-60) cells. C24-[H-3] LacCer-(N-3), but not C18-[H-3] LacCer-(N-3), induced the phosphorylation of Lyn and promoted phagocytosis. Incorporation of C24-[H-3]LacCer-(N-3) into plasma membranes, followed by illumination, resulted in the formation of several tritium-labeled LacCer-protein complexes, including the LacCer-Lyn complex, into plasma membrane lipid rafts. Administration of C18-[H-3]LacCer-(N-3) to cells, however, did not result in the formation of the LacCer-Lyn complex. These results suggest that LacCer derivatives mimic the biological properties of natural LacCer species and can be utilized as tools to study LacCer-protein interactions, and confirm a specific direct interaction between LacCer species containing very long fatty acids, and Lyn protein, associated with the cytoplasmic layer via myristic/palmitic chains.

  DOI：

  10.1194/jlr.m055319
• 作为产物：
  描述：

  十八烷二酸二甲酯 在 sodium azide 、 硼烷四氢呋喃络合物 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 、 barium(II) hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 18-aminooctadecanoic acid
  参考文献：
  名称：

  Direct interaction, instrumental for signaling processes, between LacCer and Lyn in the lipid rafts of neutrophil-like cells

  摘要：

  Lactosylceramide [LacCer; beta-Gal-(1-4)-beta-Glc-(1-1)-Cer] has been shown to contain very long fatty acids that specifically modulate neutrophil properties. The interactions between LacCer and proteins and their role in cell signaling processes were assessed by synthesizing two molecular species of azide-photoactivable tritium-labeled LacCer having acyl chains of different lengths. The lengths of the two acyl chains corresponded to those of a short/medium and very long fatty acid, comparable to the lengths of stearic and lignoceric acids, respectively. These derivatives, designated C18-[H-3] LacCer-(N-3) and C24-[H-3]LacCer-(N-3), were incorporated into the lipid rafts of plasma membranes of neutrophilic differentiated HL-60 (D-HL-60) cells. C24-[H-3] LacCer-(N-3), but not C18-[H-3] LacCer-(N-3), induced the phosphorylation of Lyn and promoted phagocytosis. Incorporation of C24-[H-3]LacCer-(N-3) into plasma membranes, followed by illumination, resulted in the formation of several tritium-labeled LacCer-protein complexes, including the LacCer-Lyn complex, into plasma membrane lipid rafts. Administration of C18-[H-3]LacCer-(N-3) to cells, however, did not result in the formation of the LacCer-Lyn complex. These results suggest that LacCer derivatives mimic the biological properties of natural LacCer species and can be utilized as tools to study LacCer-protein interactions, and confirm a specific direct interaction between LacCer species containing very long fatty acids, and Lyn protein, associated with the cytoplasmic layer via myristic/palmitic chains.

  DOI：

  10.1194/jlr.m055319

文献信息

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

  公开号：WO2018170306A1

  公开（公告）日：2018-09-20

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

  该披露涉及新型脂质和相关组合物。纳米粒子组合物包括一种新型脂质以及额外的脂质，如磷脂、结构脂质和PEG脂质。纳米粒子组合物还包括治疗和/或预防措施，如RNA，在将治疗和/或预防措施传递给哺乳动物细胞或器官方面非常有用，例如，调节多肽、蛋白质或基因表达。
• [EN] 3-MODIFIED ISO-/ISOALLO-LITHOCHOLIC ACID DERIVATIVES OR THEIR HOMO-ANALOGS FOR PREVENTING AND TREATING CLOSTRIDIOIDES DIFFICILE-ASSOCIATED DISEASES<br/>[FR] DÉRIVÉS D'ACIDE ISO-/ISOALLO-LITHOCHOLIQUE 3-MODIFIÉS OU LEURS HOMO-ANALOGUES POUR LA PRÉVENTION ET LE TRAITEMENT DE MALADIES ASSOCIÉES À CLOSTRIDIOIDES DIFFICILE
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2020260558A1

  公开（公告）日：2020-12-30

  The present invention relates to isolithocholic acid (3β-hydroxy-5β-cholan-24-oic acid) and isoallolithocholic acid (3β-hydroxy-5α-cholan-24-oic acid) together with the respective 22-homo-analogs or the deuterated analogs, which are modified in 3-position, for preventing or treating Clostridioides difficile-associated disease in a mammalian subject.

  本发明涉及孤立胆烷酸（3β-羟基-5β-胆烷-24-酸）和异孤立胆烷酸（3β-羟基-5α-胆烷-24-酸），以及相应的在3位修饰的22-同系物或氘代同系物，用于预防或治疗哺乳动物主体中的难辨梭菌相关疾病。
• 一种氨酯类化合物及其合成与应用
  申请人：华中科技大学

  公开号：CN108084059B

  公开（公告）日：2019-11-12

  本发明公开了一种氨酯类化合物及其合成与应用，该氨酯类化合物具有如式(一)或式(二)所示结构，其合成方法是以甲基丙烯酸缩水甘油酯和CO 2 为原料合成环状碳酸酯中间体，然后再与单氨基化合物发生开环反应即得到氨酯类化合物。本发明通过对其关键的分子结构，合成方法整体流程工艺设计、以及各个步骤的参数及条件进行改进，方法简单、产率高，制得的氨酯类化合物能够有效应用于聚碳酸亚丙酯的增强增韧改性中，可有效解决改性聚碳酸亚丙酯力学性能不理想等问题。
• Long chain carboxylic acid maleimides
  申请人：Kuraray Co., Ltd.

  公开号：US05360914A1

  公开（公告）日：1994-11-01

  Provided are novel superoxide dismutase derivatives represented by the following general formula (I) ##STR1## wherein [SOD] is a superoxide dismutase residue derived by removal of two mercapto groups, and W is a divalent long chain hydrocarbon residue which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom and a group of -N(R)- (R being a lower alkyl group). The SOD derivatives retain most of the enzymatic activities of unmodified SOD and have much longer plasma half-life than unmodified SOD. They are effective for treating various diseases caused by active oxygen species. Also provided are chemical modifiers to prepare the above SOD derivatives.

  提供了以下一般式（I）所表示的新型超氧化物歧化酶衍生物：##STR1## 其中[SOD]是去除两个巯基团而得到的超氧化物歧化酶残基，W是一个二价的长链烃基残基，其可以选择性地被一个或多个分别从氧原子、硫原子和-N（R）-（R为低碳基）的群组中选择的基团所中断。这些SOD衍生物保留了未经改性的SOD的大部分酶活性，并且比未经改性的SOD具有更长的血浆半衰期。它们对于治疗由活性氧物种引起的各种疾病是有效的。此外，还提供了化学修饰剂来制备上述SOD衍生物。
• [EN] DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT
  申请人：UNIV MISSOURI

  公开号：WO2009158633A1

  公开（公告）日：2009-12-30

  Conjugated compounds comprising a therapeutic or diagnostic agent linked to a substrate for a cell membrane transporter or receptor by lipophilic linker are provided.

  提供了包含治疗或诊断药物与细胞膜转运体或受体的底物通过亲脂性连接剂连接的共轭化合物。