1-octadecyl-1'-methyl-4,4'-bipyridinium bromide iodide | 1037718-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-octadecyl-1'-methyl-4,4'-bipyridinium bromide iodide
• 英文别名: 1-octadecyl-1′-methyl-4,4′-bipyridinium bromide iodide；1-methyl-4-(1-octadecylpyridin-1-ium-4-yl)pyridin-1-ium;bromide;iodide
• CAS: 1037718-00-5
• 化学式: Br*C₂₉H₄₈N₂*I
• 分子量: 631.522
• InChiKey: AKKPMNYQBOMSBF-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  7.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-octadecyl-1'-methyl-4,4'-bipyridinium bromide iodide 在 Amberlite IRA-400 resin chloride form 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  链长在甲基烷基紫精的葫芦[8]尿素络合中的作用

  摘要：

  在水中研究了烷基链长度对四种甲基紫胶单体（MVCn，n = 12、14、16、18）与葫芦[8] uril（CB [8]）结合模式的影响，揭示了从从12到16个碳原子移动的化学计量比为1：1至2：1。通过CB [8] 2 -MVC18配合物的晶体结构测定，获得了固态化学计量比为2：1的前所未有的证据。

  DOI：

  10.1002/ejoc.202100014
• 作为产物：
  描述：

  4,4'-联吡啶 以 乙腈 为溶剂， 反应 49.0h， 生成 1-octadecyl-1'-methyl-4,4'-bipyridinium bromide iodide
  参考文献：
  名称：

  The antibacterial activity of 4,4′-bipyridinium amphiphiles with conventional, bicephalic and gemini architectures

  摘要：

  Dialkyl 4,4'-bipyridinium compounds are widely employed for their useful redox properties, and are commonly known as viologens due to their intense coloration upon reduction. Despite their prevalence and amphiphilic nature, the antibacterial activity of these compounds remains largely unreported. We have thus prepared a series of mono-and bis-alkylated analogs of 4,4'-bipyridine to investigate structure-activity relationships in their inhibition of a battery of Gram positive and Gram negative bacteria. The prepared cationic compounds were conventional (one cationic head, one non-polar tail), bicephalic (two heads, one tail), or gemini (two heads, two tails) in their amphiphilic structure. Additionally, an isomeric series of six bis-alkylated compounds ranging from symmetric (PQ-11,11) to highly asymmetric (PQ-20,2) were prepared. Four themes of bioactivity emerged: (1) the most bioactive compounds were gemini in structure; (2) 22 carbons in the alkyl chains, with little to modest asymmetry, led to optimal activity; (3) bicephalic compounds were generally comparable to conventional amphiphiles, though only about 12 carbons in the alkyl chains were solubilized in water by each cationic nitrogen; (4) the effects of counterion identity were not evident between chlorides and bromides; however, the presence of the iodide counterion inhibited dissolution in all compounds tested. Three isomeric compounds with little to no asymmetry in tail length, PQ-11,11, PQ-12,10, and PQ-14,8, prepared as the bromide salts, showed comparable and highly potent activity, with MIC levels around 2 mu M against 3 of 4 bacteria tested. The simple (one-to two-step) syntheses of potent antimicrobials portend well for future optimization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.079

文献信息

• Aptamer-based self-assembled supramolecular vesicles for pH-responsive targeted drug delivery
  作者：Shuxian Wu、Juan Li、Hong Liang、Liping Wang、Xian Chen、Guixiao Jin、Xiaoping Xu、Huang-Hao Yang

  DOI：10.1007/s11426-016-0351-5

  日期：2017.5

  cytotoxic effect on target cancer cells, but not control cells. Furthermore, through simple aptamer or drug substitution, supramolecular vesicles can be applied to a variety of target cell lines and drugs, making it widely applicable. Taking advantage of the easy preparation, good stability, rapid pH response, and cell targeting ability, the aptamer-based self-assembled supramolecular vesicles hold great

  超分子囊泡由于其固有特征，包括简单的合成和可调节的两亲性，因而在生物医学应用中受到了极大的关注。尽管进行了巨大的研究，开发具有目标识别和控释的超分子囊泡仍然是主要挑战。在这里，我们通过host，紫精脂质和葫芦[8]的宿主-客体复合物构建了一种基于适体的自组装超分子囊泡，用于pH响应和靶向药物递送。提出的超分子囊泡易于组装并提供简单的药物装载。基于共聚焦荧光显微镜和细胞毒性实验，载药超分子囊泡对靶癌细胞具有高效内在化和明显的细胞毒性作用，但不控制细胞。此外，通过简单的适体或药物替代，超分子囊泡可应用于多种靶细胞系和药物，使其广泛适用。利用易于制备，良好的稳定性，快速的pH响应和细胞靶向能力，基于适体的自组装超分子囊泡在控释生物医学应用和靶向癌症治疗中具有广阔的前景。
• Supramolecular Block Copolymers with Cucurbit[8]uril in Water
  作者：Urs Rauwald、Oren A. Scherman

  DOI：10.1002/anie.200705591

  日期：2008.5.13