(4R,4'R,4''R)-N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (4R,4'R,4''R)-N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide)
• 英文别名: (4R)-N-[2-[bis[2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethyl]amino]ethyl]-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
• 化学式: C₇₈H₁₃₂N₄O₉
• 分子量: 1269.93
• InChiKey: LLSNMTOLHPUUDC-PVFNVHGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  91
• 可旋转键数：
  21
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  212
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以56%的产率得到(4R,4'R,4''R)-N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide)
  参考文献：
  名称：

  Structure and Dynamics of a Molecular Hydrogel Derived from a Tripodal Cholamide

  摘要：

  Tripodal cholamide 1 is a supergelator of aqueous fluids. A variety of physical techniques, including cryo-transmission electron microscopy (TEM), circular dichroism (CD), steady-state fluorescence, time-resolved fluorescence, and dynamic light-scattering, were employed to understand the structure and dynamics of the gel. Fluorescent probes [ANS (8-anilinonaphthalene-1-sulfonic acid) and pyrene] reported two critical aggregation concentrations (CAC(1) and CAC(2)) of 1 in predominantly aqueous media, with the minimum gel concentration (MGC) being close to CAC(2). Fluorescence lifetime measurements with pyrene revealed ineffective quenching of pyrene fluorescence by oxygen, possibly caused by slower Brownian diffusion due to the enhanced viscosity in the gel phase. The study of the gelation kinetics by monitoring the ultrafast dynamics of ANS revealed a progressive increase in the aggregate size and the microviscosity of the aqueous pool encompassed by the self-assembled fibrillar network (SAFIN) during the gelation. The striking difference between microviscosity and bulk (macroscopic) viscosity of the gel is also discussed.

  DOI：

  10.1021/ja046788t

文献信息

• Bile Acid Oligomers and Their Combination with Antibiotics To Combat Bacterial Infections
  作者：Poonam Singla、Priyanka Dalal、Mahaldeep Kaur、Geeta Arya、Surendra Nimesh、Rachna Singh、Deepak B. Salunke

  DOI：10.1021/acs.jmedchem.8b01433

  日期：2018.11.21

  Among the various antimicrobial resistant bacterial strains, methicillin and vancomycin resistant Staphylococcus aureus are among the most dreadful, causing serious complications. On the basis of the hypothesis that microbes have reduced ability to develop resistance against membrane targeting antibiotics, bile acid oligomers having unique facially amphiphilic topologies were designed and synthesized

  细菌耐药性的日益增长的风险是一个至关重要的问题。在各种抗药性细菌菌株中，耐甲氧西林和万古霉素的金黄色葡萄球菌是最可怕的，导致严重的并发症。基于微生物具有降低的针对膜靶向抗生素的抗性的能力的假设，设计并合成了具有独特的两亲两性拓扑结构的胆汁酸低聚物。具有特定接头的寡聚体对革兰氏阳性细菌表现出有效的和选择性的抗菌活性。当组合测试时，先导化合物还改善了属于不同类别的一系列已知抗生素的功效。发现活性二聚体可有效对抗金黄色葡萄球菌的抗生素耐药临床分离株，包括多药耐药分离株。对金黄色葡萄球菌有明显的抑制活性生物膜是一种高度耐药的细菌表型，通常对抗生素治疗无反应。这些二聚体在针对HEK293细胞的细胞活力测定中未观察到不利影响。