Branched lipid chains to prepare cationic amphiphiles producing hexagonal aggregates: supramolecular behavior and application to gene delivery.,Organic & Biomolecular Chemistry

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Branched lipid chains to prepare cationic amphiphiles producing hexagonal aggregates: supramolecular behavior and application to gene delivery.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-12-17 , DOI: 10.1039/c9ob02381j
Amal Bouraoui ₁ , Rosy Ghanem , Mathieu Berchel , Laure Deschamps , Véronique Vié , Gilles Paboeuf , Tony Le Gall , Tristan Montier , Paul-Alain Jaffrès

Affiliation

A ramified lipid alcohol, 2-hexyldecanol, was used as a hydrophobic moiety to prepare cationic amphiphiles on a gram scale in 3 to 4 steps, featuring either a trimethylammonium 5, dimethylhydroxyethylammonium 6 or N-methylimidazolium 7 polar head group. Compression isotherms at the air-water interface reveal that all these cationic amphiphiles collapse at a relatively low pressure indicating a weak stabilization of the monolayer via hydrophobic interactions. Ellipsometry measurements point out the presence of a thin monolayer at low lateral pressure whereas thickening of the monolayer occurs at higher pressure with a high percentage of variation of the thickness, thus demonstrating an adaptability to the constraints. 31P NMR spectroscopy of the hydrated cationic amphiphiles clearly shows that these cationic amphiphiles self-assemble in water to form hexagonal phases, irrespective of the nature of their polar head group. Furthermore, a comparison of molecular structures suggests that compounds 5-7 self-organize into an inverted hexagonal phase (HII). These cationic amphiphiles, alone or in the presence of DOPE, were evaluated for the transfection of three human-derived cell lines (i.e. A549, 16HBE and HeLa). The three compounds demonstrated high transfection efficacies in every cell line tested, 7/DOPE being the most efficient.

中文翻译：

分支脂质链，用于制备产生六边形聚集体的阳离子两亲物：超分子行为及其在基因传递中的应用。

将分枝的脂质醇2-己基癸醇用作疏水部分，以3至4步以克级制备阳离子两亲物，其特征在于三甲基铵5，二甲基羟乙基铵6或N-甲基咪唑鎓7极性头基。空气-水界面的压缩等温线表明，所有这些阳离子两亲物都在相对较低的压力下坍塌，表明单层通过疏水作用的稳定性较弱。椭偏测量法指出在低的侧向压力下存在薄的单层，而在较高的压力下厚度的高百分比变化会发生单层的增厚，因此证明了对约束的适应性。水合阳离子两亲物的31 P NMR光谱清楚地表明，这些阳离子两亲物在水中自组装形成六方相，而不论其极性首基的性质如何。此外，分子结构的比较表明化合物5-7自组织成倒六角相（HII）。单独或在DOPE存在下，对这些阳离子两亲物进行了三种人源细胞系（即A549、16HBE和HeLa）的转染评估。这三种化合物在每个测试的细胞系中均显示出高转染效率，其中7 / DOPE是最有效的。单独或在存在DOPE的情况下，对三种人源细胞系（即A549、16HBE和HeLa）的转染进行了评估。这三种化合物在每个测试的细胞系中均显示出高转染效率，其中7 / DOPE是最有效的。单独或在存在DOPE的情况下，对三种人源细胞系（即A549、16HBE和HeLa）的转染进行了评估。这三种化合物在每个测试的细胞系中均显示出高转染效率，其中7 / DOPE是最有效的。

更新日期：2020-01-02

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