Department of Chemistry, Ben-Gurion University, Be'er Sheva 84105, Israel; Department of Chemistry, University of Douala, PO Box 2701, Douala, Cameroon.
Department of Chemistry, Ben-Gurion University, Be'er Sheva 84105, Israel.
Chem Phys Lipids. 2018 May;212:96-110. doi: 10.1016/j.chemphyslip.2018.01.009. Epub 2018 Feb 2.
Based on ricinoleic acid, two asymmetric bolaamphiphiles with unsymmetrical hydrophobic skeletons and two different hydrophilic head groups were designed and synthesized. The first bola compound had acetylcholine (ACh) and maleimide (MAL) head groups while the second was derived from the first bolaamphiphile by thiol-ene conjugation of its maleimide moiety with l-glutathione and possessed ACh and l-glutathione-MAL head groups. Both synthetic bolaamphiphiles were characterized by common spectroscopic methods. The asymmetric bola compound with ACh and MAL head groups was investigated for its ability to self-aggregate into nanoparticles and showed to form in aqueous media nano-sized vesicles that were stable, positively charged and had symmetrical monolayer membrane with antiparallel packing. These vesicles prepared with or without membrane stabilizers such as cholesterol (CHOL) and cholesteryl hemisuccinate (CHEMS) were able to encapsulate carboxyfluorescein (CF), a water soluble and self-quenching marker and particularly those without additives were more CF encapsulating. The synthesis of bolaamphiphile with ACh-l-glutathione-MAL head groups gives evidence that the bola with ACh and MAL head groups can be utilized as a precursor of a plethora of asymmetric bolas.
基于蓖麻油酸，设计并合成了两种具有不对称疏水性骨架和两个不同亲水头基的不对称两性离子两亲分子。第一个两性离子化合物具有乙酰胆碱（ACh）和马来酰亚胺（MAL）头基，而第二个是通过其马来酰亚胺部分与 l-谷胱甘肽的硫醇-烯加成反应从第一个两性离子衍生而来的，具有 ACh 和 l-谷胱甘肽-MAL 头基。两种合成的两性离子两亲分子都通过常见的光谱方法进行了表征。具有 ACh 和 MAL 头基的不对称两性离子化合物被研究其自组装成纳米颗粒的能力，并显示在水介质中形成纳米尺寸的囊泡，这些囊泡稳定、带正电荷且具有具有平行排列的对称单层膜。这些囊泡无论是在有或没有膜稳定剂（如胆固醇（CHOL）和胆甾醇半琥珀酸酯（CHEMS））的情况下制备，都能够包封水溶性和自猝灭标记物羧基荧光素（CF），特别是那些没有添加剂的囊泡能够更好地包封 CF。ACh-l-谷胱甘肽-MAL 头基两性离子两亲分子的合成证明了具有 ACh 和 MAL 头基的两性离子两亲分子可以用作众多不对称两性离子的前体。
