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，设计并合成了两个具有不对称的疏水骨架和两个不同的亲水头基的不对称的双亲两亲物。第一个bola化合物具有乙酰胆碱（ACh）和马来酰亚胺（MAL）头基，而第二个bola化合物则是通过第一个bolaamphiphile的马来酰亚胺部分与1-谷胱甘肽的硫醇-烯键合衍生而来的，并具有ACh和l-谷胱甘肽-MAL头基。两种合成的双亲两亲物均通过常规光谱法表征。研究了具有ACh和MAL头基的不对称bola化合物自聚集到纳米颗粒中的能力，并显示在水介质中形成稳定，带正电荷且具有对称的单层膜且具有反平行堆积的纳米大小的囊泡。这些带有或不带有膜稳定剂如胆固醇（CHOL）和胆固醇半琥珀酸酯（CHEMS）的囊泡能够囊封羧基荧光素（CF），水溶性和自淬灭性标记物，尤其是那些没有添加添加剂的囊泡则更多地囊封CF。ACh- 1合成保兰两亲-谷胱甘肽-MAL头基团提供了证据，证明具有ACh和MAL头基团的布拉可被用作大量不对称的布拉的前体。