A bolaamphiphile is a special member of amphiphilic molecules, which contains a hydrophobic skeleton and two water-soluble groups on both ends. Bolaamphiphiles form thermally stable associates in water under lower concentration than those of typical monoheaded amphiphiles, indicating the potential usefulness of bolaamphiphiles as the component of nanomaterials. However, the structural diversity of bolaamphiphiles is limited at this moment. We recently developed the synthesis of quercetin-3-O-polyglycoside (QP) as a new entry of bolaamphiphiles via a one-pot polymerization using sugar-based cyclic sulfite initiated by quercetin skeleton. Herein, we show the bolaamphiphilic properties of QP in detail. The micellization behaviors of QP are systematically investigated through comparison with those of quercetin (Que) and isoquercitrin (IQ) to evaluate the roles of glycone on the micellization of quercetin derivatives. The morphology of the micelles bearing QP is observed by cryo-transmission electron microscopy (cryo-TEM), suggesting the formation of bolaamphiphile-specific giant ribbon-like micelles in addition to spherical micelles. The thermoresponsive micellization behaviors are also discussed through the critical micelle concentration (CMC) values, the dynamic light scattering analyses at various temperatures, and thermal hysteresis of the micellizations. It is indicated that the polysaccharide chains integrated on the surface of micelles would serve as a steric protecting group to endow the micelles with kinetic stability. These results will shed light on natural glycoside skeletons to design a new class of micelles for advanced health applications in near future.

中文翻译：

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包含Bolaamphiphilic槲皮素多糖苷的胶束的热响应结构和染料封装。

保双亲分子是两亲分子的特殊成员，它包含一个疏水性骨架和两个末端的两个水溶性基团。亲水性两亲物以比典型的单头两亲物更低的浓度在水中形成热稳定的缔合体，表明疏水性两亲物作为纳米材料的组分的潜在用途。但是，此时的保双亲分子的结构多样性受到限制。我们最近开发了槲皮素3- O-聚糖苷（QP）的合成，是通过槲皮素骨架引发的基于糖的环状亚硫酸盐通过一锅聚合来合成保兰两亲的新产品。在此，我们详细显示了QP的疏甲两亲性。QP的胶束化行为通过与槲皮素（Que）和异槲皮素（IQ）进行比较，系统地研究了甜菜碱，以评估糖苷对槲皮素衍生物胶束化的作用。带有QP的胶束的形态通过冷冻透射电子显微镜（cryo-TEM）观察到的“ X射线”表明，除了球形胶束之外，还形成了亲双亲亲状的巨型带状胶束。还通过临界胶束浓度（CMC）值，各种温度下的动态光散射分析以及胶束的热滞现象来讨论热敏胶束行为。结果表明，整合在胶束表面的多糖链可作为空间保护基团，赋予胶束动力学稳定性。这些结果将阐明天然糖苷骨架，以在不久的将来设计出一类新型胶束，用于先进的健康应用。