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Thermodynamically stable vesicle formation of biodegradable double mPEG-tailed amphiphiles with sulfonate head group

机译:具有磺酸盐头组可生物降解的双重MPEG尾两种两亲物形成热力学稳定的囊泡

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The development of efficient, biodegradable and biocompatible surfactants has become a pressing need because of adverse effects of surface-active compounds on the aquatic environment and human health. Cleavable surfactants containing a labile functional group have the ability to eliminate some of these problems. Consequently, PEGylated amphiphiles have found widespread applications in pharmaceutics, household purposes, and drug delivery. Herein we report synthesis and characterization of two novel amphiphiles which to our knowledge are the first examples of double PEG-tailed amphiphiles with an anionic head group. Considering their chemical structure, they are expected to be biodegradable, biocompatible, milder and less irritant than conventional surfactants. The solution behavior of these newly developed amphiphiles was thoroughly investigated in aqueous buffer (pH 7.0) at 25 °C. The surface activity of the compounds in aqueous buffer was studied by surface tension measurements. The self-assembly properties were investigated by various techniques such as fluorescence and NMR spectroscopy, dynamic light scattering, transmission electron microscopy, atomic force microscopy, and isothermal titration calorimetry. Both molecules were found to be surface active in water and exhibit spontaneous vesicle formation in the absence of any additives at room temperature. As in the cases of conventional surfactants, the self-assembly is driven by the hydrophobic effect. The vesicles produced in aqueous media were shown to encapsulate hydrophobic dyes and exhibit structural transitions upon addition of salts. The sensitivity of the vesicles to change in environments qualifies them for potential use in drug delivery.
机译:由于表面活性化合物对水生环境和人类健康的不利影响,高效,可生物降解和生物相容性表面活性剂的发展已成为压迫需求。含有不稳定官能团的可切割表面活性剂具有消除其中一些问题的能力。因此,聚乙二醇化两亲物在药物,家庭目的和药物递送中发现了广泛应用。在此,我们报告了两种新型两亲物的合成和表征,这是我们所知的是具有阴离子头组的双重尾尾两种的第一个例子。考虑到它们的化学结构,预计它们将是可生物降解的,生物相容性的,较温和的,而不是常规表面活性剂的刺激性。在25℃下在水性缓冲液(pH7.0)中彻底研究这些新开发的两亲物的溶液行为。通过表面张力测量研究了水性缓冲液中化合物的表面活性。通过各种技术研究了自组装性质,例如荧光和NMR光谱,动态光散射,透射电子显微镜,原子力显微镜和等温滴定热法。发现两个分子在水中是活性的,在室温下没有任何添加剂的情况下表现出自发囊泡形成。如在常规表面活性剂的情况下,自组装由疏水效果驱动。显示在水性介质中产生的囊泡被显示为包封疏水染料并在加入盐时表现出结构性转变。囊泡在环境中变化的敏感性有资格获得药物递送的潜在用途。

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