Parshad Badri, Achazi Katharina, Böttcher Christoph, Haag Rainer, Sharma Sunil K
Department of Chemistry, University of Delhi, Delhi, 110007, India.
Department of Chemical Engineering and Biotechnology, University of Cambridge, Cambridge, CB3 0AS, UK.
ChemMedChem. 2021 May 6;16(9):1457-1466. doi: 10.1002/cmdc.202100031. Epub 2021 Mar 8.
A new series of nonionic gemini amphiphiles have been synthesized in a multi-step chemoenzymatic approach by using a novel A B -type central core consisting of conjugating glycerol and propargyl bromide on 5-hydroxy isophthalic acid. A pair of hydrophilic monomethoxy poly(ethylene glycol) (mPEG) and hydrophobic linear alkyl chains (C /C ) were then added to the core to obtain amphiphilic architectures. The aggregation tendency in aqueous media was studied by dynamic light scattering, fluorescence spectroscopy and cryogenic transmission electron microscopy. The nanotransport potential of the amphiphiles was studied for model hydrophobic guests, that is, the dye Nile Red and the drug Nimodipine by using UV/Vis and fluorescence spectroscopy. Evaluation of the viability of amphiphile-treated A549 cells showed them to be well tolerated up to the concentrations studied. Being ester based, these amphiphiles exhibit stimuli-responsive sensitivity towards esterases, and a rupture of amphiphilic architecture was observed in the presence of immobilized Candida antarctica lipase (Novozym 435), thus facilitating release of the encapsulated guest from the aggregate.
通过一种多步化学酶法合成了一系列新的非离子型双子两亲分子，该方法使用了一种新型的AB型中心核，该中心核由在5-羟基间苯二甲酸上共轭甘油和炔丙基溴组成。然后将一对亲水性单甲氧基聚（乙二醇）（mPEG）和疏水性线性烷基链（C/C）添加到核心上，以获得两亲性结构。通过动态光散射、荧光光谱和低温透射电子显微镜研究了其在水性介质中的聚集趋势。通过紫外/可见光谱和荧光光谱研究了两亲分子对模型疏水性客体（即染料尼罗红和药物尼莫地平）的纳米传输潜力。对经两亲分子处理的A549细胞的活力评估表明，在所研究的浓度范围内，它们具有良好的耐受性。由于这些两亲分子是基于酯的，它们对酯酶表现出刺激响应敏感性，并且在固定化南极假丝酵母脂肪酶（诺维信435）存在的情况下观察到两亲性结构的破裂，从而促进了包封客体从聚集体中的释放。
