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Synthesis, Surface Activity, and Biological Activities of Phosphonium and Metronidazole Salts
Journal of Surfactants and Detergents ( IF 1.6 ) Pub Date : 2020-07-23 , DOI: 10.1002/jsde.12439
Miloš Lukáč 1 , Martin Pisárčik 1 , Mária Garajová 2 , Martin Mrva 2 , Aneta Dušeková 2 , Andrej Vrták 1 , Renáta Horáková 1 , Branislav Horváth 3 , Ferdinand Devínsky 4
Affiliation  

A series of phosphonium amphiphilic compounds was synthesized. Cationic parts of molecules contain triphenylphosphonium moieties. Lipophilic parts of compounds are represented by straight alkyl chain or the alkyl chains which are ornamented by benzyl or metronidazole. The physicochemical properties of phosphonium amphiphilic compounds were investigated by the measurements of surface tension and conductivity. The critical micelle concentration (cmc), the surface tension value at the cmc (γcmc), the surface area at the surface saturation per head group (Acmc) were determined. The lowest cmc value was determined for phosphonium salts with straight dodecyl alkyl chain. Its value was 1.5 × 10−3 mol dm−3. Surface tension at the cmc decreases with the addition of bulky moieties (benzyl, radical from metronidazol) at the end of alkyl chains. Biological activities of compounds were studied on human erythrocytes and strains of Acanthamoeba lugdunensis and Acanthamoeba quina. Dodecyltriphenylphosphonium bromide showed the highest activity against Acanthamoeba. To the best of our knowledge, it is the first compound of the group of phosphonium amphiphiles, which exhibited high activity against Acanthamoeba. The determined structure–activity relationship indicated nonspecific trophocidal and hemolytic activity that depends on physicochemical properties of the studied compounds.

中文翻译:

os和甲硝唑盐的合成,表面活性和生物活性

合成了一系列of两亲化合物。分子的阳离子部分包含三苯基phosph部分。化合物的亲脂部分由直链烷基链或由苄基或甲硝唑修饰的烷基链表示。通过测量表面张力和电导率来研究phospho两亲化合物的理化性质。临界胶束浓度(CMC),在CMC中的表面张力值(γ CMC),以每头组(表面饱和的表面积CMC)进行了测定。确定具有直链十二烷基烷基链的phospho盐的最低cmc值。其值为1.5×10 -3 mol dm -3。cmc处的表面张力会随着在烷基链末端添加庞大的部分(苄基,来自甲硝唑的自由基)而降低。研究了该化合物对人红细胞及棘棘棘ant棘棘棘的生物学活性。十二烷基三苯基溴化showed显示出最高的抗棘阿米巴活性。据我们所知,它是of两亲物类中的第一种化合物,它对棘阿米巴具有高活性。确定的结构活性关系表明非特异性的杀菌和溶血活性取决于所研究化合物的理化性质。
更新日期:2020-07-23
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