Kuznetsova Darya A, Kuznetsov Denis M, Amerhanova Syumbelya K, Buzmakova Ekaterina V, Lyubina Anna P, Syakaev Victor V, Nizameev Irek R, Kadirov Marsil K, Voloshina Alexandra D, Zakharova Lucia Ya
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov str. 8, Kazan 420088, Russia.
Langmuir. 2022 Apr 26;38(16):4921-4934. doi: 10.1021/acs.langmuir.2c00299. Epub 2022 Apr 11.
Novel cationic amphiphiles of the 3-alkyl-1-(4-methoxyphenyl)-1-imidazol-3-ium bromide series bearing methoxyphenyl fragments (MPI-) have been synthesized. Their aggregation properties in aqueous solutions, solubilization capacity, and hemolytic and antimicrobial activities have been investigated by a number of physicochemical methods. Using tensiometry, conductometry, and fluorescence spectroscopy, it was shown that the MPI- have lower CMCs than their nonfunctionalized counterparts. The unusual alkyl-chain-length-dependent morphology of aggregates is testified for this homological series. Amphiphiles with 12, 14, and 16 alkyl tails are characterized by the formation of micellar aggregates, while a surfactant with a decyl tail is characterized by the formation of larger aggregates with lower surface curvature. The MPI-10 aggregate morphology was rationalized in terms of the packing parameter consideration and was supported by size measurements and the fluorescence probe techniques, which showed that vesicle-like aggregates in close-packing mode probably occur. MPI- aggregates have exhibited a high solubilization capacity toward hydrophobic azo dye Orange OT. Importantly, amphiphiles studied showed (i) high bacteriostatic activity at the level of ciprofloxacin; (ii) high bactericidal action against all Gram-positive bacteria, including methicillin-resistant strains; (iii) bactericidal properties against Gram-negative bacteria; and (iv) low hemolytic activity.
已合成了带有甲氧基苯基片段（MPI-）的新型3-烷基-1-（4-甲氧基苯基）-1-咪唑-3-溴化铵系列阳离子两亲物。通过多种物理化学方法研究了它们在水溶液中的聚集性质、增溶能力以及溶血和抗菌活性。使用表面张力测定法、电导测定法和荧光光谱法表明，MPI-的临界胶束浓度低于其未官能化的对应物。对于这个同系物系列，证实了聚集体具有不寻常的烷基链长度依赖性形态。具有12、14和16个烷基尾的两亲物的特征是形成胶束聚集体，而具有癸基尾的表面活性剂的特征是形成表面曲率较低的较大聚集体。根据堆积参数的考虑对MPI-10的聚集体形态进行了合理化解释，并得到了尺寸测量和荧光探针技术的支持，这些技术表明可能存在紧密堆积模式的囊泡状聚集体。MPI-聚集体对疏水性偶氮染料橙黄OT表现出高增溶能力。重要的是，所研究的两亲物显示出：（i）在环丙沙星水平上具有高抑菌活性；（ii）对所有革兰氏阳性菌具有高杀菌作用，包括耐甲氧西林菌株；（iii）对革兰氏阴性菌具有杀菌特性；以及（iv）低溶血活性。
