Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov Str. 8, Kazan, 420088, Russian Federation.
Kazan National Research Technological University, Kazan, 420015, Russian Federation.
Chem Biodivers. 2022 Feb;19(2):e202100496. doi: 10.1002/cbdv.202100496. Epub 2022 Jan 13.
Water-soluble trialkylammonium isatin-3-hydrazone derivatives bearing phenolic substituent were easily synthesized with high yields. XRD studies confirmed the presence of these compounds as trans-(Z)-isomers in a crystal. It was shown that an increase in the lipophilicity of the cationic center leads to an increase in activity against Gram-positive bacteria Staphylococcus aureus and Bacillus cereus, including methicillin-resistant Staphylococcus aureus (MRSA) strains. The MIC values of all compounds turned out to be 2-100 times higher than the MIC of norfloxacin against the MRSA strains in the absence of hemo- and cytotoxicity. Antiaggregation and anticoagulation properties were in vitro better than for acetylsalicylic acid and sodium heparin drugs. It has been shown by UV spectroscopy and fluorescence microscopy that the mechanism of antimicrobial action of new acylhydrazones is associated with their ability to destroy the bacterial cell membrane.
水溶性三烷基铵取代的靛红-3-腙衍生物很容易以高产率合成。XRD 研究证实这些化合物在晶体中以反式（Z）异构体存在。结果表明，增加阳离子中心的亲脂性会导致对革兰氏阳性菌金黄色葡萄球菌和蜡状芽孢杆菌（包括耐甲氧西林金黄色葡萄球菌（MRSA）株）的活性增加。所有化合物的 MIC 值都比诺氟沙星对无血和细胞毒性的 MRSA 菌株的 MIC 值高 2-100 倍。抗聚集和抗凝作用优于乙酰水杨酸和肝素钠药物。通过紫外光谱和荧光显微镜表明，新的酰腙类化合物的抗菌作用机制与其破坏细菌细胞膜的能力有关。
