Sasínová Kateřina, Berčíková Markéta, Vrchotová Blanka, Hrádková Iveta, Šmidrkal Jan, Kalenchak Katsiaryna
University of Chemistry and Technology, Prague 166 28, Czech Republic.
ACS Omega. 2025 Aug 21;10(34):39236-39249. doi: 10.1021/acsomega.5c06267. eCollection 2025 Sep 2.
The growing threat of antibiotic-resistant bacteria continues to be one of the biggest challenges facing public health. As a result, there is an increasing focus on developing new substances with both antimicrobial and biofilm inhibition activities. One such group of compounds is surfactants, particularly quaternary ammonium salts (QASs), which are commonly used as disinfectants in healthcare. In this study, a three-step synthesis was used to prepare a range of QASs, including quaternary esters, hydroxyamides, and dihydroxyamides with alkyl chains of 12-18 carbon atoms. First, the initial step of the synthesis was optimized by testing various catalysts, with CHOK showing the highest efficiency and proving to be the most suitable choice for further development. Then, the antimicrobial activity was tested against , , , , and , while biofilm inhibition activity was evaluated only for the bacterial strains (, , and ). The results were compared with those obtained for benzyldimethyldodecylammonium chloride (BDMDAC), which is a commonly used disinfectant. QASs derived from myristic and palmitic acids showed the highest antimicrobial and biofilm inhibition activities, often higher than BDMDAC. Interestingly, some compounds reached maximum biofilm inhibition activity at the lowest concentration testedparticularly stearic acid quaternary hydroxyamide and stearic acid quaternary dihydroxyamide, which reached minimum biofilm inhibitory concentration (MBIC) values as low as 0.016 mmol L. Compounds derived from myristic acid showed higher antimicrobial activity compared with BDMDAC, while both myristic- and palmitic-acid-based compounds demonstrated superior biofilm inhibition activity. These findings highlight the potential of myristic- and palmitic-acid-based QASs as promising candidates for next-generation disinfectant formulations, particularly in applications where strong biofilm inhibition activity is essential.
抗生素耐药细菌构成的威胁日益增长,依然是公共卫生面临的最大挑战之一。因此,人们越来越关注开发具有抗菌和生物膜抑制活性的新物质。其中一类化合物是表面活性剂,特别是季铵盐(QASs),它们在医疗保健中常用作消毒剂。在本研究中,采用三步合成法制备了一系列QASs,包括具有12至18个碳原子烷基链的季酯、羟基酰胺和二羟基酰胺。首先,通过测试各种催化剂对合成的初始步骤进行了优化,CHOK显示出最高效率,并被证明是进一步开发的最合适选择。然后,测试了对[具体菌种1]、[具体菌种2]、[具体菌种3]、[具体菌种4]和[具体菌种5]的抗菌活性,而仅针对细菌菌株([具体菌株1]、[具体菌株2]和[具体菌株3])评估了生物膜抑制活性,并将结果与常用消毒剂苄基二甲基十二烷基氯化铵(BDMDAC)的结果进行了比较。源自肉豆蔻酸和棕榈酸的QASs表现出最高抗菌和生物膜抑制活性,通常高于BDMDAC。有趣的是,一些化合物在测试的最低浓度下达到最大生物膜抑制活性,特别是硬脂酸季铵羟基酰胺和硬脂酸季铵二羟基酰胺,其达到的最低生物膜抑制浓度(MBIC)值低至0.016 mmol/L。与BDMDAC相比,源自肉豆蔻酸的化合物表现出更高的抗菌活性,而基于肉豆蔻酸和棕榈酸的化合物均表现出优异的生物膜抑制活性。这些发现凸显了基于肉豆蔻酸和棕榈酸的QASs作为下一代消毒剂配方的有前景候选物的潜力,特别是在对强大生物膜抑制活性至关重要的应用中。