含莰烯结构的高效广谱抗菌季铵盐的制备、表面活性及生物测定,ACS Omega

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含莰烯结构的高效广谱抗菌季铵盐的制备、表面活性及生物测定
ACS Omega ( IF 3.7 ) Pub Date : 2023-09-17 , DOI: 10.1021/acsomega.3c03599
Yanqun Huang ₁ , Shangchao Huo ₂ , Junming Mo _{2,

3} , Daozhan Huang _{2,

3}

Affiliation

首次合成了一系列包含莰烯部分的新型季铵盐（QAS）（4a – 4n ）。以莰烯为原料，依次通过Prins反应、卤化、季铵化反应制备了14个实例。^{通过傅里叶变换红外光谱、 1} H NMR、¹³ C NMR 和高分辨率质谱分析了合成的 QAS 的结构。然后研究了所研究的化合物的表面活性特性、乳化能力和发泡特性。这些 QAS 对革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）、革兰氏阴性菌（大肠杆菌和肺炎克雷伯菌）和真菌（白色念珠菌、热带念珠菌和黑曲霉）的抗菌活性通过微量稀释测定方法。结果表明，化学结构因素，包括取代基类型和烷基链长度，可能与脂水分配系数（cLog P）相关，在抗菌过程中发挥着关键作用。烷基链长度（N）在10-14范围内的化合物相对活性较高，而带有吡啶鎓、苄基、甲基咪唑鎓基团或不同烷基链长度（N <5和N >16）的化合物几乎没有活性。具有十二烷基的化合物4k对几乎所有测试的细菌和真菌表现出最有效和广谱的抗菌活性，最小抑制浓度值范围为0.24至0.98 μg/mL。

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Highly Effective and Broad-Spectrum Antimicrobial Quaternary Ammonium Salts Containing Camphene Structure: Preparation, Surface-Active Properties, and Bioassay

A series of novel quaternary ammonium salts (QASs) (4a–4n) comprising a camphene moiety were synthesized for the first time. Fourteen examples were prepared from camphene through Prins reaction, halogenation, and quaternarization, successively. The structures of the synthesized QASs were analyzed by Fourier transform infrared spectroscopy, ¹H NMR, ¹³C NMR and high-resolution mass spectrometry. Surface-active properties, emulsifying abilities, and foaming properties of the investigated compounds were then studied. The antimicrobial activities of these QASs against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae), and fungi species (Candida albicans, Candida tropicalis, and Aspergillus niger) were determined by the microdilution method. The results showed that the chemical structural factors, including types of substitutes and alkyl chain length, might be correlated with the lipid–water partition coefficient (cLog P), which played a critical role in the antimicrobial process. Compounds with alkyl chain lengths (N) in the range of 10–14 were relatively more active, while compounds bearing pyridinium, benzyl, methylimidazolium groups, or varied alkyl chain lengths (N < 5 and N > 16) were almost inactive. Compound 4k possessing a dodecyl group exhibited the most effective and broad-spectrum antimicrobial activity against almost all tested bacteria and fungi with the minimal inhibitory concentration values ranging from 0.24 to 0.98 μg/mL.

更新日期：2023-09-17

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