Synthesis, Structure and Antimicrobial Properties of Novel Benzalkonium Chloride Analogues with Pyridine Rings.
Synthesis, Structure and Antimicrobial Properties of Novel Benzalkonium Chloride Analogues with Pyridine Rings.
复制标题
DOI：
10.3390/molecules22010130
复制
发表时间：
2017-01-13
期刊：
影响因子：
--
通讯作者：
Otlewska A
中科院分区：
文献类型：
--
作者：
Brycki B;Małecka I;Koziróg A;Otlewska A
季铵化合物(QAC)是一类具有重要经济意义的化合物。它们广泛用作家用和工业产品中的乳化剂、洗涤剂、增溶剂和缓蚀剂。由于其优异的抗菌活性，QAC在医院、农业和食品工业中作为抗菌剂也获得了特殊的意义。杀灭微生物的QAC的主要代表是苯扎氯铵(BACs)，它对大多数细菌、真菌、藻类和一些病毒具有杀灭活性。然而，QAC的滥用，主要是在亚致死浓度下，可能导致微生物耐药性的增加。避免这一严重问题的方法之一是引入和使用具有改性结构的新的杀生剂，而不是迄今所应用的杀生剂。因此，我们合成了新的含吡啶环的BAC类似物P13-P18。用核磁共振、红外光谱和电喷雾质谱等方法对新化合物进行了表征。对化合物P13-P18的分子结构和生成热进行了PM3半经验计算。测定了临界胶束化浓度(CMC)来表征新的BAC类似物的聚集行为。通过测定新型QAC对真菌黑曲霉、白色念珠菌、产黄青霉和金黄色葡萄球菌、枯草杆菌、大肠杆菌和铜绿假单胞菌的最小抑菌浓度(MIC)，考察了新型QAC的抗菌性能。N，N-dimethyl-N-(4-methylpyridyl)-N-alkylammonium氯化物对真菌的MIC值为0.10~12 mm，对细菌的MIC值为0.02~6 mm。
Quaternary ammonium compounds (QACs) are a group of compounds of great economic significance. They are widely used as emulsifiers, detergents, solubilizers and corrosion inhibitors in household and industrial products. Due to their excellent antimicrobial activity QACs have also gained a special meaning as antimicrobials in hospitals, agriculture and the food industry. The main representatives of the microbiocidal QACs are the benzalkonium chlorides (BACs), which exhibit biocidal activity against most bacteria, fungi, algae and some viruses. However, the misuses of QACs, mainly at sublethal concentrations, can lead to an increasing resistance of microorganisms. One of the ways to avoid this serious problem is the introduction and use of new biocides with modified structures instead of the biocides applied so far. Therefore new BAC analogues P13–P18 with pyridine rings were synthesized. The new compounds were characterized by NMR, FT-IR and ESI-MS methods. PM3 semiempirical calculations of molecular structures and the heats of formation of compounds P13–P18 were also performed. Critical micellization concentrations (CMCs) were determined to characterize the aggregation behavior of the new BAC analogues. The antimicrobial properties of novel QACs were examined by determining their minimal inhibitory concentration (MIC) values against the fungi Aspergillus niger, Candida albicans, Penicillium chrysogenum and bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa. The MIC values of N,N-dimethyl-N-(4-methylpyridyl)-N-alkylammonium chlorides for fungi range from 0.1 to 12 mM and for bacteria, they range from 0.02 to 6 mM.
登录
查看更多内容
影响因子：
3.6
作者：
Gottlieb, HE;Kotlyar, V;Nudelman, A
通讯作者：
Nudelman, A
影响因子：
0.6
作者：
Domagk, G
通讯作者：
Domagk, G
影响因子：
5.6
作者：
Kozirog, Anna;Rajkowska, Katarzyna;Gutarowska, Beata
通讯作者：
Gutarowska, Beata
DOI：
10.3390/molecules16010319
发表时间：
2011-01-05
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Brycki B;Kowalczyk I;Kozirog A
通讯作者：
Kozirog A
影响因子：
1.7
作者：
Kozirog, Anna;Brycki, Bogumil
通讯作者：
Brycki, Bogumil