Demberelnyamba D, Kim Ki-Sub, Choi Sukjeong, Park Seung-Yeob, Lee Huen, Kim Chang-Jin, Yoo Ick-Dong
Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology, 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, South Korea.
Bioorg Med Chem. 2004 Mar 1;12(5):853-7. doi: 10.1016/j.bmc.2004.01.003.
For the purpose of developing new disinfectants and antiseptics, we searched for compounds having high bactericidal activity against gram-positive bacteria, gram-negative bacteria, and fungi. Three different series of quaternary imidazolium and pyrrolidinonium salts were synthesized: series A (1-alkyl-3-methylimidazolium chlorides and bromides); series B (1-alkyl-2-methyl-3-hydroxyethylimidazolium chlorides); and series C (N-alkyl-N-hydroxyethylpyrrolidinonium). Series B and C were newly designed. These three series were tested to evaluate their antibacterial and antifungal properties for the first time. Seven microbial strains were used in the study: Escherichia coli KCTC1924, Salmonella typhimurium KCTC1926, Staphylococcus aureus 209 KCTC1916, Staphylococcus aureus R209 KCTC1928, Bacillus subtilis KCTC1914, Candida albicans KCTC1940, and Chlorella regularis. The antimicrobial efficiency was measured by bacterial and fungal growth inhibition expressed as minimal inhibitory concentration (MIC) values. Series A and B imidazolium salts had very good antimicrobial activity against the examined Gram-negative bacteria, Gram-positive bacteria, and fungi. Also the pyrrolidinonium salt was found to have low MIC for some of tested microorganisms. The antibacterial and antifungal active properties of the salts depend upon the structure of functional groups and the alkyl chain length in the imidazolium and pyrrolidinonium ring. Among the synthesized quaternary imidazolium and pyrrolidinonium salts, the imidazolium salts containing a long alkyl chain and the introduction of a hydroxyethyl chain and methyl group into the imidazolium ring structure leads to broad spectrum active antimicrobial agents which not only have bacteriostatic properties but could be powerful bactericides.
为了开发新型消毒剂和防腐剂，我们寻找了对革兰氏阳性菌、革兰氏阴性菌和真菌具有高杀菌活性的化合物。合成了三种不同系列的季铵化咪唑鎓盐和吡咯烷鎓盐：A系列（1-烷基-3-甲基咪唑鎓氯化物和溴化物）；B系列（1-烷基-2-甲基-3-羟乙基咪唑鎓氯化物）；以及C系列（N-烷基-N-羟乙基吡咯烷鎓）。B系列和C系列是新设计的。首次对这三个系列进行测试以评估其抗菌和抗真菌性能。该研究使用了七种微生物菌株：大肠杆菌KCTC1924、鼠伤寒沙门氏菌KCTC1926、金黄色葡萄球菌209 KCTC1916、金黄色葡萄球菌R209 KCTC1928、枯草芽孢杆菌KCTC1914、白色念珠菌KCTC1940和普通小球藻。通过以最低抑菌浓度（MIC）值表示的细菌和真菌生长抑制来测量抗菌效率。A系列和B系列咪唑鎓盐对所检测的革兰氏阴性菌、革兰氏阳性菌和真菌具有非常好的抗菌活性。还发现吡咯烷鎓盐对一些测试微生物的MIC较低。盐的抗菌和抗真菌活性性质取决于咪唑鎓环和吡咯烷鎓环中官能团的结构以及烷基链长度。在合成的季铵化咪唑鎓盐和吡咯烷鎓盐中，含有长烷基链的咪唑鎓盐以及在咪唑鎓环结构中引入羟乙基链和甲基会产生广谱活性抗菌剂，这些抗菌剂不仅具有抑菌特性，而且可能是强力杀菌剂。
