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Efficient antimicrobial activity and reduced toxicity of 1-dodecyl-3-methylimidazolium tetrafluoroborate ionic liquid/β-cyclodextrin complex
Chemical Engineering Journal ( IF 13.3 ) Pub Date : 2015-09-25 , DOI: 10.1016/j.cej.2015.09.041
Diana Hodyna , Jean-Francois Bardeau , Larisa Metelytsia , Sergii Riabov , Larisa Kobrina , Svitlana Laptiy , Larisa Kalashnikova , Valeriy Parkhomenko , Oksana Tarasyuk , Sergiy Rogalsky

Water immiscible ionic liquid 1-dodecyl-3-methylimidazolium tetrafluoroborate (DMIM-BF4) and its inclusion complex with β-cyclodextrin (β-CD) in molar ratio 1:1 have been synthesized. The formation of DMIM-BF4/β-CD complex was confirmed by FT-IR analysis, 1H NMR analysis, and differential scanning calorimetry data. Our results indicate that the aliphatic tail of DMIM-BF4 is included into β-CD inner cavity whereas imidazolium ring is located outside the torus. Moreover, the weak interaction between polar components of ionic liquid and hydrophilic outer surface of β-CD has also been detected. The standard agar disk diffusion method was performed to evaluate antimicrobial efficiency of the obtained compounds against Staphylococcus aureus (ATCC-25923), Escherichia coli (ATCC-25922) and Pseudomonas aeruginosa (ATCC-27853), Candida albicans (M 885 ATCC 10231) and its clinical isolate test-cultures. It has been found that both DMIM-BF4 and DMIM-BF4/β-CD complex possess high antimicrobial activity as revealed by similar zone inhibition values against all tested microorganisms. The acute toxicity studies on Danio rerio (zebrafish) model organism showed that the pure ionic liquid DMIM-BF4 is slightly toxic compound having LD50 value of 7 mg/L, whereas DMIM-BF4/β-CD complex has considerably reduced toxicity (LD50 = 100 mg/L) and therefore have potentially wider application areas.



中文翻译:

1-十二烷基-3-甲基咪唑四氟硼酸离子液体/β-环糊精复合物的高效抗菌活性和降低的毒性

合成了与水不混溶的离子液体四氟硼酸1-十二烷基-3-甲基咪唑鎓(DMIM-BF 4)及其与β-环糊精(β-CD)的摩尔比为1:1的包合物。通过FT-IR分析,1 H NMR分析和差示扫描量热法数据确认了DMIM-BF 4 /β-CD复合物的形成。我们的结果表明,DMIM-BF 4的脂肪族尾部包含在β-CD内腔中,而咪唑环则位于圆环的外部。而且,还已经检测到离子液体的极性组分与β-CD的亲水性外表面之间的弱相互作用。进行标准琼脂圆盘扩散法以评估所得化合物对金黄色葡萄球菌(ATCC-25923),大肠杆菌(ATCC-25922)和铜绿假单胞菌(ATCC-27853),白色念珠菌(M 885 ATCC 10231)及其临床分离试验培养物。已经发现DMIM-BF 4和DMIM-BF 4 /β-CD复合物均具有高的抗菌活性,如通过针对所有测试微生物的相似的区域抑制值所揭示的。对斑马鱼Danio rerio)(斑马鱼)模型生物的急性毒性研究表明,纯离子液体DMIM-BF 4是轻度毒性化合物,LD 50值为7 mg / L,而DMIM-BF 4 /β-CD复合物的毒性大大降低。 (LD50  = 100 mg / L),因此可能具有更广泛的应用领域。

更新日期:2015-09-25
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