title: Antibacterial Activity of Imidazolium-Based Ionic Liquids Investigated by QSAR Modeling and Experimental Studies.
abstract: Predictive QSAR models for the inhibitors of B. subtilis and Ps. aeruginosa among imidazolium-based ionic liquids were developed using literary data. The regression QSAR models were created through Artificial Neural Network and k-nearest neighbor procedures. The classification QSAR models were constructed using WEKA-RF (random forest) method. The predictive ability of the models was tested by fivefold cross-validation; giving q(2) = 0.77-0.92 for regression models and accuracy 83-88% for classification models. Twenty synthesized samples of 1,3-dialkylimidazolium ionic liquids with predictive value of activity level of antimicrobial potential were evaluated. For all asymmetric 1,3-dialkylimidazolium ionic liquids, only compounds containing at least one radical with alkyl chain length of 12 carbon atoms showed high antibacterial activity. However, the activity of symmetric 1,3-dialkylimidazolium salts was found to have opposite relationship with the length of aliphatic radical being maximum for compounds based on 1,3-dioctylimidazolium cation. The obtained experimental results suggested that the application of classification QSAR models is more accurate for the prediction of activity of new imidazolium-based ILs as potential antibacterials.
authors.affiliation: Department of Medical and Biological Researches, Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, 1, Murmanska Street, Kyiv, 02160, Ukraine.
authors.forename: Diana
authors.initials: D
authors.lastname: Hodyna
authors.affiliation: Department of Medical and Biological Researches, Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, 1, Murmanska Street, Kyiv, 02160, Ukraine.
authors.forename: Vasyl
authors.initials: V
authors.lastname: Kovalishyn
authors.affiliation: Laboratory of Modification of Polymers, Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, 50, Kharkivske Schose, Kyiv, 02160, Ukraine.
authors.forename: Sergiy
authors.initials: S
authors.lastname: Rogalsky
authors.affiliation: Department of Microbiology and Epidemiology, Shupyk National Medical Academy of Postgraduate Education, 9, Dorogozhytska Street, Kyiv, 04112, Ukraine.
authors.forename: Volodymyr
authors.initials: V
authors.lastname: Blagodatnyi
authors.affiliation: Organofluorine Compounds Chemistry Department, Institute of Organic Chemistry, NAS of Ukraine, 5, Murmanska Street, Kyiv, 02660, Ukraine.
authors.forename: Kirill
authors.initials: K
authors.lastname: Petko
authors.affiliation: Department of Medical and Biological Researches, Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, 1, Murmanska Street, Kyiv, 02160, Ukraine.
authors.forename: Larisa
authors.initials: L
authors.lastname: Metelytsia
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D007093:Imidazoles / Q000494:pharmacology*; D052578:Ionic Liquids; D008962:Models, Theoretical; D016571:Neural Networks, Computer; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007093:Imidazoles; D052578:Ionic Liquids
keywords: QSAR; antibacterial activity; imidazolium ionic liquids