Structure-Activity Relationships of the Imidazolium Compounds as Antibacterials of Staphylococcus aureus and Pseudomonas aeruginosa

Abstract

This paper presents the results of structure–activity relationship (SAR) studies of 140 3,3’-(α,ω-dioxaalkan)bis(1-alkylimidazolium) chlorides. In the SAR analysis, the dominance-based rough set approach (DRSA) was used. For analyzed compounds, minimum inhibitory concentration (MIC) against strains of Staphylococcus aureus and Pseudomonas aeruginosa was determined. In order to perform the SAR analysis, a tabular information system was formed, in which tested compounds were described by means of condition attributes, characterizing the structure (substructure parameters and molecular descriptors) and their surface properties, and a decision attribute, classifying compounds with respect to values of MIC. DRSA allows to induce decision rules from data describing the compounds in terms of condition and decision attributes, and to rank condition attributes with respect to relevance using a Bayesian confirmation measure. Decision rules present the most important relationships between structure and surface properties of the compounds on one hand, and their antibacterial activity on the other hand. They also indicate directions of synthesizing more efficient antibacterial compounds. Moreover, the analysis showed differences in the application of various parameters for Gram-positive and Gram-negative strains, respectively.

Rough Sets Turn 40: From Information Systems to Intelligent Systems

“…When thinking about the future it is also worth referring to the history. That reflected one more objective: acknowledging the 40th anniversary of rough sets [1], their founder [5], as well as some of relevant past and present events such as FedCSIS 2012 (rough set papers published exactly 10 years ago) [47], [48], [51], [53], [54], [57], [58], [59], [61], [64], [66], the PP-RAI 2022 rough set contest [69], [70], [72], [73], [77], [78], [81], [82], [83], [84], [89], [90], [91], [95], [96], [97], [98], [101], [105], [106] and celebration of the 30th CS&P -the event series whereby this paper's topics have been regularly addressed [36], [40], [44], [103], [116], [123].…”

“…Papers [89], [90], [91] illustrate more real-world applications of rough set methods in the area of biomedicine. The first paper uses rough set approximations built over neighborhood-based information granules [92].…”

“…As an example, let us think one more time about the task of feature selection. There are various techniques of measuring and visualizing attribute importance [88], [90], [94] but they are usually applied to report to humans the final results instead of "inviting" them into a more interactive dialogue on feature selection process. In this regard, we refer to [85] where incrementally constructed information systems are employed to guide subject matter experts through such an interactive process, letting them share their recommendations about the most relevant attributes.…”

Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

“…In recent years, our team has studied the synthesis, biological and surface activity, and structure–activity relationships (SAR) of quaternary ammonium salts. In the scope of our interest are mainly mono- and bis-imidazolium salts [ 15 , 16 , 17 ]. We found that the following structures of bis-imidazolium chlorides have the optimal antimicrobial activity: 3,3’- (α, ω-dioxaalkane) bis (1-alkylimidazolium chloride), which has at least six carbon atoms in its linker, and has a R substituent of C7 to C11; α, ω-bis [(alkane) imidazol-1-yl-3-alkoxymethyl] chloride, which has at least five carbon atoms in the linker, and has a C7 to C13; and 3,3’- (α, ω-dioxaalkane) bis (1-alkylimidazolium) chloride or α, ω-bis [(alkane) imidazol-1-yl-3- alkoxymethyl chloride], which has at least seven carbon atoms and has a substituent R of C7 to C11.…”

Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity

“…Importantly, higher antimicrobial activity of gemini surfactants is observed in some cases [ 14 , 15 , 16 ]. It is worth noting that dicationic surfactants with imidazolium head group have recently been reported: the variation of alkyl tail length and distance between cationic centers [ 17 , 18 , 19 ], introduction of substituents into the spacer fragment [ 20 ], as well as modification of the structure of the imidazolium head group [ 21 ] allows for controlling their aggregation behavior and properties, including antimicrobial activity. Previously, the biological activity of dicationic imidazolium surfactants with decyl and dodecyl tails have been studied in our research group, which showed high antimicrobial effects against a number of test microorganisms, with low cytotoxic activity observed [ 22 ].…”