Antimicrobial Activity and SAR Study of New Gemini Imidazolium‐Based Chlorides

A series of 70 new 3,3′(α,ω‐dioxaalkyl)bis(1‐alkylimidazolium) chlorides were synthesized. They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei, and Candida albicans. In this article, besides description of the synthesis, we characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkan spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, molecular area of a single particle, and free energy of adsorption of molecule). Then, we present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance‐based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds. The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds.

[1]  Salvatore Greco,et al.  Properties of rule interestingness measures and alternative approaches to normalization of measures , 2012, Inf. Sci..

[2]  J. Chlebicki,et al.  New sorbic-type quaternary ammonium single-chain and gemini polymerizable surfactants: Synthesis, interfacial properties and anti-electrostatic activity , 2012 .

[3]  Roman Slowinski,et al.  Application of Rough Set Theory to Prediction of Antimicrobial Activity of Bis-quaternary Ammonium Chlorides , 2012, Rough Sets and Knowledge Technology.

[4]  Rui Chen,et al.  Novel ionic liquid-type Gemini surfactants: Synthesis, surface property and antimicrobial activity , 2012 .

[5]  K. Patel,et al.  Surface-Active Properties and Antimicrobial Study of Conventional Cationic and Synthesized Symmetrical Gemini Surfactants , 2012 .

[6]  Sukhprit Singh,et al.  Synthesis and properties of thioether spacer containing gemini imidazolium surfactants. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[7]  Roman Slowinski,et al.  Rule-Based Estimation of Attribute Relevance , 2011, RSKT.

[8]  S. Verevkin,et al.  Building blocks for ionic liquids: Vapor pressures and vaporization enthalpies of 1-(n-alkyl)-imidazoles , 2011 .

[9]  R. Prasad,et al.  Synthesis and evaluation of new imidazolium‐based aromatic ether functionalized cationic mono and gemini surfactants , 2011 .

[10]  X. Xing,et al.  Antibacterial activity and cytotoxicity of two novel cross-linking antibacterial monomers on oral pathogens. , 2011, Archives of oral biology.

[11]  S. Al-Deyab,et al.  Syntheses, Structures and Antimicrobial Activities of bis(Imino)acenaphthene (BIAN) Imidazolium Salts , 2011, Molecules.

[12]  X. Xing,et al.  Luciferase and fluorescent protein as dual reporters analyzing the effect of n-dodecyltrimethylammonium bromide on the physiology of Pseudomonas putida , 2011, Applied Microbiology and Biotechnology.

[13]  N. Negm,et al.  Cationic schiff base amphiphiles and their metal complexes: Surface and biocidal activities against bacteria and fungi. , 2010, Colloids and surfaces. B, Biointerfaces.

[14]  K. Kuroda,et al.  Chemical structure of cationic groups in amphiphilic polymethacrylates modulates the antimicrobial and hemolytic activities. , 2009, Biomacromolecules.

[15]  H. Kourai,et al.  The mode of the antifungal activity of gemini-pyridinium salt against yeast. , 2009, Biocontrol science.

[16]  F. Guittard,et al.  Preparation and antimicrobial behaviour of quaternary ammonium thiol derivatives able to be grafted on metal surfaces. , 2009, European journal of medicinal chemistry.

[17]  E. Frąckowiak,et al.  Synthesis and properties of trigeminal tricationic ionic liquids. , 2007, Chemistry.

[18]  Seung Goo Lee,et al.  Imparting durable antimicrobial properties to cotton fabrics using quaternary ammonium salts through 4-aminobenzenesulfonic acid–chloro–triazine adduct , 2006 .

[19]  M. Berezovski,et al.  Selection of surfactants for cell lysis in chemical cytometry to study protein‐DNA interactions , 2006, Electrophoresis.

[20]  T. Maeda,et al.  Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds. , 2006, European journal of medicinal chemistry.

[21]  H. Nagamune,et al.  Biological and physicochemical properties of gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ. , 2005, European journal of medicinal chemistry.

[22]  Zdzisław Pawlak,et al.  Can Bayesian confirmation measures be useful for rough set decision rules? , 2004, Eng. Appl. Artif. Intell..

[23]  E. Urbanik,et al.  New bis-quaternary ammonium and bis-imidazolium chloride wood preservatives , 2004 .

[24]  I. Yoo,et al.  Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. , 2004, Bioorganic & medicinal chemistry.

[25]  S. Partyka,et al.  Micellar structure of gemini cationic surfactants: influence of the spacer length , 2001 .

[26]  Salvatore Greco,et al.  Rough sets theory for multicriteria decision analysis , 2001, Eur. J. Oper. Res..

[27]  M. Ferraro.  Performance standards for antimicrobial susceptibility testing , 2001 .

[28]  K. Kümmerer,et al.  Analysis of benzalkonium chloride in the effluent from European hospitals by solid-phase extraction and high-performance liquid chromatography with post-column ion-pairing and fluorescence detection. , 1997, Journal of chromatography. A.