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BioMed Research International
Volume 2015 (2015), Article ID 392326, 10 pages
http://dx.doi.org/10.1155/2015/392326
Research Article

Prediction of Antifungal Activity of Gemini Imidazolium Compounds

1Department of Pharmaceutical Technology, Nicolaus Copernicus University, Jurasza 2, 85-094 Bydgoszcz, Poland
2Institute of Computing Science, Poznań University of Technology, Piotrowo 2, 60-965 Poznań, Poland
3Institute of Chemical Technology, Poznań University of Technology, Skłodowskiej-Curie 2, 60-965 Poznań, Poland
4Department of Organic Chemistry, Nicolaus Copernicus University, Jurasza 2, 85-094 Bydgoszcz, Poland
5Department of Microbiology, Nicolaus Copernicus University, Skłodowskiej-Curie 9, 85-094 Bydgoszcz, Poland
6Systems Research Institute, Polish Academy of Sciences, Newelska 6, 01-447 Warsaw, Poland

Received 21 October 2014; Revised 13 December 2014; Accepted 23 December 2014

Academic Editor: Lei Chen

Copyright © 2015 Łukasz Pałkowski et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The progress of antimicrobial therapy contributes to the development of strains of fungi resistant to antimicrobial drugs. Since cationic surfactants have been described as good antifungals, we present a SAR study of a novel homologous series of 140 bis-quaternary imidazolium chlorides and analyze them with respect to their biological activity against Candida albicans as one of the major opportunistic pathogens causing a wide spectrum of diseases in human beings. We characterize a set of features of these compounds, concerning their structure, molecular descriptors, and surface active properties. SAR study was conducted with the help of the Dominance-Based Rough Set Approach (DRSA), which involves identification of relevant features and relevant combinations of features being in strong relationship with a high antifungal activity of the compounds. The SAR study shows, moreover, that the antifungal 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. We also show that molecular descriptors MlogP, HOMO-LUMO gap, total structure connectivity index, and Wiener index may be useful in prediction of antifungal activity of new chemical compounds.