Synthesis and in vitro antimicrobial evaluation of new N-heterocyclic diquaternary pyridinium compounds

Bianca Furdui; Georgiana Parfene; Ioana Otilia Ghinea; Rodica Mihaela Dinica; Gabriela Bahrim; Martine Demeunynck

doi:10.3390/molecules190811572

Synthesis and in vitro antimicrobial evaluation of new N-heterocyclic diquaternary pyridinium compounds

Molecules. 2014 Aug 5;19(8):11572-85. doi: 10.3390/molecules190811572.

Authors

Bianca Furdui¹, Georgiana Parfene², Ioana Otilia Ghinea³, Rodica Mihaela Dinica¹, Gabriela Bahrim⁴, Martine Demeunynck⁵

Affiliations

¹ Department of Chemistry, Physics and Environment, Faculty of Science and Environment, "Dunarea de Jos" University of Galati, 111 Domneasca Street, 800201 Galati, Romania. bfurdui@ugal.ro.
² Department of Food Science, Food Engineering and Applied Biotechnology, Faculty of Food Science and Engineering, "Dunarea de Jos" University of Galati, 111 Domneasca Street, 800201 Galati, Romania. Georgiana.parfene@ugal.ro.
³ Department of Food Science, Food Engineering and Applied Biotechnology, Faculty of Food Science and Engineering, "Dunarea de Jos" University of Galati, 111 Domneasca Street, 800201 Galati, Romania. ioana.ghinea@ugal.ro.
⁴ Department of Food Science, Food Engineering and Applied Biotechnology, Faculty of Food Science and Engineering, "Dunarea de Jos" University of Galati, 111 Domneasca Street, 800201 Galati, Romania. bahrim.gabriela@ugal.ro.
⁵ Centre National de la Recherche Scientifique (CNRS), UMR 5063, Department of Molecular Pharmacochemistry, F-38041 Grenoble, France. martine.demeunynck@ujf-grenoble.fr.

Abstract

A series of bis-pyridinium quaternary ammonium salts (bis-PyQAs) with different aryl and heteroaryl moieties were synthesized and their antimicrobial activity investigated. The inhibition effect of the compounds was evaluated against bacteria, molds and yeasts; the activities were expressed as the minimum inhibitory concentrations (MIC). The relationships between the structure descriptors (logP, polarizability, polar surface area (2D), van der Waals area (3D)) and the biological activity of the tested bis-PyQAs are discussed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / pharmacology*
Bacteria / drug effects
Chemistry Techniques, Synthetic
Fungi / drug effects
Hydrophobic and Hydrophilic Interactions
Microbial Sensitivity Tests
Pyridinium Compounds / chemical synthesis*
Pyridinium Compounds / pharmacology*

Substances

Anti-Infective Agents
Pyridinium Compounds