Antibacterial properties and mode of action of new triaryl butene citrate compounds

•New triaryl butene derivatives analogues of tamoxifen were synthesized as citrate salts.•All compounds were antibacterial at μM range against G+ and G− foodborne pathogens.•Compounds 2 and 4 showed the lowest hemolytic effect (11 & 7.8%) at 50 μM.•Bacterial cell treatment with compounds 1, 2 or 3 led to high K+ and Na+ efflux.•Compounds made severe damage of membranes in treated Escherichia coli and Listeria ivanovii cells.

The aim of this study was to evaluate the antibacterial activity of newly synthesized triaryl butene analogues of tamoxifen. Several compounds were synthesized and converted to citrate salts to ensure greater solubility. Four compounds showed significant antibacterial activity at micromolar concentrations against Gram-positive and Gram-negative foodborne pathogens including Listeria monocytogenes, Listeria ivanovii, Enterococcus faecalis, Staphylococcus aureus and Escherichia coli. Two compounds at 50 μM, caused only 7.8 and 11% hemolysis. One of these as well as the remaining two caused high K+ and Na+ efflux from bacterial cells. Ultrastructural alterations were also visible using transmission electron microscopy, which revealed severe damage of the inner or outer membrane of E. coli. L. ivanovii showed swelling, corrugations and similar damage indicating a loss of cell-wall integrity. Organometallic compounds may offer interesting opportunities for the design of novel classes of antimicrobial compounds.

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