title: Antibacterial properties and mode of action of new triaryl butene citrate compounds.
abstract: 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.
authors.affiliation: Centre de Biotechnologie de Sfax, Université de Sfax, Route de Sidi Mansour Km 6, BP 1177, 3018 Sfax, Tunisia; Chimie ParisTech, Ecole Nationale Supérieure de Chimie de Paris, Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France. Electronic address: mehdi_arbi@yahoo.fr.
authors.forename: Mehdi
authors.initials: M
authors.lastname: El Arbi
authors.affiliation: STELA Dairy Research Centre, Institute of Nutrition and Functional Foods, Université Laval, G1V 0A6 Québec, QC, Canada.
authors.forename: Jérémie
authors.initials: J
authors.lastname: Théolier
authors.affiliation: Chimie ParisTech, Ecole Nationale Supérieure de Chimie de Paris, Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Pigeon
authors.affiliation: Centre de Biotechnologie de Sfax, Université de Sfax, Route de Sidi Mansour Km 6, BP 1177, 3018 Sfax, Tunisia.
authors.forename: Karim
authors.initials: K
authors.lastname: Jellali
authors.affiliation: Centre de Biotechnologie de Sfax, Université de Sfax, Route de Sidi Mansour Km 6, BP 1177, 3018 Sfax, Tunisia.
authors.forename: Fatma
authors.initials: F
authors.lastname: Trigui
authors.affiliation: Chimie ParisTech, Ecole Nationale Supérieure de Chimie de Paris, Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
authors.forename: Siden
authors.initials: S
authors.lastname: Top
authors.affiliation: Centre de Biotechnologie de Sfax, Université de Sfax, Route de Sidi Mansour Km 6, BP 1177, 3018 Sfax, Tunisia.
authors.forename: Sami
authors.initials: S
authors.lastname: Aifa
authors.affiliation: STELA Dairy Research Centre, Institute of Nutrition and Functional Foods, Université Laval, G1V 0A6 Québec, QC, Canada.
authors.forename: Ismail
authors.initials: I
authors.lastname: Fliss
authors.affiliation: Chimie ParisTech, Ecole Nationale Supérieure de Chimie de Paris, Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
authors.forename: Gérard
authors.initials: G
authors.lastname: Jaouen
authors.affiliation: STELA Dairy Research Centre, Institute of Nutrition and Functional Foods, Université Laval, G1V 0A6 Québec, QC, Canada. Electronic address: riadh.hammami@fsaa.ulaval.ca.
authors.forename: Riadh
authors.initials: R
authors.lastname: Hammami
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D001597:Benzylidene Compounds / Q000737:chemistry / Q000494:pharmacology*; D005296:Ferrous Compounds / Q000737:chemistry / Q000494:pharmacology*; D006461:Hemolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D046529:Microscopy, Electron, Transmission; D013055:Spectrophotometry, Infrared
chemical_list: C000593213:1,1-bis(4-(3-dimethylaminopropoxy)phenyl)-2-ferrocenyl-but-1-ene; D000900:Anti-Bacterial Agents; D001597:Benzylidene Compounds; D005296:Ferrous Compounds
keywords: Antibacterial; Citrate salt; Ion efflux; Organometallic compounds; Tamoxifen; Transmission electron microscopy