J Appl Biomed 14:125-130, 2016 | DOI: 10.1016/j.jab.2016.01.005

Antimicrobial effect of salicylamide derivatives against intestinal sulfate-reducing bacteria

Ivan Kushkevycha,b,*, Peter Kollara, Ana Luisa Ferreirac, Diogo Palmac, Aida Duartec, Maria Manuel Lopesc, Milan Bartosb, Karel Paukd, Ales Imramovskyd, Josef Jampileke,*
a Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Czech Republic
b Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Czech Republic
c Department of Microbiology and Immunology, Faculty of Pharmacy, University of Lisbon, Portugal
d Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Czech Republic
e Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Czech Republic

Sulfate-reducing bacteria (SRB) are most likely involved in both the initiation and maintenance of inflammatory bowel disease (IBD); unfortunately present antibacterial chemotherapeutics used in the treatment of IBD have been ineffective. Thus, the antimicrobial activity of salicylamide derivatives against two different genera of intestinal SRB, Desulfovibrio and Desulfomicrobium, was investigated. Six 2-(phenylcarbamoyl)phenyl N-[(benzyloxy)carbonyl]alkanoates and three 2-hydroxy-N-[(2S)-1-oxo-1-(phenylamino)alkan-2-yl]benzamides showed MIC values in the range from 0.22 to 0.35 μM against Desulfovibrio piger Vib-7 and in the range from 0.27 to 8.52 μM against Desulfomicrobium sp. Rod-9, while MIC values of ciprofloxacin were 41.2 μM and 39.3 μM. The highest potency against the two strains was observed for 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide (MIC 0.22 μM and 0.27 μM). 4-Chloro-2-[(4-nitrophenyl)carbamoyl]phenyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate showed high activity against D. piger Vib-7 (MIC = 0.26 μM), while 4-chloro-2-[(4-methylphenyl)carbamoyl]phenyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-2-yl)propanoate expressed high activity against Desulfomicrobium sp. Rod-9 (MIC = 0.31 μM). Structure-activity relationships are discussed.

Keywords: Sulfate-reducing bacteria; Desulfovibrio piger; Desulfomicrobium sp.; Salicylamides; Bowel disease; Lipophilicity; Structure-activity relationships

Received: November 28, 2015; Revised: January 26, 2016; Accepted: January 28, 2016; Published: April 1, 2016  Show citation

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Kushkevych I, Kollar P, Ferreira AL, Palma D, Duarte A, Lopes MM, et al.. Antimicrobial effect of salicylamide derivatives against intestinal sulfate-reducing bacteria. J Appl Biomed. 2016;14(2):125-130. doi: 10.1016/j.jab.2016.01.005.
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