Paradoxical Effect of Synthetic Hydroxy Isothiocyanates on Antimicrobial Action of Aminoglycosides

Tajima, Hirokuni; Kimoto, Hisashi; Taketo, Akira

doi:10.1271/bbb.67.1844

Cited by 10 publications

(7 citation statements)

References 5 publications

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“…It has been suggested that ITC group covalently cross‐links to a cellular target (Tajima et al . ). ITC compounds can target a unique protein or limited number of proteins (that possess a vital function) by modifying a group crucial for the activity of the targeted protein.…”

Section: Discussionmentioning

confidence: 97%

“…The presence of an ITC group is the most crucial factor determining the compounds activity, as related cyanate or thiocyanate derivatives (compounds 23 and 25, respectively) do not inhibit bacterial growth. It has been suggested that ITC group covalently cross-links to a cellular target (Tajima et al 2003). ITC compounds can target a unique protein or limited number of proteins (that possess a vital function) by modifying a group crucial for the activity of the targeted protein.…”

Section: The Mechanism Of Itc Inhibitory Activitymentioning

confidence: 99%

“…High antimicrobial activity of many ITCs revealed in previous studies merits search for more active representatives of this class and thorough investigation of their action mechanism in order to use the compounds to combat infections. The studies of ITCs as potential antimicrobial agents are yet at the starting stage (Chmel et al 1958;Drobnica et al 1968;Johns et al 1982;Tajima et al 1998Tajima et al , 2001Tajima et al , 2003Fahey et al 2002;Johansson et al 2008;Jung et al 2010;Dufour et al 2012;Conrad et al 2013). Very limited set of ITCs have been used in these studies.…”

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confidence: 99%

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Growth-inhibitory activity of natural and synthetic isothiocyanates against representative human microbial pathogens

Kurepina¹,

Kreiswirth²,

Mustaev³

2013

J Appl Microbiol

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Aims The aim of this study was to test the growth inhibition activity of isothiocyanates (ITC), defense compounds of plants, against common human microbial pathogens. Methods and Results In this study we have tested the growth inhibitory activity of a diverse collection of new and previously known representative ITC of various structural classes against pathogenic bacteria, fungi and molds by a serial dilution method. Generally, the compounds were more active against Gram-positive bacteria and fungi exhibiting species-specific bacteriostatic or bactericidal effect. The most active compounds inhibited the growth of both drug-susceptible and multi drug resistant (MDR) pathogens at micromolar concentrations. In the case of Mycobacterium tuberculosis some compounds were more active against MDR, rather than against susceptible strains. The average anti-microbial activity for some of new derivatives was significantly higher than previously reported for the most active ITC compounds. The structure-activity relationship (SAR) established for various classes of ITC with Bacillus cereus (model organism for B. anthracis) followed a distinct pattern, thereby enabling prediction of new more efficient inhibitors. Remarkably, tested bacteria failed to develop resistance to ITC. While effectively inhibiting microbial growth, ITCs displayed moderate toxicity towards eukaryotic cells. Conclusions High antimicrobial activity coupled with moderate toxicity grants further thorough studies of the ITC compounds aimed at elucidation of their cellular targets and inhibitory mechanism. Significance and impact of the study This systematic study identified new ITC compounds highly active against common human microbial pathogens at the concentrations comparable with those for currently used antimicrobial drugs (e.g. rifampicin, fluconazole). Tested representative pathogens do not develop resistance to the inhibitors. These properties justify further evaluation of ITC compounds as potential antimicrobial agents for medicinal use and for industrial applications.

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Section: Discussionmentioning

confidence: 97%

Section: The Mechanism Of Itc Inhibitory Activitymentioning

confidence: 99%

mentioning

confidence: 99%

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Growth-inhibitory activity of natural and synthetic isothiocyanates against representative human microbial pathogens

Kurepina¹,

Kreiswirth²,

Mustaev³

2013

J Appl Microbiol

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“…However, small changes in the concentrations of both ITC and streptomycin affect their combined action from synergism to suppression of antimicrobial activity. The mechanism of synergism and suppression remains unclear (Tajima et al, 2003). AITC was effective at reducing the MIC of erythromycin against Streptococcus pyogenes (Palaniappan & Holley, 2010), and both AITC and PEITC displayed a synergy with streptomycin against Gram-negative bacteria such as E. coli and Pseudomonas aeruginosa (Saavedra et al, 2010).…”

Section: Mic Against Various Pathogensmentioning

confidence: 99%

The antibacterial properties of isothiocyanates

2015

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Isothiocyanates (ITCs) are natural plant products generated by the enzymic hydrolysis of glucosinolates found in Brassicaceae vegetables. These natural sulfur compounds and their dithiocarbamate conjugates have been previously evaluated for their anti-cancerous properties. Their antimicrobial properties have been previously studied as well, mainly for food preservation and plant pathogen control. Recently, several revelations concerning the mode of action of ITCs in prokaryotes have emerged. This review addresses these new studies and proposes a model to summarize the current knowledge and hypotheses for the antibacterial effect of ITCs and whether they may provide the basis for the design of novel antibiotics.

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“…4,5) In recent years, infectious diseases due to new types of viruses are emerging one after another, and the need for chemicals with infection-suppressive effects on viruses is well recognized. The antiviral activity of some ITCs, for example allyl ITC, benzyl ITC, horseradish extract, and so on, has been tested on herpes simplex, influenza, mouse hepatitis, human rhino virus, etc.…”

mentioning

confidence: 99%