Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

Brycki, Bogumił; Szulc, Adrianna; Kowalczyk, Iwona; Koziróg, Anna; Sobolewska, Ewelina

doi:10.3390/molecules26195759

Cited by 13 publications

(8 citation statements)

References 127 publications

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“…In the literature, the effect of anions on biological activity was also considered. Generally, it is suggested that antimicrobial activity mainly depends on the length of the hydrocarbon chains of the compound, but some studies pointed out that the type of counterion also affects MIC [ 23 , 24 ]. Anion effects are of lesser importance than those of the cations.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

et al. 2022

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In this study, a series of 10 novel 1-methyl-3-octyloxymethylimidazolium derivatives carrying various anionic moieties (4-hydroxybenzenesulfonate, benzenesulfonate, carvacroloxyacetate, chloride, formate, propionate, thymoloxyacetate, vanillinoxyacetate, eugenoloxyacetate and trimethylacetate) were synthesized. Compounds were tested for their antimicrobial activity against six microbe strains (Staph-ylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli, Enterococcus faecalis, and Candida albicans), cytotoxic activity against the mouse melanoma cell line (B16 F10), and surface active properties. All synthesized compounds exhibited antimicrobial activity (expressed as minimum inhibitory concentration; in range of 0.10–27.82 mM/L), especially against Gram-positive bacteria and fungi. In addition, all compounds demonstrated cytotoxicity on B16 F10 cells (IC50 values 0.0101–0.0197 mM/L). Surface properties defined as CMC values, ranged from 0.72 to 32.35 mmol L-1. The obtained results provide an insight into the promising activity of a novel group of quaternary imidazolium derivatives having ionic liquid properties. The most potent compounds, containing a thymoloxyacetate and eugenoloxyacetate moiety, could be candidates for new antimicrobial agents or surfactants.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

et al. 2022

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“…This means that the activity only increases to a certain tail length and then decreases. The cut-off effect of the membrane active compounds (which penetrate to the membrane and disrupt its architecture) has been well documented [14,19,20,[36][37][38][39][40][41][42][43][44].…”

Section: Chemistrymentioning

confidence: 99%

“…It can only be speculated whether the different courses of dependences of bactericidal activities against S. aureus ATCC 29213/MRSA SA 3202 (MRSA3) from isolates MRSA1/MRSA2 could be due to their differences in the composition of bacterial membranes [55][56][57][58]. The effect of changing the length of the hydrocarbon tail affecting the extent of antimicrobial activity of the compounds has been discussed (e.g., [36,37,[39][40][41][42][43][44]59,60]). The decrease in biological activity at a higher chain length as a cut-off effect is discussed above.…”

Section: Structure-activity Relationshipsmentioning

confidence: 99%

Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates

et al. 2022

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Pattern 1-hydroxy-N-(2,4,5-trichlorophenyl)-2-naphthamide and the thirteen original carbamates derived from it were prepared and characterized. All the compounds were tested against Staphylococcus aureus ATCC 29213 as a reference and quality control strain and in addition against three clinical isolates of methicillin-resistant S. aureus (MRSA). Moreover, the compounds were evaluated against Enterococcus faecalis ATCC 29212, and preliminary in vitro cytotoxicity of the compounds was assessed using the human monocytic leukemia cell line (THP-1). The lipophilicity of the prepared compounds was experimentally determined and correlated with biological activity. While pattern anilide had no antibacterial activity, the prepared carbamates demonstrated high antistaphylococcal activity comparable to the used standards (ampicillin and ciprofloxacin), which unfortunately were ineffective against E. feacalis. 2-[(2,4,5-Trichlorophenyl)carba- moyl]naphthalen-1-yl ethylcarbamate (2) and 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl butylcarbamate (4) expressed the nanomolar minimum inhibitory concentrations (MICs 0.018–0.064 μM) against S. aureus and at least two other MRSA isolates. Microbicidal effects based on the minimum bactericidal concentrations (MBCs) against all the tested staphylococci were found for nine carbamates, while 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl heptylcarbamate (7) and 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl (4-phenylbutyl)carbamate (14) demonstrated MBCs in the range of 0.124–0.461 μM. The selectivity index (SI) for most investigated carbamates was >20 and for some derivatives even >100. The performed tests did not show an effect on the damage to the bacterial membrane, while the compounds were able to inhibit the respiratory chain of S. aureus.

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“…It is worth emphasizing that gemini surfactants work effectively at a very low concentration, often several times smaller in comparison to single quaternary ammonium salts [ 59 , 60 , 61 , 62 , 63 ]. This is very important from an ecological point of view, in that to achieve the desired utility effect, the minimal concentration of compounds are used [ 64 , 65 , 66 , 67 ].…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Encapsulated Gemini Surfactants

et al. 2022

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(1) Background: Encapsulation of surfactants is an innovative approach that allows not only protection of the active substance, but also its controlled and gradual release. This is primarily used to protect metallic surfaces against corrosion or to create biologically active surfaces. Gemini surfactants are known for their excellent anticorrosion, antimicrobial and surface properties; (2) Methods: In this study, we present an efficient methods of preparation of encapsulated gemini surfactants in form of alginate and gelatin capsules; (3) Results: The analysis of infrared spectra and images of the scanning electron microscope confirm the effectiveness of encapsulation; (4) Conclusions: Gemini surfactants in encapsulated form are promising candidates for corrosion inhibitors and antimicrobials with the possibility of protecting the active substance against environmental factors and the possibility of controlled outflow.

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Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

Cited by 13 publications

References 127 publications

Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates

Fabrication of Encapsulated Gemini Surfactants

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