Synthesis, Surface and Antimicrobial Activities of Novel Cationic Gemini Surfactants

Ding, Zhaoyun; Fang, Shimin

doi:10.1007/s11743-015-1734-2

Cited by 13 publications

(8 citation statements)

References 30 publications

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“…From the obtained results, it can be stated that GS with ether groups in the spacer are more active against Gram (+) bacteria than Gram (−) bacteria. This is in line with the general relationship for gemini surfactants [ 26 , 67 , 121 ]. Dimeric alkylammonium salts belong to membrane active microbiocides.…”

Section: Resultssupporting

confidence: 89%

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

et al. 2021

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Due to their large possibility of the structure modification, alkylammonium gemini surfactants are a rapidly growing class of compounds. They exhibit significant surface, aggregation and antimicrobial properties. Due to the fact that, in order to achieve the desired utility effect, the minimal concentration of compounds are used, they are in line with the principle of greenolution (green evolution) in chemistry. In this study, we present innovative synthesis of the homologous series of gemini surfactants modified at the spacer by the ether group, i.e., 3-oxa-1,5-pentane-bis(N-alkyl-N,N-dimethylammonium bromides). The critical micelle concentrations were determined. The minimal inhibitory concentrations of the synthesized compounds were determined against bacteria Escherichia coli ATCC 10536 and Staphylococcus aureus ATCC 6538; yeast Candida albicans ATCC 10231; and molds Aspergillus niger ATCC 16401 and Penicillium chrysogenum ATCC 60739. We also investigated the relationship between antimicrobial activity and alkyl chain length or the nature of the spacer. The obtained results indicate that the synthesized compounds are effective microbicides with a broad spectrum of biocidal activity.

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Section: Resultssupporting

confidence: 89%

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

et al. 2021

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“…For the same type of the hydrophilic spacer, antimicrobial activity of geminis depends on the length of the alkyl substituent [145,154]. Gemini surfactants with higher HLB could be also obtained by introduction ester groups [160][161][162], amide group [163][164][165] or hydroxyl group [166,167] to alkyl chain. These compounds possess usually better antifungal activity than corresponding classical gemini surfactant.…”

Section: Biological Activity 61 Antimicrobial Activitymentioning

confidence: 99%

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Brycki¹,

Kowalczyk²,

Szulc³

et al. 2017

Application and Characterization of Surfactants

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Gemini cationic surfactants are compounds which are composed of two hydrophilic head groups and two hydrophobic tails linked by a spacer at the head groups or closed to them. The spacer can be either hydrophobic or hydrophilic. It can be rigid or flexible. The neutral charge of the molecule is retained by the presence of organic or inorganic counterions. Critical micelle concentrations (CMCs), surface tension (γ) and minimal inhibitory concentration (MIC) are dozen times lower than corresponding parameters of monomeric surfactants. The unique properties of gemini surfactants with a wide range of hydrophiliclipophilic balance (HLB) make them a very useful, innovative material in detergents, cosmetics, personal care products, additives for paints and coatings, biocides, material science, organic synthesis, pharmacy, textiles, enhanced oil recovery, nanotechnology, petroleum and many other branches of life. A large number of papers concerning gemini surfactants have been published so far. This review presents a synthetic look at current work devoted to structure, synthesis and applications of gemini surfactants.

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“…Until recently, research on the impact of gemini surfactants on microorganisms has focused mainly on bacteria and yeast [ 7 , 8 , 9 ]. With regard to moulds, experiments have been conducted only to determine minimal inhibitory concentration (MIC) values [ 10 , 11 ]. According to the current methodology [ 12 , 13 ], conidia are used to evaluate antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Impact of Cationic and Neutral Gemini Surfactants on Conidia and Hyphal Forms of Aspergillus brasiliensis

Koziróg

Brycki

Pielech‐Przybylska

2018

IJMS

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This study investigates the biological activity of two cationic gemini surfactants, hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) C6 and pentamethylene-1,5-bis-(N,N-dimethyl-N-dodecylammonium bromide) C5, and their two neutral analogs, hexamethylene-1,6-bis-(N-methyl-N-dodecylamine) (A6) and pentamethylene-1,5-bis-(N-methyl-N-dodecylamine) (A5). Experiments were performed with Aspergillus brasiliensis, which is used in the standard tests for biocides. The minimal inhibitory concentration (MIC) values for conidia and mycelium were determined using the dilution method. The viability of the conidia was evaluated using the plate count method. The dry mass of the mycelium was determined using the thermogravimetric method. Ergosterol was extracted from the mycelium and evaluated by gas chromatography. The effect of gemini surfactants on fungal morphology was observed using scanning electron microscopy. Cationic gemini surfactants were found to be active at lower concentrations compared to their non-ionic analogues, rapidly reducing the total number of conidia that were able to grow. They also decreased both the ergosterol content in the mycelium and its dry weight. These results suggest that cationic gemini surfactants C6 and C5 could have a wide range of practical applications as active compounds. However, it should be remembered that usage at too low concentrations, below the MIC, will only lead to short-term disturbances in the development of conidia and mycelium.

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Synthesis, Surface and Antimicrobial Activities of Novel Cationic Gemini Surfactants

Cited by 13 publications

References 30 publications

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

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

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Impact of Cationic and Neutral Gemini Surfactants on Conidia and Hyphal Forms of Aspergillus brasiliensis

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